The Wiser Financial Advisor Podcast

Get Real. Get Honest. Get Clear.

Planning The Trip of a Lifetime with Guest Cheri Smith

In this episode, “Planning The Trip Of A Lifetime”, host Josh Nelson invites Cheri Smith in for an interview to share the value of taking family, even multi-generational family, trips together to create great life-long family memories. Cheri Smith is a self taught travel agent based on her lifelong experiences with taking many family, and multi-generational family trips early in her life and later as an adult. She found herself helping friends with the scheduling and planning associated with scheduling such trips. Eventually she created her own agency, “Wishes & Waves” because she felt like she had the skills and experience to  help others in navigating the demands associated with scheduling and planning trips of a lifetime for families of all sizes. Whether your preference is for leisure or play, Cheri can handle all the arrangements for you. Check out her website below.

Cheri Smith


Wiser Financial Advisor – Planning the Trip of a Lifetime

Hi, Everyone. Welcome to the Wiser Financial Advisor 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, Certified Financial Planner and founder and CEO of Keystone Financial Services. We love feedback and we’d love it if you would pass it on to me directly: . Also please stay plugged in with us, get updates on episodes and help us promote the podcast. You can subscribe to us at Apple Podcasts, Spotify or your favorite podcast service. 

Let the financial fun begin!

This show is brought to you by Keystone Financial Services, a wealth management firm based in the land of Love, Loveland, Colorado. At Keystone Financial Services, our mission is to bridge the gap between knowing and doing in the financial lives of our clients. We are here to provide unbiased advice and guidance. We are an independent fiduciary and all of our wealth advisors are certified financial planners, the gold standard in the financial planning industry. Take the guesswork out of your financial future and contact us today by visiting .

Today we’ll be talking with Cheri Smith, the founder and CEO of Wishes and Waves Travel. Cheri is an expert at planning the trip of a lifetime, something I talk about with clients all the time as a way to bless people with gifts and experiences during our lives instead of just leaving everything at the end. Why not create some magic moments—some memories for our family that they can carry on for hopefully generations to come because of those experiences. Cheri has plenty of ideas around planning trips not only with Disney but also cruises and other experiences families have done and what that’s meant to them, especially in cases where people have passed away not long after the trip, so join us on this journey and think about how this applies to you or what that means in 2022. Thanks and enjoy.

Josh: We have Cheri Smith with us from Wishes and Waves Travel. What we’re going to be talking about is how to plan the trip of a lifetime. Here at Keystone Financial, we’ve worked with many clients on wealth management, and a lot of them have reached the point where they’re financially successful. Now they’re kind of wondering, “Well, what’s next? What does my life look like and what’s my bucket list look like?” And as we talk to Cheri, we’re going to find that there’s a lot of planning that goes into that. You can just show up, but it will be a different experience if you do some planning ahead. So, welcome Cheri.

Cheri: Thank you for having me.

Josh: You’re a Disney specialist—that’s a big part of what you help people plan for. Disney might not be everybody’s thing, but it’s definitely our thing. We like to do that. What other types of travel do you tend to plan for people?

Cheri: My focus is really on multigenerational family travel, so a lot of Disney, yes. Disney World, Disneyland, Aulani, which is Disney’s resort in Hawaii, and Disney Cruise Line. But additionally, I plan a lot of trips to Mexico and the Caribbean for all-inclusive resorts and also cruises worldwide. Alaska is a popular destination for a lot of families, too, but there are a ton of Caribbean cruises.

Josh: Sounds like a lot of bucket list types of trips. I like that you’re multigenerational. What does that mean when you’re talking to folks?

Cheri: Many of my clients are in their 50s, 60s, 70s and wanting to plan travel with their kids, their grandkids, and oftentimes their great-grandkids. There are plenty of opportunities. Resorts and cruise lines as well as Disney have all become aware that families want to travel together and have these experiences together. So, it’s a different kind of trip because you’re planning for a group that’s often over ten people. It’s helpful to working with a travel agent who understands what’s involved—and I have personal experience with it because I travel with my in-laws and my parents and my son. You want to work with a travel agent who specializes in this because they know how to plan the trip. They know that maybe not everyone wants to do everything together in a day—or maybe they do. So I’m kind of the middleman when grandparents don’t want to be in in the parks at Disney World every day. I’m able to plan activities for them to do on their own and then meet up with their kids and grandkids later in the day. Or I can guide them through taking breaks, all so they can have that trip of a lifetime.

