The Best Caribbean Sailing Tours & Trips

The Caribbean has so many fantastic sailing tours and trips. In Antigua, you can enjoy a full-day trip around the island or go to the Bahamas to enjoy a swim with the swimming pigs. In Barbados, you can swim with turtles and around a shipwreck.

Visit Grenada to see the Underwater Sculpture Park. Stop off in Guadaloupe for a swim around the mangroves. In St. Lucia, you can enjoy Sulphur Springs. These are just some of the best sights among the Caribbean islands.

The Caribbean has over 700 islands spread across a beautiful shimmering blue sea. Exploring this magnificent group of island chains is best done by sea.

The idea that sailing in the Caribbean is only for the rich and famous is luckily far from the truth. Many single-day and multiple-day tours and trips are open to those who don’t own a superyacht.

Sometimes choosing where you are going to visit can be a hard decision. To help you with this choice, I have included a few of the best Caribbean sailing trips. It will help make your decision that much easier.



Many consider this little island the Caribbean’s sailing capital. Antigua has some lovely beaches, and some of the planet’s rarest animals call it home.

The sailing facilities on this island are highly rated. There are a few sailing tours you can join in on, of which these are two of the best:

The Extreme Circumnavigation – With Adventure Antigua, you can explore Antigua’s coastline for a day. Hop on board to enjoy a swim at Stingray City Marine Park and lunch at Green Island. You will also enjoy a snorkel at Nelson’s Dockyard and a stop-off at Rendezvous Bay.

Mystic II Sunset Cruise Tour Tropical Adventures tour company will take you on a 2.5-hour sunset cruise. There is an open bar aboard the Mystic II catamaran, and the cruise includes some snacks.

The crew will give you a glass of wine to enjoy when you board. Then it’s off for an evening of romance and relaxation as you take in all that Antigua’s sunset offers.

Sunset views from Shirley Heights, Antigua (Photo credit: Unsplash)


There are many lovely things to see while sailing around the Bahamas. There are birds, beautiful reefs, pink sand beaches, and old shipwrecks.

With so many sailing trips and tours around the Bahamas, the following two are some of the best:

Swim with the Pigs Exuma Tour – This full-day tour has it all. You will get to swim with the swimming pigs at Big Major Cay and feed the Iguanas at Allen’s Cay.

From there, you will enjoy a swim with the Nurse Sharks at Compass Cay and snorkel on the Aqua Shores. Aquashores Luxury Powerboat Tours will make sure that your trip is a memorable one.

Eleuthera Adventure with Swimming Pigs and Turtles – You can enjoy a full day on the water with Born Free. You can swim with the pigs at Meeks Patch, tour the Spanish Wells in Eleuthera, and snorkel at a coral reef.

You will taste local food and drinks on an Eleuthera beach. Stop for lunch on Rose Island, and swim or snorkel with wild turtles.

See also: [9] Things to know about Bahamas sailing trips

The famous Eleuthera swimming pigs, Bahamas (Photo credit: Unsplash)


Barbados is one of the ideal places to sail with its calm Caribbean seas and almost constant trade winds.

A few fantastic sailing tour companies offer trips in and around Barbados. You can enjoy various sights and experiences. Although, some stand out above the rest:

5-Hour Turtle & Shipwreck Cruise – On this tour, you will get to cruise along the west coast of Barbados. Some fun things you will do on this trip are swimming with turtles and tropical fish.

You will also get to snorkel over a shipwreck. El Tigre Catamaran Sailing Cruises will take you on an adventure. With snacks and drinks provided.

Sunset Cruise – The trip will take around 3 hours. You will sail along the coast with Calabaza Sailing Cruises Barbados.

This adults-only trip has two snorkel stops along the way. You can swim around a reef and a shipwreck and snorkel with turtles. The boat has an open bar onboard and provides some tasty finger foods.

(Photo credit: Tom Jur)

The British Virgin Islands

The British Virgin Islands (TBVI) beaches are beautiful, with white sand and huge granite boulders.

Although there are a few charters available at TBVI, there are only a few tours perfect for solo travelers, couples, or small groups. The following tour is a highly-rated choice:

Sunset Sail – Leaving from St. Thomas, this tour with Stormy Pirates only has room for 12 people. It is a seven-hour trip, starting around midday and ending in the evening.

On this fantastic trip, you can snorkel around a shipwreck at Christmas Cove or a colorful reef. Afterward, you will head to World Famous Pizza Pi to enjoy pizza.

Then, you will sail past Cinnamon & Trunk Bay along the Northern Shore of St. John. You can swim with turtles and enjoy the sunset with a glass of bubbly at the end.

