Cruises in the Caribbean

Cruise in the Caribbean: Top Sailing Tips

On a cruise on a catamaran or sailboat in the Caribbean, you’ll encounter a plethora of idyllic islands, such as Barbados, the Bahamas and Martinique. Set sail for breathtaking beaches as you navigate these spectacular shores in luxury.

Where
Dates
Add your dates
Boat
All boat types
Rental type
With or without a skipper
Capacity
Add people

Cruise on a sailboat in the Caribbean

The best selection of sailboats for your holiday with family and friends

Sailboat Elan GT5 13.2m (2018)

Antilles
9

From €1,000 per day

Sailboat BENETEAU OCEANIS 41.1 12.43m (2018)

Saint Thomas
6

From €569 per day

Sailboat Jeanneau Sun Odyssey 449 13.34m (2018)

Saint Thomas
10

From €828 per day

Harmony 52 Sao Jorge (2007)

Road Town
10

From €745 per day

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

Tortola
13

From €1,056 per day

Welcome on Felicity (2001)

Saint Barthélemy
6
 3

From €743 per day

Beneteau First 40.7 (2008)

Saint Barthélemy
10

From €929 per day

Beneteau Oceanis 48 2017 (2011)

Saint Martin
8

From €714 per day

Sun Odyssey 45.2 (2003)

Bonaire
2

From €726 per day

Sailboat Jeanneau Sun Loft 47 monocat 14m (2020)

Jolly Harbour
13

From €988 per day

Sailboat Dufour Yachts Dufour 425 GL 12.9m (2012)

Jolly Harbour
8

From €679 per day

Sailboat Dufour Yachts Dufour 41 12m (2023)

Jolly Harbour
8

From €941 per day

Racing Boat Escapado (2008)

Saint John
10

From €929 per day

Private Sunset Cruise for couples & groups in Curacao (1999)

Curaçao
5

From €993 per day

Sailboat Bavaria 50 cruiser 15.4m (2008)

Casa de Campo
12

From €1,800 per day

Discover more boats for this destination

Cruise on a catamaran in the Caribbean

The best collection of catamarans for your dreamy sailing experience

Leopard 48 catamaran (2014)

Saint Thomas
10

From €1,097 per day

Catamaran Lagoon-Bénéteau Lagoon 42 - 3 + 1 cab. 12m (2022)

Saint Thomas
9

From €1,211 per day

Catamaran Catana Group Bali Catspace OW 12m (2023)

Saint Thomas
6

From €1,090 per day

Catamaran Lagoon-Bénéteau Lagoon 46 - 4 + 2 cab. 13.99m (2024)

British Virgin Islands
12

From €1,633 per day

Catamaran Lagoon-Bénéteau Lagoon 51 - 6 cab. 15.35m (2024)

British Virgin Islands
13

From €2,603 per day

Catamaran Fountaine Pajot Fountaine Pajot Astrea 42 - 4 + 2 cab. 12.58m (2020)

British Virgin Islands
12

From €1,322 per day

Catamaran Fountaine Pajot Fountaine Pajot - Tanna 47 - 5 cab. 13.94m (2022)

British Virgin Islands
10
 1

From €1,276 per day

Catamaran Catana Group Bali 4.8 - 4 + 1 cab. 14.86m (2024)

British Virgin Islands
9

From €2,220 per day

Catamaran Catana Group Bali 4.8 - 6 cab. 14.86m (2024)

British Virgin Islands
14

From €2,220 per day

Catamaran Lagoon-Bénéteau Lagoon 46 - 4 + 2 cab. 13.99m (2024)

British Virgin Islands
10

From €1,633 per day

Catamaran Lagoon-Bénéteau Lagoon 46 - 4 + 2 cab. 13.99m (2024)

British Virgin Islands
12

From €1,633 per day

Catamaran Island Spirit Yachts Island Spirit 525E 15.77m (2024)

British Virgin Islands
14

From €2,220 per day

2021 Lagoon 46 (2021)

Road Town
6

From €2,087 per day

BRAND NEW 2023 Lagoon 40 for weekly charter! (2023)

Road Town
4

From €1,223 per day

2021 Lagoon 46 for 7 people! (2021)

Road Town
4

From €1,785 per day

Discover more boats for this destination

Cruise catamaran and sailboat

Want to plan a cruise?