Josh: And how did you get into doing what you do?

Cheri: I grew up traveling with my grandparents and with my parents. My husband and I traveled a lot before we were married and before we had kids. When I had my son, we started going to Disney. Then people started asking me to help them plan their Disney trips and so it was just a natural fit. I started a travel agency and it’s grown from there. But I’ll always have those memories of the trips we took with the grandparents, and it’s those that I remember the most.

Josh: On that note, you know we do a lot of financial planning with people to make sure they’re not going to run out of money in retirement. That’s the biggest fear for retirees—fear of running out and then not being able to take care of themselves. So, once we figure out things to the point that they have some abundance and they’re not likely to spend all their money, then it comes down to, “Well, do I just leave a bunch of money to people or do I invest in memories?” And I’m a big fan of investing in memories. Good example there with your grandparents, right? That’s just priceless to have those memories you had with him.

Cheri: Yes, and my parents and my in-laws have actually continued on that path, so my father-in-law takes us on a big trip every other year. His thought is, “Either I can leave you this money or I can spend it while I’m still alive to enjoy it.” And I think it’s great. I enjoy traveling with my husband’s family and it’s brought us closer together.

Josh: So what advice would you give somebody getting ready for a major Disney World trip or a cruise or something? It’s not just, “Hey, let’s buy a plane ticket and go someplace for the weekend.” It’s a major undertaking, especially Disney World as opposed to Disneyland, right? That’s a whole different experience. What advice would you give them on where to start if they’re just at the very beginning of trying to plan something multigenerational?

Cheri: I think the most common thing people do is turn to Google. Which is great, but overwhelming. There’s a lot, and so finding a trusted travel advisor, someone who has done this for a while and understands, is the first step. When you’re looking at a big trip, a bucket list trip, it’s helpful to be working with the advice of someone who can not only help you plan, but also help you with travel protection trip insurance. When you’re spending 10 or 20 or 30 thousand dollars on a trip, you need to make sure that your investment will be protected. Trip insurance is very important and understanding what will and what won’t be covered. Additionally, working with someone who understands how to put these trips together and knows the destination and knows the options available to you and what’s going to be best.

For example, if you’re planning a trip to Alaska—if it’s just two people and you’re in your fifties or sixties, I’m going to be looking at one cruise line. But if you’re bringing your kids and your grandkids, I’m probably looking at another. So, it helps to work with someone who understands your needs and what you’re looking for and your expectations, so they can match you with the right destination, the right resort, the right cruise line—those kinds of things.

Josh: Yeah, I can speak from experience with this recent Disney World trip we took in October. I planned it myself and I shouldn’t have done it that way. I’ve been to Disney World before and thought, “I got this, I can do this.” But it had been four or five years since the last time, and things have changed a lot. It was overwhelming. We had a great trip; it was an awesome experience and everything, so in the end it was all good but there was more stress than there needed to be in that planning process because it was just confusing. There was so much information and I needed to figure out things that had changed as far as needing to make park reservations. You can’t just show up, and some of the technology has changed as far as how to book experiences and things like that. We found out pretty quickly that it’s literally impossible to actually get hold of somebody at an 800 number at Disney. So, in the future I will not do that again. I absolutely will use a travel agent.

So, let’s say that somebody is listening to this and saying, “You know what—we want to do something like this, but they’re not sure what.” How far in advance would you recommend somebody start planning?

Cheri: I think six to eight months is probably best. You can start planning about a year in advance if you have your heart set on a specific resort such as Disney World; if you have to stay at this resort or you have to have a certain type of room, then the earlier the better. Right now at Disney World, there is limited availability. Demand is high, inventory is low, and people are ready to travel. So, six months is a good amount of time, which is not to say that if you call me today and say you want to come in January that it’s not going to happen. It can happen. But that six to eight month mark is the sweet spot in planning.

Josh: Okay, and I’m sure there’s quite a price range for experiences like this. If you throw in a couple families, kids, grandkids, grandma, grandpa, that sort of thing—what’s the craziest you’ve ever seen, like at Disney World for somebody who goes all out?

Cheri: I just had a five room trip where Grandma took the entire family for a week, and that was about 40,000 dollars. Because of school schedules, some people stayed for seven days and some for four days so there was a mixture of number of days. That was 40,000, but you know it was the trip of a lifetime. They stayed at the Grand Floridian which is the flagship hotel at Walt Disney World. They spent some days in the park. They rented a poolside cabana. They had a fantastic time, and that was with four generations.

