How To Save Money Booking Your Winter Escape

Hyatt Andaz Papagayo scenic view
Gorgeous views of the water from the Hyatt Andaz Papagayo
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Now that I’m living in Nashville, I understand why people feel the need to travel someplace warm in the winter. We were definitely spoiled in California with mild winters. When the temperatures drop, I’m ready to escape the winter chill and hit the beach someplace warm. We’ll look at some winter escapes, then we’ll share ways to cut costs and save money so you can thaw out without breaking the bank.

I’m working with the Dosh cash back app to share these warm-weather destinations and ways to save money on your travels.

Destinations to escape the winter chill

These are a few of the most popular destinations for winter escapes that are affordable and relatively close by. I wanted to share some places that you can do a quick getaway from the U.S. (long weekend anyone?), yet are still good if you can take the full week off.

Puerto Rico

The Caribbean is a popular destination with warm water and sandy beaches. However, most Caribbean islands require a passport and use a different currency. Puerto Rico is part of the U.S., so you don’t need a passport and it uses the dollar.

The capital of San Juan is wonderful to explore, but you’d be missing out if you didn’t check out the rest of the island. Rent a car and drive around to see what wonderful natural attractions it has to offer. Listen to my podcast interview of Conrado Asenjo for his tips when you visit San Juan, Puerto Rico.

Dosh cash back hotel San Juan Puerto Rico January 2020
Use the Dosh cash back app to receive up to 40% cash back on your hotel room


When I lived in California, Cabo San Lucas was our go-to spot for long weekend getaways. Now that we’re in Nashville, Cancun is closer and just as fun. You can’t go wrong with either location for excellent food, great beaches, and friendly service. Listen to my podcast episode with Jay Kali about the best things to do in Cancun.

You do need a passport to visit Mexico, so plan ahead. Although Spanish is the local language, most of the people we’ve met spoke at least a little bit of English.

Westin Lagunamar margaritas at Taco y Tequila Lee and Anna with food
Anna and Lee enjoying tacos at Taco y Tequila in Cancun.


The Hawaiian islands are always near the top of bucket list destinations for American travelers. It is popular because the weather is always nice and you don’t need a passport to thaw out in their tropical weather. Because it is so far out in the Pacific Ocean, I would only consider it for a quick getaway if you live on the West Coast.

There are several airports and major cities to choose from. My cousins love Maui, but my experience has been with Honolulu. Timmy and I traveled there with my buddy David a few years ago. We had an awesome time in the water, at the Dole pineapple plantation, and climbing some of the local mountains.

Grab some inspiration by listening to my podcast interviews with Doug Nordman about Oahu (Honolulu) and Kim Julen about Maui.

Dosh cash back hotel Honolulu Hawaii January 2020
Dosh offers competitive rates to other online travel agencies at over 60,000 hotels around the world

Costa Rica

Timmy and I flew to Liberia, Costa Rica a few years ago and stayed at the Hyatt Andaz Papagayo. It was an incredible property that is very eco-friendly. The hotel rooms are built into the side of the mountain and overlook the bay. It now offers an all-inclusive option as well. Free nights with points are 20,000 each.

You do need a passport to travel to Costa Rica. However, everyone we encountered at the resort spoke English.

Hyatt Andaz Papagayo dinner
Dinner at the Andaz Papagayo

How to save money on your winter escape

Whether you’re getting away for the weekend or can take the entire week off, you want to save some money on your vacation. This is especially true when you’ve been spending money during Black Friday and all of the other sales leading up to Christmas.

Here are a few of my favorite ways to reduce the cost of our trips.

Get up to 40% cash back with Dosh

Whenever I book a vacation, I first turn to Dosh to see what hotel options are available and how much cash back I can earn. Dosh gives users up to 40% cash back on the price they paid for their room. Plus, the prices are competitive with online travel sites like Expedia and TripAdvisor so you’re not overpaying for your room.

For a limited time, you’ll receive an additional $30 cash back when you book your first hotel booking with the Dosh cash back app. You have until January 3, 2020 to book your reservation. Currently, you can book dates into November 2020, so there’s plenty of opportunity to earn this bonus.

Use hotel points to book your hotel

Once I know how much I can book a room for cash, I compare that to the options available when using hotel points. I like to save my points for longer stays so I can cash in on 4th night free with IHG (if you have the IHG card) and 5th night free with Marriott and Hilton. Plus, it makes sense to book with cash instead of points when I’m traveling for business or the hotel I really want is asking for too many points for the stay.

Book flights using airline miles

I almost always using airline miles to book our flights. Our family doesn’t have status with any airline, so we’re not focused on spending money to maintain that status or earn those perks.

Instead, we earn airline miles across several different loyalty programs. This allows us to compare prices between them to figure out which one offers the best route, lowest prices, or most desirable departure and arrival times. We also factor in the opportunity to use airport lounges to make our trip more comfortable.

Get cash back on your meals automatically

When I get new credit cards, one of the first things I do is register them for cash back apps and rewards programs. This ensures that every time I use them, there’s an opportunity to stack rewards and earn extra points for my purchases.

Dosh offers cash back on meals at participating restaurants. Most of the time, I’ll earn anywhere from 5% to 10% on my meals just from Dosh. This is in addition to the rewards I get from my credit cards and miles from Rewards Network (e.g. Southwest, American, Delta). Use a credit card that offers bonus rewards for dining, like the Capital One Savor Card (4% cash back), to maximize your restaurant and fast food expenses.

Choose hotels that have a kitchen or include breakfast

Because we use Dosh or points to book hotels and miles for flights, our biggest expense while traveling is often paying for food. This is especially true as our kids are growing up and eating meals like grownups. I can’t even imagine what it will be like when they’re teenagers.

One of the ways that we save money on food while traveling is booking hotels that offer free breakfast, include lounge access, or have a kitchen. Even if the kitchen is only a mini-kitchen, you can still make a couple of eggs and pour some cereal to eliminate the cost of one meal each day. That adds up over a week-long vacation.

The Bald Thoughts

When it gets cold outside, it is time to book a winter escape and head someplace warm. With these tips, you can book this getaway without busting your budget as we head into the new year. You’ll be on the beach with a cold drink in your hand and your toes in the sand in no time.

What’s your favorite winter escape? Let us know in the comments below.


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