Long Stay Vacations: The Best Caribbean Islands for Snowbirds

Have you ever thought of spending a few weeks or even the entire winter in a warmer climate? That’s exactly what “snowbirds” do. If you’re considering long stay vacations someplace warm, you’ll love this list of the best Caribbean islands for a winter getaway. The only trouble you may have with these options is picking which one is right for you. So, read on for information that will help you decide where to take a warm winter vacation.

long stay vacations: the best Caribbean Islands for snowbirds

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CONTENTS: In this article, you will learn about 15 Caribbean Islands that make good candidates for long stay vacations, including:

What is a Snowbird?

A snowbird is someone, usually an empty-nester or retired person, who travels to someplace warm for an extended stay during the winter months.

How To Pick The Best Destination for Long Stay Vacations

Some of the top destinations for snowbirds include Arizona, Florida, Hawaii, Mexico, Spain–and our favorite, the Caribbean. That’s what we’ve focused on here. You might consider these factors when you pick a snowbird destination:

  1. Warm Weather: What is the average temperature between late December and early March when most snowbirds are looking to get away?
  2. Affordability: Is this island paradise affordable?
  3. Attractions: What is there to do on long stay vacations?

In this guide, we’ve addressed these questions as they relate to wintering over on a Caribbean Island.

You’ll find the average temperature range from December to March listed in Fahrenheit and Celsius. Affordability is a relative term and prices are always changing, so you’ll find we’ve rated affordability in relative terms. For instance, the most affordable island destinations have a single ‘$’, while pricier destinations are shown as ‘$$$’. You can see we’ve also highlighted some main attractions and activities you might enjoy that might help you decide whether this destination a good fit for you.

Now that you know what to expect from this list of long term vacation destinations, go ahead and dive right into your options! You’ll find them listed below, alphabetically.

Important Notice: Check with each island’s travel authority for the latest information about whether you are permitted to travel from your country of origin.

1. Anguilla

Anguilla beach scene (long stay vacations)
Anguilla averages about 80-degrees Fahrenheit year round and offers near-constant sunshine.

Average Temperature in Anguilla (Dec. to Mar.): 75-82°F / 24-28°C

Anguilla’s Affordability: $$$

What to Do in Anguilla

Anguilla is famous for its gorgeous coral reefs, public sandy beaches, and laid-back atmosphere. You’ll find it located in the Eastern Caribbean.

When you visit, you might like to tour Anguilla’s historical churches or try snorkeling in its turquoise-blue waters. You might also enjoy tasty drinks on the beach in Anguilla’s near-constant sunshine.

You’ll find a luxury golf course on the island. (Incidentally, CuisinArt Golf Resort & Spa is rated as one of the best course in the Caribbean).

You can also tour several wildlife sanctuaries on the small offshore islands and cays that comprise Anguilla.

If you stay until late March in Anguilla, you can experience a two-day fun-filled “celebration of the sea” known as Festival Del Mar.

Related: Read about a tropical getaway to The Bahamas Out Islands here.

2. Aruba

Architecture in Oranjstad, Aruba (best snowbird destinations in the Caribbean)
Aruba is one of the safest Caribbean destinations.

Average Temperature in Aruba (Dec. to Mar.): 77-88°F / 25-31°C

Aruba’s Affordability: $$$

Things to Do in Aruba

Aruba is best known for its breathtaking white sand beaches, rich culture, and consistently beautiful weather. In fact, it’s known to have the lowest rainfall of any island in the Southern Caribbean.

Aruba is a constituent country of the Kingdom of the Netherlands, and measures about 20 mi. long by 6 mi. at it’s widest point. With Bonaire and Curaçao, it’s considered one of the “ABC” islands and is part of the Dutch Caribbean.

When you’re not enjoying the gentle trade winds at the beach, you’ll want to visit Aruba’s capital, Oranjestad. There, you’ll see bright and beautiful architecture, plenty of shops, and museums. 

Aruba also offers spectacular opportunities for golf as well as a line of casinos on Palm Beach.

And in January, you won’t want to miss the festival of Carnaval.

Plus, it’s good to know it’s one of the safest destinations in the Caribbean.

3. Barbados

Long stay vacations: Barbados underwater scuba diving scene with three divers, coral, and red fish
Barbados’ beautiful reefs attracts scuba divers from around the world.

Average Temperature in Barbados (Dec. to Mar.): 74-85°F / 23-29°C

Barbados’ Affordability: $$$

Things to Do in Barbados

You’ll find Barbados is a perfect winter getaway for active and laid-back travelers alike. This small Caribbean island is about 166 square miles–which makes it perfect for exploring by land or sea.

