The Wiser Financial Advisor Podcast

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Navigating the New Waves of Travel with Cheri Smith

In this episode, host Josh Nelson, CFP®, welcomes back Cheri Smith the founder of Wishes and Waves Travel. Dive into the dynamic world of travel post-pandemic, exploring how Cheri turned her passion for Disney vacations into a thriving travel business. Cheri shares insights on the latest travel trends, from the rise in cruising to navigating crowded tourist hotspots like Italy and Greece. Discover her expert tips on planning memorable, budget-friendly trips and hear about her own globe-trotting adventures. Whether you’re dreaming of a multi-generational family vacation or an exotic getaway, Cheri’s advice will help you turn your travel wishes into reality. 


Wiser Financial Advisor – Interview with Cheri Smith of Wishes and Waves Travel
Hi everyone, welcome to the Wiser Financial Advisor show with Josh Nelson, where we
get real, we get honest and we get clear about the financial world and your money. This
is Josh Nelson, founder and CEO of Keystone Financial Services. Let the financial fun
I am happy to welcome back our guest, Cheri Smith, the founder of Wishes And Waves
Travel, an awesome travel agent who happens to be our personal travel agent. So
welcome back, Cheri.
Cheri: Thank you for having me.
Josh: It’s travel season right now, coming up into summer. We’re going to talk about
what’s the latest in travel, and for a lot of our clients, travel is a big part of their life,
either while they’re working or with family or maybe part of a bucket list that they’re
trying to hit in retirement. But what inspired you originally to become a travel agent and
to found your company called Wishes and Waves? How did you get inspired to start that
Cheri: I don’t think I ever imagined myself as a travel agent. I always worked in
advertising and marketing, and my family and I had traveled quite a bit. When my son
was 3, it felt like every six months or so we were going to Disney. Then friends and
family were asking me to help them plan trips. And in the advertising business, when an
agency loses a client, they also lay people off. So, I was laid off, and my husband said
to me, “You know, you are helping all these people planning Disney trips. You could get
paid for that.” And that’s how the agency was founded. I called it Wishes And Waves
because when I started the agency, I was planning mostly Disney trips and cruises.
Those first couple years I was booking a lot of Disney trips, probably 80% of my
business. Today, that’s maybe 5% of my business. Now, 61% of my business is cruises.
So it’s changed quite a bit.
Cruising in general is on the rise, and there are a lot of reasons for that. I’m booking a
lot of family and multi-generational trips, and cruising is the best value vacation for your
dollar right now. I think that’s why it’s grown so much. And then the rest of the business
is 5% Disneyland, Disney World. A big chunk of what’s left is Europe and Asia and then
the other portion is all-inclusives. I’m not booking as many all-inclusives as I was a few
years ago. A lot of people are moving to cruising and part of that might be cost. Flights
are expensive right now, and getting to the Caribbean to go to an all-inclusive, the
sticker shock is there. I’m a one-woman show with two assistants, and we get it all done
and help hundreds of people every year with their travel needs.
Josh: You’ve done a great job for us, and it’s very obvious that you love what you’re
doing. You travel extensively yourself, right?
Cheri: I do. In fact, last year was my biggest travel year. I went on four cruises—to
Dubai, Germany, and safaris in Tanzania and Zanzibar, Africa.
So far this year I’ve been to Amsterdam to the River Cruise Conference. I’ve been on
two cruises. I’ve gone to Ireland, and next week I leave for Bali. Then I come home and
have a family cruise. Also, I’ve been invited to the pre-inaugural sailing for Utopia of the
Seas, a Royal Caribbean ship, which I’m very excited about. And then in September, I
will be going on a cruise to Norway, to a point as far north as you can go before you hit
the North Pole for an expedition cruise. So this year will be 5 cruises and three
long-haul trips.
Josh: When you’re talking to people, it’s a whole different story when you can say, “I’ve
been on this ship,” or “I’ve been to this location,” as opposed to it just being something
you’re researching.
Cheri: Absolutely, it does make a a big difference to be able to talk to a client and talk
them through the process. L:ike “If you’re going through customs and immigration, this
is what it looks like,” or “That particular flight really wasn’t that bad,” or “I prefer this
hotel; I prefer this region, and this is why.” It does really make a difference in the type of
trips that I plan, and it makes a difference for my clients because I’ve been there, I’ve
done it, and they know they can trust me.
Josh: Yeah. So, let’s talk about what trends you’re seeing right now, and we’ll get into
cost too, because that’s one thing that’s changed a lot. You started your business right
before the pandemic, right? And so it’s been crazy ups and downs over the last five
years, but yeah, let’s talk about what you’re hearing about what people are interested in,
and maybe some of the things that you’re helping people avoid?
