66. You Don't Need to Use Points for Every Trip with Dr. Laura Jana

Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher-than-average expenses to travel the world. I'm your host, Devon Gimbel, and I believe that your expenses are your greatest untapped asset if you know how to leverage them. Ready to dive into the world of credit card points and miles so you can travel more, travel better, and travel often? Let's get started.

Welcome back to the podcast, everybody. If you're anything like me, you probably have one or two or 17 different trips that you're dreaming of booking at any given time. The beauty of points and miles, of course, is that for certain wish list travel experiences, points can significantly defray your travel costs and save you thousands or even tens of thousands of dollars on aspirational travel. 

But of course, not all wish list travel experiences can be booked using points, but part of the beauty of having points and miles is that every dollar you save by booking travel with points instead of cash is a dollar that you can allocate somewhere else, including towards those travel experiences that aren't possible to book with points.

In today's episode, you're going to hear all about an unforgettable trip taken by a member of the Point Me To First Class community, Dr. Laura Jana, that I know is at the top of so many people's wish list when it comes to unique travel experiences that may not be bookable actually using points, but is still an incredible trip to consider taking, and that is a cruise to Alaska.

But we are not talking about your standard mega ship cruise experience. Today, you are going to hear all about what it's like to charter a small private Alaskan cruise, including why Dr. Jana chose to go this route instead of a traditional cruise, the benefits and unique experiences available on a chartered boat, why this can be a great option, even for folks who don't consider themselves cruisers, and her most memorable experiences traveling seeing Alaska by boat.

Whether you've never even considered going on an Alaskan cruise or knew it was possible to charter a private boat to create a completely personalized cruising experience, you're not going to want to miss this conversation. 

My guest today, Dr. Laura Jana, is an Omaha based pediatrician, social entrepreneur, and award-winning children and parenting book author who first gained international recognition working with world renowned pediatrician, Dr. Spock. Now on faculty at PSU, she has 20 plus years’ experience working with parents, educators, media, academia, government, nonprofits, and corporations alike. 

From early literacy advocate and nine year owner of a 200 student educational childcare center to advisor to Mattel Primrose schools and spokesperson for the American Academy of Pediatrics, she's dedicated to addressing the most pressing needs of children, families, and communities. She also loves photography, fitness, books, and bargain hunting, and is faithfully committed to reading the weekly travel section of the Sunday paper. I hope you all enjoy this conversation with Dr. Laura Jana. 

Devon: Welcome to the podcast, Laura. Thank you so much for joining me today.

Laura: Oh, I'm excited to actually join you on this. I'm a big fan. 

Devon: Amazing. So let's start out real quick with a little bit of background before we dive into this one specific trip that you recently took and all about it. First, I'm just curious to hear from you. How long have you been in the points and miles hobby? 

Laura: Actually, not long enough seeing as how the trip we're going to talk about, I didn't use points for but easily could have used some. But it was about November, December of last year. So not that long, just at the end of 2023.

Devon: Yeah that's one thing that I think is really interesting about this conversation and why I wanted you to join me today because I think sometimes there's this perception that if you're new to points or miles that until you get really, really great at it, or until you have built up this huge stockpile of points and miles that you're sort of not doing it, quote unquote, right. 

I really want to dispel some of those common myths. I think that there are so many different advantages to having points and miles. But I don't think that even if you've been in this hobby for years and years and years that that means that you should only ever travel using points and miles for all of your trips from here to the end of eternity. I think there are absolutely times and trips and circumstances where points can be enormously helpful and enormously valuable. But not every single type of trip is easy to book using points and miles. Certainly some aspects of travel lend themselves so much better to being having the cost afraid by using points or miles.

One type of trip in particular that I think a lot of people are really, really interested in taking and sort of wondering how do we make this work in the bigger travel picture is a trip that you recently took. So can you tell us a little bit more about where you went and just how did you decide to take this trip? 

Laura: Well, absolutely. I'll tell you, but I'm going to start by saying just so people kind of have the right mindset around this. I have always loved travel. So I already feel like I found my people. I had to remind myself. I'm like, should I say something about this trip to the group because it wasn't a points trip, but it has points opportunity. I was like, but wait a minute, what ties us all together is that we love to travel. I have always been a bargain hunting traveler who thought I was very good at it until I got introduced to Point Me to First Class. Then I realized that there was so much more that I could be doing. 

So, as I said, I started in November, December. I sat and watched. I read all the comments. I made notes. I saved posts so I could come back and like do these things. But it all stuck, and I was resisting the urge to jump in until the 250,000 Amex Business Platinum deal popped up. I was like I was getting jittery before that. I said okay, that's it. I can't hold out anymore.

But the point being, I love to travel, and I was a bargain hunter. So the trip that I took, the one that you're referring to, was one that I never thought I would take because it wasn't inexpensive, right? Like this wasn't like the big bargain deal trip, which means that when I say that it was probably one of the best trips I and my family have taken and that I felt compelled to find who would want to know about this, it's that context. 

So the trip we took was this past summer in July. My family, so I've got my husband, who's also a physician, he's a surgeon, and our three kids who are now all in their 20s. We were going to be empty nest when the pandemic hit. So that got postponed a few years, but we're empty nest. So we actually really prize the time that we get to spend with all three kids coming together with them scattered around the country. We took an Alaskan cruise. 

