Jamaica · SAILING

15 Sailing Trips in Jamaica, Compared on Price and Drive Time

49 tours  ·  from $70

The 15 sailing trips below are the ones travellers come back happy from, with the price per head, the hours it takes and who each one suits. Number one is first for a reason.

Reggae Catamaran and Snorkeling Open Bar Cruise Montego Bay - When the reggae party takes over
Catamaran Cruises, Catamaran Cruises in Montego Bay, Cruises & Boat Tours, Montego Bay Tours, Sailing, Snorkeling, Snorkeling in Montego Bay, Tour Reviews

Reggae Catamaran and Snorkeling Open Bar Cruise Montego Bay

1.Reggae Catamaran and Snorkeling Open Bar Cruise Montego Bay

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

Cruise Jamaica’s north coast from Montego Bay on a lively catamaran with hotel pickup, reggae music, snorkeling near Doctor’s Cave Beach, an open bar, fruit, pastries, and appetizers. This is an 18-plus party cruise, not a quiet sightseeing trip. Bring sunscreen, a towel, swimwear, and dry clothes.

“The Reggae Catermaran was wonderful. We really enjoyed it. The drinks was great they were on time. We stopped at margaritaville. To swim. The weather was wonderful.The staff was great. I highly recommend this tour for everyone . It was too short. I wish it was longer, 5 hours. The water was blue.”

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NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe Adults only ALL HOTELS - What the $88 price really covers
Catamaran Cruises, Catamaran Cruises in Negril, Cruises & Boat Tours, Evening Experiences, Evening Experiences in Negril, Negril Tours, Rick's Cafe & Seven Mile Beach Tours, Rick's Cafe & Seven Mile Beach Tours in Negril, Sailing, Tour Reviews

NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe Adults only ALL HOTELS

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

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

Cruise Negril’s coast with an onboard DJ, rum punch, snorkeling at Sandy Cove Reef, and a sunset stop at Rick’s Cafe. The lively crew, including MCs such as Chocolate Thunder and Danca Mon, keeps the party moving. Transfers cover Negril, Lucea, and Montego Bay, but you must walk through the sea to board.

“There's not enough amazing things to say about this crew and the trip itself! We left from Margaritaville and from there it was non-stop music, shenanigan's and booze! I would call this the rated R version of the Booze Cruise Negril! Lol. So many enjoyed the snorkeling (I'm not a strong swimmer, so I didn't go), but the summary on the boat and at Rick's was amazing! We even got our picture taken ❤️”

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Catamaran Cruise Full Day Tour to Reef, Caves and Negril Beach - Boarding the catamaran means getting wet
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Catamaran Cruise Full Day Tour to Reef, Caves and Negril Beach

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 free time near Margaritaville and Seven Mile Beach, then board a catamaran for snorkeling, reef views, drinks, reggae, and sunset near Rick’s Cafe. Guides such as Washington, Garfield, Kevin, and Elvis have been praised for keeping the day organized. Expect a long road journey and wet boarding.

“I gave 3 stars for a few reasons: 1. The company presented a pickup location different from my residing hotel which led to much confusion. 2. The itinerary doesn’t specify time frames for travel, margaritaville, catamaran and ricks cafe. 3. Didn’t really get the full ricks cafe experience as we were only there for 1 hr. However, the driver Elvis was super cool and made the overall experience ok. My friend was able to get the clear boat photo experience which was really nice. The catamaran crew was pleasant and fun!”

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Catamaran Cruise with Snorkeling and Dunn's River Falls - The 65-foot catamaran is transport and entertainment
Catamaran Cruises, Cruises & Boat Tours, Dunn's River Falls Tours, Dunn's River Falls Tours in Ocho Rios, Ocho Rios Tours, Sailing, Snorkeling, Tour Reviews

Catamaran Cruise with Snorkeling and Dunn’s River Falls

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

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

Sail from Ocho Rios or Montego Bay on Chukka’s 65-foot catamaran, snorkel over Caribbean reef, climb Dunn’s River Falls, and return to music, lunch, rum punch, and Blue Mountain coffee. Hotel pickup, equipment, guides, and entrance fees are included. Expect a lively group outing, not a quiet sailing trip.

