Sailing Holidays Caribbean

Sailing Holidays in the Caribbean: Top Tips

During a sailing holiday in the Caribbean, there are a plethora of islands to explore that are isolated but idyllic, such as Barbados, the Bahamas, Martinique, and more. Set sail for breathtaking beaches on a luxurious cruise you’ll never forget.

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Cruise on a sailboat in the Caribbean

The best selection of sailboats for your holiday to paradise

Sailboat Jeanneau 44 14m

St. Thomas

From £940 per day

Sailboat Jeanneau Sun Loft 47 - 6 + 1 cab. 14.42m (2020)


From £545 per day

Welcome on Felicity (2001)

Saint Barthélemy

From £633 per day

Beneteau Oceanis 48 (2011)

Saint Martin

From £511 per day

Sun Odyssey 45.2 (2003)


From £649 per day

Sunset Cruise or Day Charter with 15m Sailing yacht in Curacao (1999)


From £888 per day

Enjoy your trip in a 0 metre sailboat (2000)


From £537 per day

Sailboat Bavaria 50 cruiser 15.4m (2008)

Casa de Campo

From £1,610 per day

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Cruise on a catamaran in the Caribbean

The best catamarans for your holiday with family and friends

Catamaran LAGOON LAGOON 450 F 13.96m (2017)


From £753 per day

Catamaran Fountaine Pajot Lipari 12.5m

St. Thomas

From £1,159 per day

INSTANT BOOKING: Sailing Around Paradise in Your Own Private Yacht!! (2003)

Charlotte Amalie

From £1,516 per day

Catamaran Lagoon Lagoon 52f 15.84m (2017)

Saint Thomas

From £2,556 per day

Catamaran Catana Group Bali Catspace OW 12m (2022)

British Virgin Islands

From £658 per day

Lagoon 24 (2019)

British Virgin Islands

From £607 per day

Catamaran Catana Group Bali 4.8 - 5 + 1 cab 14m (2022)

British Virgin Islands

From £1,521 per day

Fountain Pajot 2022 TANNA 47 (2022)

British Virgin Islands

From £1,533 per day

Catamaran Catana Group Bali 4.8 - 6 + 1 cab. 14m (2022)

British Virgin Islands

From £1,877 per day

Bella (2018)

Road Town

From £1,039 per day

Boomerang (2017)

Road Town

From £1,284 per day

Seventy Six (2018)

Road Town

From £983 per day

Claro Que Sea (2018)

Road Town

From £1,039 per day

Dawn Star III (2018)

Road Town

From £1,202 per day

Lone Star (2018)

Road Town

From £1,240 per day

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Cruise catamaran and sailboat

Interested in a sailing holiday?

Our sailing advisors are at your disposal to organise the perfect sailing holidays.

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Best time to sail in the Caribbean

The Caribbean has good weather year-round. To avoid hurricane season, we recommend travelling from November to May. Annual temperatures are from 32°C to 23°C depending on the region! The temperature and rain season changes depending on the region you are visiting, so make sure to look into the specific island or islands you are sailing in.

Places to visit in the Caribbean

In the Caribbean you will find many islands and dream destinations. There are plenty of islands to choose from in this Caribbean paradise! We recommend visiting the Dominican Republic, Martinique, Barbuda, the Bahamas or the Mexican coast. Utopia is a few clicks away, explore more with us.

Luxury Caribbean Sailing Holidays in a Catamaran or Sailboat

There are a plethora of idyllic islands in the Caribbean, with a diverse combination of cultures that promise to make your sailing holiday in the Caribbean one you’ll never forget. On a bespoke cruise in a catamaran or sailboat, you can go island hopping or try a variety of different water sports, all with a skipper and crew, who will attend to your every need on board. Set sail for destinations beyond your wildest imagination as you navigate these coastlines in complete comfort.

Get ready to make some memories with family and friends!

A sailing holiday in the Caribbean guarantees an experience full of excitement and adventure that is perfect to share with family and friends. There is something for everyone in the Caribbean, whether you want to lounge around on the breathtaking beaches, or explore the more remote yet equally idyllic islands. Take salsa classes on the beach in the Dominican Republic, or go snorkelling on any of the islands for an experience that you will never forget. On board, the kids will love to play with the inflatable toys, while adults will enjoy other watersports, such as water skiing, paddle boarding, and sea kayaking.

The Caribbean is a melting pot of different cultures, with influences from Spain, France, the Netherlands, and also the UK. This mismatch of different cultures promises a unique experience on each island that will leave you wanting to visit over and over again. No matter who you’re going with, you will surely have a fantastic time on your sailing holiday in the Caribbean so don’t hesitate to set sail straight away!

What are some of the best destinations and sailing routes for your sailing holiday in the Caribbean?