Now we had talked about, I had planned a very nice, like bucket list trip to Tanzania, two weeks safari, and I hit purchase on all, no points because big decision back before I knew about this group. Back right in, let's see, was February of 2020. Hit purchase, we're good to go. Kids can all get together, time off of school, time off of work, all those things. Then the pandemic hit, had to cancel the entire thing. Now we're facing this, I don't think we could all get two weeks off together or 10 days if we tried. 

So we thought, okay, the other one on our list is Alaska, and we're going to do a cruise. So we started looking for a cruise. My husband, who's, like I said, he's a surgeon. He's a joint replacement surgeon. Has a tendency to go to work and survey everybody he talks to about like, where do you like to eat? What's the best dry cleaner? So he started saying, have you taken an Alaskan cruise? Where did you go? Did you like it? 

Fortunate for us, another surgeon who we knew liked to take very high-end trips with his family had done all the research and found a private charter that did customized experiences in Southeast Alaska. We had already started looking at the prices of cruises. We thought, well, if we're going to do this, we're sort of at the stage. We'll spend up for at least one room with the balcony and the open, whatever. We'll stick the kids in a smaller, less expensive room, get two of those, and then we're good. But this is going to be a week-long, amazing trip, and we're just going to spend what we need to spend.

That's when we found out about this week-long private charter. It was certainly more. I posted to the group. It wasn't an inexpensive trip. If you had just said to me, would I ever spend that much on a cruise? I'd be like, no, I'm going to go find a good bargain with the free airfares that come along and the whatever. It proved to be unbelievable. 

So that's what we did is we took this Alaska Bound Charters group. The couple that owns the boat, we kind of got lucky because we found out about it. This was their second year, this past summer. It was their second year in operation. But they'd been on other people's boats doing charters. The husband, Jim, has lived his whole life in Alaska. I think his father worked for the Department of Natural Resources or whatever it was in Alaska. He'd done commercial fishing. He knew the area. 

His wife had spent over 20 years, Alisa, as a chef in the Seattle area and on whale watching trips and things. She is an unbelievably good chef. It was the two of them who run this trip. So I kind of thought, these are like people we would actually want to travel with anyways. Then they ran the trip for us. So it was a week. We went from Juneau to Petersburg, all three kids plus my daughter's fiancée in a three-state room, 92-foot yacht with all sorts of amenities and things that we can talk about. But it was fun. 

Devon: Oh, yeah. We're definitely going to get into everything that you guys did and what was really special about the amenities that were available on this cruise. But for people who are thinking about doing a cruise, and I am not a cruiser. I know very, very little about it. I am intensely introverted. I don't like being around people. So really, cruises and Disneyland are my two versions of existential hell. So they're not things that I have looked into a lot. 

Laura: I am so glad you said that because my husband and I, for his 50th birthday, we took a cruise. We thought, oh, we'll go do one of the ones, a little calmer cruise. So we did a Viking cruise, and we did the Rome to wherever, Barcelona, or whatever we did. It was nice because we got to stop in a bunch of places that we probably wouldn't have gone to otherwise. But we concluded we're not cruise people. We eat relatively healthy. I don't drink alcohol. He doesn't hardly drink. We get up really early in the morning, and we don't like touristy, stand in line, kitschy things. 

Disneyland, we're not fond of either. We once convinced our kids when they were like two and three years old, hat the area outside of Disney World, where they've got the Legos and things, we went there. They thought they went to Disney World, and we left and we didn't go in.

So we had already concluded we weren't cruise people. We were going to Alaska on a cruise because I convinced two of my kids long ago to be photographers with me because I love photography. It was like nature, photography, hiking, doing the outdoor stuff. For Alaska in particular, the ability to get around Alaska on a boat was what we liked. 

For introverts or people who like peaceful, quiet, think they're not cruise people, this is the trip for you in that sense. We spent, for example, one morning, it was very clear to our hosts, Jim and Alisa, that we really were excited about whales and that we could sit and listen to whales for a very long period of time because they filled the whole bay. We were mostly in places where there wasn't a single other boat around us ever.

So they said, okay, and you're up early. So, we'll get up early, and we'll serve you breakfast on the bow of the boat while you're drinking your tea watching the whales. We spent three hours in a bay and it was like, they sounded practically like elephants, right? Like you could hear them all around you in this bay, but you're by yourself.

If you want Jim and Alisa to disappear, they don't have to spend any time around you. If you want to hang out with them or hang out with Alisa while she's making unbelievably good food in the kitchen and see how she does it, you can. But that's where this was the cruise for people who like the peace, the quiet, the customized schedule, wake up early, stay up late. You like hot tubs. You want to play games. You want to watch TV. Whatever you want to do, you can do. 

For us, we spent a whole lot of time following whales at a very respectful distance. We went to see the glacier, and they pointed out to us where the cruise ship stopped. It seemed so far back behind us because a 92-foot boat can get in. We went almost all the way up to the glacier and then they put their three kayaks in the water for us. We kayaked through the icebergs up to the calving glacier while we photographed seals sitting on the ice 10 feet away from us.