Our experts are at your disposal to organise the perfect cruise with you.

Learn More

Best time to sail in the Caribbean

Although the Caribbean has good weather year-round, we recommend travelling from November to May in order to avoid hurricane season. In the Caribbean, December and January are the high season for charters, meaning that renting a boat at this time will be more expensive.

Places to visit in the Caribbean

In the Caribbean Sea you will find many islands and dream destinations. The Antilles with their 'Leeward' and 'Windward' Islands are very popular amongst sailors who are looking to plan a holiday in the Caribbean. We also recommend visiting the Dominican Republic, Martinique, Barbuda, the Bahamas or the Mexican coast - paradise awaits you!

Cruise in the Caribbean: Holidays in Catamarans and Sailboats

The Caribbean is an area consisting of many islands. The diverse combination of different cultures promises a sensational sailing holiday, full of island hopping and water-based adventures. Experience the Caribbean like never before with a bespoke cruise in a sailboat or catamaran, complete with a skipper and/or crew who will make sure you want for nothing on board. Set sail for only the most desirable destinations as you navigate these coastlines in complete comfort.

Get ready to make some memories with family and friends on a bespoke cruise in the Caribbean

There is no better way to spend the holidays than with a custom cruise in the Caribbean, no matter who you’re planning on spending it with. If you’re planning a Caribbean cruise with the family, the possibilities are endless. You can go island hopping, with many amazing islands in the vicinity, each one offering a unique character that will enchant all who visit. However, you can also try out a number of different water sports, including water skiing, windsurfing, scuba diving, and snorkelling. The Caribbean sea is rich in marine life making the latter two activities a sure way to ensure that your cruise in the Caribbean is one that the whole family will remember for many years to come. You can even add some inflatable water toys to your charter for the younger children. These are certain to provide hours of enjoyment.

If you are planning a romantic getaway with your partner in the Caribbean, you should opt for a crewed charter. In this way, you can enjoy an intimate meal for two onboard, catered by your own personal chef. The Caribbean is known for being an amazing place to witness sensational sunsets, which will only add to the romantic atmosphere along with the captivating views of the Caribbean coastline.

What are some of the best destinations and sailing routes for your Caribbean cruise in a catamaran or sailboat?

The Caribbean has long been a dream destination for people all over the world, with over 7000 islands and islets total, although most are uninhabited. With so many islands at your disposal, it’s natural that you might need a little help deciding where to go and it’s for this reason that we have made a list of some of the best destinations and sailing routes for your Caribbean cruise in a sailboat or catamaran.

Some of the best places to visit in the Caribbean include the US and British Virgin Islands, Martinique, Antigua and Barbuda, St Lucia, St Vincent and the Grenadines, Grenada and St Martin. The US and British Virgin Islands have well over 100 islands and islets between them and so may be worth a separate trip to some of the other areas of the Caribbean. Meanwhile, Martinique perfectly blends French and Caribbean culture, Antigua and Barbuda are home to an impressive selection of reefs and rainforests, and St Lucia is lined with unique volcanic beaches and luxury resorts. In St Vincent and the Grenadines, you will find the transcendent Tobago Cays, a key Caribbean dive site, whereas Grenada is home to numerous nutmeg plantations, and on St Martin, you can sample the famous fusion cuisine or visit old forts. Naturally, the Bahamas are another amazing area to go sailing in the Caribbean, but with over 700 islands and islets, we feel this group of islands deserves its own boating holiday, separate from the rest.

