How to Travel Cheap In Retirement with Jillian Sidoti
Creating Meaningful Travel Expenses Before and During Retirement
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Jillian Sidoti is an entrepreneur, traveler, and co-founder of Last Life Ever, a platform built on the idea that you shouldn't wait for retirement to live well. A mom of three based in Rincón, Puerto Rico, she shares her adventures at @lastlifetravel and helps people design lives full of meaning experiences. Thank you for joining us here today, Jillian. Excited to talk to Jillian. She is, quote, "a travel expert." So we're talking about traveling today. And I know many of us, as we head into retirement, that is something we really think about are thinking that's what we're gonna do. So I thought, you know what? Jillian would come and share. She's set up some amazing travel trips. I'm sure she'll share those with you, and then- Yeah ... basically how to plan and prepare. So Jillian, before we jump into the questions I have to get us talking about those things specifically, share who you are and what you do and how you got into the, really, the travel side of it all. Yeah. So it's interesting. I was an attorney for 15 years, and my life was, like, pretty, pretty miserable. It was interesting because I was having this really great career, and yet I found myself just wishing I didn't have it anymore, I was making a ton of money and I just didn't wanna have it anymore. I ended up going to a conference, and I met this guy who's now my business partner, and he said to me, "Oh yeah, I used to be a lawyer." And I remember thinking "Oh yeah, I wanna be a used to be a lawyer." And he told me a story about how he... And this is his story, but I'm gonna tell it anyhow. He told me a story about how he was a bankruptcy attorney, a very successful bankruptcy attorney, and he- Got really sick when he was in Peru at Machu Picchu. Got home and found out he had leukemia- Oh ... and thought he was gonna die, and went through all of that, the chemo treatment and whole thing, things. And when he came out of the fog of leukemia, he realized, "I'm just, I'm not gonna do this attorney stuff anymore." Not only that, he had to file for bankruptcy, right? So it was like this whole what am I doing with my life? And he was already committed to traveling. And for me, I wanted my kids to have a life of travel that I did not get when I was a child. I grew up in a very middle-class situation but I was also the oldest of five kids, so our idea of travel was getting in the station wagon and driving, fighting the entire, down the I95, and fighting the entire way, and then ending up somewhere. Or a minivan, whatever it was that year. And I remember thinking, when my kids were born, you're not waiting... I think I was 20 when I got my passport for the very first time. And I remember when my youngest was born, I have three kids, my youngest was born, he literally, he was fresh out of the womb, I still have his first passport, and I got him a passport almost immediately. And that's really when I started going, "I'm going to travel and I'm going to travel hardcore. I'm never gonna say no to travel opportunities." And that became even more clear when my husband and I planned a trip that we had been planning, for all intents and purposes, our entire lives together, right? We'd probably been together at that point in time my oldest was seven. So we'd been together for about 15, 16 years at that point in time. We won an auction, a church auction for a trip to Italy and this was a trip that we had planned to take before my oldest was even born, right? We bought the auction and then we still had to plan the trip. We still had to plan when we're gonna go, when to take the kids out of school, that kind of thing so we ended up planning 18 months out and a month before, my husband he'd kill me if I told you this. My husband had a yoga accident- and tore his labrum in his hip so badly that he couldn't even sit in a car, let alone be on a plane for eight hours. So- that was a moment in time where I had to make a decision. Was I gonna take three kids to Italy by myself, or was I gonna sit at home, and feel sorry for myself? And my husband's "You're going on that trip." And so that's what I did. I took... I think I said the wrong thing, my son was seven. He was not seven. He was 10. So my oldest was 10, and then I had a seven-year-old and a three-year-old, and we went to Italy, and we spent two weeks in Italy by ourselves. My aunt came out and met with us for a little while, and she hung out with us for a little bit, which was great, because I had an extra room. I had a extra hotel room that I already paid for. Yeah. So somebody might as well use it. Yeah. And and after that I've figured out every trip I've ever wanted to take I've figured it out "How are we gonna do this? Am I paying for it with points? Am I gonna save for it? What are we gonna do?" And that's it. And then there's gonna be those times where you're like, "Okay, maybe I can't afford the, the $15,000 Tahitian vacation." That's okay. You don't have to go to Tahiti. You can find other things to do. There's a big, wide world out there. You just have to figure out what you're gonna do and how you're gonna do it. I love that, and I love that you said, Tahiti, people talk about, and if you can't afford that which I've been working with a client, and she's got on her radar this big trip. So I Googled something similar, and I'm like, "Oh, there's tons of places local that wouldn't cost her as much." Yeah. And so it's looking at the options and things like that. So I love that story. I love, taking your three kids by yourself. I'm glad your aunt could go and support you. Yeah. So for someone who dreams of traveling more but doesn't know where to begin, they didn't get thrown into the auction, thrown into the fire of, "I gotta take my three little ones by myself," what are the first few steps you recommend? The first thing is you gotta have a goal in mind. You... I absolutely have to... I wanna go to blankety blank, and the word someday should never come out the end of that sentence. It always should be just a definitive, "I want to go to X." And then you have to set yourself a deadline of when you're gonna go by. It's not someday. Someday is never. You might as well just say, "I wanna go to..." And I'll use... Right now we have a big trip to Egypt planned, so I'll say, "I wanna go to Egypt" never is the same as saying, "I wanna go to Egypt someday," 'cause you'll just... if you live in that kind of like- unknown it will be a never. That I'll tell you what the known is. The known is that it's never gonna happen. And I've met a lot of people in that particular situation. So the big thing is to set your mind on a goal, and then set a date for that goal, just like any other goal that you would set. Whether it's a career goal, or a retirement goal, or, a housing goal. Whatever your goal is- Yeah ... it's no different for travel. I like that. That's huge. That's insightful. So what are some ways people can travel without feeling like they have to spend a fortune? The first the first thing you wanna check out is where is it cheap to travel? There are some really exotic places that are crazy cheap to travel. Vietnam, Bali, Egypt. Now, there, there's certain things you have to know before you go type of things in going to all of those places, but all of those places are relatively expensive. You could go to Tanzania for relatively low money if you do it correctly. If you find the right plane ticket at the right... the most expensive thing in Tanzania is the plane ticket. You can stay in some really nice places for low money in a place like Tanzania, and go on safari. So those are the things you want to explore, is where is your dollar, your your good old US American dollar gonna go the farthest- and then where can you get a good a great deal on plane tickets? And are you willing to go when everybody else isn't willing to go? Some of the best trips I've taken, especially with my kids, were the week before Thanksgiving, right? And not Thanksgiving, excuse me, Christmas, right? I remember this one particular time we were, like, in Cabo San Lucas, Mexico, and or it was either Cabo or somewhere in Mexico, Ca- Cancun, some big tourist destination. And we were staying at one of those all-inclusive resorts, and- We were there until the 18th of December, and the 18th of December was when we were leaving, and the 18th of December is when that resort got crazy busy. And it was like, "Oh, I'm so glad I'm leaving right now." And those people paid a premium for being there that week, and it was way more expensive. A- it was not just way more expensive, the staff is more taxed, your service isn't gonna be as good, the food's probably not gonna be as good because everything's rushed and there's so many people. Those are the things you really wanna consider. Am I willing to go when others aren't? Like for example, going to Paris in November as opposed to in the springtime, right? If Paris is your dream to, to go there. And by the way I'm actually going to Paris in a week. There's a lot of cheap things you can do in Paris if you do it right. I've stayed at a ton of Airbnbs in Paris as opposed to hotels, which is super helpful. Are you gonna get a view of the, the Eiffel Tower? Yeah. I have some news for you. You can see the Eiffel Tower from all kinds of different places in Paris. You don't need to be looking out your hotel window at it. You can stay at a decent Airbnb and do okay or even, stay at an efficiency motel- hotel that like, is just great. One of my favorite hotels is a budget hotel in London, and it's called Premier Inn, and it's absolutely fabulous and you can get family-sized rooms and things like that for the cost of a regular hotel room that has, more frills. You really gotta consider how much time am I spending in my hotel room? Do I need a decent night's sleep with clean sheets and a clean bathroom that's safe? Yeah. That's really what you need. I agree. It's like making those adjustments and really fleshing that out. We ended up because of different reasons, not 'cause we chose to go there, we ended up in South Carolina in December. Beach was empty. Yeah, right? We were... It was like the week before Christmas, and, it was 60 degrees. It