Money + Fun Part I: Setting an Itinerary for Savings

About the Episode

Over two-thirds of Americans are budgeting for their travel this year, and more than half have cut back or changed their plans due to the economy. But no matter your budget, you can still plan a great vacation—and this episode of Making it Count will teach you how! With the help of Donna Shields, a vacation planning expert and travel blogger, Cristina and Randy take a deep dive into how you can turn travel planning from a chore into part of the fun while saving money along the way.


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All About Travel Planning on a Budget


Randy asks Question 1: “Donna, let’s start with the first thing you have to decide when you’re trying to plan your trip: where you’re going. What’s the best way to pick a destination on a budget?”

Donna responds: “The first thing I ask is who's going on the trip? Because that really dictates an awful lot. Because if you're a couple, if it's a family trip, a multigenerational family trip, you know, your best friends down the street, that really determines where you want to go and what you want to do.”

“Once you've nailed that down, then consider what your budget is. We travel for different reasons all the time. Sometimes we want adventure, sometimes it's an educational, historical kind of a trip. Other times it's a road trip to go see the grandparents and we're going to put some fun into it as well on the way. So it kind of depends on what the purpose of the trip is. And then once I know that, then I think about what destination fills that particular need.”

“I am all about maximizing your time and your dollar, and especially if you're going to visit people, you have a free place to stay in most cases. So, you know, you've saved some money right there. And then that leaves a little more to go on tours and maybe splurge on something else that you might not have.”

Read More: 12 Budget-Friendly Travel

Destinations for Your Next Vacation


Cristina asks Question 2: “So let’s say we got the destination in mind, we know the purpose of why we're going. What’s your hot take? Flights first or hotels first?”

Donna responds: “I am a flights-first person because that is a big ticket item, right? Maybe more so than even your accommodations. And we have a lot of options with where we're going to stay. But we have a more limited set of options with how many flights are going to the place I want to go to.”

“I always start at a high level and I start looking at things on Google Flights and Skyscanner. Google Flights in particular, if you have flexibility with your time, because that allows you to look at say, a whole month and you can eyeball what part of the month is cheaper. And if you can work your trip around that, well, all the better. Once you've narrowed that down, then I start looking at things like Kayak and Expedia and Hopper and Skyscanner to actually see where I can get the best deal on booking the tickets.”


Randy asks Question 3: “In terms of the strategy of that, are there certain days of the week that are cheaper or certain times of the year that are cheaper?”

Donna responds: “There used to be this thing about, ‘Oh, they're always cheaper on a Tuesday and a Thursday.’ And while there sometimes is credence to that, what I find is if I'm planning a trip, I go in every morning about the same time and I do a quick scan of my favorite three or four booking platforms because things change constantly with flights. There's so many different factors that go into pricing with airlines. And people say, ‘Well, I don't have time every day.’ And I'm like, ‘Listen, five minutes, you can do a quick scan.’ And I have found that it really varies.”

“Sometimes people think, ‘Oh, it's more expensive to fly on the weekend.’ Not necessarily. If you put a little up-front work into this daily scanning while you're really in the thick of planning a trip, I think that can be well worth your time. And then with respect to time of year, I mean, it's always going to cost you more in the winter. If you want to come down here to Key West where I am, or go somewhere warm, it's going to cost you more.”

Cristina follows up: “I have two kids, so I’m bound to the school calendar. I feel like I'm traveling at the most expensive times of year because everybody's traveling with kids in the summer and around the holidays and spring break.”

Donna responds: “No, you're absolutely right. School schedules are definitely a challenge because you don't have a lot of wiggle room. Having said that, schools around the country often vary a week or so in either direction of their winter breaks or their spring, and particularly with spring breaks, depending on where you live in the country. You know, not everyone has the same exact spring break.”

“It is a challenge for parents, I won't lie about that. Sometimes, though, [it’s easier] finding locations that aren't on the must-do list and finding more off-the-beaten path things. And again, it depends on what kind of kids you have. One year, for example — I live here in Key West, which of course is a big tourist destination. But we get out of here to avoid the crowds and go to other places in Florida. And when my son was younger, we would come up to Central Florida to go panning for shark's teeth in a river. It was a lot of fun and way cheaper than going to Disney.”

Read More: How to Plan a Family Vacation on a Budget


Cristina asks Question 4: “Let's switch gears and talk about accommodations. When do you decide between a hotel—a budget-friendly hotel, a swanky hotel—an Airbnb or VRBO. How do you make that decision?”

Monica responds: “If you're with an adventurous crowd, I've booked staying in a teepee on Airbnb and I think it's so much fun. But that's not for everybody, right? So you have to know the crowd that you're traveling with. My overall answer to your question is if you're going with a few people or if you're going for a slightly longer period of time, an Airbnb can certainly save a lot of money because you can buy groceries, you can at least make breakfast. And, you know, sometimes you go out for breakfast and you can spend 20 bucks a person. So you need to think about that cost-saving, factoring in with some meals cooked in.”

