If you are anything like me, you always have a list of places you’d be okay with jet setting off to at a moment’s notice. I love to travel, so I can’t help it! Lately, my list has been all about finding the best Caribbean destinations for a fun in the sun getaway. I don’t know if its something in the Chicago water, if being cooped up at home is getting to me, or if my body just needs some Vitamin Sea but I am craving a tropical getaway.
Beautiful Tropical Destinations in the Caribbean

The Caribbean is a region that is made up of the Caribbean Sea, its islands and the surrounding coasts. It has more than 700 islands, reefs, and cats making it the perfect option for a tropical getaway. If you want sand, sun, and fun, look no further than the Caribbean! Here are the best Caribbean destinations to keep in mind for your next trip.
St. Bart’s
St. Bart’s has a reputation for being the Caribbean’s most expensive and elite destination. But don’t let this posh reputation scare you away if you, like me, aren’t friends with Leo DiCaprio and his circle of rich and famous peers. There is still plenty to win over us normal folk!
St. Bart’s has 22 white sand beaches which are generally much less crowded than other Caribbean destinations. In Gustavia, the capital, you’ll find gingerbread-trimmed beach cottages and a yacht-filled harbor. There are shops and restaurants as well to check out. On the opposite end of the island is St.-Jean. This tiny strip is often compared to St.-Tropez with its colorful boutiques and tropical drink serving beach bars. All over the rest of the island, there are resorts that cater to every demographic and include everything under the sun.

Best time to go to St. Bart’s
The best time to visit St. Bart’s is from November until June. Just keep in mind that from December to April the sun is out on full display, ready to scorch! High season in St. Bart’s is in December. If you plan on spending your winter holiday there, make sure you plan at least 6 months in advance. Reservations and bookings fill up fast so this isn’t your last-minute winter getaway. You’ll want to avoid traveling to St. Bart’s in the rainy season (September – November) as many establishments usually close this time of year.
Know Before You Go
Weather
June through September are St. Bart’s hottest months. During this time, the island has an average high of 90°F (32°C). The coolest months are January through March with an average high of 84°F (29°C).

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Transportation on St. Bart’s
St. Barts has no public transportation so many visitors tend to rent a car. If you aren’t comfortable driving (or don’t want to) there are licensed taxi drivers. Your hotel will be able to call one for you should you need one.
Language:
French is the official language but English is widely spoken.
Dominican Republic
The Dominican Republic is truly a unique Caribbean destination. And it is also one of the most geographically diverse countries in the region. There really is something for everyone in the DR, from stunning mountains to white-sand beaches.
The Dominican Republic has hundreds of miles of coastlines that draw visitors from all over the world. The ocean is the heartbeat of the island. Whether you are in a small fishing village peppered with boats or snorkeling in the underwater playgrounds, rows of palm trees and rocky cliffs provide you with dramatic landscapes. This natural heritage is protected by way of parks and preserves, including coves where thousands of humpback whales migrate to year after year.

In the capital city of Santo Domingo, romance is in the air! Stroll along cobblestone streets where conquistadors once walked and take in the beautifully restored buildings. In Puerto Plata and Santiago, you can see homes built in a more prosperous time. This area reminds me of Cuba where decades of mismanagement have left beautiful gingerbread homes crumbling.
Beyond the capital, much of what you’ll find in the Dominican Republic is rural but not without charm. You’ll see trucks packed with fresh produce heading to market and cows grazing along the sides of the road. You’ll go from rivers and lush jungles that lead to water falls one minute and the next you’ll be reminded of the European Alps as you go further inland. Four of the five highest peaks in the Caribbean are located in the area surrounding Santiago!

In the Dominica Republic, you are sure to encounter a lot of culture! All night merengue blasts from corner stores and bars, all over the country. Carnival celebrations are held through out the country in February. If you happen to visit during this festive time, you can expect a fun time!
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Best time to go to
The best time to visit the Dominican Republic is in the spring. Keeping the weather and crowds in mind, spring is the perfect time. April and May have lovely weather without being overly crowded. Something else to keep in mind is the hurricane season! As a tropical destination, your vacation can be impacted by storms.
Know Before You Go
Weather
The weather in the DR is generally hot with your typical tropical temperatures year around. It does vary from region to region but you can expect 75-85 degree weather.
Language:
Spanish is the official language but English is widely spoken in the tourist areas.

Martinique
Martinique is a place that has it all! There is breathtaking beauty, Creole culture, and a bunch of opportunities to explore the outdoors. Pretty much every water sport can be done in Martinique. The island was made by volcanic activity from Mont Pelée that whipped out St-Pierre, the former capital, in 1902. Its geographical features and origin mean that Martinique is mountainous and has a diversity of landscapes.