was not, 80, 90. But from where we were from, which was 30 at the time, 60 was really quite pleasant and enjoyable. Yeah. And we didn't have to fight the tourists. So I love that suggestion as well. I know you mentioned travel points. How does somebody go about that if they're unfamiliar, or maybe some tips and tricks on that? This is where AI is like a your super best friend at this... ask me two, three years ago about this tip and of course it didn't even exist. But now you can gather points somewhere. And my, my point gathering of choice is American Express Platinum, which not everybody is gonna be like, is gonna wanna do that because American Express Platinum also comes with a very hefty yearly fee. But American Express Platinum has paid itself in s- spades. It really has. But you can also do the Chase Sapphire Preferred card or the Capital One, Oh, I forget the name, but one of the Capital One cards, so you just wanna kind of research that. But then what you can do with AI is go, just ask them, "What can I do with all these Platinum points that I have?" 'Cause rarely is the good deal that you can just buy travel on American Express travel site. Except, and this is one of the reasons I love American Express travel points so much, the Platinum card so much They have a thing where every half year, they give you a $300 credit on their, on their Fine Hotels or Hotel Collection hotels which you can find on their website and you book it through their website. I got a hotel in Dubai for pretty much free that was a Hilton Canopy, beautiful hotel right on the water. With $100 hotel credit as well. If... I wish I could show you pictures. I know we're on- Like, we don't have a... It but this, this hotel was gorgeous. It was in an incredibly great location with amazing food. I went there during Ramadan they had when you go to the Middle East and there's Ramadan's happening, the food after sundown is like nothing you've ever had in your life. It's amazing. Wow. It's amazing. And it's everywhere. I couldn't even believe it. My son and I could not spend the money fast enough because also the dollar goes, even though Dubai UAE is a very wealthy country, the dollar does still go pretty far. So my hotel room, I think, for one night was, like, $100. We stayed there for two nights. It was, like, 100 or $150. I actually booked it last minute, so it was a little more expensive than it usually was, and then I got the $300 American Express hotel credit. And then on top of it, I got a $100... Because I booked through American Express, I got a $100 credit with the hotel and an upgraded room. Things like that where, you say, "Okay, I'm going on, I'm going on vacation for two weeks," and you can stay, two nights on on a bookend of your vacation at a really nice place, it makes it worth it. That's usually something I do. For example last time I went to Tanzania on safari, safari can be like I don't wanna say it's rough on your body, but you're in a safari truck, for eight to 10 hours a day. Wow. So it's a lot of driving and it's a lot of being out in the Serengeti or some of the other parks. And so it's just ti- it's tiring. It gets exhausting. It's a little dirty and a lot... Even though Tanzania is an incredibly clean country, believe it or not. So what did we do? We stayed at, a five-star resort at the beginning and the end of our trip, so it felt like a little luxury- in, in the trip. And it was just the perfect end to the trip. And still the hotel 'cause it's Tanzania, the hotel, even though it was a five-star resort was really inexpensive. One of my friends who was with us, literally every night he was there got a massage because it was so cheap. Wow. So but, li- listen, for... I have a lot of friends who are... we're talking pretty, we're talking some pretty exotic places. And I have a lot of friends who go, "I can't travel that far. Just can't do it. I can't do it." Or, "I don't wanna be on a..." My husband's a perfect example. Ever since that trip to Italy, now he will not get on a transatlantic flight. He's like, "I don't have to do it. It's not something I have to do. You don't need me to go." And he's right, I don't. I have plenty of travel partners and companions- ... and I like to stay married. And it's not for him. But I have other friends who are... It's not that they don't like to get on planes they're downright afraid of planes, or they're afraid... I've had a, a couple of family members who tell me straight out they're afraid to leave the country. Which- yeah ... listen, I can't help you overcome that. I can just tell you what my own personal experience is, especially that last trip to Tanzania, I took my 11-year-old with me, and we were fine. And we went all over the Middle East and Africa by ourselves, and we were fine. But that's not the point of this. The point of this is to tell you, you don't have to you don't have to go to, super exotic places to have a super exotic time. And and one thing I would say to people is that if you are worried about retirement and saving for retirement and still experiencing life to the fullest, is to really look in your own backyard. Because that 11-year-old who