Thanks to its great weather all year long, turquoise seas, white sandy beaches, lively nightlife, and tropical flavors, the Caribbean is the ideal place to escape with your friends for an unforgettable holiday.
If you intend to rent a sailboat to the city, we will certainly suggest island hopping so that you can experience as much as possible.
Jamaica
Where are we even starting?
Jamaica is a perfect place for someone who loves to wake up in a tropical paradise after a rough party.
One of our favorite beaches in Jamaica is the Seven Mile Beach in Negril.
The beach is popular not only for its stunning sunsets and long-haired windsurfers but also for its legendary parties.
This is not a peaceful spot (the Blue Lagoon could be a better place to spend a relaxing day at the beach) – Seven Mile Beach is full of bars serving ice-cold Red Stripes, people from all over the world, live music, and street vendors selling skewers and fresh fruits.
There are open fireplaces and grills selling Caribbean-style food and serving very heavy cocktails served in pineapples and coconut shells.
There are multiple activities taking place every week – you’re sure to make new friends and have a lifetime party anytime you want to come.
Fun fact: this is the longest beach in Jamaica.
The Trinity
If you want to party in Trinidad,
you’re going to have to learn some slang.
If you want to go out and enjoy the nightlife and music, you might say that you’re “limin’ heavy.” If you’re looking to kick back at the outdoor bar, you might say that you’re limin’ gentle.
And happily, in the larger island of Trinidad and Tobago, you have several chances to do all of these things.
If you’re with a band, head to Rust Street, where dance hall music from local bars fills the streets with energy.
Or get dressed and dance the night away at any of the nightclubs in Port of Spain or San Fernando.
Close the night with the sweet promise that you can rest your body on the beautiful beach of Trini the next day.
Aruba
Aruba, best known for its rum and intimate settings, is also an excellent choice for partygoers.
Beautiful sandy beaches, palm trees, massive palapas (shade huts) filled with people dancing to the rhythm of island beats, coconut rum, blue curacao, tequila and peach snacks, cool bar workers who know their cocktails: Aruba has it all.
There’s even a party bus (the Kukoo Kunuku Party Bus).
Puerto Rico
The best time to rent a boat in Puerto Rico?
Every time, of course.
However, if you love festivals, make sure you schedule your visit around January or June.
The San Sebastian Festival is taking place in January – perfect if you’re into stuff like Mardi Gras.
In June, the entire island becomes an all-night party for the Noche de San Juan.
Puerto Rico is not only the capital of the Caribbean nightlife but also the birthplace of Piña Colada, a quintessential island cocktail.
Antigua
Whatever your mood, Antigua is sure to keep you amused.
If you’re dancing the night away at one of the island’s top clubs, bar-shopping or trying your luck at a casino, the island is sure to please your senses.
Recover the evening festivities at Shirley Heights Lookout for their Sunday afternoon BBQ, a perfect meeting place for locals, celebrities, and tourists.
Take a drink and some food and enjoy the sounds of the Caribbean as you dance, mingle, and relax under the sun.
St. Barts
Get ready for an evening party-hopping on luxury yachts and private villas on the Caribbean’s most chic island and one of its best-kept secrets.
Often known as the Caribbean French Riviera, the island is full of gourmet restaurants, top-notch bars, and gorgeous people.
Spend your Christmas holidays in St. Barts and join other sailors as the whole island becomes a giant open-air party.
Grab a cocktail in one of the island’s beautiful beachfront bars and get ready to spot celebrities as private jets and mega yachts arrive on this tiny island of paradise.
Jost Van Dyke’s
Jost Van Dyke is the perfect destination for partygoers and sailors searching for the best tropical beverages.
Relax on the white sandy beaches throughout the day and enjoy the island’s relaxed lifestyle.
At night, get ready for bar-hopping around some of the finest bars in the British Virgin Islands.
Cruise to Jost Van Dyke for the Caribbean’s finest New Year’s Eve and Halloween parties at the infamous Foxy’s Bar or enter one of the many yacht parties in the Great Harbor.
Swim to the Soggy Dollar Bar, the birthplace of “The Painkiller,” the most popular cocktail in the Caribbean.
In the past, the bartender would hang your soggy dollars (wet from the swim to the bar) to dry while you enjoy a concoction of premium dark Rum, Coconut Cream, Pineapple, and Orange Juice, topped with freshly grated Grenadian Nutmeg.
Barbados
Barbados is the place to get away from it all.
Host to some of the best nightlife in the Caribbean, you’ll be swept away by local beats that have inspired the music icon of Rihanna.
Enjoy sunbathing on pristine beaches and surfing throughout the day, then head south to find the best rum bars (Barbados is supposedly the birthplace of rum), beach clubs and open-air parties, or head to St. Lawrence Gap and grab a pint at one of the many English-style pubs.
St. Maarten, St. Martin’s
Cure the winter blues by moving to the beautiful metropolitan island of St. Maarten (Dutch side) or St. Martin (French side), where you can experience sandy beaches, delicious food, and lively nightlife on this island.
Legend has it that the French / Dutch border on the island was created after a drinking competition in the 18th century.
Martin is said to have more bars per capita than any other Caribbean island today.
The island is also home to Las Vegas in the Caribbean, with 14 casinos on the Dutch side.
Martin likes to get the party started early, so head to the beach for a BBQ as the sun sets, enjoy some delicious concoctions during the island’s happy hours and rejoice in the sounds of reggae as the stars come out, and the real party begins.
St. Lucia
St. Lucia is well known for its sandy beaches, authentic culture, and unspoiled landscapes, but it is also the ideal destination for adventure and partygoers.
You’ll be sure to enjoy alluring tropical plants, flowers, and flavors while exploring historic fortresses, tiny villages, and orchards full of exotic fruits such as coconuts, papayas, and mangoes.
In the evening hours, you’ll find a lot of stuff going on at Rodney Bay Village.
Try local Piton beer on the island, savor local treats every Friday night in the fishing village of Gros during its lively street parties.
Do you like our list of the best islands in the Caribbean party?
Speak to our staff about sailing routes and boat holidays in the Caribbean.