Josh: How cool. And we don’t know how long we’re going to be around. Depending on her finances, maybe Grandma could do that again in the future, but none of us knows how long we are going to be around—and not only be around but be in good health. Hopefully, if somebody is listening to this and thinking, “Gosh, I don’t know; it’s expensive. Should I do this or not?” My encouragement would be to definitely be thinking about that. And if you haven’t done your own bucket list, you should.

I have and I redo it every now and again, but I think it’s some good perspective.

So, when it comes to planning, when you’re thinking about financing on the low end, for somebody who just heard that 40,000 number and said, “Well, that’s way out of my price range; I can’t spend forty grand on this thing,” –at what price do you think somebody could have a really nice experience at one of these places without going all in? What’s the price level?

Cheri: The average for a family of four for a six to seven day trip is around $3000. That’s going to include your transportation, your park tickets, and your accommodation staying on site. So for three families, that would be about $12,000. There are additional options. You can always stay off property and rent some type of a villa. Hotels are a little bit less expensive, so I always say $3000 to $5000 per family is a pretty good trip for a week. Sometimes people only want to go to two parks and be there for five days the first time because it’s too overwhelming. And for cruises, that oftentimes is a little bit less. Cruises also offer you that all-inclusive deal. Your food is included, and so depending on which cruise line (Disney Cruise Line is a little more expensive), but Royal Caribbean is a great option for families and multigenerational travel—and that would be about half that per family.

Josh: So things are starting to open back up. What are you experiencing right now? If somebody contacts you and says, “We want to do a cruise?”

Cheri: The Caribbean is probably easiest at this point. Most of the cruise ships are sailing in the Caribbean and Mexico, so that has been fairly easy. The European cruises are more difficult right now; that inventory is a bit more limited. There are also more restrictions on traveling to Europe right now.

The Alaska season is shorter; it’s the early summer months and that is a little harder for inventory as well. There is still inventory for 2022, but we’re really looking out at 2023.

Josh: Yeah, Disney in particular will book up way far out for things like dining reservations. Talk about that a little bit, as far as somebody who’s never experienced Disney World and wants to be thinking about planning now. What would they miss out on if they say, “Hey, we want to go next month.”

Cheri: You can’t just show up to a park. Even if you have a park ticket, that does not guarantee admission. You have to make a park pass reservation because they’re limiting capacity at the parks, and those can book up. The week of Christmas there is little to no availability for any of the parks. The couple weeks of Spring Break are filling up as well. Dining reservations open up 60 days prior to your arrival. They open at 6:00 AM Eastern time, and people are up making reservations at 6:00 AM because if you want to eat at that sit-down restaurant, you need a dining reservation. Anytime kids are out of school—Christmas, Spring Break, Presidents Day weekend, 4th of July and into the summer, if you want to eat at a sit-down restaurant, they are going to book up. So you need to go in with a plan and make those dining reservations in advance. Otherwise you’re at a counter service restaurant, which is fine, but you’re not having a sit-down meal every day, which not everyone likes.

Josh: Right. So, to turn back to investing in memories, what are some special experiences that really would need to be planned further in advance? Things that you’ve found that were fun for a family and they were able to get some great memories; what are a couple of things you’ve helped people experience?

Cheri: VIP tours, which means you get a private VIP tour guide and they take you around to any of the parks and give you a history of the parks. They point things out to you and you’re able to walk on rides so you’re not standing in line—which for a lot of people is just priceless. That’s a popular one.

And there are dessert parties. Both Magic Kingdom and Epcot Center have dessert parties where for an additional fee you’re able to enjoy a private area to have wine and beer and desserts and light orders. You get to enjoy that and then get preferred standing area for the firework shows, which is really special. Epcot also has dining packages where you get preferred seating and dine and watch the fireworks, which is a nice way to regroup at the end of the day. It’s nice not to have to fight the crowds to find a place for the fireworks.

Another one that’s been pretty popular lately is called “capture the magic” where you can have family photos taken inside the parks and have your own private photographer to capture the moment.

Josh: Yeah, and for things like that, unless you were working with somebody who knew what they were doing, you probably would never even know that that was a possibility.