can't take it when I leave without him, he can't... he thinks I have audacity when I travel without him now. Yeah. As a matter of fact, he doesn't understand why I didn't plan a trip to Australia this summer. He swears I promised him a trip to Australia this summer. That did not happen, but he swears it did. But that same 11-year-old was- But swear words are appropriate here, but I will not use them. That same 11-year-old was the worst toddler on the planet. He was a nightmare. He was a nightmare to bring anywhere, long road t- I could not possibly bring him on a plane. He would terrorize everyone he would come in contact with. So when he was that age and so impossible, I just knew I couldn't bring him on a plane, so I didn't. And what we did instead for my kids who were older and, they wanted to adventure, we just went to the biggest city for me at the time was San Diego. And just once a week we'd go down to San Diego and find a new international restaurant and eat at that international restaurant and then go and do something in San Diego. And usually what we did, because I had a nightmare child, usually what we did is we would go to the... It was during the summertime, we'd go to the outdoor symphony. And so we would have a dinner at a international restaurant. If my kid was acting out, I would just take him out of the restaurant, and then we'd go to the outdoor symphony, and that was somewhere where he could run. We could sit in the back, he could run around, make all the noise he wanted, and bother nobody. And I know we're talking, to people who are not, raising hellions. They've raised their hellions, right? We're talking to people who are looking to retire. But my point is like you don't have to get on a long plane ride, travel to exotic destinations, move points all over the place, or, save for years and years to really experience international cuisine or really experience adventure in your life. And you can do it right in your own backyard. You just gotta find it. During COVID I had... My oldest son was crazy sick with... He got crazy sick with COVID- ... and was pretty convalescent for many months. Just wouldn't move off the couch 'cause he hadn't moved in months. So he got COVID in March of 2020, and- July of 2020 rolled around and he was still, like, sleeping 10 hours a day. It was awful. He was a 12-year-old boy, so it was pretty scary. And then if he wasn't sleeping, he was just laying and staring, not doing anything. And so I just threw him in the car. Again, we lived in Southern California. I threw them all in the car and I said, "Get in the car, we're going on a trip." And I just drove to Yellowstone. "We're just gonna drive to Wyoming." That's a long drive. Yeah. "And you're gonna get some fresh air." Yeah. And honestly it, a- and so we stopped at a couple places on the way. We stopped at Zion National Park. We stopped at a couple other places and then we made it to Yellowstone. We went to Teton and we went to Yellowstone, and then we came back And on our way back, we stopped in Vegas, and I have the greatest video of my son jumping on the bed. And again, American Express points paid for that hotel 'cause I, I got the credit, and it was COVID so everything was cheap. I have the greatest video of my 12-year-old jumping on the bed at the Wynn Hotel in Vegas during COVID because it w- just getting him out of the house and getting him moving and that's how, travel and seeing something new can really revitalize you, for the next part of your journey. I love that. I know, and we'll, I wanna talk about that, that you've done some adventurous trips, but I love that you can share how to find adventure without... M- like my husband, my daughter, they do not wanna fly over water, they don't wanna be on the plane for that long, two hours is just so much for them. But yet you can find it a lot, closer through different means, so I love that. But what I would love for you to share with listeners now are the adventures that you're planning, and I know the one trip is booked, but, some other ways that maybe they can connect with you in the future. Oh, absolutely. The first one that I wanna encourage people to come and join us is an incredible Dominican Republic trip that we're doing in the northern... It's not in a to- One of the things we don't do is anything My business partner, the one who had leukemia that I talked about, one thing that we don't do is anything that you'll typically find anywhere else. That's the whole point of what we do. It's supposed to be an adventure that is bespoke and you can't get anywhere else. And he and I have done the adventure some, at some point in time, so we know all the ins and outs. And so one we're doing in October if you guys wanna join us is at the Dominican Republic, but not in any of the n- very well-known tourist destinations, but in the northern part of- the Dominican Republi- public ca- in a place called Las Terrenas. And we're gonna stay at a really small resort that I actually happen to be an investor in, and we're gonna go adventuring around and see waterfalls, and beautiful white sand beaches, and go on a catamaran, and go to the national park, and