Then my kids decided to do a polar plunge, which was not my thing, never will be my thing. Then quick run up to the top deck and jump in the hot tub, right? I mean, that kind of cruise. So it's not what people think of as cruising in the sense of we had already decided we weren't cruise people. We were just going to do the Alaska cruise because of Alaska, not because of the cruise. 

Devon: Yeah, I think that there's going to be so many people who can relate to that type of sentiment. Certainly in terms of areas that are just known for their natural beauty. I think Alaska is at the top of so many people's list to do this type of experience, and especially the type of experience where you can be boat-based rather than land-based. Then just the activities and the viewing that that affords versus taking a, quote unquote more, traditional trip where you don't have access to a boat. 

Now for people who, again, where an Alaska cruise is kind of top of their mind and when they've thought about that, maybe the only consideration they've ever had is a more traditional, very large boat, major cruise line type of experience. What kind of tips or what advice would you have for people in terms of going about how do you think it's wise to choose a charter boat for your trip? Or are there certain elements that you think it's important for folks to consider if they are looking into this more private charter type of experience? 

Laura: Sure. Let me just say again, we never considered ourselves private yacht charter boat people. Did not know that was a thing, thought it was way more than I thought it was worth spending. So I don't presume to know a whole lot about it. We kept thinking it's too bad Jim and Alisa don't go around the world on their boat because we would just take trips with them all over the place. 

Now I did get invited back on their boat because I took photos for them. Since they're a new business, I was all excited. I'm like you can have my photos, use them. So they've been using all my photos. So they invited me back for another week to come take pictures in Sitka for a week on their boat. So I took my 24-year-old son with me, who's a photographer now, and we took pictures for them there. 

So what I would look for is obviously where they go, where the boat goes, if it's where you want to go. Obviously, I would think most of them customize because that's part of the appeal to it. But we thought about it as our family, we like to do things as a family, sort of private. Don't want to stand in line touristy, wait an hour at a restaurant at an all-inclusive resort if we don't have to. We got to spend the time together but not too close.

I have one son, my 26-year-old, whose regular schedule would be he'll wake up around 11 in the morning, and he'd like to go take his polar plunge at 10:00 at night, jump in the hot tub, have a few drinks, and hang out until one in the morning. My husband and I are like, it's 9:00. We're ready for bed. We like to wake up at sunrise, catch some photos, like that kind of thing. So the ability on a private boat to have enough space where you can kind of be doing your own things, but have enough that everybody could be happy was a big one for us.

Also that we liked, now we didn't know that we liked Jim and Alisa when we went out there, but fortunately this other surgeon, my husband's colleague, had already done all the research, talked to them many times, and scheduled their trip already. So we got a whole lot of insight from that.

Then the last thing for us that's really partly what makes vacations for us is we like, my husband in particular, very likes good food, very into good restaurants. So we spend every year, we go at Christmas time to Grand Cayman. Expensive restaurants, but we get somewhere way up the beach that's kind of secluded, and every day we go out to a fancy expensive restaurant. Like that is my husband's dream vacation. 

So figuring out what you're going to eat on the boat is not insignificant, especially in somewhere like Alaska where you don't just pop over to a different restaurant if you don't like what they're serving. These guys, Alisa, I mean, they had a big long kind of form you filled out of what do you like to eat? What do you like to drink? What is your schedule? Do you have a schedule? Do you want to participate in the, would you like to go hang the crab pots off the little boat, go back out with us and pull them in? Would you like to have it served on the back deck? Would you like informal buffet? What would you like?

When we looked at that form, we're like oh, this is the boat for us, right? We were like this is amazing. So we did shrimp. We did crab. We did fishing. They said would you like a barbecue on the beach, or would you like to stay on the boat? We're like yeah, no, that's great. Private secluded little island beach.

But it's not just like your run of the mill food. It was like seasoned like salads with homegrown herbs on the boat. She has an herb garden. Homemade sourdough bagels with lox that they had made themselves with. I mean, so the food was not insignificant for us. I certainly would find out what the options were or are somebody looking for a trip like this.

Then the last thing, just because I didn't want to forget, space. We sort of envisioned, I, as a kid, when I was in high school, my mother got invited by a colleague to come on a boat in like the British Virgin Islands. I don't think it was quite as big as this one, but probably close, some 90 some feet. I remember we had one of those little tiny showers where like you kind of fit in, and you kind of hosed yourself off a little bit. I think that's what I had in my mind for this boat. 

Like I said, there were three state rooms. My husband and I obviously got the master suite. It was a king sized bed with a sofa on one side, a dresser, a desk, cabinets on the other, a walk-in closet, and a full granite bathroom with a regular shower. They had a washer and dryer on the boat. They don't say like oh, just do all your laundry because they have to conserve water and things.

Well, we, as a family of five, we know how to travel light and conserve water. So by the end, they're like do you have any laundry you want to do? Like, go ahead and do laundry. Never had to worry about it. But each of the three state rooms had their own bathroom. I mean, they weren't huge in the other two rooms, but they were like regular bathroom, regular size shower. To me, it felt like we were staying in a hotel rather than roughing it on a boat. 

