Sailing trip Caribbean

Plan your sailing trip in the Caribbean now

Cruise on a catamaran or sailboat in the Caribbean and you’ll encounter many idyllic islands, such as the BVIs, the Bahamas, and more. Explore the Caribbean by boat for breathtaking beaches and spectacular shores in luxury.

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Sail on a sailboat in the Caribbean

The best selection of sailboats for your vacation to paradise

Sail on a catamaran in the Caribbean

The best catamarans for a vacation with your family and friends

Cruise catamaran and sailboat

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Best time to sail in the Caribbean

The Caribbean has good weather year-round. To avoid hurricane season, we recommend traveling from November to May. Temperatures range from 75°F to 90°F during this season. It is important to note that the temperature and rain season ranges depending on the region. Make sure to look at the specific island you will sail to!

Places to visit in the Caribbean

The Caribbean is home to countless islands and dream destinations. From Anitgua to Tobago there are plenty of islands to choose from! We recommend visiting the Dominican Republic, Martinique, Barbuda, the Bahamas or the Mexican coast. Paradise awaits you, don't miss your dream sailing trip in the Caribbean!

Sailing trips in the Caribbean: Cruises on catamaran and sailboat

A sailing trip in the Caribbean offers a diverse combination of different cultures. The Caribbean promises a sensational experience, full of island hopping and water-based adventures. Experience the Caribbean holiday with a cruise in a sailboat or catamaran, complete with a captain and/or crew who will make your stay desirable and unforgettable. Cruise in the most desirable destinations navigating stunning coastlines in complete comfort. Cruise in a sailboat in the Bahamas and get into an adventure of a lifetime with your friends and family. Or cruise on a catamaran in the Bahamas and experience comfort and luxury.

The Caribbean: A holiday paradise for you, your family, and friends

Delight in the tropical utopia that is the Caribbean, making the most unforgettable memories with your children, family, or friends. The plethora of sandy beaches and miraculous sunsets will leave you nothing short of amazed. Make this vacation twice as special and book a sailing trip for you to enjoy with your loved ones.

As you cruise on a sailboat or catamaran around the Caribbean, gaze off of the deck and spot a multitude of islands and islets. If you are lucky you will be able to observe the incredible biodiversity of the sea: from whales to damselfish and everything in between! The Caribbean is absolutely perfect for your family, it really is a veritable heaven on earth for everyone, no matter the age.

Sailing trip in the Caribbean with a captain and crew

You can choose to cruise in a catamaran or sailboat with a captain and crew in the Caribbean. Click&Boat recommends cruising with a captain and crew so you can discover the 7,000 islands and islets the Caribbean has to offer without worries. If you have no sailing experience, a captain and crew will take care of all of the sailing technicalities and problems, as well as guide you through places that only locals and experts know! Moreover, the crew will cook delicious meals for you and your family and friends making this trip feel like an all-inclusive moving hotel.

If you book your sailing trip in the Caribbean with a captain and crew, the cost is normally divided into the price of renting a boat and the additional services, and the additional provision of funds for the trip. The additional funds are the money that the captain would use to pay for the extras such as gas, food, and drinks.

You can also choose to cruise on sailboats in the Caribbean with only a captain. No need to worry about navigating the boat while you are exploring the coastlines. Comfort, tranquility, and safety in the palm of your hands. Cruising in a catamaran in the Caribbean with a crew is a great idea!

You can also choose to cruise without a captain or crew if you have a valid boating license for the boat you would like to rent.

Is a cruise in a sailboat or catamaran better?

A sailing trip in the Caribbean gives you lots of freedom to explore many islands, islets, and beaches alike. Are you wondering what boat would be best for you and your group? Let us help you decide! Whether you choose a spacious catamaran or a fast sailboat, each boat type has its own advantages and disadvantages. If you have any further questions, Click&Boat is here to help!

A cruise on a sailboat in the Caribbean is typically more affordable and faster due to the size of the boat. Therefore, the sensation of sailing is intensified with a stronger breeze, making it also more fun and exciting for sailing enthusiasts. Sailboats are also easier to maneuver compared to catamarans. Likewise, due to this boat having one hull and typically being smaller, living spaces are narrower and you are more likely to get seasick.

Cruising on a catamaran in the Caribbean is highly recommended for large family groups with small children. The spacious nature of these two-hulled boats facilitates coexistence and gives your group more room. This ensures you are comfortable as well as makes it easier to move around and carry out different tasks onboard such as cooking. Likewise, the draft of the boat is smaller allowing you to get closer to shallow coves. This also makes catamarans slower and more difficult to maneuver, in addition to having a higher price than other boats.

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 7,000 islands and islets to explore. Most of these islands and islets are uninhabited, and others are well-known worldwide for a great escape. 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 the British Virgin Islands, Martinique, Antigua, and Barbuda, St Lucia, St Vincent, and the Grenadines, Grenada, and St Martin. The US and the British Virgin Islands have well over 100 islands and islets between them and so it may be worth a separate trip to some of the other areas of the Caribbean. The clear blue water and the mountain-filled coastline are as dreamy as can be. 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 to discover. 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. The Bahamas is another option for a sailing trip in the Caribbean, but with over 700 islands and islets, this group of islands deserves its own boating holiday.

Sailing around the BVI

There are many itinerary options for your sailing trip in the Caribbean. The first route centers wholly around sailing for a week in the US and British Virgin Islands. 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. 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, Martinique and Guadeloupe, stopping off at the island of Dominica along the way. 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 sail to 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

Are you planning a longer cruise on a catamaran in the Caribbean? Or just want to cruise on a sailboat in the Caribbean for 14 days uninterrupted? Head south from Martinique until you reach the spectacular coastline of 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 trip in the Caribbean cost?

When considering a sailing trip in the Caribbean, there are many different factors that can affect the price. This includes the length of your trip, the season, the size and type of boat, as well as the amenities on board. Renting with a captain and crew can also affect the price. A cruise on a catamaran in the Caribbean costs from $2260 per week. A cruise on a catamaran instead can cost from $5645 per week.

Usually, when looking at rental 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 extras 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, fuel, food, and drinks bought during your stay. You usually also need to leave a deposit, which will be given back after your trip once the boat is checked for any damages.


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