The Caribbean · SAILING

Sail Charters in the Caribbean, 15 Ways

35 tours  ·  from $65

The 15 sail charters below are ordered by how consistently travellers rate them. Price, duration and the one thing to check before you commit sit on every entry.

Historical San Juan Bay Sunset Sailing Tour - The sunset portion is the real payoff
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Historical San Juan Bay Sunset Sailing Tour

1.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115Our pick

You’ll sail San Juan Bay for about two hours aboard a 30-foot J/30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, local history, and sunset photos. Beer, sangria, rum and Coke, water, and light refreshments are included. The boat is small and sporty, not a yacht or party catamaran.

“Unfortunately, we were not able to sail with this company and ultimately we were not able to communicate with them at all about our problem with the excursion.”

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50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience - How the snorkeling usually fits into the day
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50′ Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

2.50′ Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

★★★★★★★★★★5.0 · 606 reviews Top rated

Charter the 50-foot SY Sirena from Red Hook for four to seven hours with up to 12 people. Your captain chooses calm coves and snorkeling sites around St. Thomas and St. John, while the crew supplies gear, floats, soda, beer, rum punch, and water. Pickup in Cruz Bay may be possible by advance request.

“This activity was the highlight of our stay in St. Thomas. We were a family of six, including an 7 and 2 year old. Everything from the booking to checking-in was smooth. The captain and first mate were accommodating and very knowledgeable. Read more”

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Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten - Little Bay adds the island’s unusual side
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Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

3.Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

★★★★★★★★★★5.0 · 402 reviews

Sail privately around St Maarten with Captain Mike and Elmira aboard a catamaran for up to eight people. Expect a safety briefing, coffee and croissants, snorkeling at Long Bay and Little Bay, paddleboarding, beach time, a charcoal BBQ lunch, and an open bar with rum punch, mimosas, beer, and mixed drinks. Stops can change with the weather.

“We had a wonderful experience! Michael was very helpful! There was a issue with the catamaran needing work done, but Michael went the extra mile and got us set up with another catamaran. We had the best experience, delicious lunch, beautiful beaches and an authentic Painkiller!”

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Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. - Building your route around St. Thomas
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Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

4.Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

★★★★★★★★★★5.0 · 386 reviews

Spend up to seven hours aboard S/Y Pisces, a private 47-foot Leopard catamaran for up to 12 people. Your captain may plan stops at Buck Island, Water Island, Honeymoon Beach, Shipwreck Cove, or quieter coves for snorkeling, swimming, and beach time. Snorkel gear, floats, drinks, Bluetooth audio, and a restroom are included. Lunch is not.

“This trip was perfect. The captain and 1st mate were knowledgeable and personable. We traveled to two islands. The 2nd island we stopped at to swim and snorkel was great. Funny enough there were about two hundred little fish that circled under the boat. We loved it! Rum punch was a +.”

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Tropical Catamaran Snorkeling & Sailing - Little Bay gets you into the water fast
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Tropical Catamaran Snorkeling & Sailing

5.Tropical Catamaran Snorkeling & Sailing

★★★★★★★★★★5.0 · 353 reviews · from $132

Spend about six hours aboard a spacious catamaran from Bobby’s Marina, sailing St Maarten’s French and Dutch sides. You’ll snorkel at spots such as Little Bay, swim from calm beaches, watch planes near Maho Beach, and enjoy barbecue lunch, snacks, and an open bar. Crews may include Captain Josh, Charlie, Fritz, JP, and others.

“Captain Josh and Fritz were amazing! We have done many catamarans and this was by far the best! Service, beautiful turquoise water and overall experience! Snorkeled with plane wreck, saw beautiful fish and relaxed! Thank you so much for making this so memorable for my family! Btw all other charters were booked and our charter had least amount of people made it almost seem private!”

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Afternoon Luxury Catamaran Sailing and Charter Cruise from Bridgetown - Hotel pickup between Speightstown and Oistins
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Afternoon Luxury Catamaran Sailing and Charter Cruise from Bridgetown

6.Afternoon Luxury Catamaran Sailing and Charter Cruise from Bridgetown

★★★★★★★★★★5.0 · 269 reviews · from $175

Join Calabaza Sailing Cruises for a 3.5-hour afternoon catamaran from Bridgetown. You will snorkel with turtles, explore a reef or shipwreck, enjoy canapes and a premium bar, then watch the sun set over the Caribbean. Crews have included captains such as Danny and Chad, with hotel pickup between Speightstown and Oistins.

