Top 7 Jamaica Sailing Trips

1.Reggae Catamaran and Snorkeling Open Bar Cruise Montego Bay

★★★★★★★★★★4.0 · 453 reviews · from $125Our pick

Spend about three hours cruising Montego Bay’s north coast, snorkeling near Doctor’s Cave Beach, then dancing to reggae with unlimited drinks and onboard snacks. Hotel pickup is offered, but the party atmosphere, possible crowding, and choppy water make this best for adults seeking music and fun rather than quiet sightseeing.

“When the driver came to pick me up he tried telling me that I canceled my tour. I showed him my booking and confirmation showing that I never canceled. He calls someone and after 10 minutes it was confirmed that I never canceled my excursion. When we arrived to get our wrist bands and sign in shanice was rude making rude comments. She tells me my name was not on the list because I booked late but I had a family member that booked after me and her name was on the list. It was very embarrassing will not recommend or book again”

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2.NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe Adults only ALL HOTELS

★★★★★★★★★★4.0 · 390 reviews · from $88Best value

Cruise Negril’s coast with an energetic crew, onboard DJ, open bar, light snacks, and snorkeling at Sandy Cove Reef. You’ll stop at Rick’s Cafe for sunset and cliff jumping, though rough seas can require a bus transfer and time there is limited. Hotel pickup is available from Negril, Lucea, and Montego Bay.

“You have to walk through the sea to get on the boat, snacks are not provided if you call a packet of cheap crisps a snack then fair play. Not worth the money at all, not enough time at ricks cafe, very dangerous in awful weather. (They didn’t cancel even in awful conditions)”

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3.Catamaran Cruise Full Day Tour to Reef, Caves and Negril Beach

★★★★★★★★★★4.0 · 378 reviews · from $90

Travel by air-conditioned bus from Ocho Rios to Negril, spend time near Seven Mile Beach, then board a catamaran for snorkeling, reef views, an open bar, reggae music, and sunset near Rick’s Cafe. Adults-only sailings run Tuesday, Thursday, Saturday, and Sunday.

“This is my second time on this boat And it was just as amazing as the 1st time. Music is amazing and drinks are bomb!”

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4.Catamaran Cruise with Snorkeling and Dunn’s River Falls

★★★★★★★★★★4.5 · 358 reviews · from $139

Join Chukka’s 65-foot catamaran from Ocho Rios or Montego Bay for snorkeling, lunch, and a guided climb up Dunn’s River Falls. Expect lively music and rum punch on the return sail. Water shoes, breakfast, and patience with group logistics will make the day much easier.

“Lunch wasn’t the best.. too spicy and no drinks included. But overall everything else good and a lot of fun on the catamaran.”

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5.OpenBar, Music, Negril Beach, Caves, Snorkeling

★★★★★★★★★★4.0 · 299 reviews · from $90

Travel by air-conditioned bus from your north coast hotel to Negril, spend time on 7 Mile Beach, then board a music-filled catamaran for snorkeling, unlimited drinks, and Rick’s Cafe. Dex, Thunder, and other hosts keep the party moving, but expect a long day and waist-deep water boarding.

“This was too much fun! The snorkeling was a good experience even though we didn't get to many fish or other sea animals. The boat was fun we danced and partied the entire time. I do wish we had more time at Rick's, didn't get to jump. Overall a great experience and I would definitely do it again”

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6.Montego Bay Reggae Sunset Catamaran Cruise

★★★★★★★★★★4.0 · 99 reviews · from $125

Set sail from Montego Bay at about 3 pm for a three-hour reggae catamaran cruise with a live DJ, open bar, fruit, pastries, appetizers, and Caribbean sunset views. Hotel pickup is available from selected hotels. Expect a lively party atmosphere, limited seating at times, and possible weather changes.

“This excursion was better than I thought it would be. We will definitely take the same one again. The staff on the boat was excellent.”

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7.Reggae Catamaran 18+ Cruise with Open Bar

★★★★★★★★★★3.8 · 87 reviews · 3 hours · from $125

Spend three hours on an adults-only catamaran off Montego Bay, with hotel pickup, a short reef-snorkeling stop, open-bar cocktails, appetizers, music, and access to Margaritaville. The return trip becomes a floating dance party, with a DJ and Caribbean rhythms.

“An absolutely blast! Very chill and also very fun!”

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