The Caribbean is one of those destinations that everyone dreams about visiting, with over 7000 islands and islets in total, although the majority are completely deserted. With so many islands that you can visit at the drop of a hat, you might need some help deciding which of them you should visit during your cruise in a sailboat or catamaran. For this reason, we’ve made a list of some of our top destinations and sailing routes to visit as you set sail for a tropical utopia.

Although there are many amazing places to visit in the Caribbean, some of the best include the US and British Virgin Islands, St Lucia, St Vincent and the Grenadines, St Martin, Antigua and Barbuda, Grenada, and Martinique. The USVI and BVI have over 100 islands and islets between them, so we usually suggest taking a separate trip here in order to see all the treasures this area has to offer. In Martinique, you can experience an exquisite blend of French and Caribbean culture, while Antigua and Barbuda offer an impressive range of landscapes, from reefs to rainforests, and St Lucia is home to unique volcanic beaches and luxurious hotels and resorts. If you go to St Vincent and the Grenadines, you will have the pleasure of diving into the depths of a key Caribbean diving site, the Tobago Cays, whereas on Grenada, you can visit the nutmeg plantations and St Martin is famous for its fusion cruising and the spectacular selection of old forts that you can visit.

When it comes to sailing itineraries, we have a few different routes you can take. Naturally, you can adjust or change these itineraries depending on the duration of your trip as well as what you want to see. The first route is based completely around a week in the US and British Virgin Islands. We recommend that you start your journey in St Thomas, where you can enjoy the warm, sparkling seas before officially setting sail. From here, you can go to the smallest of the three main USVI, St John, where you can visit the captivating Caneel Bay, with its wondrous white sand and border of lush, green vegetation. It truly is the perfect place to relax with family and friends. After you feel fully refreshed, you should head northeast out of USVI territory, until you reach Guana Island in the BVI. After Guana Island, you will set sail south-east, past Barracouth Point, before going northeast again, until you reach Marina Cay. Marina Cay is very small, and so after a quick exploration, you will move on to Virgin Gorda, one of the four main BVI, which lies to the east. After Virgin Gorda, you will make a quick stop at Necker Island, before continuing north to Anegada, which lies the furthest north out of all the BVI. From Anegada, you will start heading back to St Thomas, with just a brief stop at Peter Island and Norman Island on the way.

If you want a completely different Caribbean experience, you should visit the French Caribbean islands of Martinique and Guadeloupe, stopping off at Dominica on the way. If this appeals to you, start your sailing holiday at Le Marin, a cruise port in the south of Martinique. From Le Marin, set sail to the west until you reach Les Anses d’Arlet, a charming coastal town, known for its resplendent landscapes and diverse marine life. Then, head north to St Pierre, where you will make a brief stop before continuing on to Portsmouth in the north of Dominica. After Portsmouth, continue on your northbound navigation until you reach a group of small islands just south of Guadeloupe, known as Les Saintes. These islands will leave you awestruck as you take in the rocky, volcanic landscapes and coral-rich seas that are perfect for a quick dip among the plethora of tropical fish. Once you’ve had your fill of the seas of Les Saintes, you should start to navigate your way to the south, heading to Dominica’s capital city, Roseau. Here, you can fully immerse yourself in the Dominican culture, with a visit to the delightful Dominica Botanical Gardens. These gardens display an impressive selection of local flora and fauna, including the Sisserou parrot, which is endemic to the island of Dominica. On the final day of your Caribbean cruise in a sailboat or catamaran, you will head back to Le Marin, to return your boat.

If you want to cruise in a catamaran or sailboat for 14 days, instead of just 7, you should go south from Martinique until you reach St Lucia. From St Lucia, go south to St Vincent, on your way to the islands of Bequia and Baliceaux. Although small, the beauty of these diminutive islands should not be understated and you should be prepared to spend an hour or two on each. From here, keep going south, via Mustique, Canouan, Mayreau, and Tobago Cays, until you get to Petit Saint Vincent and Petite Martinique. You will then start to return to Martinique, sailing first to Union Island, and then stopping quickly at St Vincent and St Lucia, before returning your boat.

Each and every one of these sailing routes guarantees a Caribbean sailing holiday full of complete tranquillity, with just a dash of adventure so pick a route, select your boat, and set sail on your nautical adventure right away.

How much does it cost to go on a sailing holiday in the Caribbean?

If you are thinking about a cruise in a sailboat or catamaran in the Caribbean, there are many things that could potentially influence the cost. Some of these factors include the duration of your trip, the season, and the size and type of boat, as well as the amenities on board. The decision of choosing if you want to find a boat charter with a skipper or crew can also greatly influence the price, although we do feel like the extra costs are worth the added level of luxury and comfort. Even if you are an experienced sailor, skippers can teach you a lot about the area you’re sailing in that only the locals are usually aware of.

As a rough guide though, a Caribbean cruise in a catamaran can cost around £3805 per week, while a Caribbean cruise in a sailboat costs around £1744 per week in low season, or £3281 per week in high season.

