Sailboat Cruises Tortola

Plan Your Custom Cruise in Tortola

Tortola, the biggest BVI, is filled with a spectacular selection of white sand beaches and mountains covered with lush green vegetation that ensure a captivating cruise for all. From snorkelling to sunbathing, there’s something for everyone here.

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Cruise on a sailboat in Tortola

Discover your perfect holiday experience with family and friends

Cruise on a catamaran in Tortola

The best catamarans for your sailing holiday

Catamaran Lagoon-Bénéteau Lagoon 42 - 4 + 2 cab. 12.8m (2024)


From €649 per day

Turquoise Turtle Voyage 500 Catamaran (2001)


From €2,142 per day

Catamaran Catana Group Bali 4.4 - 4 + 1 cab. 13.5m (2024)


From €777 per day

Catamaran Catana Group Bali 4.2 - 4 + 1 cab. 12.85m (2024)


From €675 per day

Catamaran Catana Group Bali 4.2 12.85m (2022)


From €1,029 per day

Catamaran Fountaine Pajot Fountaine Pajot Astrea 42 Quatuor 12.58m (2023)


From €702 per day

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


From €793 per day

Catamaran Fountaine Pajot Fountaine Pajot Elba 45 - 4 + 1 cab. 13.45m (2024)


From €858 per day

Catamaran Catana Group Bali 4.2 12.85m (2023)


From €649 per day

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


From €793 per day

Catamaran Catana Group Bali 4.2 OW 12.85m (2024)


From €649 per day

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


From €793 per day

Catamaran Catana Group Bali 4.2 12.85m (2023)


From €1,020 per day

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Best time to sail in Tortola

The best time to sail in Tortola is in May, October or November as you avoid tourist season. However, due to the light breezes and pleasant climate, conditions are good for sailing all year round. Be a little careful sailing between June and November as this is the Caribbean hurricane season. Hurricanes don't often hit Tortola, but the weather can still be a little erratic.

Places to visit in Tortola

Tortola is a nature lover's paradise - don't miss out on exploring Cane Garden Bay, Josiah's Bay, and many of the island's other gorgeous wonders. One of the best things about visiting Tortola, though, is that it puts you in the perfect position to go on an island-hopping adventure throughout not just the BVI, but also the USVI, depending on the duration of your trip.

Catamaran and Sailboat Cruises in Tortola

Tortola is an idyllic island in the Caribbean Sea, full of unique opportunities for exploration that make for a truly sensational sailing holiday. Set sail with a skipper who can ensure you visit only the most desirable destinations, not just in Tortola, but also in the rest of the BVI and some of the other Caribbean territories, such as the USVI and Puerto Rico. Embark on an island-hopping adventure quite unlike any you’ve had before and get ready to make some memories.

Get ready to make some memories on your cruise in Tortola with friends and family

No matter who you embark with for your cruise in Tortola, we are sure you will have a fantastic time. Adults will love to try out the plethora of different water sports available, while children will love to splash around with the inflatable water toys.

If you’re travelling with your partner and have opted for a crewed cruise in Tortola, complete with a personal chef, you can also enjoy a fully catered intimate dinner for two on board. With a plethora of breathtaking backdrops at your disposal and sensational sunsets almost every evening, this is an amazing opportunity to do something special with your significant other.

Whether you want a romantic trip or something more family-friendly, you will certainly have a fantastic time.

Set sail with a skipper and crew for the ultimate relaxation

You can’t go wrong with a skippered cruise in Tortola. Even if you have a lot of sailing experience, a skipper has an intimate knowledge of the area that can only really be acquired by years of exploration. Your skipper will take you to all the best locations in the area, while still making time for things that you want to do.

If you want to further enhance the comfort of your trip, you can even opt for a crewed cruise in Tortola. A crew typically consists of four to six people and will include a chef, one or two hostesses, and one or more deckhands. This crew is on board to make sure you want for nothing throughout your trip and will guarantee the ultimate level of luxury.