“But what I have found too when I'm deciding between Airbnbs or VRBO and, I often have found places less expensive on And I say this because I'm also a host on Airbnb, so I know my costs. I have to pay taxes, I have to pay a cleaning fee and all of that has to get rolled into what you're charging the guest.”

“I have often found now that private hosts are also putting their properties on People think is just for hotels—not necessarily. You really have to do your homework with this stuff. And if you're going for three nights and it's just the two of you, then fine, get a very cool hotel and splurge a little bit.”

“I just came back from a four month trip—I was on the road for four months in Mexico, Spain and Portugal. So the budget was paramount. We could not spend more than $50 to $60 a night on lodging. And I had to stick to it. And when you're in cities, of course, it's more expensive. You know, Madrid and Lisbon are more expensive than what I was paying anywhere in Mexico. So you have to balance it out, too. You splurge here, you cut back there.”


Randy asks Question 5: “Donna, a lot of my friends use reward points or loyalty programs. They save money on traveling. Do you have any recommendations for the most generous programs that you've heard of?”

Donna responds: “Well, I personally am not a hotel loyalty point person because we tend to stay more frequently in little small places and Airbnbs. I don't typically stay in larger hotels that have loyalty programs, but I know a lot of people do, and they get a good value out of it.”

“When it comes to airline miles—I mean, on this trip, I booked us business class. I felt like I was living large, but I only did that because I had enough miles. It's way too expensive to pay for those tickets. So I have accumulated a lot of miles through airlines. But I also use credit cards that have pretty robust reward programs. And credit card programs don't tie you to one airline, which is a nice feature of getting your rewards on a credit card rather than one that's just tied to an airline.”

Randy follows up: “That's a really good tip. I have the Southwest card with Chase, and every time I buy something, I accumulate points that I can eventually use on flights.”

Donna responds: “That's great if you're flying on Southwest. But if you envision that you're going to be taking a trip in the future somewhere else and you're going to need to rack up some miles some other way, then yeah, you may want to think about getting [a credit card with travel rewards]. I only get a new credit card if there is some fantastic bonus sign up. Like I just got the Chase Sapphire card because right now it has an 80,000 mile bonus sign up. Those are the kinds of deals you want to be on the lookout for.”

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Making It Count Essentials


Randy asks Quick Question 1: “Do you have any recommendations for bag checking?”

Donna responds: “I never check bags, but that's me. I travel very lightly. If you can get away with not checking a bag, you can save money and also save hassle and time. And also then you eliminate the possibility that maybe your bag isn't going to show up when you do.”


Cristina asks Quick Question 2: “Do you have any favorite vacation planning success stories that you can share with us?”

Donna responds: “Well, this trip I just came back from was really the first time I had done a trip that long. And one of the things that I did on this trip was in order to save money on lodging, I had signed up for a website called Trusted House Sitters and we stayed for one whole week in a beautiful home in exchange for watching someone's dog.”

“And there's other platforms where homeowners who are also pet owners are looking for someone to come take care of their pets while they go away. You get free lodging. Many of the homes are in great locations. This was my first time trying that and it was a really great experience.”

“The other thing I would suggest to people, which I have been doing for years, is trying home exchanges, and that's where you mutually are staying in someone else's home and they are coming to yours and there's no exchange of money. So that can save a tremendous amount on lodging costs. I've done it for years, both in the States and abroad, and it's a great cultural immersion, too. You know, it's a very different experience than staying in a hotel. You're in someone's neighborhood. You're meeting their neighbors. You're shopping where they shop.”

Read More: The Cheapest Ways to Travel Young

& Still Experience It All


Cristina asks Quick Question 3: “If you could pick any type of vacation—are you a relax and chill at the beach type? Are you an adventure seeker or are you one that wants to be immersed in the culture? What is your favorite type of vacation?”

Monica responds: “Well, okay, this will answer your question because last year we did a 10,000 mile motorcycle trip through Mexico. So I'm an adventure seeker. I like to do different things and I like the cultural immersion aspect when I'm traveling. That's not for everyone. And, you know, that's why when I travel, I don't tend to sit and read on the beach because I can read at home. I want to experience the place as fully as possible when I travel.”

“If your life is in a high-powered, high-stress crazed career, then for you sitting on the beach and reading is a vacation. So I think it depends on where you're coming from. You know, what is your normal, and then you kind of have to take it from there.”


You can book Donna to plan your next vacation at


On this episode, Cristina and Randy shared a free vacation budget template. Fill out the details in each column to get daily totals, then add those up to get an estimate of your total vacation cost to start saving for your next getaway.

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