things like that. Things that you typically wouldn't do, you know, going to a all-inclusive resort in Punta Cana, right? Yeah. Yeah. So that's one. The one you're referring to, And by the way, if you're really interested in this particular trip, to anybody who's listening I wanna encourage you to reach out to me because we're actually going to Egypt next week to see if we can get more spaces available. So if you're interested, please reach out to me and we'll see if we can squeeze you on. But we are going to Egypt to see a once in a civilization event, and that event is, The solar eclipse over Luxor. This has actually never happened in recorded history and won't happen for thousands more years. And so this is a luxury trip that we are gonna be taking. We start in Cairo, and then we're gonna do some Cairo things, and then we are going, we're gonna go see the pyramids in Giza, and we're gonna take a boat ride down the Nile River, and we're gonna... Yeah, and we're gonna fly back from Luxor to... But when we get down to Luxor, we're gonna see the eclipse. And you just, you... There's no other time you're ever gonna be able to see this again in your life. So if you wanna join us for that, you can. And yeah, that's in 2027. So that's in August twen- that's a year away, and we already sold out of that trip because that's just such a... I can't. I can't reproduce it. Yeah, that's amazing. I love that about how you guys are setting up trips and creating different adventures, but also how you shared with us that you can find adventure in your own, local, not too far, maybe even a, I'm guessing, 18-hour drive that you took from Southern California- Yeah to Yellowstone, right? Making it happen. So yeah. How can listeners connect with you, learn more about you? Yeah, I would love that. Just check us out at lastlifeever.com. And you can sign up for our mailing list, and you can reach out to me directly. And I love connecting with people particularly on Facebook. So if you'd like to come and friend me on Facebook, it's Jillian Sidoti on Facebook. Awesome. We'll make sure those links are down in the show notes. And so if you're thinking about traveling before or after retirement, I hope this was helpful. I hope you reach out with Jillian. And I wanna thank you for being here. Is there any one last word, piece of advice that you wanna share with our listeners, Jillian? Just get out there and start small. If travel seems scary and expensive, then just start small. Do something small, but make it extraordinary and I swear you'll never stop after that. I love that. Thank you, and thank you for taking the time with us today. I appreciate it. Absolutely.
Many people dream about traveling more in retirement. They imagine exploring new countries, visiting family, relaxing on beautiful beaches, or finally taking the trips they have talked about for years.
But there is often one thing standing in the way:
"We'll do that someday."
Someday when we have more time. Someday when we have more money. Someday when we retire. The problem with someday is that it often never arrives.
In this episode of Wealthy After 40, I sat down with travel expert Jillian Sidoti, co-founder of Last Life Ever, to talk about how to create meaningful travel experiences, how to travel cheap, and why you don't have to wait until retirement to start enjoying the adventures you dream about.
Whether you are preparing for retirement or already enjoying retired life, the goal isn't just to save enough money to stop working.
The goal is to create a life you love along the way.
Why Travel Often Gets Pushed to "Someday"
Jillian's travel journey started with a powerful realization.
After spending 15 years as an attorney, she had built a successful career but realized she wasn't happy. She found herself wishing she could leave the career behind and create a different kind of life.
A conversation with her future business partner helped shift her perspective. He had been a successful attorney, became seriously ill, and after recovering from leukemia realized he didn't want to continue living the same way. He wanted to experience more.
For Jillian, that became a reminder that life isn't guaranteed, and waiting for the "perfect" time to travel can mean missing out on experiences you truly value.
When she had children, she decided travel would be part of their lifestyle. Her youngest child had a passport almost immediately after being born because she wanted her kids to experience the world in a way she hadn't as a child.
That mindset continued when she and her husband planned a dream trip to Italy. After years of planning, her husband injured his hip shortly before the trip and couldn't travel. Jillian had a decision to make:
Stay home and wait for another opportunity?
Or take her three children to Italy herself?
She chose adventure. She traveled to Italy with her 10-year-old, 7-year-old, and 3-year-old children and created memories they still talk about today.
The lesson? You don't need everything to be perfect before you start living.
How to Travel Cheap Without Sacrificing the Experience
One of the biggest misconceptions about travel is that it has to be expensive.
