15 Best Caribbean Islands For A Winter Vacation

Are you wondering which Caribbean islands are the best for a winter vacation? Then this article is exactly what you need to read.

The Caribbean has over 700 islands, reefs and cayes and thus there are numerous options to consider for your winter getaway.

In this article we will highlight some of the best places to visit for a winter vacation along with various cultural , historic and other activities that makes each destination special.

So let’s dive into this article.

1. Grenada

Affectionately known as the isle of Spice, Grenada is a marvelous destination to visit for your winter vacation.

The island is loved for its gorgeous white sand beaches, waterfalls, lakes, rivers and exotic cuisine.

Often regarded as the best beach in Grenada, Grand Anse beach located in the South of the island is a gorgeous one mile stretch of white sand with turquoise waters.

Grenada is also loved for chocolate products which can be readily found in a café in the capital city called House of Chocolate.

So definitely consider adding Grenada as a strong contender a place to visit during your winter vacation.

Where To Stay In Grenada

Grenada has a wide cross section of accommodation options for you to make your selection. There are guest houses, apartments, cottages and hotels.

The South of the island is the perfect place to stay as you will be within close proximity to malls, supermarkets, the iconic Grand Anse beach, restaurants and banks.

For hotels within walking distance to these amenities mentioned above, we recommend Siesta Hotel and Blue Horizon Hotel.

These are also near the public transportation which is ideal for budget travelers interested in using the local buses.

For adults only all-inclusive experience, we recommend the luxurious Sandals La Source Grenada which is located a short five minutes from the Maurice Bishop International Airport.

If you are spending time in the Northern part of the island especially for hiking trails, waterfalls and lakes, Petite Anse Hotel is great for easy access to these excursions.

2. Barbados

Loved for its white sand beaches and exciting nightlife atmosphere, Barbados is a superb option to consider for your winter getaway.

Accra Beach, Miami Beach and Carlisle Beach are some of the best spots to visit while on the island.

Barbados is also loved for its robust nightlife activities and Fish Friday which is one of the major events on the weekly entertainment calendar.

Fish Friday is a street party hosted in Oistins where local vendors come together to prepare traditional Bajan meals with fish as the main ingredient.

The island has a great range of international flights when compared to regional counterparts such as Grenada mentioned above.

Amenities are also more diverse when compared to other islands in the Southern Caribbean.

Where To Stay In Barbados

The South Coast is an excellent region to stay as there are a number of restaurants, bars, grocery stores, fast food chains which makes life without a car seamless.

On a whole, hotels in Bridgetown and Christ Church are excellent regions to consider as they are near to the city centre and other amenities.

Budget Options– Pirate’s Inn and Coral Mist Beach Hotel

Mid-Range Options– Coral Sands Beach Hotel and Coconut Court Beach Hotel

Luxurious Options– Savannah Beach Club, Hilton Barbados Resort, Courtyard By Marriott Bridgetown

3. Jamaica

Fondly known as the land of wood and water, Jamaica is one of the most visited islands in the Caribbean.

Travelers love to flock to Jamaica due to its culture, history, white sand beaches, music and unique cuisine.

With only less than two flying time from Miami International Airport, Jamaica is a great choice for individuals seeking a shorter winter vacation.

Jerk chicken, festivals, bammy, ackee and saltfish are some of the dishes unique to the island and these are must try should you visit.

Dunns River and Falls is one of the most iconic attractions in Ocho Rios as well as the Blue Hole.

The island also boasts of many festivals throughout the year. The National Pantomime which commenced in 1941 begins on Boxing Day (December  26) annually.

A must do activity during your stay in Jamaica.

Where To Stay In Jamaica

If you are considering spending time in Negril and the iconic Seven Mile Beach, we recommend Negril Treehouse Resort, Merrils Beach Resort II and Negril Palms.

Furthermore, to enjoy the countryside of Montego Bay, Toby’s Resort and Altamont West Hotel are excellent accommodation providers.

For all inclusive options in Montego Bay, S Hotel Jamaica and Riu Reggae are two amazing choices.

Alternatively, if you are interested in staying in Ocho Rios, Ocean Palms, Hibiscus Lodge Hotel and Pineapple Court Hotel are places that we recommend.

4. Turks & Caicos Islands

An overseas territory of the United Kingdom, Turks and Caicos Islands are exceptional places for persons who enjoy white sand beaches.

Located less than two hours flying time from Miami International Airport, this destination is suitable for persons traveling with toddlers.

The award winning Grace Bay Beach on the island of Providenciales is often regarded as the best beach on the island.

As a general rule, Turks & Caicos is not a destination for nightlife and entertainment.

Nevertheless, if you are on the island, be sure to check out the Fish Fry which occurs every Thursday evening.