Cheri: As we came out of the pandemic, we saw what industry insiders were calling
“revenge travel,” where people were taking these big bucket list trips and spending a
ton of money. But coming out of COVID, prices were lower. Hotels and flights were
looking to attract people, and it was just less expensive to travel. Personally, I have not
really seen a slowdown in the amount of trips people are taking. I’m still seeing those
bucket list trips. But I’m also seeing prices rising. I wouldn’t characterized this as
revenge travel. The world has changed and people have changed, and they realize that
tomorrow is not promised and they’re taking these trips.
When you look at our country, you see that a lot of retail is suffering. People aren’t
spending as much money at retail. I’m not seeing that in travel. People are still spending
a good amount of money. Some of it’s because it’s more expensive and some of it’s just
because they want to do it and they’re going to take that trip now. So I think people are
shifting spending their money to travel. I don’t think prices are rising because hotels or
airlines are being greedy. It’s all supply and demand. The demand is so high that the
prices are rising and it is just more expensive to travel. I’m seeing people wanting to go
on longer trips, farther away, more unique destinations, more of what we call “bespoke
itineraries.” They want private tours; they want a very unique experience, and they’re
willing to pay for it. Pre-COVID, I only had a couple years under my belt. I was not
booking a lot of first class tickets. These days, I book more first class tickets than any
other kind of ticket, and people don’t balk at the price.
Josh: We had some clients a number of years ago who went to Europe for a kind of
celebration—I think they had a big birthday or retirement or something like that. They
said “Alright, we’re gonna go first class.” And when they got back, they said, “We’ll
never go any other way.” So, once you’ve had that experience, especially on the long
haul flights, it makes a big difference. That first day that you’re there, you don’t end up
Cheri: Right. My family and I have a rule that when going on an overnight flight, we’ll fly
first class or business on the way there and then economy coming back, to try to
mitigate some of that cost. But there are things you can do. We buy a main cabin ticket
and then we’ll use miles to upgrade to business or first class. A lot of the airlines are
calling it business class now with the lay-down bed. You have to look at the plane that
you’re on and understand what business or first class means, but a lot of times it’s
cheaper to buy the main cabin ticket. Just make sure there’s no restrictions, and then
upgrade to business or first. Even if you do it both ways, it’s less expensive than buying
into first class or business.
Josh: We’re hitting travel season for the US, with kids out of school and people in that
travel mode. So, what are the trends that you’re seeing of what people want to do? I’ll
be chaperoning on an Italy trip here in a couple of weeks. We talked about this before,
that there are certain destinations that are a little crazy because everybody wants to go
there. So what are you encouraging people to avoid just so they don’t have a bad
experience? They end up some place that they’re just in complete chaos with crowds.
What do you recommend?
Cheri: For the last couple of years, we’ve seen over-tourism in Italy and Greece in
particular. In Venice, they’re imposing a day tax. So, people not staying in Italy pay a tax
to get into the city. And part of that is to combat some of the over-tourism. For my clients
asking for Italy and Greece, we have real conversations about what that is going to look
like. I ask if they want to be at the Trevi Fountain with 1000 other people at 10:00 AM,
because that’s the reality of what they’ll experience. Or maybe they’re OK with getting
up at 6:00 AM and getting to the fountain before it’s really crowded. Are they OK
standing in line for two hours to get into the Vatican? Because even if you have skipped
the line tickets, so have 100 other people, and they’re waiting to get in. And are they
willing to pay for more private tours to get to the front of those lines? If they say “no,”
then I think the best thing to do is look at an alternate destination.
I’m seeing a lot of people going to Croatia. Croatia has definitely been under the radar
for a while, but growing in popularity. The beaches in Croatia are incredible and it’s
relatively inexpensive to rent a yacht for a couple of days and island hop. It’s a less
crowded experience. I’m also recommending people go to Portugal or Spain instead of
Paris this summer. Everybody wants to go to Paris, and not everyone realizes that the
Olympics are going to be in Paris in a few weeks, so you cannot get a hotel in Paris this
summer, because they’re booked out. So, what about going to Buenos Aires? The
architecture is the same. You’re getting some of that same taste of culture that maybe
you were looking for in Paris.
Because it’s all over Instagram, everybody wants to go to the Maldives, which is a
nation of islands in the Indian Ocean. The Maldives are expensive, and a lot of people
don’t realize where they are.
Josh: That’s on my on my bucket list.
Cheri: It’s a fantastic experience, no doubt, but you’ll go via Qatar or Dubai, which from
the Midwest is a 16 hour flight. From Denver, you’re probably looking at 20 hours or
more and then taking another flight to the Maldives. There are other islands. Tenerife is
someplace that is not as popular. It’s up the coast of Africa, kind of near Morocco. I’m
going to Bali in a couple weeks because it’s one of the last of the exotics. The flight
there is 30 hours, but when you get there, it is a very inexpensive destination where you
get culture and beaches. Madeira, off the coast of Portugal is an easy flight. You’re
flying into a little island, which is a little scary, but you can be in a tropical paradise in 8
hours from the East Coast.
So, it’s helpful to be flexible and work with someone or do the research to know that
these places are not what you see on Instagram. That can make the difference in your
vacation. Maybe put off Italy or Greece for a couple of years when they lose popularity.
If you look historically, these cities in Europe in particular are cyclical, so certain
countries are hot for a few years and then drop in popularity because everybody went
there. Then other countries rise in popularity.
It’s knowing where to go and it’s also knowing the season. I mean, Italy in August is
brutal. Greece in August is very hot. So, go in October. The prices are less and there
are less people.
Josh: Social media over the last couple of decades must affect trends as far as causing
some of these surges to certain locations.
Cheri: Yes. There are certain influencers who have very large followings. I’ll get calls
saying, “Ooh, what about this resort?” And I Google it and think, Yep, that’s why
everybody’s asking about this. Don’t believe everything you see on social media. A lot of
these influencers are paid to go to these locations, and they’re not giving you what it’s
like and what it costs. You’re better off looking at alternatives and really understanding
what they’re posting about.
Josh: I recommend working with somebody like you who knows what they’re doing and
hopefully has actually experienced it. So what about budget-wise ways that people can
still travel right now? Because inflation has been a real thing. So when people come in
with a budget and say, “Alright, we’re gonna spend X number of dollars,” is that your
starting point?
Cheri: Absolutely. Usually when I have a call with a client, we talk about where they
want to go and why they want to go there, and what they want to see. That helps me
understand whether there is an alternative that I can present. And what is the budget?
Sometimes, people will say, “Well, I don’t really have a budget.” Then I will come back
and say, “OK, so you’re fine with spending $30,000?” No, no, no. Everyone has a
budget. It helps me select locations and form a trip.
If you want four people to go for a week to Italy, and your budget is $8000, then you’re
going to be staying in 2-star hotels and you’re not going to be having private tours and
you’re going to be roughing it. The budget is a big part of the trip. If people have a
smaller budget, we can work with that, but those people will not be planning a
last-minute trip. The best thing to do is plan early. The earlier you book, the better
pricing you get. I already have cruises on the books for spring break of 2026—because I
have a lot of clients who love to cruise but they can’t afford to do it every year. So we
plan spring break cruises every other year. Not only do they get the best pricing, but
then they’re able to make payments on it. I have quite a few clients who pay a deposit
and then once a month make a payment for $100 or $200. In 2 years, they’ve paid that
trip off. They’re able to afford an experience that would not have been possible if they
would have tried to plan last minute.
The nice thing about cruises is you can reprice them. I go in periodically when sales and
promotions change, to spot check them. And when you’re able to reprice those cruises,
I can shift thousands of dollars off a trip, which makes a huge difference. But booking
early is key and the same goes for flights. Flights are expensive right now, and there’s
just no way around that. I booked flights for you just last week but instead of booking a
round trip flight, I booked the same flights one way, and saved about $800.00. I know
what to look for to save you money.
Josh: Absolutely. I appreciate that. But yeah, it’s kind of a game, right? But the common
person doesn’t have the time and the experience to understand the rules of the game,
so tricks like that—for the same flight, the same seats, and $800 cheaper, who would
Cheri: And I think you know, that’s the beauty of working with an experienced travel
agent. You’re able to tell me what you’re looking for, and I’m able to make it happen at
the best possible price. Does it always work out like that? No, sometimes things are just
expensive. But I know what to look for to see if I can get it for you cheaper.
Josh: That’s one of the things that we definitely appreciate about you, is that you have
an opinion and you’re not just an order taker. In other words, the advice part of it is huge
as far as the value that you provide.
And I think you’re right, people are willing to spend the money to go to Mexico, do an
all-inclusive, bring all the family together. It’s a shift in perspective from before COVID
because back then you could just travel whenever you wanted. Then all of a sudden,
that was taken away. So, maybe it’s not revenge, but I think there’s still kind of a pent-up
attitude in people’s minds, of wanting to get out there and have these experiences.
Cheri: And I’m definitely still seeing the trend of multi-generational travel. I have a
handful of families, sometimes 4 generations, who have decided they’re no longer doing
traditional Christmas, and the Christmas present is to themselves to travel together.