When is the best time to go for a cruise in Tortola?

As it is located in the Caribbean, the weather is beautiful and ideal for a cruise in Tortola for most of the year. However, the sailing season really starts in mid-November and lasts until the end of May, with high season running from mid-December to March, when the weather conditions are perfect for a boating holiday full of comfort and luxury, with just a dash of adventure. The trade winds are strongest and most predictable in December and January and have thus earned the rather apt name of Christmas Winds. The only issue with going for a cruise in Tortola during the high season, is that it is likely to be a lot more crowded and there is a possibility that you won’t find a boat that suits all your needs unless you book months in advance.

If you are prepared to sacrifice some of the hotter weather in favour of a calmer nautical experience, you should instead opt to go from March until the beginning of June. During this period, the weather will still be nice enough for you to enjoy a pleasant boating holiday, but there should be fewer holidaymakers and as a result, the boat prices should also be a little lower.

The only time we would actively avoid going on a cruise in a catamaran or sailboat in Tortola is during the hurricane season, which runs from September until mid-November. During these months, the weather will be erratic and at times, a little dangerous and it is even possible that your trip may have to be cancelled as a result of the poor weather, which would be disappointing for everyone.

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

There are a wealth of desirable destinations around Tortola, not just in the BVI, but also in the USVI. If you fancy a slightly longer trip, you could even make the journey as far as Puerto Rico to experience even more of the different cultures and atmospheres in the Caribbean.

One possible itinerary if you want to explore the BVI and USVI starting from Tortola is as follows:

Day 1: Tortola to Jost Van Dyke (6.3 nautical miles)

Jost Van Dyke is one of the four main islands in the BVI and is known for being crime-free, so you literally couldn’t pick a safer place to start your sailing trip.

Day 2: Jost Van Dyke to Great Tobago to Little Tobago to St Thomas (12.4 nautical miles)

The second day of your Virgin Island cruise is packed to the brim with new opportunities for exploration as you prepare to sail first from Jost Van Dyke to Great Tobago and then cross over into USVI territory to visit St Thomas, stopping off at Little Tobago National Park along the way. St Thomas is easily the most cosmopolitan of the USVI and is also home to the territory’s capital city, Charlotte Amalie, where you can mingle with many of the islands residents.

Day 3: St Thomas to St John (9.5 nautical miles)

St John will be your last major stop in the USVI and you should definitely spend at least a day here, exploring the Virgin Island National Park and discovering the ruins of the plantations that were once a main feature of the island. St John is also the perfect place to go snorkelling or scuba diving, given that it is surrounded by coral reefs which are teeming with life.

Day 4: St John to Leduck Island to Norman Island (7 nautical miles)

From St John to Leduck Island, it’s just a short trip and although there isn’t much on land at Leduck Island, the underwater sights more than make up for it. Often overlooked by people visiting the USVI, Leduck Island is actually one of the best places to go snorkelling in the whole of the Caribbean. When you’re done snorkelling, you should head back into BVI territory to Norman Island, the supposed inspiration for the novel Treasure Island by Robert Louis Stevenson. Around this island, not only is there a wealth of marine life, but also hidden caves which you can explore.

Day 5: Norman Island to Dead Chest National Park to Peter Island (6.4 nautical miles)

From Norman Island, you should sail along the east coast of Peter Island and then north until you reach Dead Chest National Park, which has three main dive sites, suitable for people of all levels. After immersing yourself in the warm waters in this area, you should back to Peter Island, where you can enjoy a nice meal in one of the many beach bars while soaking yourself in a tranquil atmosphere.

Day 6: Peter Island to Virgin Gorda (10.4 nautical miles)

From Peter Island, you should head up north to Virgin Gorda, another of the main islands in the BVI. If you have time, you can stop off at some of the smaller islands along the way, such as Salt Island, Cooper Island and Ginger Island, but you may want to save as much time as possible to explore the Virgin Gorda Baths and the Devil’s Bay National Park, which will undoubtedly take a lot of time to truly do them justice.