Many future retirement travelers believe they need a large budget to explore the world.
But according to Jillian, the first step is changing the way you think about travel.
You don't have to start with: "How can I afford the most expensive trip?"
Instead, start with: "Where can my money go the farthest?"
Choose Destinations Where Your Money Has More Value
Some destinations offer incredible experiences without the high price tag.
Places like:
Vietnam
Bali
Egypt
Tanzania
can provide amazing cultural experiences while allowing your dollar to stretch further.
The key is researching where your money will have the most purchasing power. A luxury experience in one location might cost significantly less than a similar experience somewhere else.
Travel isn't always about spending more. It's about choosing intentionally.
Be Flexible With Your Travel Dates
One of the best ways to learn how to travel cheap is to avoid traveling when everyone else is traveling.
Peak seasons usually mean:
Higher airfare
More crowded destinations
Higher hotel prices
Less personalized service
Jillian shared how some of her favorite trips with her children happened right before major holidays when fewer people were traveling.
Instead of paying a premium to be somewhere during the busiest week of the year, they enjoyed a quieter experience for less money.
Flexibility can be one of your biggest travel advantages.
Retirement Travel Ideas Don't Have to Be Exotic
When many people think about travel in retirement, they picture international destinations.
Maybe it's a European vacation. Maybe it's an African safari. Maybe it's exploring somewhere they've always dreamed about.
And those are amazing goals. But travel doesn't have to mean a 12-hour flight across the world.
One of Jillian's biggest messages is that adventure can be found much closer to home.
When her son was recovering from a difficult case of COVID and had spent months inactive, she decided they needed a change. She loaded her kids into the car and drove from Southern California to Yellowstone.
Along the way, they visited places like Zion National Park and the Grand Tetons.
That trip wasn't about luxury. It was about creating movement, memories, and a new experience together.
Sometimes the best retirement travel ideas are closer than you think.
Adventure can look like:
Visiting a nearby city you've never explored
Trying restaurants featuring different cultures
Exploring national parks
Taking a weekend road trip
Finding unique experiences in your own area
You don't have to wait for a major international trip to start living adventurously.
Use Travel Points Strategically
Another way Jillian recommends reducing travel costs is by learning how to use travel rewards.
Travel points can feel overwhelming at first, but they can create incredible opportunities when used intentionally.
Jillian shared how she has used credit card rewards and travel benefits to create luxury experiences at a fraction of the cost.
Her recommendation? Do your research and understand how your points work.
Programs like travel rewards cards can provide benefits such as:
Hotel credits
Flight rewards
Room upgrades
Travel perks
She also mentioned that AI tools can now help people understand how to maximize their points.
Instead of collecting points without a plan, ask: "How can I use these points to create the travel experience I want?"
The key is making sure your financial decisions align with your goals.
Plan Travel Like Any Other Retirement Goal
One of my favorite things Jillian shared was this:
Your travel dreams deserve a goal and a deadline.
Instead of saying: "I want to visit Egypt someday."
Say: "I want to visit Egypt in 2027."
Then create the plan. This is the same approach you use with retirement planning.
You identify what you want, determine what it will take, and create steps to make it happen.
Travel is no different.
If travel is important to you, include it in your financial planning.
Ask yourself:
What experiences matter most to me?
Where do I want to go?
When do I want to go?
How much will I need to save?
The sooner you create clarity, the easier it becomes to make progress.
Don't Forget to Enjoy Life While Preparing for Retirement
One of the biggest mistakes people make when preparing for retirement is believing life begins after work.
But retirement planning isn't just about building a financial future. It's about creating a meaningful life.
Your future retirement lifestyle should include the things that bring you joy. For some people, that's travel. For others, it's family, hobbies, community, or experiences.
The important thing is knowing what matters to you and intentionally making room for it. You don't have to wait until retirement to start practicing the lifestyle you want.
Start Small and Make It Extraordinary
Jillian's final advice was simple:
Start small. If travel feels intimidating, expensive, or overwhelming, begin with something manageable. You don't have to start with an international adventure.
You don't have to wait until you have unlimited time or money. Start with something that feels exciting.
Because once you experience the joy of exploring somewhere new, you may find yourself wanting more.