Sailing around the BVI

In terms of sailing itineraries, we have a few different options for you. The first route centres wholly around sailing for a week in the US and British Virgin Islands. For this route, we recommend that you start your cruise in a catamaran or sailboat in St Thomas, where you will have plenty of opportunities to splash about in the water before starting your nautical adventure in earnest. From here, you should head to Caneel Bay on St John, the smallest of the three main USVI. Caneel bay is a gorgeous white sand beach surrounded by lush green vegetation and the perfect place to relax a little with your family and friends. From Caneel Bay, you should sail northeast out of USVI territory, until you reach Guana Island in the BVI. Then, sail southeast past Barracouth Point, before heading northeast again until you reach Marina Cay. As Marina Cay is rather small, you won’t spend long here before moving on to the much larger Virgin Gorda to the east. You will then set sail due north for another quick stop at Necker Island, on your way to Anegada, the most northerly of this island group. From here, you will start to navigate your way back to St Thomas, stopping off at Peter Island and then Norman Island to the south of the BVI on the way.

A seven-day cruise of the French Caribbean (and Dominica)

If you want a slightly different vibe for your Caribbean cruise, you should set sail for the French Caribbean islands of Martinique and Guadeloupe, stopping off at the island of Dominica along the way. If you decide on this course of action, you should start your cruise in a sailboat or catamaran at Le Marin, a cruise port in the south of Martinique. From here you should sail west until you reach the charming coastal town known as Les Anses d’Arlet, known for its picturesque charm and the diversity of its marine life. After Les Anses d’Arlet, you will start to navigate your way north, stopping off at St. Pierre on your way to Portsmouth in the north of Dominica. Next, you should set sail for Les Saintes, a group of small islands just south of Guadeloupe with impressive volcanic landscapes and coral-rich waters that are perfect for a quick swim. When you’re done soaking in the warm waters of Les Saintes, you should start sailing south again until you reach the slightly more cosmopolitan capital of Dominica, Roseau. In Roseau, you can fully immerse yourself in the Dominican culture while strolling through the Dominica Botanical Gardens, which hold an impressive display of local flora and fauna, including the native Sisserou parrots. Finally, you should head back to Le Marin on Martinique to return your boat.

A 14-day cruise

If you want a slightly longer, 14-day cruise in a catamaran or sailboat, you can instead head south from Martinique until you reach the spectacular St Lucia. Then, continue sailing south to St Vincent, on your way to the much smaller and yet equally impressive islands of Bequia and Baliceaux. From here, keep navigating your way south, via Mustique, Canouan, Mayreau, and Tobago Cays until reaching Petit Saint Vincent and Petite Martinique. You will then start your return trip, sailing first up to Union Island, and then making quick pit stops once again at Saint Vincent and Saint Lucia, before returning your boat to Martinique.

Any of these three sailing routes promise a trip full of complete relaxation and tranquillity, with just a dash of adventure thrown in for good measure. Naturally, these are also just suggestions, you can add in and take out parts of the itineraries depending on what you want to see.

How much does a sailing holiday in the Caribbean cost?

When considering a sailing holiday in the Caribbean, there are many different factors to consider with relation to cost. Some of the things that can affect the price of a sailing in the Caribbean include the length of your trip, the season, and the size and type of boat, as well as the amenities on board. Whether or not you want to charter with a skipper or crew can also greatly affect the cost, although, for a more comfortable and luxurious trip, this is one that we think is worth spending a bit more on. Even sailors who have been navigating the seas for years can learn a lot from skippers who will know things about the area you’re sailing in that only locals do. In general, a Caribbean cruise in a catamaran costs around €5000 per week, while a Caribbean cruise in a sailboat costs around €2000 per week.

Included services and additional costs

Usually, when looking at charter prices, the base price listed on the website only includes the basic rental of the boat so check with the owner which additional costs you may face before deciding on a boat. Additional charges are usually split into mandatory and optional extras. Mandatory extra usually include things like administrative expenses, the final cleaning of the boat and things you need to use while on board such as kitchen utensils and bed linen. You will usually also have to pay for fuel and a diving inspection of the boat after your trip to check for any damage that may have been done during the trip.