The most easterly island of the Caribbean, Barbados offers a mix of surfable waves and calm waters. You’ll find natural wonders, like Harrison’s Cave or Hunte’s Gardens, along with beautiful reefs that attract scuba divers from near and far.

Look for the most gorgeous beaches on Barbados’ southern and western shores.

You’ll find the rum is fine and the people are friendly on this island country located in the Lesser Antilles of the West Indies.

Foodies will be happy to find their share of Zagat rated restaurants and excellent street food. There are plenty of festivals throughout the year in Barbados, too!

4. British Virgin Islands

British Virgin Islands scenic overlook with lush mountains and aqua water make it a perfect candidate for long stay vacations
The British Virgin Islands (BVI) include four main islands and 50 smaller islands and cays you can explore.

Temperature in BVI (Dec. to Mar.): 72-85°F / 22-29°C           

BVI’s Affordability: $$$

Things to Do in the British Virgin Islands

With its lush green landscapes, colorful coral reefs, and numerous beautiful beaches, the British Virgin Islands (BVI) is a perfect snowbird destination for adventure and soaking up the sun. This 60-isle paradise is well known for its boating scene, so make sure to take a day trip around the area on a luxurious yacht!

You might not know that BVI includes the main islands of Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, as well as 50 smaller islands and cays. Tortola hosts the capital (Road Town) and is the largest of the islands in this volcanic archipelago, and measures about 12 mi. long and 3 mi. across at its widest point.

The temperature remains fairly constant here year-round, as Barbados has a tropical climate soothed by trade-winds.

Garden lovers will love the J.R. O’Neal Botanical Garden, a well landscaped park with tropical plants including some rare varieties.

In Wreck Alley, you’ll find purposely-sunken vessels which makes for an incredible diving experience!

5. Cuba

A visit to Cuba can feel like stepping back in time.

Average Temperature in Cuba (Dec. to Mar.): 77-81°F / 25-28°C           

Cuba’s Affordability: $

Things to Do in Cuba

Cuba is known for its rhythmic music, rich Latin American culture, and friendly locals. Cuba was once restricted to visitors but is now is more open to snowbirds and other travelers.

Your visit to Cuba can feel like stepping back in time with its 1950s style cars and colorful colonial architecture. You’ll find sunshine and beaches and a number of cultural influences.

But did you know Cuba is home to 9 UNESCO heritage sites? That’s more than any other Caribbean island!

In fact, there’s a lot about Cuba that might surprise you.

For instance, it’s made up of the larger island of Cuba as well as several smaller archipelagos and the Isla de la Juventud.

While you’re there, you’ll want to visit Cuba’s capital, Havana, to experience some of the best of what Cuba has to offer, including some quirky establishments and a very active nightlife. Or, plan a visit to Baracoa, the oldest city in the country. If its a white sand beach you’d love, look to Playa Paraíso.

Wherever you go, you’ll discover that Cuba has a culture rich in music, food, culture, and traditions that’s hard to beat.

6. Curaçao

Curaçao is just off the coast of Venezuela and outside “the hurricane zone.”

Average Temperature in Curaçao (Dec. to Mar.): 76-88°F / 24-31°C

Curaçao’s Affordability: $$$

Things to Do in Curaçao

Curaçao is best known for its stunning cove beaches and warm, aqua blue waters. You’ll enjoy warm weather as you gaze at the vibrant, dutch-inspired architecture or attend one of the many festivals that occur frequently throughout the year.

This is one of the Dutch Caribbean islands (and the “C” of the “ABC” islands). It’s just 37 miles off the coast of Venezuela. This island has its fair share of tourists, but is largely residential, making it especially attractive for long stay vacations.

While you’re there, you’ll want to check out the Handelskade, which are the colorful buildings along the waterfront in Punda. You’ll also find opportunities to swim with the dolphins along with water sports like:

  • scuba diving
  • snorkeling
  • surfing
  • windsurfing, and
  • kitesurfing.

Plus, you’ll find lots of budget-friendly places to eat a range of cuisines, including small bars called “Snacks,” which serve Chinese food.

If tropical storms and hurricanes worry you, you’ll be glad to hear that Curaçao is outside what’s known as “the hurricane zone.”

7. Dominican Republic 

Dominican Republic beach scene with cabanas
The Dominican Republic is one of the most affordable and diverse places for long stay vacations.

Average Temperature in the Dominican Republic (Dec. to Mar.): 72-88°F / 22-31°C

Dominican Republic’s Affordability: $

Things To Do in The Dominican Republic

One of the most visited islands in the Caribbean, the Dominican Republic (DR) is home to stunning white sand beaches, world heritage sites, and of course, baseball. It’s the second largest island in the Caribbean and just two hours from the coast of Miami. It’s also a top destination for snowbirds.