That made, I mean, we walked to the state room. My husband and I, were like this is crazy. We never expected that. Even though it was coming at a premium price, we were expecting much smaller.

Devon: Yeah. That sounds absolutely amazing just in terms of accommodations because for being on a boat where, again, that's basically where you are living the entire time that you're on this trip. Certainly you want to have a space where you're going to be comfortable enough. So it's really great to hear sort of what the layout was like, something that someone can expect. 

Of course, this may differ based on other companies or other charter options that people look into, but just hearing kind of what you all encountered on your specific trip is, I think, helpful to paint a picture for what other people might be able to expect. 

You may have mentioned this. I'm sorry if I didn't catch this, but how long was your actual trip? I'm really curious about where did you go? Did you actually stop at a certain number of ports or destinations, and how did you all pick the itinerary that you ended up taking for your trip? 

Laura: So this is also in line with what we look for, which was we didn't have to do all of it ourselves. We could tell Jim and Alisa what we liked. They typically sail out of Petersburg, but because they do trips between Petersburg and Juneau, sometimes it's Juneau to Juneau, sometimes it's Juneau to Petersburg but in that sort of Southeastern Frederick Sound part of Alaska.

So they said, fly in. We've got this week still available. We were late to the party, right? Like they'd had almost their full summer schedule. They had a week that we could all make work. They said okay, fly into Juneau, and here's where it was really nice. They picked us up at our hotel. So we flew into Juneau. We'd never been there before. We walked around that evening. The next morning, they drove and picked us up, drove us over to the boat. Then we went out.

We didn't have to pay attention to the itinerary any more than we said we’d love to get off the boat and go hiking. We would love to go kayaking. I love paddle boarding, but didn't really see myself wanting to fall into icy cold water. So I didn't do that. We said we love fishing. Yes, we'd like to go onto the beaches and wander around and take pictures and do stuff. They planned the whole thing for us. 

But half an hour on our trip, like half an hour out of Juneau, 45 minutes, there was a pod of whales, and they were bubble feeding. Now, I don't know about you. I did not know about bubble feeding. Picture a whole bunch of whales going down deep, blowing a whole bunch of bubbles that make a ring that traps the fish in it, then they all come bursting through the water at the same time. I was like okay, we don't need to go any further. Like 45 minutes out, and we're good. I'm like, let's just stay here. 

Got the most unbelievable photos. It was mesmerizing. They had an underwater microphone for us. So they can put the microphone in the water, and you could hear the whales, and then you'd hear the different sound then you'd be waiting for them to come up. My son who's not the photographer, obviously anyone who's a photographer, like this is like dream vacation 45 minutes in. My other son, first of all, loved the whale. Thought they were the coolest thing ever. But I mean, he was mesmerized. So we spent a good three hours. 

This is where they even said to us on a regular cruise, you pull up to the glacier, you see whales, and you look 15 minutes. They turn the boat around, the other side of the boat gets to see it for 15 minutes, and you keep going to your next port. 

These guys, what we really liked was that if the water was choppy, and they didn't want to go around the outside of an island, they could go on the inside. Or they'd go to a bay, but somebody was in it, and we wanted secluded private. So they'd go to another one and find a place. So that's where we didn't have to do a really rigid port of call. When are you going to be here? When do you have to be back on the boat again? 

When we went out in the kayaks, again, my son who's the least into photography and stuff, he sat in the back paddling for me while I sat in the front with my big lens. I'm like okay, here's a seal on the ice, best picture I've ever taken. My son's trying to whack ice off the, like floating by icebergs. But we were out for almost three hours. He said that was his second favorite thing next to the whales.

So it's not that I can't find things to do with that son, but he has less in common with me, like schedules, interests and things. That was the best part of the whole trip. It was unplanned, which means we just didn't leave the bay as soon as we thought we were going to. Then they adjusted for us afterwards. 

Devon: Yeah I think it's really that kind of two themes that I feel like have come up just in our conversation so far that really stand out to me in terms of kind of the advantages of this type of trip are the personalization and the customization. I think that all of us, I'm sure, have experienced when we've traveled, we go to a place where yeah, it's not really about what do you personally want to do or how do you want to make this experience customized to you or your different family members. You just kind of have to go where they say you're going to go or do what they say you're going to do. 

I think one of the enormous advantages of booking this type of experience is the fact that it sounds like you can personalize so much of your experience, and you can customize it to just what your interests are. Like you said, you're not bound to sticking to one set schedule. 

That if you find the things that are really appealing to you, that you actually have the latitude to linger there. I think that's what makes this type of experience so unique, especially to share as a family, as a group of people, like you said, different ages, different interests. But to be able for you all to have this one shared experience, it sounds like an enormous advantage.

Laura: Well, and one of my sons had a wedding he had to go to, and this was the only week that they had available that we could go. Then my one son said, well, I may not be able to go because I've got that, at the end of the week, I've got to be back for a wedding. We were like but you need to go because it's like you pay one flat amount for the boat, and it's up to six people. They can accommodate up to 10 if there's children or if you don't mind somebody sleeping or whatever. 

But we were like okay, we're not going to take this without him because that'd be stupid. Plus it's supposed to be like meaningful family trip together. So we thought well, what are we going to do? Because we don't want to cut it short by a day. It's an expensive trip, right? Flying out there, because I didn't have points at the time, flying out to Alaska for all of us coming from East Coast, Arizona, Nebraska, and Wisconsin. 

They said, well, when does he need to be out? What we figured out was that we were going from Juneau to Petersburg. They said well, you know what we'll do? We'll pull into Petersburg the day before, we'll run him to the airport. Then we'll spend that last 24 hours doing stuff around Petersburg. We thought oh, we're just going to, like it's going to be like us sitting in a port somewhere. 

No, because they're from there. I can't remember what the kind of boat is. It's like one of those like jet boat swamp kind of boats that you can go fast through like shallow water in like the marshy areas. Well, Jim grew up there. So he said well, we haven't done this with like clients on the boat before, but if you want, we can go do this. We're like zipping through these marshy areas with bald eagles and bears and all these things. Then we went and did a picnic, and we went to a waterfall and hot springs and all these things. 

They had not actually done it with other people before, like paying customers, but they did it so that we could drop our son off the day before at the airport and then stay there. 

So, again, the customization, personalization, not spending time doing things you don't want to do, not standing in line, and not leaving when you're doing the absolute thing you love most. Like for me and my two kids, it's the photography. If there's good photography and animals and nature and things, we'll spend hours. If my husband and my son didn't want to, they could go inside in the living room on the boat and watch TV, like watch the tennis, or whatever the tennis tournament was on, Wimbledon or something was on at the time. So.

Devon: So I'm really curious. It sounds like there was so much that you all did customize in terms of your trip, the itinerary, the activities that you did. Is there anything that you wanted to do or requested that just wasn't possible in terms of just logistics or what they were able to accommodate? Or I guess for other people who are planning on a trip like this, do you think that there are types of requests that people should not expect would easily be fulfilled? 

Laura: Well, what we loved about this was these guys, I mean, the only work or effort we put into it was filling out their forms. Then we were like, well, this is amazing because they totally followed it. I mean, they had like a whole spread out for food that we wanted, like kind of a breakfast bar area, but with snacks and treats, all the stuff that we would like, all the drinks that we would want in a refrigerator that was stocked. 

So the request, I mean, not really. What I know now, now that I've gotten to know Jim and Alisa and have gone on these two one-week trips with them, is they've had people come with like elderly grandparents who can't really, aren't very mobile. They've gone on trips with people with four and five-year-old, six-year-old children, and they can accommodate a lot. So I'm imagining there's some things they can't, and sometimes it's weather, but that would just be what you'd expect going to Alaska. 

But whether you want to have what you want to do, what your schedule is, what they have on board the boat before you get there. So they've got the kayaks, they've got the hot tub, they've got those sorts of things. But I think they're really into and we'll get you where you want to go. If you want to go do something else, we could even get you somewhere. If you want to do the helicopter ride somewhere, I don't know. I don't even know if they do helicopter rides in Alaska or if they just do the seaplanes, they could get you there. 

One of the other things that I think would be really good for someone doing this, especially in an area like Alaska, where it seems a lot of people know each other. What we found is Jim and Alisa know a lot of people, right? Because they've been there for so long, and they've worked on other boats, and they know the research vessels.

Just as a fun story, by the way, here's how well they know people and what they do sharing ideas about travel and experiences and weather and whales and things. Alisa, like I said, fabulous cook. So she made cookies. I'm not a big dessert person. I eat healthy. I'm into fitness.

But these cookies were so good, and they were actually, on the scale of cookies, relatively healthy, but they were so good. So she bakes these cookies. We're like coming up on the boat, we're like someone's making cookies. Like this, the whole boat smells good. She’s like yeah, I made them for all of you. But I also made some for the people on the research vessel, right? It looked like a big National Geographic-like boat. 

Because here's the thing because they swap information, right? They stop in, they check in, they see it. They said, so they said okay, we're going to pull up the boat, not take the little one, but we're going to pull up the boat. Here's how they swapped cookies. The guys on the other boat, they look like the fishermen with the rain suits and the big gear and everything. They take their big giant fishing net. Alisa has wrapped the cookies in foil, in a plastic bag, saran, all these things. She throws the bundle into their fishing net. 

Okay, because the big boat, they have two big boats next to each other. A couple hours later, we get a call from that fishing vessel. I mean, the research vessel. They said there's like 100 whales in a bay over whatever. There you go. We're off to go watch whales in the bay because they tell you where they are, what to look out for, what the weather's like. So anyways.

That's where they had said if they need something or we have to find something, they know people to ask, or they'll probably know the operator of the seaplane or somebody who has a truck they can borrow if they need to go park in Juneau somewhere and go pick people up or drop you off at the shops or I don't know. So yeah, that was a big feature for us is we didn't want to have to do the planning. For our purposes, there was nothing we wished we had done that we couldn't do on this boat. 