“Loved the staff on the Catamaran. Chukka was awesome. I do wish they had rinsed the floor off while we were climbing the Falls, it was covered in hair and it would have been nicer to have it rinsed as we were all barefoot.”

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Party Catamaran: OpenBar, Music, Negril Beach, Caves, Snorkeling - Music, dancing, and an open bar at sea
Catamaran Cruises, Catamaran Cruises in Negril, Cruises & Boat Tours, Negril Tours, Rick's Cafe & Seven Mile Beach Tours, Rick's Cafe & Seven Mile Beach Tours in Negril, Sailing, Snorkeling, Snorkeling in Negril, Tour Reviews

Party Catamaran: OpenBar, Music, Negril Beach, Caves, Snorkeling

5.Party Catamaran: 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 at 7 Mile Beach, then wade aboard a music-filled catamaran. You’ll get snorkeling gear, unlimited onboard drinks, and a stop at Rick’s Cafe when weather allows. Adults-only sailings run four days a week, with family cruises on the others.

“We did not get picked up to 2 hours after we arrived back to Margaritaville. They voiced that the bus broke down. We could not eat once we got bavlct to resort because we missed the time.”

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Dunn's River Catamaran Cruise From Ocho Rios - A catamaran ride with a party soundtrack
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Dunn’s River Catamaran Cruise From Ocho Rios

6.Dunn’s River Catamaran Cruise From Ocho Rios

★★★★★★★★★★4.5 · 114 reviews · from $141

From Ocho Rios, you’ll sail by catamaran to Dunn’s River Falls, snorkel a protected reef, and climb the 600-foot cascade in a linked human chain. The boat adds a live DJ, open bar, pastries, fruit, and appetizers. Pickup is available from selected hotels, and the tour lasts about four hours, not including transfers.

“Excellent moment sur le catamaran, festive avec de la bonne musique et super équipe, snorkeling et le top gravire la cascade de dunn's juste magnifique”

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Montego Bay: Reggae Sunset Catamaran Cruise - A catamaran ride with a club-on-water mood
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Montego Bay Reggae Sunset Catamaran Cruise

7.Montego Bay Reggae Sunset Catamaran Cruise

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

Set sail from Montego Bay around 3:00 pm for roughly three hours of reggae, dancing, Caribbean views, appetizers, and an open bar. Selected hotels receive round-trip pickup. Expect a lively party boat rather than a quiet sail, with timing, crowd size, weather, and the Margaritaville stop subject to change.

“This trip was so fun—nice long cruise, beautiful scenery, good drinks and great music. If you like to sail this is a must do!”

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Montego Bay: Reggae Catamaran 18+ Cruise with Open Bar - Snorkeling over coral and fish
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Montego Bay: Reggae Catamaran 18+ Cruise with Open Bar

8.Reggae Catamaran 18+ Cruise with Open Bar

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

Spend three hours cruising Montego Bay on an adults-only catamaran with a snorkeling stop, appetizers, unlimited cocktails, and reggae-led dancing. Hotel pickup is included from selected Montego Bay hotels. You will also stop at Margaritaville, while driver Cory has earned praise for smooth, friendly transfers.

“THIS WAS LITTTT! I could do without the paper cups but I understand why they do it that way. The drinks were good but some were took strong that my cup discentigraded by the time I was able to drink it lol. But overall an amazing time!”