The Dominican Republic has nearly 1,000 miles of coastline along the Atlantic and Caribbean. It’s located on the Hispaniola Island in the Greater Antilles archipelago, which it shares with Haiti.

Every Sunday in February, you’ll find a different Carnival featuring:

  • Festive parades
  • Colorful masks
  • Fun music
  • Lively dancing, and
  • Delicious food!

Related Article: Check out this world-famous Carnevale in Venice, Italy.

Most of the bigger resorts of the Dominican Republic are located in Punta Cana. But, there are some hidden gems you’ll want to explore:

  • Azua, where you’ll find ocean vineyards and wine tours
  • La Romana, if you’re looking for great golf courses
  • Samana, where you may see hundreds of hump back whales off the coast

You might also love a visit to Damajaqua cascades, where you’ll see more than 27 waterfalls and can swim in the natural limestone pools.

There’s so many things to do in the Dominican Republic that these ideas only scratch the surface.

More on Visiting the Dominican Republic

To make the Dominican Republic even more attractive, the cost of living is quite affordable. If you’re looking to rent an apartment for your long stay vacation in the DR, you’ll want to look to Sosua and smaller towns near the Santo Domingo

Finally, you won’t need a Visitor Visa or Tourist Visa for your long stay vacations to the Dominican Republic. You’ll just need to purchase a Tourist Card on arrival, which is good for 60 days, and then pay a small extension fee for longer stays. (For the most up-to-date information on visa requirements, check here.

8. Grenada 

Colorful houses on the hillside in Granada overlooking an aqua harbor with boats - best Caribbean long-stay vacation spot
Grenada is known as “Spice Island.”

Average Temperature in Grenada (Dec. to Mar.): 74-86°F / 23-30°C

Grenada’s Affordability: $$

Things to Do in Grenada

Known as the Isle of Spice, Grenada is home to numerous diving sites, lush rainforests, breathtaking waterfalls and of course, spices.

It consists of the island of Grenada plus six smaller islands north of the main island Grenada is about 133 square miles in size.

In the capital city of St. George, you’ll see colorful houses that climb the hillside from the waterfront. This harbor is the yachting center of the eastern Caribbean.

El Albaicin is one of the most picturesque and budget-friendly destinations. It was built by the Moors in Medieval times. You’ll also find a vibrant Jewish neighborhood in El Realejo.

If you’re a cricket fan, be sure to plan a visit to The Grenada National Cricket Stadium.

On Friday nights from 6pm, you can enjoy Fish Fridays, where you’ll find an abundance of all tasty things from the sea, lamb dishes, and tin-pan music.

In addition, you’ll find a variety of other festivals in Grenada throughout the year, like the Sting Band Festival and the Grenada Music Festival.

Don’t be surprised if you detect the scent of nutmeg and vanilla in Market Square and the spice plantations. In fact, make sure to take a tour of the Nutmeg Plant while you are there; there’s a reason it’s known as the Isle of Spice!

Do you love sweets? Then you’ll want to make a stop at the House of Chocolates.

You might also brave a sample of River Antoine Distillery‘s 150-proof rum!

9. Jamaica

Colorful towels hang to dry on the beach in Jamaica (Caribbean long stay vacations)
Jamaica is known for its Reggae music, golden sand beaches, and its everlasting sunshine.

Average Temperature in Jamaica (Dec. to Mar.): 72-88°F / 22-31°C

Jamaica’s Affordability: $

Things to Do in Jamaica

One of the most popular Caribbean Islands, Jamaica is known for its Reggae music, golden sand beaches, and its everlasting sunshine. It’s located off the North American Coast and is part of the great Antilles. It’s the third largest Caribbean island, behind Hispaniola and Cuba.

Jamaica is quite affordable. You’ll find no shortage of beautiful resorts as well as great accommodations in some of the smaller hotels and villas.

If you’re looking to connect with other snowbirds, you’ll most likely find them in Montego Bay, Ocho Rios, Negril, and Kingston.(If you favor white sand beaches and pristine water, look to Negril.)

You’ll find nature trails and island jungles at Port Antonio.

Foodies will find plenty of delicious dining options in Jamaica, but for the most authentic cuisine, you’ll want to have a taste of the goat curry with rice and peas.

While you’re in Jamaica, be sure to enjoy a boat tour on Blue Lagoon, sunbathe on Seven Mile Beach, or go for a hike in the Blue Mountains National Park.

And of course, you must visit the Bob Marley Museum!