This is a great opportunity to sample the cuisine and music on the island as well as mingle with the locals.

Where To Stay In Turks & Caicos

Turks and Caicos Islands are loved for the iconic Grace Bay Beach which is ideal for beach bums and families.

For stay on the beach we recommend, Windsong on the Reef and Wymara Resort and Villas. For an all-inclusive stay on the beach, we recommend Alexandra Resort.

The capital city of Providenciales is another excellent location to consider. We recommend, Zenza Boutique Hotel and Rock House.

Beaches Turks and Caicos Resort Villages and Spa is an ideal all inclusive hotel to consider in the capital city.

5. Antigua & Barbuda

If you are a beach lover, Antigua and Barbuda is the perfect winter vacation escape.

Known as the Caribbean island with 365 beaches being one for every day of the year, Antigua and Barbuda boasts of having white sand, black sand and even exotic pink sand beaches.

Dickensen Bay Beach, Half Moon Bay Beach and Darkwood Beach are some of the principal spots to visit on mainland Antigua.

For more secluded and private beach experience, head over to Barbuda which is only 62 square miles but has some of the best pink sand beaches in the Caribbean.

Though small, Barbuda is the home of thelargest frigate bird colony in the entire Western hemisphere.

This makes it an excellent Caribbean island for bird watching.

Where To Stay In Antigua

For an adult only all-inclusive, Cocobay Resort Antigua and Escape at Nonsuch Bay are excellent options.

For proximity to the famous Dickenson Bay Beach, Trade Winds Hotel, Buccaneer Beach Club and Yellow Maison are outstanding options.

Royalton Antigua is a high end option to consider near this beach.

Alternatively, if you will love easy access to the capital city, Hodges Bay Resort & Spa as well as Heritage Hotel are great options to consider.

6. Aruba

Next up is Aruba which is known as the Happy Island. Aruba is a Dutch Caribbean island is loved for its beautiful white sand beaches.

Furthermore, Aruba is an exceptional destination for luxury shopping with  fashion designer retailers such as Cartier, Adidas, Michael Kors and Carolina Herrera all have retail stores at the Renaissance Mall.

Aruba is also perfect for golf enthusiasts as the island has two main gold courses being The Tierra del Sol Resort & Golf and The Links At Divi Aruba.

Additionally, the island is a great destination for hiking, parasailing and nightlife.

Where To Stay In Aruba

The best place to stay in Aruba is the capital city of Oranjestad or at a resort on the famous Eagle and Palm beaches.

To enjoy the white sands and turquoise waters of these above beaches, we recommend Coconut Inn, MVC Eagle Beach and Board Walk Boutique Hotel Aruba.

For high end accommodation on Eagle and Palm beaches, The Ritz Carlton, Aruba and Bucuti & Tara Boutique Beach Resort are two premium options.

For accommodation options in the capital city of Oranjestad, we recommend Wonders Boutique Hotel and Hyatt Place Aruba Airport.

For a private island escape where you can take instagrammable pictures with the pink flamingos, we recommend Renaissance Wind Creek Aruba Resort.

7. St Lucia

Known globally for its exotic twin peaks called the Pitons, St Lucia is truly an island for nature and coffee lovers.

St Lucia is home to its own brand of gourmet coffee called Green Gold Mountain Coffee which you can buy as a souvenir or try while on island.

The main hiking trail on the island is the Gros Piton is the designated hiking trail.

However, it could be strenuous and more suited for intermediate to advanced hikers.

Tet Paul Nature Trail is better for beginners and takes less than an hour to complete.

St Lucia is also a great island for bird watching and relaxing at beautiful waterfalls.

Where To Stay In St Lucia

The best place to stay in St Lucia is in Gros Islet as there are many restaurants, marinas, bars, banks, malls and supermarket all in the vicinity.

Additionally, it is easy to access the capital city, Castries from Gros Islet.

Bay Garden Hotel, Coco Palm and Harbor Club, St Lucia Curio Collection by Hilton are all phenomenal locations to stay in the heart of Gros Islet with easy access to buses to the capital city, Castries.

Royalton St Lucia is also another premium property ideal for an all-inclusive stay.

For an upscale and world class experience, we recommend Jade Mountain with stunning views of the Pitons.

This location is perfect for an unforgettable romantic honeymoon.

8. St Vincent & the Grenadines

St Vincent and the Grenadines is one of the islands in the Southern Caribbean that is loved for its hiking trails, waterfalls, white sand beaches, black sand beaches and cuisine.

The island is recognized as the world’s largest supplier and processor of this root starch and trying the famous madungo bakes.

Hiking the La Soufriere Volcano is one of the most famous things to do in St Vincent & the Grenadines.

The mountain stands at an elevation of 4,048 feet and though active is safe for exploration.