It certainly helped to have people where even just the simple logistics of we get into Juneau, and we're like okay, are there Ubers in Juneau at this time of night? Or Sitka. Like they're like yeah, no. We'll come pick you up. When I went to Sitka with my son, they said, well, technically we won't have finished the week before, but it was just friends on the boat with us. So one couple will still be with us, two have left already. I said well, do you want us to stay in the hotel at Sitka? They said oh no, we'll come get you. You won't find an Uber or anybody at night in Sitka. It's small. Then we just went to the harbor and stayed on the boat like it was a hotel the night before we were going to start. 

So that's where even the logistics of where do you stay? How far is it? How much does it cost? Are you going to be able to get somebody to drop you off or pick you up? How long does it take at the airport to get through? What kind of, we did not know when we went out there. They have a storage area for big suitcases. So we're like, we're going to be on this boat. We got to take small things and whatever. 

Now, not that I would take massive suitcases, but you want to take your rubber boots for hiking in the mud because we did a seven hour hike through the woods and the mud and the whatever, you could fit them, and they can stick your suitcases away for you. Not even in your room on the boat. 

Devon: Yeah. That's so convenient to know. Now you've mentioned, it sounds like a lot of incredible activities that you all did on this cruise. You talked about kayaking, photography. You just mentioned a seven hour hike that you went on.

Can you give me an idea of was there an even broader range of activities that were available that you guys did on this cruise or that would have been available to you if you had requested it? You've already mentioned some incredibly memorable ones, but I'm curious if one really stands out to you as the most memorable experience you had while you were on this trip. 

Laura: Well, for me, I have to say because I hadn't been to Alaska before, the whales had to be it. I mean, it was just, for anyone who likes nature, relaxing, like tuning out the rest of the world, just being, it's peaceful, but the marvel of the whales. I mean, huge. They would come right up to the boat. I mean, five feet off the. We're like, are they going to hit the boat? Cause when you see whales breaching in the videos and things. So it had to be that.

But I also like to get out and explore, like to actually feel like I went somewhere as opposed to just looked at something. So getting off the boat, the hike that I just did in Sitka on the second trip, we got off. We had to hike through. Like they, they pulled a little skiff boat, like kind of like rowboat size thing up to the water, but it was still about eight inches of water. Had to stop there. My son and I did not have like Pacific Northwest boots up your calves that you can walk in water and mud.

So one of the other couples who was there who was friends with Jim and Alisa, they're like here, get on my back. First of all, I've got my camera bag on. It's heavy. I'm like I don't know these people. I'm like well, now I feel like I know you very well right because you just took me 10 feet to the shore. It's very muddy. But we went through what looked like moon landing, rocks, mud, barren. Then we walked through like kind of river areas. It was still cold when we first started at the bottom of the mountain. So 32 degrees, a little bit icy.

Then we're through what looked like a rainforest, right? Some hot springs along the way for this hike then we got to the most secluded sort of deserted beach. It looked like it was an ocean beach after hiking all the way there, but like 10 times larger than any beach I've ever been to. With the woods and forest all around it, you could see animal prints and bear prints and things. Sand dollars showed up on the beach. 

Jim, who's a very funny guy, by the way, the captain, knows what he's doing, but he's also got a great sense of humor and very funny. But he's like, what do you mean you found a sand dollar? Where'd you find that? Like as if I was holding out on him. Because I'm like well, you're walking so far back from the waterline, you'd never find them but found 15. He's like, I didn't even know there were sand dollars in Alaska. Right.

But because people were just enjoying walking along this expansive, massive beach in the middle of the woods that you didn't even know was there. That, to me, was another memorable one. It was just get away. For anybody who's got stress in their lives, right? Busy work, kids, juggling lots of things. It's like I forgot about everything else. Those two things were just everything. The paddling through the icebergs. 

See, there's so many things. Paddling through the icebergs up to a calving glacier where the ice would come down from the glacier into the water, and you'd wait for like a minute, and you'd feel the waves coming by you in a kayak. So that was another one. 

Devon: Those all sound absolutely incredible. I have never really thought I need to go to Alaska on a cruise. I've heard so many other people who've done it and said great things about it, but hearing your stories are really making me reconsider. That idea that this really sounds truly like a once in a lifetime type of experience, especially to be had with a larger group of people, with a family or close friends. It's really got me thinking about when my kids are just a little bit older, a little bit more tolerant of just things in general, that this could be a really incredible option.

I'm just curious to hear from you. For other people who might be listening to this and maybe have never considered either going on a cruise to Alaska or never considered doing what you did, hiring a private charter for your Alaskan cruise. Do you think that there are any last tips or recommendations that you have for anyone interested in planning a similar trip that you think will make it easier for them to make this type of trip a reality for themselves? 

Laura: Well so the first thing is we had the benefit of word of mouth referral, which, and this is where I'm like I've written some books. I've done some other things. I'm terrible at selling my own stuff. I'm really good at selling other people's stuff. I want these guys to succeed. But the idea that when you get somebody authentically supporting, I always say, I'm not paid. Like I should be getting a commission for, but that's because I'm authentically excited about it just love, I want to see them succeed just like I like to see other people succeed doing good things.

But word of mouth would be a good one because I've been to plenty of places where it sounds good, looks good, whatever. We've all looked at TripAdvisor. Then you go how many of those were paid for? Or somebody asked you to fill out the form, but they're watching you while you fill it out. I just did a tour last week, and I'm like well, now you don't want to say bad things about it. It wasn't that great, but they're sitting right there, and you're going to hand the clipboard back to them. So that would be a big one.