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Montego Bay Private Yacht Tour with Open Bar and Lunch - Cruising Montego Bay Harbor
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Montego Bay Private Yacht Tour with Open Bar and Lunch

9.Montego Bay Private Yacht Tour with Open Bar and Lunch

★★★★★★★★★★5.0 · 67 reviews Top rated

Cruise Montego Bay with Captain Owen, Reynaldo, and Shauna on a private yacht for up to seven passengers as described. You’ll snorkel with supplied gear, enjoy jerk chicken bites and cocktail patties, sip sparkling wine or rum drinks, and stop near the Hip Strip before returning to the yacht club.

“The crew was super helpful from start to finish and the food and drinks were amazing! Everything was beyond expectations!!”

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PARTY Catamaran Cruise with Snorkeling Rick's Cafe ADULTS ONLY - Boarding from the beach at Margaritaville or Jam West
Catamaran Cruises, Catamaran Cruises in Negril, Cruises & Boat Tours, Negril Tours, Rick's Cafe & Seven Mile Beach Tours, Rick's Cafe & Seven Mile Beach Tours in Negril, Sailing, Snorkeling, Snorkeling in Negril, Tour Reviews

PARTY Catamaran Cruise with Snorkeling Rick’s Cafe ADULTS ONLY

10.PARTY Catamaran Cruise with Snorkeling Rick’s Cafe ADULTS ONLY

★★★★★★★★★★3.5 · 26 reviews · from $88

Spend about four hours sailing Negril’s coast on an adults-only catamaran with reggae music, open-bar drinks, light snacks, snorkeling at Sandy Cove Reef, beach time, and a visit to Rick’s Café for cliff jumping and sunset views. Transfers from most Negril hotels are included, but rough seas may require a bus transfer to Rick’s Café.

“Amazing experience! Snorkeling, drinks, cliff diving, ricks cafe too good! Highly recommend! Can’t wait to come back!”

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3.5hr Private Catamaran Cruise with Snorkeling, DJ, Bar, Food - Boarding at Wild Card Charter Yacht Club
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3.5hr Private Catamaran Cruise with Snorkeling, DJ, Bar, Food

11.3.5hr Private Catamaran Cruise with Snorkeling, DJ, Bar, Food

★★★★★★★★★★5.0 · 20 reviews

Take your private group of up to 10 from Wild Card Charter Yacht Club into Montego Bay waters for 3.5 hours of snorkeling, swimming, music, and open drinks. Captain CJ and the crew handle the boat, bar, and safety while the DJ sets the mood. Snacks and two hors d'oeuvres are included, but eat beforehand.

“We had a marvelous time Dj Quan was theeee best he should be the top Dj in Jamaica. The crew we had was top notch couldn't ask for a better crew.”

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Sail Away in Montego Bay on a Private Catamaran - Three Hours Along Montego Bay’s Coast
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Sail Away in Montego Bay on a Private Catamaran

12.Sail Away in Montego Bay on a Private Catamaran

★★★★★★★★★★5.0 · 20 reviews

Spend about three hours aboard Gypsy Soul, a private catamaran for up to 12 people. Captain Peter and his crew sail Montego Bay’s coast, stop for swimming and snorkeling, serve drinks, fruit, Jamaican patties, and smoked marlin dip, and play your playlist through Bluetooth speakers. The route is flexible, and the boat returns to Doctor’s Cave Beach.

“Sailing on the catamaran was the highlight of our time in Jamaica. Capitan Peter and his crew were excellent. Would highly recommend!!”

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4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food - Cocktails, food, and the onboard party
Cruises & Boat Tours, Food, Food & Drink, Private, Sailing, Snorkeling, Tour Reviews, VIP

4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food

13.4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food

★★★★★★★★★★5.0 · 19 reviews

Book a private four-hour catamaran cruise from Montego Bay Yacht Club for your group. You’ll get a DJ, bartender, premium open bar, food, coastal views, swimming, and snorkeling near Doctor’s Cave Beach Club. The 47-foot yacht is listed for up to 10 people at $4,300 per group, with another description noting space for up to 15.

