Where to charter a sailboat in 2020

With fall upon us, our thoughts are turning to the new year and sailing destinations for 2020.

27th Sep 2019

With almost 100 days to go until the new year, our thoughts are turning to future plans for sailing and where in the world to charter a yacht in 2020.

If you want to try somewhere different for your sailing vacation next year, let us inspire you. 

In our guide we run you through the most popular Caribbean sailboat and catamaran charter destinations, as well as some more further flung exotic countries. 

Maria Soleil, Senior Marketing Executive

LateSail Caribbean and exotic destinations

British Virgin Islands

Virgin Gorda, British Virgin Islands

Famous for its teal blue clear waters, spectacular diving, white sandy beaches and vibrant nightlife, the British Virgin Islands are also known for their welcoming atmosphere for visiting sailors. If you charter a sailboat or catamaran in the BVIs, you will experience easy sailing with line of sight navigation, short legs and lots of time to relax (and party!)

When to go to the BVI

Late November to early December for lighter crowds. Or mid-April to June for cooler temperatures. December to January brings crowds over the holiday season. Hurricane season is from June to October, rainy season is August to November. The BVI Spring Regatta is in March.

Sailing and weather conditions in the BVI

The reliable trade winds and year-round tropical climate of around 86°F make this a popular place for cruising. From November to June, the trade winds blow from the north-east, averaging 15 to 25 knots. The winds can be stronger between December and January, known as the famous Christmas wind.

Ports and facilities in the BVI

There are superb marinas and yacht clubs on Tortola, Virgin Gorda, Peter Island, as well as hundreds of picturesque anchorages and bays dotted around the islands

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Green Cay BVI



Antigua is one of the most exciting places in the Leeward Islands to charter a boat. Its 365 beaches means there are more than enough sheltered coves and bays to settle for the night. Relics from its colonial past dot the island and sit alongside typical colorful Caribbean villages. And there is plenty of English Harbour rum to go around…

When to go to Antigua

We recommend visiting between December and April. 

Antigua Sailing Week is at the end of April in 2020.

Sailing and weather conditions in Antigua

As among all the Leeward Islands, Antigua is warm all year round, reaching a peak of 88°F in August. 

The trade winds blow year round in from the northeast at 15 to 20 knots between November and May.

Ports and facilities in Antigua

A world-class sailing destination, you can expect the best marina facilities in Antigua, including at Antigua Yacht Club Marina in Falmouth, Jolly Harbour Marina and Nelson’s Dockyard Marina.

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St John's Antigua
Shirley Heights English Harbour Antigua

St Vincent and the Grenadines

Tobago Cays, Grenadines

Between the volcanic island of St Vincent and Grenada lie 32 islands that are home to white-sand palm-fringed deserted beaches. Abundant wildlife and some of the best snorkelling spots in the world make St Vincent and the Grenadines perfect for a sailboat charter in 2020.

When to go to St Vincent

The dry season is January to April, while the rainy season and risk of hurricanes is between June to October/November respectively.

Sailing and weather conditions in St Vincent

Prevailing winds are north-easterly and range from 10 – 20 knots from June to October and 15 – 25 knots from November to May. 

The tidal range is approximately 45cm.

Ports and facilities in St Vincent

There are plenty of adequate marinas on the larger islands of the Grenadines. 

Most charters would start from Blue Lagoon on the south west coast of St Vincent; while the passage through the Grenadines would see you anchor among stunning archipelagos such as Tobago Cays.

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Mustique the Grenadines


Seychelles boat charter

The Seychelles truly are a tropical paradise lying 1000 miles off Africa’s east coast. You can expect fine powder beaches, verdant hills and the freshest seafood dishes, all with a dash of French, Indian and African influence. 

When to go to the Seychelles

Sailing is great all year in the Seychelles, but there are two disctinct seasons: May to September is dry, whereas November to April has more rainfall.

Sailing and weather conditions in the Seychelles

May to September sees cool south-easterly tradewinds of 10 to 20 knots. 

October to March sees a north-westerly of between 8 to 12 knots. 

Expect water temperatures of up to 86°F!

Ports and facilities in the Seychelles

Eden Island Marina on the main island of the Seychelles, Mahé, is a well equipped and comfortable marina. 

Praslin Marina is convenient and has adequate facilities.

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Thailand boat yacht charters
Phuket, Thailand

A myriad of exotic islands with fascinating limestone landscapes and some of the best beaches in the world await you on a yacht charter to Thailand. Enjoy cliff jumping and swimming at Koh Phi Phi, scuba diving at Similan Islands national park and aromatic fresh food at Phuket’s beach bars.

When to go to Thailand

The most popular time to charter a yacht in Thailand is November to March.

Sailing and weather conditions in Thailand

Thailand has two distinct seasons – one is the dry season of November to April with hot weather and north-easterly winds averaging 10 to 15 knots. 

May to October is the wet season, with stronger winds and some afternoon rain. Winds rarely exceed 25 knots this time of year. 

Thailand is a tidal nation with a range of 2m in Phuket

Ports and facilities in Thailand

Marinas are plentiful on Phuket, which is the base for most charters on Thailand’s west coast. 

The main marina at the north east, Phuket Yacht Haven Marina, is well managed and has great facilities.

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Thailand sailboat charter

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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