Where To Stay In St Vincent

The best place to stay is on the Windward side of the island. The Villa and Arnos Vale areas are near to the principal beaches as well as hotels on the island.

The Joshua Centre which was the former E T Joshua Airport is now a mall. There is a large Massy Supermarket as well as Kentucky Fried Chicken in the vicinity.

Mariners Hotel and Paradise Beach Hotel are two excellent locations to consider on the Windward side.

Access to public transportation is easy from these locations.

For a more upscale and private experience, Young Island Resort is a great location to consider.

A five minutes boat ride is required to access the island which consists of only 13 acres.

9. St Kitts & Nevis

Known as Sugar City, St Kitts and its dependency Nevis is home to the first ever hotel in the Caribbean.

The island is loved for its scenic hiking trails, UNESCO Heritage site Brimstone Hill and the railway train which is the last remaining of its kind in the West Indies.

Furthermore, the island is situated in close proximity to St Maarten and there is a ferry service which provides transportation to and from St Kitts.

Makana Ferry Services which is the provider also has onward connections to Dutch Caribbean islands of Saba and St Eustatius.

From St Maarten there are also connections to the French territory of St Barths and the British dependency, Anguilla.

Where To Stay In St Kitts & Nevis

The best place to stay in St Kitts and Nevis is at a hotel in the capital city of Basseterre.

Ocean Terrace Inn which is walking distance from the city is a perfect for persons seeking to explore the island without a car.

If you are booking a taxi you can consider Seaview Inn or for a more upscale experience the Marriott Resort in Frigate Bay.

The Frigate Bay area is a great place to night time entertainment and many bars and restaurants are within walking distance.

On the beautiful island of Nevis, we recommend Mount Nevis Hotel and Montpelier Plantation Beach which are perfect for beach lovers.

For a high end experience, Four Seasons Resort on the famous Pinney’s Beach is the place to stay with golf course, infinity pools and spa facilities.

10. Dominica

Fondly known as the Nature Island of the Caribbean, Dominica is an excellent destination for hikers and outdoor enthusiasts.

The island is home to second largest boiling lake in the world which is situated in the UNESCO Heritage Site Morne Trios Pitons National Park.

Dominica is an excellent destination for budget travelers and individuals seeking to island hop.

L’Express Des IIes provides ferry services which seamlessly connects travelers to Dominica from St Lucia, Guadeloupe and Martinique.

Where To Stay In Dominica

Fort Young Hotel is the best place to stay in the capital city of Roseau. There is an excellent restaurant on site, an outdoor infinity pool and spectacular views of the Caribbean Sea.

For a breathtaking beach front 5 star stay in Portsmouth, The Intercontinental Dominica Cabrits Resort & Spa is the ideal place to stay.

Nestled in the historic Northern region of the island, the hotel is equipped with fitness centre, kids club and restaurant.

For an eco-friendly stay, Rosalie Bay Eco Resort is an outstanding choice. The property features stunning river, sea and mountain views. There is a fitness centre, spa facilities and garden.

11. Dominican Republic

Often confused with Dominica mentioned above, Dominican Republic provides a range of activities to visitors.

The island is Spanish speaking and is home to the tallest peak in the Caribbean being Pico Duarte which stands at 10,125 feet.

Most notably, Dominican Republic is also home to the tallest waterfall in the Caribbean Salto de Jalda.

It is a breath taking 400 foot drop and is situated about two hours’ drive from Punta Cana.

Dominican Republic is also home to the gorgeous Bavaro Beach which is one of the longest in the Caribbean.

With uninhabited island getaways, white sand beaches, cenotes, waterfalls and excursions, you are in for a threat if you choose this Caribbean destination.

Where To Stay In The Dominican Republic

We recommend the capital city of Santo Domingo for persons interested in sightseeing.

Catalonia Santo Domingo and Radisson Hotel Santo Domingo are two locations to consider for stay in the capital city.

Alternatively, Punta Cana is one of the most popular areas to stay in Dominican Republic for beaches and a bustling nightlife atmosphere.

Hotel Marimba, Punta Cana and Hotel and Casino Flamboyan are great places to consider for your stay on Bavaro Beach which is one of the longest in the Caribbean

For all inclusive experience, we suggest Catalonia Royal Bavaro, RIU Palace Bavaro and Bahia Principe Grand Aquamarine.

12. Belize

Our next recommendation is the exotic island of Belize which is an excellent destination for diving and snorkeling experiences.

Some of the top spots in the country to consider include Turneffe Atoll, Belize Barrier Reef, Hopkins and Placencia.

Furthermore, Belize has 300km of barrier reef system which is part of the Mesoamerican Barrier Reef which is the second largest system in the world.

