How to Escape the Cold Winter 101

Me and cold weather are not BFFs. You will catch me avoiding cold, winter weather like it's the plague. So instead, I like to spend the cold months of the year in warm, tropical destinations.

Here's a quick lesson — How to escape the cold winter 101, as taught by me: 

Step 1: Find a Tropical Destination

Look at Google Maps and find somewhere close to the equator that piques your interest. Make sure to do some research on what there is to do in that destination and what people are saying about safety. If you want to be a beach bum and not explore, than it may not matter how much else is close by to do.

Recommended Tropical Travel Destinations

Cancún, Mexico

Cancún's hotel zone makes for a perfect winter getaway. Miles and miles of shoreline on this island give you plenty of beach spots for a nice, lazy beach day. Or if you want to branch out, there are numerous tours you can take that pick you up from your hotel or you could rent a car and explore surrounding areas at your own pace.

Starting on December 15, 2023, the Maya Train will connect Cancún to Chichén-Itzá, Valladolid, and many other parts of Mexíco. Later on, the train will also connect Cancún to Playa Del Carmen and Tulúm and other areas down the coastline.

San Juan, Puerto Rico

No passport needed for U.S. citizens to travel to this tropical destination and have the ideal winter getaway! If you've got the budget for it, I recommend splurging and staying in Old San Juan, where you'll find colorful streets filled with Spanish charm. Otherwise, another great option is to stay in San Juan, specifically in Santurce close to Calle Loiza. Both spots are very walkable areas with plenty to see and do, and there's access to the beach just about anywhere.

Here you can spend all your time lounging around on the beach, or you could rent a car and travel to other parts of the island. I recommend getting a rental car for at least a small part of the trip to branch out to other beaches that aren't in the tourist area. Those beaches are worth the trip!

Additional Considerations

Make sure you consider weather patterns for the colder months. This can be more of the rainy season for a lot of places closer to the equator, so you'll want to keep that in mind. Plus if you're going to the Caribbean, keep in mind that hurricane season runs until the end of November, and there's occasional tropical storms trickling into December (although not as likely). 

Step 2: Book a Flight to that Destination

There are many websites you can use to look up a flight to whatever destination your heart desires. I like to check out sites like Google Flights and WayAway as a starting point just to check out what current flight prices are looking like. Once I find out what airlines service that destination, I also like to go directly to their site to see prices.

Pro tip: go into an incognito tab first or use a VPN.

Step 3: Make a Reservation for a Place to Stay at that Destination

You're going to need a place to stay while you're enjoying warm temperatures. Hopefully this is just a place where you sleep, shower, and keep your belongings -- and that you spend most of your time with your toes in the sand and a drink in your hand.

Lucky for you, there are plenty of options when it comes to choosing what type of place to stay in — a hostel, a short-term rental unit, or a hotel — and there's pros and cons to each.

When it comes to a vacation, I consider staying in all three types of places. However, if I'm traveling for longer periods of time, I typically end up in a short-term rental.

Before I book anything, I shop around throughout my option quite a bit. At a minimum, I check out Airbnb, VRBO, Expedia,, and It's probably a few too many sites, but I like to explore my options, and then I end up with too many which makes it hard to decide, but I know I'm going to end up in a great place. You're bound to find something too!

Step 4: Pack your Bags, Get on Your Flight, and Go

It's as simple as that. And if you need some packing tips, check out this blog post.


What are you waiting for? Winter is coming, and your next tropical destination is waiting on you to arrive.

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