5 Stunning Caribbean Islands You Need to Sail on a Charter in 2020

Blissful turquoise blue lagoons, swaying palm trees and temperatures in the high 80s. You really are spoilt for choice when it comes to sailboat charters in the Carribean in 2020.

8th Jan 2020

From sailing through the vibrant British Virgin Islands, exploring Puerto Rico’s beautiful natural landscape, or designer shopping on St Martin, there is something for everyone when sailing in the Caribbean.

Take a read through and be inspired for your sailboat vacation in 2020 and beyond.

Maria Soleil, Senior Marketing Executive

British Virgin Islands

Best for: Partying at beach bars

It’s no surprise that the British Virgin Islands are the top sailing destination in the Caribbean for vacationers.

The 60 islands and islets provide easy line-of-sight sailing and are the perfect mix of pristine white sandy beaches, lively nightlife and lots of snorkeling stops.

Bareboat charter BVI
A sailing paradise | Necker Island, BVI

Throw in the ever popular Soggy Dollar Bar and Foxy’s Bar – both on Jost Van Dyke – and you’ve got the makings of a vacation to remember. 

There are plenty of options for a sailing charter in the BVI – from catamarans such as a Nautitech, Lagoon or Bali, or monohulls including Dufour or Jeanneau.

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Best for: A family vacation

Most people familiar with the Caribbean islands will know that Antigua is famous for its 365 beaches – one for every day of the year. This makes it ideal for a bareboat charter with a family – you’ll have plenty of places to anchor up and spend the day.

Swim in the luscious calm shores at Ffryes Beach and enjoy barbecued local fish for lunch. Or try beachcombing on the sweeping golden sands at Darkwood Beach.

Antigua sailboat charter
Ffryes Beach

Go to the viewpoint at Shirley Heights overlooking English Harbour – the site of hundreds of years of naval history – and try an old fashioned punch using the local dark rum.

Most sailboat charters in Antigua start from Jolly Harbour Marina, which is very well placed to sail out of and circumnavigate the island on a 7 day vacation. It also has plenty of restaurants and shops for provisioning.

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Puerto Rico

Best for: Nature and wildlife

Nature lovers will love sailing the coastline of Puerto Rico on a bareboat charter. Its diverse habitat is full of forests and rocky outcrops home to a variety of flora and fauna.

Take a charter out of San Juan or Fajardo and sail east to wild uninhabited Isla de Culebra – a haven for turtle and seabird populations. Snorkel off Punta del Soldado and see ray, blue tang and barracuda. 

Puerto Rico bareboat charter
See the colours of Puerto Rico’s nature

On the way back, live stories of pirate legend and sail to Pirates of the Caribbean filming locations Isla Palominos and Palominitos and swim ashore through the breathtaking azure blue and sea green waters.

Although Hurricane Maria devastated much of Puerto Rico in 2017, the island is on its way to recovery and visits from tourists will give a much-needed boost to the economy.

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Best for: Snorkeling

Hilly and colorful Grenada is a favorite among our team here at LateSail, and it’s not hard to see why. The ‘Spice Isle’ and its surrounding islands is a world-class sailing destination, with a rich history and plenty of impressive coral reefs.

Most bareboat charters in Grenada start out of the capital of St George’s. From there you can enjoy a 7 day itinerary and take in Carriacou and Petit Martinique. The tiny island of Petit Martinique is a hidden, relaxed and unspoilt paradise.

Grenada bareboat charter
Don your snorkeling gear and dive into the sea in Grenada

Hire a stand-up paddleboard and don your snorkeling gear to take in the amazing underwater seascape, where you can spot turtles, lobster, rays, seahorses and eels.

Why not sit back and relax by taking advantage of a crewed catamaran charter and sail through the Grenadan island chain in style. 

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St Martin/St Maarten

Best for: Shopping

A blending of Dutch and French heritage on one landmass makes St Martin and St Maarten a fascinating island to visit on a bareboat charter.

It is also excellent for those looking for a bargain or daytime activities. Said to be the Caribbean capital of duty free, St Martin has plenty of designer shops offering discounted goods and other places to keep visitors entertained including casinos and many beach bars. 

St Martin bareboat charter
There is plenty to keep you occupied in St Martin

St Martin is a great base to make a sail over to its diverse neighboring islands of St Barts and Anguilla

Just 12nmi to the south west lies stylish St Barts, a haven for the rich and famous. An even shorter passage across to British Overseas Territory Anguilla to the north brings wide sweeping beaches and a laidback vibe.

Search for boats in St Martin

Want the best sailboat charter offers?

Get in touch


With a combined 50 years of experience, our team knows all there is to know about the world of boat chartering.

If you want to know more about bareboat, flotilla, or by-the-cabin charters, speak to one of our experts who will be happy to share their knowledge with you. 

Use our price comparison tool to search for charters by date or destination, request a quote or contact our team on 877-292-0737.

We love being on the water and it’s our ambition to enable others to share our love of sailing.

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