Nightlife in Belize is concentrated more in the San Pedro region on the island of Ambergris Caye.

Sunset Lounge and Carlo & Ernie’s Runway Bar are two locations to check out for entertainment in San Pedro.

Where To Stay In Belize

If you are searching for a hotel in Belize City, then we recommend The Great House Inn, Best Western Plus Belize Bitmore Plaza or Radisson Fort George Hotel & Marina.

For stay in Caye Caulker, Tropical Paradise or Blue Wave Guest House are options to consider.

If you main travel motivation is nightlife and entertainment, San Pedro is the best place to stay.

Hotel Del Rio and Ambergris Sunset Hotel are two amazing properties.

For stay in San Ignacio if you are visiting Mayan ruins, Venus Hotel and Rumors Resort Hotel are outstanding places to stay.

13. Bahamas

The Bahamas is a remarkable destination for persons seeking white sand beaches, unique pink sand beaches, nightlife, private island experience and to swim with the iconic pigs.

Gold Rock Beach, Cable Beach and Tropic of Cancer Beach are three of the amazing spots to visit for beautiful white and powdery sand in the Bahamas.

The Bahamas is also known for having pink sand beaches with one of the most famous one being Pink Sand Beach on Harbour Island.

This island is only 3.5 miles long and 1.5 miles and is popular stop for affluent visitors.

The sand on pink sand beach has its distinct pink color due to the presence of foraminifera.

For a unique experience, Pig Beach on the island of Exuma is the perfect for those who want to swim with pigs.

Where To Stay In The Bahamas

The best place to stay in the Bahamas for easy access to a range tours and proximity to key landmarks as well as the night life hotspots is the Nassau.

For more budget friendly accommodations, we recommend Ocean West Boutique Hotel and Orange Hill Beach Inn.

For a high end premium experience in Nassau, we suggest Grand Hyatt Baha Mar and SLS at Baha Mar.

Paradise Island is also a great location to stay.  We recommend Comfort Suites Paradise Island, The Coral at Atlantis and The Royal at Atlantis.

14. Puerto Rico

If you are considering visiting the Caribbean for the first time, Puerto Rico is one of the best Caribbean islands to visit.

Puerto Rico is an outstanding destination for private island getaway, white sand beaches, historical landmarks and so much more.

Flamenco beach is one of the best beaches in Puerto Rico which is loved for its calm waters which makes it perfect for swimming and snorkeling.

Puerto Rico is the more superior destination when it comes to nightlife. It is a larger island and hence has more entertainment options.

There are several night clubs, bars and lounges in the city. Some of the places to visit include La Factoria, La Cubanita, Club Brava and Club 77.

La Placita de Santurce is a popular nightlife spot to meet locals on the island to eat relax and salsa dance in Puerto Rico.

Where To Stay In Puerto Rico

The capital city of Old San Juan is a great place to stay for sightseeing, soaking up the culture, and visiting historic landmarks.

We recommend Sheraton Old San Juan Hotel and CasaBlanca Hotel for your stay in San Juan.

Alternatively, if you are thinking of spending time at the beach and enjoying fine dining, we recommend that you stay in Condado.

For accommodations, we recommend El Canario Lagoon Hotel and Acacia Boutique Hotel.

For a more upscale experience, we suggest AC Hotel By Marriott San Juan Condado and Condado Palm Inn San Juan and Tapestry Collection By Hilton.

15. Curacao

Our final suggestion is the Dutch Caribbean island of Curacao which is known for its exciting dive sites and nightlife experience.

Some of the popular beaches on the island include playa piskado which translates to fisherman’s beach where you get to swim with sea turtles in Curacao.

 In addition, you can swim with dolphins at Jan Thiel beach.

Peradventure, you are a nature enthusiasts, Christoffel National Park is an outstanding place to visit.

The park is home to several species of flora and fauna at the park as well as birds.

There are eight hiking trails which you can explore as well as the Savonet Museum is located at park where you can learn more about the history of Curacao.

Where To Stay In Curacao

The capital city of Willemstad is the best place to stay for history, culture, restaurants and entertainment.

We recommend City Suites and Beach Hotel, Saint Tropez Boutique Hotel and Curacao Marriott Beach Resort for your time in Willemstad.

Alternatively, if you are primarily interested in spending time at the beach and snorkeling, we suggest that you stay in Sabana Westpunt.

Great resorts in this area include Marazul Dive Resort and Rancho el Sobrino.

Frequently Asked Questions

Final Thoughts: Best Caribbean Islands For A Winter Vacation

The Caribbean has so many islands with a wide range of activities and hence it’s an exceptional option to consider if you are seeking a winter getaway.

Perchance, one of the destinations that you have an interest in visiting was not mentioned in the list above, feel free to continue reading using the search bar at the top of this page.

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