Cheri: Absolutely, those things do need to be booked in advance, and they aren’t something that Disney advertises per se. I mean, if you comb through the site you can definitely find information about it, but when you work with a travel advisor, I’ll be talking to you about your trip and what you’re looking for and the kind of memories you want to make, so these are things that I can suggest to you.

Josh: Yeah, the Internet is a good thing; Google is a great thing, but I remember when I started as a financial advisor in the late 90s, a lot of people were telling me, “I’m not sure if this career could be long term. This industry might go away because now there’s E-trade and people can just do their own stuff and all the information is out there.” But the exact opposite has happened, in that people are just overwhelmed. There’s just so much information out there, and so little wisdom as far as guidance on what to do with it. That’s why we still have jobs.

Cheri: Right, and I’ve found that especially after COVID a lot of people who had trips planned and went through the process of trying to cancel or postpone them and spent hours and hours on hold with the 800 number, definitely felt it. Whereas when you work with a travel advisor, you just call me and I take care of it for you. Many families will email or text me a photo while they’re traveling, and a lot of times I I get choked up because I see these kids and the magic they’re experiencing. I really like to see families experience the magic of traveling together that I experienced.

Josh: I’m sure you can channel yourself as a young kid doing this and having those experiences.

Cheri: I do, and I often share these stories with my clients because it was just so special. I had a client last summer whose father had cancer and he wanted to see his granddaughter. She loved princesses and he wanted to see her dress up as a princess and go to the Magic Kingdom. Unfortunately, two weeks after their trip, he passed.

Josh: So I think for a lot of us it’s a perspective changer as far as saying, “Maybe you need to take the trip. Maybe you need to do something that you’ve been putting off for a long time that was really important.” I would encourage you to think about that.

Cheri, you’ve got some fun things happening. You’ve got a YouTube channel and Facebook. Tell me about some of that and how people can find you.

Cheri: You can find me on my website and there’s a link to my Facebook page where I share different travel-related news. But I also have a YouTube channel. My family and I do travel quite a bit and I’ve logged all our trips. I film all kinds of videos to prepare people for travel, whether it be cruising or Disney or other places. I do packing tips and tricks, everything that you need that’s travel related. and there’s a link on my website to my YouTube channel. I think people want to see what it’s really like and so I try to document that for real.

Josh: Yeah, especially if they’re going to be investing not only their time, but potentially $20,000 – $40,000, depending on the size of the family and what the accommodations are.

So, we have a broad range of listeners all the way from folks that have been retired for years to young people just starting out. I’m curious what advice you would give to a smart, driven college student, someone just about ready to enter the real world. What advice would you give them as they’re getting started?

Cheri: Take every opportunity that comes your way. I didn’t think that this would be the future of my life. Be a sponge and absorb everything that comes your way. Take the opportunity to learn something from everybody that you meet.

Josh: Along those lines, what advice should they ignore?

Cheri: One thing we see quite a bit in our industry is that a client will ask us a question and then we see that same person asking a question in a travel Facebook group and getting a lot of wrong answers. I’m doing this every day, all day long. Rules are changing, things are changing. Should you ask your Facebook friends for a destination? Absolutely. Should you ask them for the entry requirements to get into a certain country? Probably not.

Josh: I think that’s to a large extent why you and I still have jobs, right? People still want to use somebody that they can trust. They know that this is important enough to get it right and not be just winging it based off what somebody said on the Internet. And now, people have a trusted source on travel with you. So again, the best way to contact you is probably your website, right? They’ll find your YouTube channel and Facebook at your website.

Cheri: Absolutely. . There’s a contact page there and links to my Facebook and Instagram and YouTube.

Josh: The reason we’re talking about this today is for perspective. Do you want to leave people the wealth that you’ve built up? We hope you’re getting to that point where you really have the choice; you have that abundance and you can be thinking about that bucket list and what kinds of experiences you want to create. Ask yourself, “What memories do I wish people would have?” Take the time, think about it and then make a contact. Cheri is a great resource from a travel perspective. The contact could be just an email saying, “I don’t know what I’m doing here but I know I need to do something.”

Thank you Cheri, appreciate it.

Cheri: Thank you so much for having me.

The opinions expressed in the Wiser Financial Advisor show with host Josh Nelson are for general information only and not intended to provide specific advice or recommendations for any individual. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing. Investment Advisory services offered through Keystone Financial Services, an SEC registered investment advisor.