If things like WIFI and towels aren’t included in the mandatory extras, you can usually add them on for an additional fee. Sometimes, you will have the option of adding water sports onto your boat charter experience. Some of the water sport equipment which is usually available on demand includes kayaks, donuts, surfboards, and snorkelling and diving equipment. Some boats will even come with some of these things included, so make sure you thoroughly check through the selection of boats available before making your selection.

When is the best time to go on a Caribbean cruise in a catamaran or sailboat?

The Caribbean generally benefits from great weather all year round, but the sailing season typically runs from mid-November until the end of May, starting pretty much as soon as the hurricane season ends. High sailing season is between mid-December to March, when the conditions are perfect for sailing, with strong trade winds and hot weather. Due to these idyllic weather conditions, however, the Caribbean islands are also often pretty busy around this time, full of holidaymakers trying to escape the harsh winter conditions of their home countries. For this reason, if you want to set sail during this period, you should book a boat months in advance to ensure you find a boat that meets all your needs.

Alternatively, if you want a slightly more peaceful trip, you should either go at the beginning of December, or between March and May. During these periods, there will be fewer people to compete with for a prime space on the water.

The only time we would advise against sailing in the Caribbean is during the hurricane season, from September to mid-November. During this time the weather conditions will be a lot more erratic and your trip may be cancelled to avoid putting you in danger. The conditions also won’t be so good at this time if you want to try out the various water sports that are sometimes available during your nautical adventure.

What are the best things to do while sailing in the Caribbean?

This really depends on where you go. Some general activities that can be enjoyed throughout the Caribbean include things such as scuba diving, snorkelling, kayaking, and horseback riding along the beach. However, you should also definitely explore the Virgin Gorda baths or visit the famous Ixora Spa if you go to the BVI, and kite-surfing in St Martin is always a treat. Equally, although there are plenty of amazing snorkelling destinations throughout these idyllic islands, Norman Island offers you the chance to experience the underwater world like never before as you propel yourself around the island that inspired the famous ‘Treasure Island’ novel by Robert Louis Stevenson.

Is a cruise in a sailboat or catamaran better?

Both catamarans and sailboats are amazing options if you want to go on a luxury Caribbean cruise, but both also have pros and cons. Sailing boats are typically more affordable as they are able to cover more space more quickly using less fuel. You can comfortably go on a cruise in a sailboat with a smaller group than in catamarans, creating an itinerary that suits the individual needs of the passengers on board. Furthermore, sailing boats give you a more authentic sailing experience making them better for sailors who want to develop their skills. However, there isn’t as much space on board sailing boats on account of their monohull structure, so if you are looking for a holiday where luxury and comfort are the priority, these may not be the boats for you.

Cruises in a catamaran, on the other hand, provide a more luxurious and spacious trip, ideal for larger groups who can share the cost. They are also more stable, which is better for those who suffer from seasickness and can enter shallower waters, which allows access to more areas. They are also faster than monohull boats, which allows you to visit more places. Having said this, catamarans do not provide an authentic sailing experience and also require more docking space than sailboats, which can make mooring expenses more costly.

Cruise with a skipper and crew for the ultimate relaxation

If you want your Caribbean cruise in a catamaran or sailboat to be a truly relaxing experience where you don’t have to lift a finger, you should definitely find a boat charter with a skipper and maybe even a full crew. Even if you are an experienced sailor, you can learn a lot from a skipper who will also have an intimate knowledge of the area, and can take you to all sorts of places that only the locals really know about.

If you want to further increase the level of luxury and relaxation, you can opt for a crewed charter. Typically, the members of the crew can include a cook, a maid, and one or more deckhands. Usually, each member of the crew will come at an extra cost but the additional charge really is worth it as your crew will ensure that you want for nothing throughout the entire voyage.


Our client reviews
4.9 / 5
Score calculated based on 433041 reviews
See all reviews

These cruise destinations can also interest you