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5 Caribbean Island Escapes for Your Next Vacation

Need a winter escape? Get inspiration from these top Caribbean island destinations that will keep you warm and won't break your budget for your next winter vacation.

Calling all beach bums, sunbathers, snorkellers, and explorers! Escape the cold weather and head to one of these five Caribbean island destinations and find the perfect spot for your much-needed winter vacation. 

Many destinations in the Caribbean are a direct (or via Miami) flight away from major Canadian cities. In less than five hours of travel time, you can find yourself in paradise! And our search engines will help you find cheap flights to these sunny and affordable destinations. With more and more flight deals happening to the Caribbean, now is the time to book your sunny winter getaway!

Caribbean Flight Deals of the Week
Two people relaxing in beach chairs during a beach sunset. caribbean vacation spots.
Caribbean Winter Escapes | Skyscanner Canada

Vacation in Grenada

The country of Grenada is actually made up of several small islands. It got its nickname “The Spice Isle” from the many spices produced on the island like nutmeg, cinnamon, cocoa, ginger, and cloves. This means there are plenty of spice estates and spice gardens for you to discover!

There are also lots of waterfalls, lakes, gardens, and rum distilleries (like the River Antoine Rum Distillery). There is even a fort that overlooks the capital, Saint George, called Fort Frederick.
Fun fact: The restoration of the fort was helped by the Canadian government!

Beach and island lovers can spend days on the beautiful beaches or snorkelling in the gorgeous water, but you should also not miss out on the Annandale Falls, a 30-foot high waterfall. You can swim in the water surrounded by tropical plants and the water is deep enough for you to jump in!

How to Get to Grenada:

Travellers typically arrive at the Maurice Bishop International Airport and then proceed to take ferries to different islands like Grenada, Carriacou and Petit Martinique. Search for cheap flights to Grenada here.

Where to Stay in Grenada:

Blue water and green hills in Trinidad.
Caribbean Winter Escapes: Trinidad and Tobago | Skyscanner Canada

Fly to Trinidad and Tobago

Unlike other Caribbean island destinations, tourism is not a large part of the Trinidad and Tobago economy, making it a unique choice on our list of top spots in the Caribbean. The country has two main islands, three different mountain ranges and a ton of untouched wilderness. Trinidad and Tobago is a great winter vacation destination for people who love hiking, biking and hanging out on the beach.

In the capital city, Port of Spain, there are plenty of activities, including a walk along the waterfront park, the National Museum, the Botanical Gardens, and the 260-acre park (Queen’s Park Savannah).

While you’re on your winter getaway in Trinidad and Tobago, make sure to eat one of the local rotis, which are flatbreads stuffed with different fillings. The rum is worth trying too!

How to Get to Trinidad and Tobago:

Piarco International Airport in Trinidad is most likely where you will land. There is also the ANR Robinson International Airport in Tobago. In order to get between the two islands, you can take a flight or a ferry (two ferry options). Search for cheap flights to Trinidad and Tobago here.

Where to Stay in Trinidad and Tobago:

Colourful Dutch-style homes in Aruba.
Caribbean Winter Escapes: Aruba | Skycanner Canada

Relax in Aruba

One of the top Caribbean islands to explore this winter? Try relaxing in beautiful Aruba! Head to this warm and balmy country for your fill of sun and beaches. Being one of the most touristy spots in the Caribbean, there is plenty of infrastructure and activities for you to pass an amazing sunny vacation.

Stick to the southwest coast of the island for warm water and amazing beaches. The northeast coast is a bit rocky with rougher seas, which makes it not recommended for swimming. Many of the popular winter vacation activities in Aruba are ideal for beach and island lovers! Activities include scuba diving, snorkelling, cave exploring, kayaking through mangrove forests, fishing, and lying on the beach.

Walking around the capital city, Oranjestad, will have you admiring all of the Dutch influence. As a large tourist destination in the Caribbean, Aruba has a mix of high-end shops and unique local boutiques, five-star restaurants with spectacular views, a casino, and activities like parasailing.

How to Get to Aruba:

To get to Aruba, head to the Queen Beatrix International Airport. Search for cheap flights to Aruba here.

Where to Stay in Aruba:

Green hills and blue water in Saint Kitts.
Caribbean Winter Escapes: Saint Kitts and Nevis | Skyscanner Canada

Explore Saint Kitts and Nevis

This Caribbean country is made of two islands: the larger island of Saint Kitts and the smaller island of Nevis. Nevis is only around 3 km southeast of Saint Kitts, located across a channel called “the Narrows.”

Nevis has one volcanic mountain, a bunch of beaches, and a small capital called Charlestown. It is the more secluded of the two islands, focusing on mountain biking, hiking, deep-fishing, and windsurfing.

St Kitts is larger and has a wider selection of restaurants, hotels, and bars. However, it’s still is a small island. The island’s first traffic light was only installed at the start of 2018! The main attractions promoted on this island are golf, scuba diving, and an emphasis on eco-tourism. Of course, you can always enjoy the Brimstone Hill Fortress!

Both islands of this Caribbean destination have rainforests, beaches, and historic ruins, making this a great destination for beach and island lovers who want to stay away from any crowds.

How to Get to Saint Kitts and Nevis:

There are two airports: Robert L. Bradshaw International Airport (SKB) on St. Kitts and Vance W. Armory International Airport (NEV) on Nevis. There is a ferry that runs between the two islands. Search for cheap flights to St Kitts and Nevis here.

Where to Stay in Saint Kitts and Nevis:

White sand and blue water in Barbados.
Caribbean Winter Escapes: Barbados | Skyscanner Canada

Escape to Barbados

From luxury resorts to local rum bars, the Caribbean island of Barbados should be on most lists of best winter escapes!

Barbados is home to pristine beaches, excellent snorkelling opportunities, cave tours, rum factories, gardens, and wildlife preserves. There are beaches that perfectly complement some of the all-inclusive resorts and the many east coast beaches of Barbados offer a little something for everyone. Head to Bathseba for some of the best surfing in the world. Rent a car and drive to Cattlewash or Bath Beach to experience that picturesque beach scene and make the most of your winter getaway.

Barbados is also known as one of the nightlife capitals of the Caribbean, so you will be able to dance the night away in open-air dance floors, nightclubs, and more. Make sure to head to Oistins Fish Fry for dinner at drinks at least one night – preferably on a Friday. 

The island of Barbados is small enough for you to circle the entire island in a day! Alternatively, explore some of what Barbados has to offer via a catamaran trip.

No matter what activities you choose to do, Barbados is one of the best Caribbean islands for a sunny holiday.

How to Get to Barbados:

Fly into Grantley Adams International Airport. Search for cheap flights to Barbados here.

Where to Stay in Barbados:


Ready to book your next winter vacation destination? Find cheap flights to all Caribbean vacation spots and popular destinations with the Skyscanner search engine. You can even score deals on hotels! Not sure how Skyscanner works? Check out our Frequently Asked Questions

Get even more inspiration for warm places to travel this winter: