5 exotic sailboat charter destinations to visit on a vacation in 2020

Do you want to try somewhere different for your sailboat vacation in 2020? We can help inspire you.

10th Dec 2019

We’ve picked out some of the best cruising grounds in the Caribbean, Central and South America and further afield into the South Pacific.

Read why these destinations should top your sailing vacation bucket list.

5. Ilha Grande, Brazil

Get away from the crowds and discover tropical beaches and untouched rainforest on a sailboat vacation to south-eastern Brazil.

Lagoa Azul, Ilha Grande
Lagoa Azul, Ilha Grande

A two hour drive from Rio de Janeiro lies Marina Velrome, a popular charter base in the Angra dos Reis municipality. From there it’s easy to sail to tranquil islets found all along this part of the coastline, including Ilha de Paqueta and Ilha da Gipoia.

The larger car-free pristine island of Ilha Grande is perfect to explore by boat over several days. It features long, sandy beaches which are said to be among the best in Brazil. It’s no surprise that visitors come here from Rio for a weekend break.

Enseada das Palmas, Ilha Grande
Enseada das Palmas, Ilha Grande

Take a hike ashore and see an old abandoned prison called Instituto Penal Candido Mendes, at Dois Rios. Or walk one of the many jungle trails and go for a cooling swim in the natural pool at the Cachoeira Da Feiticeira – a 50ft waterfall which has stunning views over the island.

Sailing in Brazil means one thing – enjoying the local waterfront nightlife after the sun goes down. In the main town of Vila do Abraão on Ilha Grande, dance along with the locals to live music such as bossa nova and samba.

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4. Saint Martin, Caribbean

St Martin is one of the most popular bases for a sailboat vacation in the Caribbean and it’s not hard to see why. The dual-nation island combines some of the best cruising conditions with designer shopping, luxury restaurants and fantastic nightlife.

Anse Marcel, St Martin
Anse Marcel, St Martin

You’ll start your charter from one of these bases on St Martin: Simpson Lagoon, Anse Marcel, and Oyster Pond. From here you can head north to the quiet but stunning Anguilla or south to luxurious French-speaking St. Barts.

Relax on the fine beaches at uninhabited Prickly Pear Cays, just six miles offshore north-western Anguilla, or try a distinctly different vibe on St Barts. 

Beach on Anguilla
Beach on Anguilla

Known as the St Tropez of the Caribbean, St Barts is a slice of cosmopolitan France in the West Indies. It’s popular with Americans and multi-millionaires who come over here in the holiday season. 

If you’re looking for a vacation with a mix of culture, you’ll find it here. There is a blend of African, French, Dutch and British heritage, and unsurprisingly that means that foodies will love it here as well. You’ll find a melting pot of Creole, French and West Indian cuisines.

You’ll love sailing in St Martin, with trade winds ranging from 10 to 25 knots blowing north-east to east in the high season, and temperatures of 27°C.

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3. Belize

A sailboat vacation in Belize would create memories of a lifetime, especially for fans of scuba diving and snorkeling. 

Caye Caulker Belize
Caye Caulker, Belize

Belize is home to one of the longest coral reefs in the world, the 190-mile long UNESCO World Heritage Site of the Belize Barrier Reef

Stretching from Bacalar Chico in the north to Sapodilla Cayes in the south, the reef is home to hundreds of mangrove and coral islands that make up the cays along the coast of the country. Its offshore Blue Hole is a sinkhole famous for its size – measuring 100ft across and 400ft deep.

Blue Hole, Belize
Blue Hole, Belize

Glover’s Reef and Turneffe Atoll are closest to the sailboat charter base at Placencia. These protected areas are home to sharks, rays and turtles and a local skipper is required to access these places (along with the Blue Hole), since they are outside the main reef.

On land, the cultural melting pot of Spanish, French, Mexican and Caribbean influence combines to make a fusion everywhere, from the language to the food.

Trade winds averaging 10-13 knots and calm waters mean you can be confident of comfortable passages when sailing in Belize.

At just over a 2 and a half hour flight from Miami, Belize is a great alternative to Mexico for those looking for a Central America yacht charter with a difference.

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2. The Exumas, Bahamas

The clear aquamarine waters of the Exuma Island chain’s 365 cays make the Bahamas an ideal destination for a sailboat charter in 2020.

Sandbar Bahamas

Although the Abacos and Grand Bahama Island were devastated by Hurricane Dorian in 2019, the other 14 major islands of the country were unaffected. The Bahamian Prime Minister Hubert Minnis invited tourists come to the Bahamas in a speech to the UN: “Please come and visit one or more of the 14 other major islands in The Bahamas not affected by Hurricane Dorian.”

As tourism is one of the main contributors to the economy, by taking a sailing vacation in the Bahamas in you’ll be helping communities recover from the effects of the hurricane.

Bahama pigs, Big Major's Cay
The swimming pigs at Big Major’s Cay

Fly into Nassau, which lies around 35 miles north-west of the Exumas, and pick up your boat before exploring three main areas of the Exumas – Little Exuma, Great Exuma and Exuma Cays.

Beaches upon beaches of flawless powder white sand will welcome you at this celebrity hotspot and haven for the rich and famous.

On a sailboat vacation in the Exumas you can take a trip to Big Major’s Cay, which is home to the famous swimming pigs. South of Big Farmer’s Cay you can venture onto your own piece of paradise – the mile-long sandbar which appears at low tide.

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1. Tahiti and the Society Islands

Top on our list is Tahiti. Sailing in Tahiti and the Society Islands is truly a once in a lifetime experience. Expect to glide through dazzling lagoons in multiple shades of blue, with soaring green mountains in view and lush beaches bordering every isle.

Bora Bora, Tahiti
Bora Bora, Tahiti

If you charter a sailboat from the base on Raiatea, you’ll be just 20nm from one of the most breathtaking paradises on Earth – Bora Bora. Its famous picturesque Blue Lagoon is home to colorful tropical fish, black tip reef sharks and stingrays. 

You’re spoilt for activities in the Society Islands. Swim ashore to one of the tiny ‘motus’ – Polynesian for small island – that are found all over the South Pacific.

Gaze at the nearly 2400ft high Mount Otemanu – a magical ancient volcano which soars above Bora Bora in the centre of the lagoon.

Sunset from Raiatea
Sunset from Raiatea

You can also create incredible memories by swimming with humpback whales between August and October.

Try exploring some of the lesser known gems in the Leeward Islands (or Îles Sous-le-Vent) by mooring at Taha’a – a serene island north of Raiatea. Taha’a produces 80% of Tahitian vanilla, so you’re sure to catch a vanilla-scented hillside breeze.

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Get in touch


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