In the north of the island, you’ll find mountainous rainforests. And in the south, there are miles of gorgeous beaches and bays. Fort-de-France, the capital, is an urban city with plenty of shopping, restaurants, and things to do. As you get away from the capital, life becomes less busy.
Best time to go to
May is the best time to visit Martinique. During this time of the year, the temperatures are consistently in the 80s. But you have to keep in mind that hurricane season can sometimes crash your vacation if you go in the summer or fall. Peak season in Martinique is from December to April which can mean marked-up prices for hotels and accommodations.

Know Before You Go
Weather
Martinique’s peak season is from December to April where you will find temperatures in the low 80s. In May, the island is pretty quiet after the Carnival season ends. During this time, you’ll see temperatures in the mid-80s. From June to November, many hotels shut down. Any hotels that are open during the rainy season don’t offer as much of a discount as you would hope. By the end of November, the island is starting to open back up and prepare for peak season to start!
Language:
The official language in Martinique is French, and Creole is widely spoken. English is not.

Grand Cayman
When it comes to Grand Cayman, you can expect quite the package! On this island, art and culture come alive while nature mesmerizes you. On the west side of the island, you’ll find Seven Mile Beach. This crescent-shaped white sandy beach is award-winning! North Sound is where a large number of stingrays can be seen. There are so many of them that they call it Stingray City! With everything the island offers visitors it is easy to see why Grand Cayman is our on list of best Caribbean destinations.

If the beaches aren’t calling your name, maybe duty-free shopping in George Town is. You can shop duty-free at stores like Versace, Gucci, and Tiffany. There are also local craftsmen who provide amazing handmade gifts. Across the island, you can see the Blue Iguanas of Queen Elizabeth II Botanic Park. While you’re in that area, stop to eat freshly caught fish at one of the nearby restaurants.

Grand Cayman has a few must-sees, you can’t miss. To experience the natural and cultural history of the island, head to The National Museum of the Cayman Islands. Rum Point is a great spot to hang out after snorkeling. If you’re looking to hike, The Mastic Trail will not disappoint. This trail takes you through the jungle!
Best time to go to
Try to plan your trip to the Cayman Islands sometime between March and June. During this time, hotel rates usually drop. The islands are warm all year so you don’t have to worry about planning around the weather. The islands western Caribbean location shields them from being hit too hard by hurricanes.

Know Before You Go
Weather
The island is a tropical paradise year around. You can find 80 degree weather pretty much anytime. The coolest months of the year are January and February where the average lows are generally in the high 60s.
Language:
English is the official language.
Anguilla
Anguilla is the kind of island that offers visitors a mix of everything. Unlike many islands in the Caribbean that have seen a growth in properties along the beach, Anguilla still has its small island charm. Local authenticity can be hard to find but not in Anguilla. It is the kind of place where you can lounge with a drink in hand, ride horses on the beach, or enjoy the water. You can enjoy the coral reefs by snorkeling or diving in Anguilla’s crystal blue waters. And if history is more your thing, you can learn about the island’s local history at the Heritage Collection museum.

Best time to go to
Year-round, Anguilla has great weather which is one of the reasons it is on our list of best Caribbean destinations. Just keep in mind that peak season is from December to mid-April. During this time, prices increase considerably. If you want more of a budget trip, consider visiting between May and August.
Know Before You Go
Weather
During the high season, you can expect average temperatures in the high 80s. From May to August, there is a little more rain so you can expect it to be humid.
Language:
Most people in Anguilla speak English.

Cartagena
Cartagena is a gorgeous city that has become one of the best Caribbean destinations in Colombia for local and international visitors alike. The historic city is a UNESCO World Heritage Site. With cobblestone streets, balconies covered in flowers, and stunning old monasteries that have been converted to hotels and restaurants.
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Cartagena is the kind of place where you can let go of your normal sightseeing routine. Here you can go with the flow. You can spend the day sitting in a plaza people watching or explore the culinary wonders of the Old Town. The city charms you, it draws you in. And it is hard to walk away without falling in love. Cartagena is one of the most well preserved historic cities. It is a great destination for families, couples, or friends looking for a tropical getaway.
Best time to go to
The best time to visit Cartagena is from December to April. The dry season for Cartagena is from December to April which is also the city’s summer season. During the summer is when Cartagena sees the most visitors. It is worth fighting the crowds since winter can bring constant rain and insane humidity.
Know Before You Go
Weather
The city has a tropical climate so temperatures tend to stay around the mid-80s. What does vary, is rain! The rain does drop the temperature a bit so make sure you pack a light jacket just in case.
Language:
Spanish.

These tropical places are the best Caribbean destinations. Each one has a lot to offer visitors but some are better fits than others depending on what you are looking for. No matter which one you visit, you’re sure to have a great time. So grab you sunscreen and get ready for fun in the sun!