10. Martinique

Average Temperature in Martinique (Dec. to Mar.): 71-85°F / 22-29°C

Martinique’s Affordability: $$

Things to Do in Martinique

This French-owned island is home to some incredible natural landscapes and a rich history. From its capital, Fort-de-France to Les Trois-llets, you will find a mix of lush gardens, delicious French and Creole cuisine, and stunning white-sand beaches in Martinique.

If you’ve never seen black sand, you can find it on Martinique at Grand’Rivière, a small fishing village located in northern Martinique.

Martinique has a rugged beauty and a unique blend of West Indian and French influence. It’s especially suited to nature-lovers, foodies, and francophiles.

The markets also hold loads of spices, exotic fruits, medicinal herbs, and Martinique’s ubiquitous “ignames” or yams. You’ll find fine dining in Fort-de-France, where restaurants combine fish and local cuisines with a French flair.

This island in the lesser Antilles relies heavily on France for imports. That’s part of the reason why you’ll find boutiques, artwork, and the latest French fashion in the markets. Martinique may be one of the best shopping destinations in the Caribbean!

11. Nassau

Pink building with white statues in Nassau, a great winter getaway
You’ll find charming pastel colored houses and government buildings in Nassau.

Average Temperature in Nassau (Dec. to Mar.): 66-81°F / 19-27°C

Nassau’s Affordability: $$

Things to Do in Nassau

As the capital of the Bahamas, Nassau is an extremely popular spot for tourists with its cruise ship port and countless attractions. Experience its modern resorts on Paradise Island, shop duty-free at the downtown markets, or take in the beauty of the old, brightly colored colonial buildings.

Nassau is the capital city and the largest and most populous island in the Bahamas. Located on the island of New Providence, it offers easy access to Paradise Island via the Nassau Harbor bridges.

When you visit, you can’t miss the pastel colored houses and government buildings that are so typical of the Bahamas.

In addition to the beaches, diving excursions, and snorkeling along the offshore coral reefs, you’ll find countless things to do in Nassau. From city tours to jeep adventures to the Heritage Museum of The Bahamas, it’s safe to say you’re unlikely to run out of things to do in this urban setting.

Like many urban settings, Nassau is known to have its share of crime, but this hardly offsets this vibrant destination. In any case, check with the US Department of State for travel advisories before you go.

12. Puerto Rico

San Juan Puerto Rico, red dome and historic fort overlooking water
Fort San Cristobel is the largest Spanish Forts in the New World.

Average Temperature in Puerto Rico (Dec. to Mar.): 72-85°F / 22-29°C

Puerto Rico’s Affordability: $$

Things to Do in Puerto Rico

Puerto Rico is known for having it all. It’s Spanish Caribbean culture, vibrant colonial architecture, lush vegetation, golden-sand beaches and surfable waves are only a few things that draw tourists to the island.

When you visit, make sure to visit its sunny capital San Juan for dining and shopping by day and experience the magic of Bioluminescent Bay by night.

You’ll also want to spend some time exploring Old San Juan, where you’ll find interesting art galleries, historic churches, and museums.

By visiting during the winter, you’ll be glad to know you’ll miss a lot of the rain. And, even though it’s a little cooler than other tropical destinations at this time of year, it’s still a great destination for sun-lovers. Plus, the food is phenomenal and English is widely understood.

If you love whale-watching, head over to the Rincón Lighthouse in February and March where you’ll see migrating humback whales on their way back to North America.

Finally, one of the great advantages of wintering in Puerto Rico is that since it is a US territory, you won’t need a visa. Plus, you’ll enjoy all the liberties and protections of the US Constitution while you visit Puerto Rico for the winter (or any time).

13. Roatan, Honduras

Colorful buildings on the harbor in Roatan Honduras, makes for a great snowbird destination
Roatan is a hidden tropical gem off the coast of Honduras

Average Temperature in Roatan (Dec. to Mar.): 72-85°F / 22-29°C

Roatan’s Affordability: $

Things to Do in Roatan

Just off the northern coast of Honduras, Roatan is an island paradise that offers a mix of adventure and serenity. While you’re there, you might encounter some of the island’s exotic animals like monkeys, sloths, and iguanas, or try snorkeling and scuba diving in its beautiful reef-lined waters. 

Plus, it’s easy to find monthly leases on properties in Roatan, whether you’re looking for a condo, house, or apartment. Real estate is so affordable for a winter stay! In addition to beachfront properties, you’ll find properties with hillside views and lush green landscapes. Roatan is one place where nature reigns supreme!

In fact, Roatan has several popular expat communities from from West Bay to Camp Bay, to Port Royal.

Here are some other experiences in Roatan you might enjoy:

  • Take a glass-bottom boat tour
  • Paddle through the mangroves, or
  • Dive into Mayatlantis, an underwater museum replicating Mayan civilization.

If safety is a concern, you’ll like to know that this beautiful island paradise located about 40 miles off the coast of Honduras is very separate from–and much safer than–the Honduras mainland.

Instead, you’ll find magnificent white-sand beaches, pristine water, and beautiful sunsets!

Related Articles: Read about more the best islands for wildlife vacations.

14. St. Barts

A deck overlooking St. Barts waterfront with palm trees (Caribbean getaway)
St. Barts ranks as one of the safest destinations in the world.

Average Temperature in St. Barts (Dec. to Mar.): 75-85°F / 24-29°C

St. Barts Affordability: $$$

Things to Do in St. Barts

St. Barts is known to be a prime spot for the rich and famous. While you bask in the sun among the world’s top A-listers, you can also enjoy duty-free shopping, ride a jet-ski on the glistening waters, or enjoy-fine dining by the sea. You’ll find a celebrity hideaway, at the Hotel Isle de France, which also holds a popular weekly fashion show on the beach.

The tiny volcanic island surrounded by shallow reefs is more formally known as Saint Barthélemy, and it belongs to France. It offers an expansive shoreline and is not nearly as crowded as other party-islands.

You might get some afternoon thunderstorms in “The Lent” as they call the winter season, and as a winter snowbird, you’ll find it’s a cooler climate, averaging 73°F. But some might find that pleasantly refreshing!

A few points of interest in St. Barts:

  • One of the prettiest beaches on the island might be Flamands Beach.
  • Nature lovers can see a collection of over 9,000 seashells at the Inter oceans museum.
  • A visit to the 18th-century fort, Fort Gustave will give you the best view of the harbor.

The St. Bart’s Film Festival takes place at the end of April, if you’re still on island. And if not, there are plenty of festivals throughout the year, including the February Carneval.

Plus, St. Barts ranks as one of the safest destinations in the world!

15. St. Lucia

Soaring twin mountains arise from the water in St. Lucia, Caribbean vacation for warm winter getaway
The twin Piton Mountains of St. Lucia.

Average Temperature in St Lucia (Dec. to Mar.): 73-84°F / 23-29°C

St. Lucia’s Affordability: $$

Things to Do in St. Lucia

With its twin Piton Mountains setting it apart from other Caribbean islands, St. Lucia is home to some of the Caribbean’s most stunning views. Set in the lower Antilles, this 238-square-mile island may just be the most low-key destination for snowbirds.

In St. Lucia, you’re sure to find vibrant sunsets, fresh coconuts (expertly split and prepared for drinking for a small fee), and the most dramatic landscapes. You’ll also find some of the best snorkeling, especially at Anse Chastanet Coral Reef.

While visiting, make sure to grab a kayak to visit Pigeon Island, bike through the lush forest, or scuba dive in the crystal clear waters.

At the Sulfur Springs Park, you’ll discover steaming hot geothermic springs, and you might even take a soak in the nearby therapeutic springs. You can also take a drive to La Soufriere, a volcano which hasn’t erupted in years, but you can still see the boiling pools and sulfur springs.

Finally, garden lovers might like to tour the botanical gardens, which offer tropical beauty along the trail to the diamond falls.

Though the official language is English, the locals also speak speak a Creole dialect–a further confirmation that you’re on a faraway vacation!

Final Thoughts on Long Stay Vacations in the Caribbean

Aren’t each of these topical islands perfect for a warm winter getaway? You can see now why it might be so hard to pick just one from these 15 best Caribbean islands for snowbirds.

If you can’t decide, we think the best plan of action as a snowbird is to line up several long stay vacations, perhaps with a new one each year. 😉

That way, if you decide to call one of them your permanent home, you’ll know what to expect as an expat.

Which of these best Caribbean Islands would be the perfect winter getaway for you? Which have you been to? Are some of these snowbird destinations high on your bucket list? Let us know in the comments below.

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Contributors: Michaela Shimkus contributed to this story.

Photo Credits: Angilla – jaegeranna1; Aruba – falco; BVI, Granada – Richard Todd; Cuba – ?; Curaçao – Steven Bol; DR – Martin Str; Jamaica – Peggy und Marco Lachmann-Anke;  Martinique, Nassau – skeeze;  PR – AndPon; Roatan – Michelle Maria; St. Barts – franckchisinau; St. Lucia – mimics (all courtesy of Pixabay); Barbados – VisionPic.net (via Pexels);

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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.

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