Then this one, I also don't mention it without realizing it was an expensive trip, right? I mean, here's the way we looked at it afterwards, which was, first of all, by the time you're looking at an Alaskan cruise with a balcony, like that you've got some sort of the nicer things, at least for one of our rooms even if we didn't do it for our kids. We'd been looking at that. Well, you're talking like what, $7,000 for a week long, $7,000, $8,000 is what we were seeing for the same comparable time. 

To jump up to $10,000 a person, big jump for people where $2,000, you don't have it. But if you're looking at like, this is going to be the one big family trip, bucket list trip once in a lifetime, it didn't seem like as big a jump. But then also, I would say you have to compare apples to apples because we would be the people who'd pay extra for paddle boards and for kayaking and for going on a hike, like take a tour, go to Viator and take a tour and do those things. We didn't do any of that. No food, no transportation, no nothing. Like they took care of all of it for us.

Then we went wow. When I told some people who are more used to taking this kind of high end trip than I am, they're like wow, that's really not that expensive at all like when you factor in those other things. So that's what I would tell people is one is obviously I wouldn't be telling everybody to take this because I am very aware that not everybody is in a position to do that. I always say my three kids are now out of college, right? So at least that helps.

But also look what you want to get out of it. If it fits with your defined idea of like the perfect vacation, this had every element for us. For people like you who say, and like us, not a cruise person, this is the cruise for not cruise people. This is how you would go do get the benefits of what is cool about being at a cruise and going to different areas and seeing a bunch of things and seeing the sites, but without having to do these stand in line with a whole lot of people all, so.

Devon: Yeah, those are really, really great points to bring up. I think again, travel. I think personal finance is personal. I also think travel is personal. So when we share stories like this on the podcast, it's not because I think that every single person on earth should want to take any one of these types of trips or experiences that we highlight. 

It's more that let's share stories so that if you hear one that does resonate with you, or you hear one that opens up your mind to the possibility of something that otherwise never would have thought about that could end up being the trip of a lifetime for yourself or your family, then the better for everybody.

Laura: Devon, I love the group for that. I have to tell you just last week, I was on a relatively short birthday trip to Costa Rica with my husband. We were sitting in the airport. Of course, my now instead of doom scrolling, I scroll through all the comments on Point Me to First Class, and I saw somebody had said something about Costa Rica. 

Someone said they'd taken a nighttime frog tour. I'm like well, that sounds cool, like fascinating. Never would have thought of it, wouldn't have done it, and wouldn't have planned it for the night that we arrived, right? Because we land at the airport. We have to drive three hours. It was an amazing tour. But the fact that somebody who already probably was likely to have similar interests to me because they're part of the group. They like to travel, physician, mom, all those things, increased the odds that I was going to like what somebody else likes. 

So I look all the time when people talk about the Maldives, or they're at the Park Hyatt in, wherever, Tokyo. I'm like I'm making notes because I'm like those kind of discussions. I love when people post the details of their trips because I'm like cool, gives me ideas. I know I save it. So I'm like we want to go there. Now I don't have to go figure out what we should do.

So yeah, there's definitely that component of it, which is see if it's for you. But if for anyone who loves travel, even if this isn't for you, I would imagine people could understand why we were as enthused about it as we were. 

Devon: Absolutely. Again, for people who loved hearing this story and the experience that you describe is one that they are really interested in, I would love for you to be able to share the name of the husband and wife couple, again, who actually offered this opportunity, the name of their business. Again, for full transparency and disclosure, I have no affiliate links or arrangement nor do you for talking about this company. This is just a genuine, wonderful travel experience that you had that you would love to share with other people. 

I'm a huge fan and supporter of small businesses and small business owners. So when someone's had a fantastic travel experience, I'm more than happy to share that, again, with anybody in this audience who would benefit. But I do like to be totally transparent about the fact that these people don't even know that we're talking about their charter boat or their charter experience on this podcast. This was just a story that we wanted to share with you.

But for people for whom they, like you said, really like relying on word of mouth and don't necessarily want to start research from scratch about how would they go about organizing a trip like this, please share with us sort of the name of this couple, the name of their charter company for anyone who is interested in looking into this a bit more. 

Laura: Sure. To your point, by the way, I do get very excited about helping other small businesses. I've owned a small business. I've done a bunch of things where I'm like it's so nice when somebody does that, got very enthused about it. But it also reminds me for a lot of these private charters, especially when they're getting started like Jim and Alisa are, they were telling us while we were traveling together that they had to pay the brokers who helped them get customers, right? They have to pay like sometimes 30, 40, 50% to the broker. 

So I'm always like okay, if you're going to look them up, it's Alaska Bound Charters. So that's their website. Make sure you're not going through a broker. Because I felt, when we heard that, we're like that's terrible. But how are you going to get off the ground? We kept thinking you're not going to be able to get in on this boat once people know about it, but they have to build up word of mouth. 