Smuggler’s Cove in the BVIs (Photo credit: Unsplash)


You can enjoy lovely experiences in and around the many islands in Grenada. If you are traveling alone, in a small group, or as a couple, you should book your trip with Tours Grenada. This company has a few great options for you to join:

Snorkel Trip “Double Dip” – 4-hour trip with only up to 40 people. Includes sailing to the world-famous Underwater Sculpture Park to enjoy a fully guided snorkeling tour.

Private Sailing & Snorkeling Tour – This trip takes around 8 hours and seats up to 40 people. You will see the famous Underwater Sculpture Park and stop at Mango Bay for a lunch buffet. For extra fun, you will snorkel along the reef at Flamingo Bay and sail through the bay at sunset.

Private Luxury Sunset Cruise – 3-hour trip with only up to 40 people. The trip includes sailing just off the coast of Grand Anse beach. You will enjoy the views, sunset, and an open bar with appetizers.

Grand Anse beach, Grenada (Photo credit: Unsplash)


The islands around Guadeloupe have beautiful forests and coastlines.

There are a couple of great sailing trips and tours that you could enjoy. Two stand out above the rest, and these include:

Sailing and Snorkeling Day Tour to Les Saintes – The crew of Reve de ‘Nav Croisiere will take you on a sailing adventure from Basse-Terre to Les Saintes. This 9-hour trip will also take you around Cabrit Island and Terre-de-Haut. You will stop along the way to swim and snorkel.

Small Day Cruise (Islet Caret, mangrove, coral reef) – If you want to sail through the mangroves, Ti-Kata Caraibes is the sailing company for you. You will stop to swim at Caret islet and islet La Biche and snorkel in a coral reef, around a shipwreck, and at starfish. 

Guadeloupe is a history buffs dream (Photo credit: Unsplash)

St. Lucia

St. Lucia features some lovely majestic mountains perfect for viewing from the sea. The following two sailing tours should be on your bucket list if you visit St. Lucia.

St. Lucia Catamaran Day Sailing and Sightseeing Tour – The guys at Barefoot Holidays Saint Lucia Day Tours will take you on a trip of around 8 hours. You will see some top spots along the way. These top spots include the Sulphur Springs, the Pitons, and Diamond Botanical Gardens.

St. Lucia Full-Day Catamaran Sightseeing Cruise with Snorkeling – This Sea Spray Cruise tour takes about 8 hours. You can use the onboard snorkeling equipment. This equipment will help you to enjoy the underwater views of Marigot Bay and Anse Cochon.

On this trip, you will explore places like Morne Coubril Estate and Sulphur Springs. You will also stop at Toraille Waterfall and the town of Soufriere.

Also see: St Lucia’s best sunset cruises

Seeing More Than One Island

The following tour might interest you if you wish to spend more than one day sailing around the Caribbean.

Caribbean Sojourn – This tour is part of an Ocean Cruise and is 13 days long. You will start in the Bahamas and move on to Long Island, Little Inagua Island, and Puerto Rico.

From there, you will sail to Isla de Culebra, the British Virgin Islands, Saint Barthelemy, Antigua, and Barbuda. You will sail to Saint Vincent and the Grenadines, Mayreau, and Barbados in the last few days.

❓ FAQs

For interest’s sake, the answers to the following FAQs should help you to plan your perfect sailing trip or tour in the Caribbean.

What Are The Best Months To Sail The Caribbean?

The best months are between December and June, outside the hurricane season. Yet, you could shorten this time frame to December to March. This will ensure the weather is dry, clear, and sunny.

Many believe February is the best month. This belief is because the crowds who frequent the Caribbean during Christmas are beginning to leave.

Are The Seas Rough In The Caribbean?

The general agreement is that the Caribbean features calm and smooth sailing conditions. Although, as with most significant bodies of water, conditions can change according to the weather.

The water in the Caribbean can get choppy in places where one body of water runs into another. An example is where the smooth waters of the Caribbean meet the Atlantic Ocean.

Also, during hurricane season, you can expect the waters to get rougher than in the calmer months.

💭 Final Thoughts

Caribbean sailing vacations are ideal for winter holidays. With calm, smooth waters (ideal for sailing vacations) and unique islands.

Whether your dream is to swim with pigs or turtles, or you wish to see the coral reefs up close. Maybe you want to sip some champagne on a catamaran while watching the sunset. The touring sailing companies around the Caribbean islands have something for you.

I don’t know about you, but I can hear the warm waters calling. It’s time to start turning plans into action and get out there to enjoy a few of the best Caribbean sailing tours and trips.

I’m the founder and chief editor here at Sailing Savvy. I spent a decade working as a professional mariner and currently, I mix those experiences with digital publishing. Welcome, and I hope that we can be the hub you need for safe passage.