Most of the time that’s cruises, but sometimes it’s all-inclusive, sometimes it’s taking a
Disney trip or going to Europe. It’s because you can’t get the time back, and it’s really
special. I know we’ve had a podcast about this before: Traveling multi-generationally is
just a special experience. And if I can share a personal story about your family, you’re
personally traveling with both your parents and your in-laws next year.
Josh: Yeah, absolutely.
I had a conversation with your father-in-law—a good 15 to 20 minute conversation,
when he was telling me how special it was that you invited them to go with you on a
cruise. They only get so much time with their grandchildren. On your cruise, you don’t
have the phone interruptions, you don’t have the TV interruptions, all of these different
interruptions that we have in life. You’re isolated from that, if you want to be, so you can
have that quality family time.
Josh: Yeah, you’re right. I’m a big fan of investing in experiences and memories as
opposed to stuff. I like stuff too, but what’s more valuable? In the end, it’s the time you
get with people. And as people get older, you don’t know how much time you’re going to
have left. You and I don’t have any idea how long we have, right? But having those
memories and being able to be intentional about getting people together, I call the
pre-heritance. I’ll ask clients, “Do you want to leave a big inheritance at the end?” If
we’re doing our job right and being prudent, then there’s probably gonna be some
inheritance assets. That’s all good. But maybe if we invest in more experiences with the
family, they would appreciate the time and the experience more than getting more
money when probably the kids are retired and don’t necessarily need money. So yeah, I
call that a pre-heritance, to give a gift of an experience and making those memories.
Cheri: And I think we see cruise lines understanding these multi-generational trips.
When I was at the River Cruise Conference in Amsterdam earlier this year, a lot of the
river cruise ships are understanding that. Twenty years ago, river cruising was for old
people. That’s not the case anymore. Now they’re making family suites because they
understand there’s that need. River cruising takes you into the cities that you can’t get to
on the ocean liners. Even resorts in the Caribbean are doing more suites with more
rooms that accommodate multiple families.
Josh: My parents have gone on a river cruise with friends. It’s cool that they’re opening
that up for families. We haven’t done that; we’ve just been on the big ships. But yeah,
they’ve had a great time, and when they talk about their next travel, they’re saying it’s a
river cruise.
Cheri: If you want to visit multiple places in Europe, it’s much easier than traveling over
land to multiple cities because you’re not having to go from hotel to hotel or fly or take
the train between places. Talk about over-tourism, navigating the train system with
suitcases in Europe can be hairy. I’ve done it multiple times and even as an experienced
traveler, I’m looking googly-eyed at some of these train lines. By going on a river cruise,
you unpack once and hit multiple cities. While you’re not in the city for as long on the
river cruises because they’re smaller ships, they’re able to dock in the heart of the city.
So you’re able to quickly get off and really have some amazing experiences.
Josh: So those are some of the more common things to do. What are a couple of really
exotic, out-there things that you’ve booked for people?
Cheri: Well, places that a few years ago were more exotic are becoming more of the
norm, like the Maldives. Bali, Tahiti, Bora Bora are still pretty big bucket list trips. Part of
that has to do with Instagram. Everyone’s showing those over-water bungalows. But I’ve
been getting a lot of requests for Iceland. Part of that I think, was the volcano that
erupted there last year. That on the news always brings curiosity.
I would say the places today that seem a little more exotic, five years ago would have
been super exotic. Now they’re a bit more mainstream. If we’re looking towards the
future, I think in the next couple years we’re going to see a real resurgence in Asia.
They’re just opening up really from COVID now. Japan is probably the number one
tourist destination this year. People want to go places where their friends haven’t been.
Josh: Hmm. Yeah. Very good. Well, thank you for taking all your time and certainly
thank you for helping our family. You’ve been just a huge resource to us and again, it’s
not about the money as much as it’s about the experiences of getting to do stuff
together, but also to have things go a little bit smoother, smoothing out the rough edges
of what could be stressful. Thank you for that. How do we find you?
Cheri: Absolutely. So we’re most active on Instagram. My handle is there.goes.Cheri.
My agency is Wishes And Waves Travel. I’m on Instagram with my agency as well, but
I’m more active on my personal site where I share my adventures. My website is and you can send me a message there.
Josh: Thank you so much. Appreciate your time and I hope you have a great trip to Bali.
Cheri: Thank you. I’m excited.
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This episode has been prepared for informational purposes only and is not intended to
provide or should not be relied upon for tax, legal or accounting advice. You should
consult your own tax, legal or accounting advisors. Investment Advisory Services
offered through Keystone Financial Services, an SEC registered investment advisor.