Day 7: Virgin Gorda to Scrub Island to Guana Island to Tortola (11.9 nautical miles)

Depending on what time you have to check back in, you may have to miss out on either Scrub Island or Guana Island, but considering they should be more or less on your way back, it was worth including them, even if you can only glimpse them from onboard your boat. Scrub Island is a fantastic place to go swimming with sea turtles, while Guana Island has plenty of nature trails, perfect if you want to spot some of the unique wildlife of the island, such as iguanas and the red-legged tortoise. Either would be a perfect way to end your cruise in a sailboat or catamaran before sailing back to Tortola, for a nice meal in one of the beachside restaurants.

What different activities are available during your cruise in Tortola?

There are many different activities and other holiday experiences available to you when you set sail for a cruise in Tortola. Obviously, you can take the opportunity to explore the BVI and USVI, using our sailing itinerary detailed above. However, if you would prefer to stay a bit closer to Tortola, you can also try a number of different water sports by simply adding equipment onto your charter. Some of the water sports available to you include waterskiing, windsurfing, paddleboarding, snorkelling, and scuba diving. The oceans surrounding the island are rich in marine life so the latter two will surely be a treat.

How much does it cost to go on a cruise in a catamaran or sailboat in Tortola?

There are many things that can affect the price of a cruise in a catamaran or sailboat in Tortola, such as the size, model and amenities of the boat. The type of boat and whether or not you want to charter with a skipper can also affect the price. As a rough guide, though, a cruise in a catamaran in Tortola can cost anywhere from around €6486 per week in high season or about €4106 per week in low season, while a cruise in a sailboat can cost anywhere from around €3282 per week in high season or about €2133 per week in low season.

What is included and what comes as an additional charge?

The only way to know for certain what extra costs you may have to face is to ask the owner directly. However, we can give you some idea of things that you may have to pay extra for. In general, extra costs will fall into one of two categories: mandatory and optional extras. The base price only usually includes the basic charter of the boat, as well as mooring fees at the port of origin. Some examples of possible mandatory extras are the charter package, mooring fees if you dock at any other marinas than your starting port, and fuel. The charter package will include a final clean of the boat, administrative costs, a diving inspection of the boat to check for any damage, and maybe some basic necessities, such as kitchen equipment and bedsheets.

If things like towels and wifi aren’t included in the charter package, you can usually add these on as optional extras. Another optional extra is a skipper, although this may be mandatory depending on whether or not you have a boating licence, and whether or not you need one for the boat you’ve chosen. A catamaran or sailboat charter is always more luxurious and comfortable with a skipper and crew though, who can attend to your every need while on board, so it may be worth opting for these additional features, even if you do have a boating licence. Other optional extras are things like water sport equipment, such as kayaks, snorkelling and scuba diving equipment, and inflatable toys.

Which is better, a cruise in a sailboat or catamaran?

Both cruises in a sailboat and in a catamaran can be truly spectacular and which you should rent depends a lot on you and your sailing history. If you are an experienced sailor, for example, and are therefore after a fully authentic sailing experience, you should opt for a cruise in a sailboat. Sailboats are definitely the more affordable option, given their ability to travel large distances without consuming too much fuel and are suitable for both small groups and larger ones. Having said this, they aren’t the most spacious boats and so if you are looking for a luxury holiday, they may not be the boat for you.

A cruise in a catamaran is definitely the more luxurious option, the double hull structure providing more space than monohull sailboats and making them perfect for larger groups and families. They are also faster than sailboats, allowing you to cover more ground, and offer access to shallower waters. However, with the luxury comes higher prices, not just in terms of the boat itself, but also when it comes to finding moorings at marinas, as they require more docking space than regular sailboats.

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