“Swimming with the turtles and swimming around some shipwrecks was awesome. The crew who worked that night was also amazing , the food was great and so were the vibes. Not my first time and definitely not my last time.”

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St Lucia Catamaran Day Sailing and Sightseeing Tour - Soufriere Bay and the Pitons from the water
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St Lucia Catamaran Day Sailing and Sightseeing Tour

7.St Lucia Catamaran Day Sailing and Sightseeing Tour

★★★★★★★★★★4.5 · 198 reviews · from $138

Spend about eight hours sailing St. Lucia’s west coast by catamaran, with hotel pickup from North Island properties. Visit Soufriere, the Pitons, Sulphur Springs, a tropical waterfall, and possibly Diamond Botanical Gardens, then enjoy a Creole buffet, drinks, swimming, and snorkeling at Anse Cochon or another beach stop.

“I would not recommend this tour with aviator and Barefoot Holidays to my enemy let alone a friend! There was conflicting information about the pick up location for the tour, we ended up in the wrong place on the wrong tour and had to pay for that tour after having already paid for the one through victor. When I reached out to ask about a refund since we never made it to the tour at all I was told it was my fault I was in the wrong place and because they sent a driver for us I would not get my money back. This is after someone was supposed…”

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Sailing Discovery Day Tour in Martinique - Seeing Martinique from the Caribbean coast
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Sailing Discovery Day Tour in Martinique

8.Sailing Discovery Day Tour in Martinique

★★★★★★★★★★5.0 · 195 reviews · from $155

Spend about 7 hours and 45 minutes sailing from Case-Pilote aboard Fildou, a racing trimaran limited to nine people. Captain Pol shares his love of Martinique, teaches sailing, leads a snorkeling stop near Îlet Ramiers, and serves a local lunch with drinks. You must arrange your own transport to the meeting point.

“Perfect tour! Paul was a very friendly and authentic guide and engaged the guests (max. 8 people) in the sailing experience. Brilliant choice of spot for snorkeling and free time (the given equipment was very good) and a lot of knowleRead more”

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Full-Day Sailing and Snorkeling Excursion to Les Saintes - The crossing from Basse-Terre to Les Saintes
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Full-Day Sailing and Snorkeling Excursion to Les Saintes

9.Full-Day Sailing and Snorkeling Excursion to Les Saintes

★★★★★★★★★★5.0 · 177 reviews · from $179

Join Reve de Nav at 9 a.m. in Gourbeyre for a nine-hour sailing trip to Les Saintes. Skippers such as Mathieu, Didier, Raphaëlle, and Olivier guide the boat, explain local sights, and let willing passengers take the helm. Expect snorkeling, a shipwreck swim, snacks, punches, and chicken colombo served onboard.

“Super sortie en mer avec possibilité de prendre la barre, rhum colombo et snurkling. Bonne ambiance et personnel très professionnel. Traversée et visites des saintes depuis le bateau. N'hésitez pas à aller voir sur Google ou j'ai laissé un avis avec une belle description”

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Day Yacht Excursions throughout the US or British Virgin Islands - Choosing Between the US and British Virgin Islands
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Day Yacht Excursions throughout the US or British Virgin Islands

10.Day Yacht Excursions throughout the US or British Virgin Islands

★★★★★★★★★★5.0 · 164 reviews

Set out from Compass Point Marina in St. Thomas on a private 45-foot yacht for six to eight hours. Choose a custom route through the US or British Virgin Islands, with options such as snorkeling at Norman Island or relaxing on Sandy Cay. Hotel pickup and meals may be available, while fuel and customs fees require careful checking.

“Great Snorkeling and great sightseeing. Caring crew with great hospitality and lots of fun adventures”

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3 ADVENTURES: Sailing Catamaran Cruise - Hooka Diving - Snorkeling - What the catamaran ride feels like
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3 ADVENTURES: Sailing Catamaran Cruise – Hooka Diving – Snorkeling

11.3 Adventures: Sailing Catamaran Cruise – Hooka Diving – Snorkeling

★★★★★★★★★★5.0 · 162 reviews · from $105

Spend about four hours off Punta Cana on a catamaran with hotel pickup, an open bar, snorkeling, and guided hookah-style underwater time near Bávaro’s coral reef. The crew handles the equipment and safety briefing, while you enjoy music, dancing, and a short ocean adventure with up to 40 people.