Included services and additional charges

Typically, the charter price listed on the website only covers the basic rental of the boat, so make sure you check with the boat owner which additional costs may crop up before deciding on a boat, to avoid any unpleasant financial surprises. Additional charges will usually be divided into two categories: mandatory and optional extras. Mandatory extras are usually things like administrative expenses, a diving inspection of the boat to check for any damage that may have been done during the trip, a final clean of the boat, and necessities that you will need to use during your trip, such as cutlery, crockery, and bed linen.

If things like wifi and towels aren’t included in the mandatory extras, you will usually be able to add them on at an extra charge. Sometimes, you will even be able to add water sports equipment onto your boat charter, including but not limited to kayaks, inflatables, surfboards, and snorkelling and diving equipment. You should check with the boat owner though, as some boats, especially larger ones come with some of these things included.

When is the best time for a sailing holiday in the Caribbean?

In the Caribbean, the weather is usually fantastic throughout the year, but the sailing season runs from mid-November until the end of May, the second hurricane season ends. High season in the Caribbean is from mid-December until March, when the sailing conditions are perfect, with strong trade winds and hot weather. Due to these idyllic weather conditions, the islands can be very busy during this period, full of holidaymakers trying to escape the cold wintry weather of their home countries. For this reason, you should make sure you book a boat months in advance if you have your heart set on sailing in these months.

If you would prefer a more peaceful trip, free from the hordes of tourists, you should go instead either at the beginning of December or between March and May. In these periods you will see fewer crowds, without sacrificing the good weather.

The only time when you shouldn’t plan to go sailing in the Caribbean is during the hurricane season, which runs from September until mid-November. During this period, the weather conditions will be a lot more erratic and it is possible that your cruise in a catamaran or sailboat may be cancelled to avoid endangering you. The conditions also wouldn’t be as ideal in these months for trying out the various water sports that can enrich your experience at other times of the year.

What are the best things to do during your Caribbean nautical adventure?

What you should do during a sailing trip in the Caribbean depends on where you go. Naturally, some of the more general activities can be enjoyed throughout the Caribbean, such as scuba diving, snorkelling, kayaking, and even horseback riding along the beach. However, there are some activities that you can only do on specific islands, such as exploring the Virgin Gorda baths or visiting the famous Ixora Spa in the BVI, and in St Martin, the conditions are perfect for kitesurfing. You should also definitely go snorkelling in the seas surrounding Norman Island, which is home to an underwater world quite unlike what you’ll find anywhere else and is even the inspiration for Robert Louis Stevenson’s ‘Treasure Island’.

If you’re going on a romantic sailing holiday in the Caribbean with your significant other and you opted to set sail with a crew, you might also want to enjoy an intimate dinner for two onboard your vessel, while watching a spectacular sunset. The views in the Caribbean truly are the perfect backdrop for this sort of experience and having your personal cook on board will ensure that you don’t have to lift a finger.

Should you go on a cruise in a sailboat or catamaran?

Although both types of boats are perfect for a luxury sailing holiday, they also have advantages and disadvantages, depending on the type of trip you’re after. Sailing boats are generally cheaper to rent due to their ability to cover more ground more quickly using less fuel, as well as the fact that they require less docking space than the double hull catamarans. Cruises in a sailboat are also perfect for smaller groups, and you can create an itinerary that caters to the interests and needs of everyone on board. Sailboats also give you a much more authentic sailing experience than catamarans, making them more suited to sailors who want to develop their skills. The main drawback of hiring a sailboat is that they are less spacious due to their monohull structure, and this also makes them less stable, resulting in a higher risk of seasickness. If you want a holiday of luxury and comfort, these may not be the boats for you.

Cruises in a catamaran, however, are synonymous with luxury, having much more space onboard due to their double hull structure. They are more stable than sailboats, decreasing the likelihood of seasickness and have access to areas that sailboats don’t, as they are able to enter shallower waters. They are also faster than the monohull alternative, which enables you to visit more places. However, they do not provide passengers with an authentic sailing experience, and are more costly, especially when it comes to mooring, as they require more docking space. These boats are better for larger groups, who are able to share the cost.

Book your sailing holiday in the Caribbean with a skipper and crew for the ultimate relaxation

For the most luxurious boating holiday in the Caribbean, you should charter a boat with a skipper and full crew. If you have a lot of sailing experience, you may assume you don’t need a skipper, but even if they won’t teach you much about sailing, they will still have an intimate knowledge of the area, which will be invaluable when it comes to deciding on the best itinerary, as they will be able to suggest places that only the locals know about.

To further increase the level of luxury and relaxation, go for a crewed charter, which can include staff such as a cook, a hostess, a maid, and one or more deckhands. Each crew member will usually come at an additional cost, but we would say that the added comfort is worth it, as you really will want for nothing during your voyage.

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