“Great boat crew that was attentive and helpful they helped create a wonderful experience. Exceptionally clean boat. It was spacious and the open bar drinks were great. The DJ kept us up and moving the entire time. Would book again in a heartbeat.”

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Reggae Family Catamaran Cruise From Montego Bay - Leaving from the private dock
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Reggae Family Catamaran Cruise From Montego Bay

14.Reggae Family Catamaran Cruise From Montego Bay

★★★★★★★★★★4.0 · 19 reviews · from $125

Sail Montego Bay on a family-friendly reggae catamaran with a live DJ, snacks, adult drinks, and a 30-minute snorkeling stop near Doctor’s Cave Beach. The crew provides equipment and instruction, and the cruise includes time to relax on deck, see fish, and enjoy a lively boat ride. Pickup is offered, but transfer time is separate.

“Great crew! Amazing sites. Family loved snorkeling and crew made sure than even those of us that stayed on the catamaran got to see sone fish!!! Good food and drinks too!! Would definitely do it again!!”

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Negril Catamaran: Adults Sunset Party with Drinks & DJ - Getting checked in at Margaritaville Negril
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Negril Catamaran: Adults Sunset Party with Drinks & DJ

15.Negril Catamaran: Adults Sunset Party with Drinks & DJ

★★★★★★★★★★3.5 · 19 reviews · from $89

Set sail from Margaritaville Negril at 2:30 pm for a four-hour adults-only catamaran party. Swim at a snorkeling stop, enjoy Red Stripe, rum, vodka, juices, sodas, Jamaican snacks, and DJ music, then watch the sunset near Rick’s Cafe. You must walk through waist-deep water to board.

“We had an amazing experience great music! This is my third time doing this catamaran's cruise an this time we seen dolphins jumping in an out of the water!!🥰”

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New in Sailing

★ 4.5Family Catamaran Cruise from Jamwest Beach Negril HotelsFrom $907 reviews
★ 5.0Sailing Adventure Cruise from Montego BayFrom $1386 reviews
★ 5.0Zipline, Horseback Ride, ATV and Catamaran from Montego BayFrom $4407 reviews
★ 5.0Sunset Catamaran cruise, Snorkeling and Rick’s Cafe from MobayFrom $2904 reviews
★ 4.0Negril 7 mile Beach, Party Catamaran Cruise , Snorkeling and Ricks Cafe ComboFrom $1184 reviews
★ 5.0Bamboo Rafting, Catamaran Party Boat & Snorkeling In Montego BayFrom $2803 reviews
★ 5.0Party Catamaran Cruise with Open Bar and Snorkeling Montego BayFrom $1807 reviews
★ 5.0Negril Private Day Tour: ATV Ride, Party Catamaran & Ricks CafeFrom $1504 reviews
★ 5.0Catamaran, snorkeling & Dunn’s River FallsFrom $2156 reviews
★ 5.0Party Catamaran with Dunns River Climb from Montego BayFrom $1698 reviews
★ 4.5Catamaran Party Cruise and Snorkeling from Montego BayFrom $2607 reviews
★ 3.5Half Day Catamaran Party Boat, Snorkeling and Hip Strip TourFrom $1755 reviews
★ 4.0Bamboo Rafting, Catamaran Party Boat & Snorkeling In Montego BayFrom $1205 reviews
★ 5.0Bamboo Rafting, Catamaran Party Cruise and Snorkeling in JamaicaFrom $1047 reviews
★ 4.5Bamboo Rafting, Catamaran Party Cruise and Ricks CafeFrom $1109 reviews

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Cruises & Boat Tours77Catamaran Cruises46Snorkeling41Clear Kayak Tours22Canoes & Kayaks24Rick's Cafe & Seven Mile Beach Tours115Bamboo Beach Club Tours19
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Explore Jamaica

Pick a river, a reef or a cliff.

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On the water

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After dark

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Inland and up

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