The boat's name is Dauntless, D-A-U-N-T-L-E-S-S. The couple's name, it's Jim and Alisa. So Jim Edgers and Alisa Jessel. But they are the warmest, nicest, easy to connect with people. You can connect right through Alaska Bound Charters on the website for them. 

Devon: Amazing. We'll have all that information linked up in the episode show notes and the episode description. So it's easy for people to find and just click on links, again, if you do want to learn about scheduling or planning your own trip like this. Also, Laura, for people who are interested more in following you, learning more about what you do, where can people find you on the internet? 

Laura: Well, the easiest way is I actually have a woefully neglected website, but it's at drlaurajana.com. So it's just the D-R-L-A-U-R-A-J-A-N-A.com I mostly leave it up there because I have a contact us kind of page for a lot of my engagements and things, but the emails just come straight to me. So no formality. Just fill out whatever sections you have to get the email to send, but you can reach me directly. Obviously through the group because I'm on it every day scrolling through, but people can always direct message me. 

The other thing, you know what Devon, I forgot to mention, which would be I actually was like I don't want to spam the group. I'm relatively new, and I didn't know if this was going to be of interest. But the thing I also got very excited about was while I was spending my time sitting on the boat, looking at things, because I had just gotten my first couple of credit cards, and I was doing my points and things. I was telling Alisa about them. She said well, they take credit cards.

I had just been reading all these things about because your stuff on how you pay your taxes, and if you can only pay this percent for your taxes, it's worth it because you get this. So we did a couple of test purchases because I was buying some of their, like they got cool hats and sweatshirts and things. 

I said okay, put one on my Amex Gold and put one on my Chase Sapphire Reserve because they were both my new cards. The CSR put them as a travel category and did 3X. Then I said hey, what percent do you charge for credit cards? What are you charging? They were relatively new with it. They said oh, we just got a vendor to set it up for us and stuff. I just connected them with a credit card vending company that does charitable give back called Give Local. 

Give Local has just, they've just turned in their paperwork. So they're going to get a lower credit card fee. I was like well, at least I'm contributing for anybody who actually does want to do this trip. You could pay it, which would make it much more easy to like kind of manage the price of it if you're also getting a whole lot of points for it. 

Alisa was like, now, when I get the time to do this, you're going to have to tell me which credit cards to sign up for. I was already calculating what she could do if like she had the gas card. If she got 4X on gas when we're pulling up to the big 92 foot boat fueling station, seeing if they take it. So that's the other thing I wanted to make sure I mentioned to people, which is why I thought okay, I don't want to just post it and spam people with another trip because everybody's taking cold trips. 

Although it is very cool and I did want to share it, but also this idea of imagine because we didn't know that. I wasn't in on the game when we had paid our stuff. I was like I would have charged it on my CSR card and then I would have gotten all those points for it at the same time, which would have even been better.

Devon: Absolutely. I think in terms of the world of travel, when I look at booking trips or when I look at where we've allocated our travel budget and how we want to spend it, both our cash budget as well as our points budget, I really see basically all things that we spend money on is either a points earning or a points redeeming opportunity. I'm either going to get value from my points and offset the cost of travel, or I'm going to do my very best to leverage the spend that I've intended to have by earning as many points as possible.

I think this is such a great example of one of those trips that can be a combination of both. Where we didn't really get into flights and positioning and being able to use points for that aspect of a trip, but for any type of travel experience that you want to have that isn't necessarily one where you're going to be able to use your points for the booking of some aspect of the trip, like booking a charter cruise, certainly that can become an amazing points earning opportunity. I'm just thrilled to hear that they're accepting credit cards and they're coding as travel. 

So for people for whom, again, already wanted to take a trip like this, already have the budget set aside for it, absolutely make sure that you optimize that spend either by getting new credit cards or using a credit card that's going to bonus you for travel spend so that you can turn that cash portion, payment portion of your trip into a future flight or hotel stay somewhere else.

Laura: You've ruined me now because I literally was sitting on the boat thinking, oh my gosh, you can get several sign up bonuses, and you can do your points on your CSR. I'm like you can do all these things with this. Alisa was just laughing, but she was all in on it. Like figure out how to get the amount down so that it's a smaller percentage. 

I think she's just turned in her paperwork to get it to, I don't know what it is yet. She hadn't gotten the number back, but I don't think it was more than 3%. But I think she was trying to get it down to 2 point something percent for credit cards. So that was my small contribution. If anybody does end up taking the trip is to get the credit cards to go through. 

Devon: Absolutely. Well, Laura, thank you so much for joining me today. Thank you for sharing about this really, really incredible trip of a lifetime. I hope that, again, this gives people inspiration for either taking a similar trip or just a really, really great thing to imagine and what it would look like for their family, what version of this they can do for themselves or their family. So thank you so much for joining me today. It was an absolute pleasure talking to you.

Laura: All right, well thank you, and thank you for the group because I have to say, I love the culture and the sharing and my people. So it's great to join you. 

Devon: All right, well, everybody have a fantastic week. We will see you again, same place, same time next week for another episode of the Point Me to First Class podcast.

Thank you for joining me for this week's episode of Point Me to First Class. If you want more tips on turning your expenses into travel, visit pointmetofirstclass.com to learn more. See you next week.