“It's not what I expected. The crew on the boat was great and upbeat and awesome. But the diving wasn't worth it. We hooked up, went down and did a circle around the boat, that was it. The snorkeling was around a lot of boats so there were some fish but nothing great. Overall it was ok but not worth money.”

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Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba - Spanish Lagoon and Arubas shoreline
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Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba

12.Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba

★★★★★★★★★★5.0 · 151 reviews · from $135

Spend about four hours sailing from Varadero Marina, passing Spanish Lagoon and Flamingo Island before snorkeling at Mangel Halto Reef. Choose a morning BBQ lunch or an afternoon BBQ dinner with sunset views. Pickup is available, and the small group size, attentive crew, and onboard drinks make this a relaxed alternative to a large catamaran cruise.

“We had a blast from start to finish. The sailing was fun, snorkeling and dinner/drinks incredible. Best time ever.”

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Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico - Snorkeling at quieter reef sites
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Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

13.Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 144 reviews · from $285

Spend about five hours sailing from Puerto del Rey Marina to Piñeros or Palomino Island with a group of no more than six. You can snorkel, swim, visit a white-sand beach, relax on the catamaran trampoline, and use a floating lily pad. Lunch, snacks, drinks, and snorkeling gear are included. Captains and mates may include Ricardo, Ashley, Bill, Monica, or Scott.

“Absolutely wonderful day on the water. Ricardo and Ashley made the day so easy and pleasant. They suggested things we could do and pointed out marine life. Motored out to the island for snorkeling, visited a beautiful beach. Visited a sanRead more”

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Sunset Sailing Cruise with premium drinks and bites - A slow look at Curaçao’s eastern coast
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Sunset Sailing Cruise with premium drinks and bites

14.Sunset Sailing Cruise with premium drinks and bites

★★★★★★★★★★4.5 · 141 reviews · from $82

Sail from MOOD Beach Curaçao at 5:30 PM for a 2.5-hour evening cruise along the east coast, Caracas Bay, Fuik Bay, and Spanish Water. You’ll have a spacious catamaran, sunset views, music, light bites, a premium open bar, and onboard restrooms. The cruise returns at 8 PM.

“The Crew was awesome. Great atmosphere, great drinks. A must do experience. The sunset scenery was spectacular.”

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Luxury Private Yacht Charter Aruba - Eden Luca Yachts - Comfort on the Eden Luca I
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Luxury Private Yacht Charter Aruba – Eden Luca Yachts

15.Luxury Private Yacht Charter Aruba – Eden Luca Yachts

★★★★★★★★★★5.0 · 135 reviews

Book the 45-foot Eden Luca I for a private Aruba cruise from Varadero Marina. Your captain plans the route around wind, waves, and time available. Johan, Jimmie, or another crew member may serve your group of up to 10 with drinks, music, WiFi, snorkeling gear, and a floating mat.

“Super recomendable esta actividad. Barcos nítidos, todo en tiempo, tripulación de primera, servicio top!!!! 😎”

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New in Sailing

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★ 5.0Private 1/2 Day Yacht Charter in Bonaire – Customizable!40 reviews
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★ 5.0Private Sailing Catamaran55 reviews
★ 5.0Montego Bay Private Yacht Tour with Open Bar and Lunch67 reviews
★ 5.0Vi Top Taxi &Tours -Airport Transfer Bluebeard’s/Yacht Haven57 reviews
★ 5.0Jost Van Dyke – Sandy Spit & Soggy Dollar Sailing Tour in the BVIFrom $22831 reviews
★ 5.0Norman Island – The Indians & The Caves Sailing & Snorkel TourFrom $19837 reviews
★ 5.0Stroll and Initiation to Sailing in the Baie des SaintesFrom $8980 reviews
★ 5.0Day Lagoon 100% Sailing stops Snorkelling PaddleFrom $11370 reviews
★ 4.9Sailing and Snorkeling Day Tour to Les SaintesFrom $15357 reviews

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Cruises & Boat Tours362Catamaran Cruises112Sunset Cruises79Party Boats & Booze Cruises36Speedboat Tours21Boat Charters62Island Hopping15Shore Excursions40
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