5 Best Vacation Destinations for Retirees To Travel This Winter

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You don’t have to go into hibernation this winter, especially when there are plenty of vacation destinations ready to welcome retirees. Trade those icy driveways for sunshine or a slower pace somewhere new and warm. These retiree-friendly destinations deliver warmth, charm and a change of scenery without breaking the budget. Each offers a mix of affordability, comfort and easygoing adventure that makes traveling after 65 doable and delightful.

Costa Rica

In the Guanacaste or Central Valley regions of Costa Rica, you’ll enjoy a warm climate that’ll help you shake those winter blues. December to April is Costa Rica’s dry season and the temperatures usually range from 70 to 95 degrees during these months, according to TripSavvy. There are plenty of gentle adventures to explore, like nature walks, birding, hot springs and small towns. So you won’t be stuck with high-adrenaline activities unless that’s something you’re looking for. 

It helps that the cost of living in Costa Rica is relatively low compared to the United States, so it’s an affordable vacation pick. For example, International Living estimated that monthly expenses in Costa Rica total about $2,240. Common vacation expenses like entertainment, transportation and food make up $900 worth of that calculation. Obviously, those costs would be lower if you’re only traveling for a week or two, but it’s a prime illustration of what you can expect to pay if you’re planning to visit Costa Rica this winter. 

Arizona

If you’re looking for a domestic destination, Phoenix or Scottsdale, Arizona, might be a solid choice for your next winter vacation. Arizona summers are notoriously unbearable, but the winters are far more mild with plenty of sunshine and comfortable temperatures in the 60s and 70s during the daytime, according to Visit Phoenix. It’s perfect for outdoor activities like golfing, which is likely why the PGA tour holds the WM Phoenix Open here from Feb. 2 to Feb. 8, 2026. 

You’ll be in the good company of other snowbirds if you visit during the winter months, since there’s a thriving senior culture and community here. There are plenty of sporting events and festivals held during the winter months, including the Arizona Balloon Classic, where you can witness hot air balloons race across GoodYear Ballpark. There’s also the Waterfront Fine Art & Wine Festival from Jan. 31 to Feb. 2. The only downside is that Arizona’s peak tourism season is from November to April, which means you’ll typically see higher prices. 

Cozumel, Mexico

Planning a cruise to Cozumel, Mexico, takes much of the work of vacation planning off your plate. Cruises are an especially good choice for retirees since your lodging and meals are already handled while you move from point A to point B. Plus, it’s easy to scale your activity levels according to your mood. Low energy day? You can relax on the beach, do some light snorkeling or take a cultural tour. 

A cruise to Cozumel might even cost less than you think. For example, Virgin Voyages has a five-day cruise that travels round-trip from Miami, Florida and stops at Cozumel, Mexico and Bimini, Bahamas. This package costs as low as $1,190 for two people during the 70% off second sailor promotion. Your food options are included in the fare and you can purchase a drink package for as low as $200 per person.

Myrtle Beach, South Carolina 

Myrtle Beach is a classic destination that’s perfect whether you want to relax on the beach by yourself or with the family. There are tons of senior-friendly activities like golfing, coastal walks, nature reserves and theaters. It’s not balmy Caribbean weather by any means, but it’s still warmer than a New England winter. Since the winter months are the off-season in Myrtle Beach, you could save money on lodging and other costs compared to summer pricing. Plus, you won’t have to deal with the hassle or complications of international travel. 

Madeira, Portugal

For a vacation spot across the pond, Madeira, Portugal, might be worth it for retirees who want to embrace the slow life. Madeira is a slightly less populated tourist destination compared to Lisbon, but you’ll still find that English is widely understood, so there’s a little less friction when it comes to languages. The flight there is about nine hours from the East Coast, so it’s a proper getaway and the climate is similar to Hawaii’s. 

There’s a diverse food culture, wineries, museums and tons of natural beauty to explore. In terms of affordability, Madeira offers a lower cost of living compared to many Western European nations, as well as the United States, so your money may stretch a little further. According to Global Citizens Solutions, monthly expenses for a single person, excluding rent, cost 630 euros or about $737.

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