Top Caribbean Sailing Trips

Q: What are the best options for Caribbean Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Sailing Trips are: Jost Van Dyke - Sandy Spit & Soggy Dollar Sailing Tour in the BVI Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. No1SXM Day Sailing Experience in St. Maarten St. John Days End Sunset Sail with Open Bar from the Westin Live Music Sunset Sail

Q: What are the best kid-friendly options for Caribbean Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Sailing Trips are: St. Martin Sunset Sail Half Day Party Boat and Snorkeling in Punta Cana Parasailing in Bavaro Full Day Excursion to Isla Saona from Punta Cana Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran View all kid-friendly Tours →

Q: Which Caribbean Sailing Trips have Instant Confirmation?

Caribbean Sailing Trips with Instant Confirmation include: San Juan: Snorkeling with Turtles and Complimentary Videos St. Martin Sunset Sail Half Day Party Boat and Snorkeling in Punta Cana Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult Beach Buggy Excursion in Punta Cana Bavaro View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Sailing Trips have Hotel Pickup?

No problem. These Caribbean Sailing Trips include Hotel Pickup: Half Day Party Boat and Snorkeling in Punta Cana Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult Beach Buggy Excursion in Punta Cana Bavaro Parasailing in Bavaro Full Day Excursion to Isla Saona from Punta Cana View all Tours with Hotel Pickup →

Q: Got any more Caribbean trip ideas?

We sure do. Check out our curated lists of hand-picked Caribbean Tours. Top 10 Caribbean 2026 Senior-friendly tours Caribbean The best tours and activities for culture lovers in Caribbean Top Day Trips from Caribbean Things to do in Caribbean this summer View all Caribbean Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Caribbean?

Based on our sales data over the past year, the most popular styles of tours and activities in Caribbean are: Caribbean Luxury & Special Occasions Caribbean Luxury Tours Caribbean Tours & Sightseeing Caribbean Shore Excursions Caribbean Port Transfers View all tour styles in Caribbean →

Aruba Sunset Catamaran Sail with Appetizers and Open Bar

Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the open water as you sip a cocktail and watch the …More

4.6 (2,268)

Aruba Sunset Catamaran Sail with Appetizers and Open Bar

Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the open water as you sip a cocktail and watch the...

2 hours Free Cancellation

4.6 (2,268)

from
$92

Sailing lagoon day: slide between mangrove & reefs

Morning boarding in a calm sea, with a simple welcome over coffee. From the first edges, sailing sets the pace. The lagoon, protected by the …More

Basse-Terre Island, Guadeloupe

5.0 (62)

Sailing lagoon day: slide between mangrove & reefs

Morning boarding in a calm sea, with a simple welcome over coffee. From the first edges, sailing sets the pace. The lagoon, protected by the...

8 to 9 hours Free Cancellation

5.0 (62)

from
$94

You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and sensual seascapes as we sail in …More

4.8 (59)

Catamaran Sunset Sail

You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and sensual seascapes as we sail in...

1 hour 30 minutes Free Cancellation

4.8 (59)

from
$94

Saona Island Excursion by Catamaran and Speedboat (Full Day)

Morning pickup in Punta Cana or Bavaro means you begin the day stress-free. Enjoy the scenery on the way to Bayahibe, where you board either …More

4.8 (5)

Saona Island Excursion by Catamaran and Speedboat (Full Day)

Morning pickup in Punta Cana or Bavaro means you begin the day stress-free. Enjoy the scenery on the way to Bayahibe, where you board either...

10 hours Hotel pickup offered Free Cancellation

4.8 (5)

from
$95

Sharks & Stingrays Encounter and Small Boat Ride from Punta Cana

Come and live this emotion and enjoy a fun and completely safe trip. From young children to adults can participate in these incredible adventures. Enjoy …More

3.8 (15)

Sharks & Stingrays Encounter and Small Boat Ride from Punta Cana

Come and live this emotion and enjoy a fun and completely safe trip. From young children to adults can participate in these incredible adventures. Enjoy...

2 hours 30 minutes Free Cancellation

3.8 (15)

from
$96

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical …More

Isla Verde, Puerto Rico

4.7 (1,432)

San Juan Sunset Harbor Boat Ride

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.7 (1,432)

from
$99

Board your Catamaran for the sailing, snorkeling and beach experience you will never forget! Snorkel in a secluded cove, with all equipment supplied, and attentive …More

4.9 (450)

St Kitts Full Day Catamaran to Nevis

Board your Catamaran for the sailing, snorkeling and beach experience you will never forget! Snorkel in a secluded cove, with all equipment supplied, and attentive...

7 hours Free Cancellation

4.9 (450)

from
$99

San Juan Historical Bay Daytime Sailing Tour

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no …More

4.8 (191)

San Juan Historical Bay Daytime Sailing Tour

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no...

1 hour 30 minutes Free Cancellation

4.8 (191)

from
$99

San Juan Bay Day Sail with Drinks Included

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze …More

5.0 (569)

San Juan Bay Day Sail with Drinks Included

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze...

1 hour 30 minutes Free Cancellation

5.0 (569)

from
$99

Caribbean Escape: An Adults-Only Ocean Experience (15+) Light

Escape the crowds on this premium catamaran experience in Punta Cana, limited to just 35% of the boat's capacity for maximum comfort and personalized service. …More

Punta Cana, Dominican Republic

4.9 (519)

Caribbean Escape: An Adults-Only Ocean Experience (15+) Light

Escape the crowds on this premium catamaran experience in Punta Cana, limited to just 35% of the boat's capacity for maximum comfort and personalized service....

4 hours Hotel pickup offered Free Cancellation

4.9 (519)

from
$99

St. John Days End Sunset Sail with Open Bar from the Westin

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full …More

4.8 (313)

St. John Days End Sunset Sail with Open Bar from the Westin

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full...

1 hour 30 minutes Free Cancellation

4.8 (313)

from
$99

Grace Bay Luxury Catamaran Reef Snorkel Sail

Imagine a blissful snorkel stop in the crystal-clear waters in Turks & Caicos aboard a luxury catamaran. As the catamaran gently glides over the turquoise …More

4.9 (18)

Grace Bay Luxury Catamaran Reef Snorkel Sail

Imagine a blissful snorkel stop in the crystal-clear waters in Turks & Caicos aboard a luxury catamaran. As the catamaran gently glides over the turquoise...

2 hours 30 minutes Free Cancellation

4.9 (18)

from
$99

Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds, …More

Ocho Rios, Jamaica

5.0 (1)

Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds,...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$99

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta Cana. Get up close and personal with …More

Punta Cana, Dominican Republic

4.4 (78)

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta Cana. Get up close and personal with...

3 hours Hotel pickup offered Free Cancellation

4.4 (78)

from
$100

3 ADVENTURES: Sailing Catamaran Cruise - Hooka Diving - Snorkeling

Discover the amazing underwater world at Punta Cana on this 4-hour party cruise. Enjoy the open bar, snorkeling, and hooka diving with a professional guide. …More

Punta Cana, Dominican Republic

4.9 (164)

3 ADVENTURES: Sailing Catamaran Cruise - Hooka Diving - Snorkeling

Discover the amazing underwater world at Punta Cana on this 4-hour party cruise. Enjoy the open bar, snorkeling, and hooka diving with a professional guide....

4 hours Hotel pickup offered Free Cancellation

4.9 (164)

from
$105

Aruba Snorkel Cruise with Open Bar and Lunch

Sail, snorkel, swim and swing in Aruba aboard an impressive 85-foot teak Schooner. Snorkel and Swim at three sites: You will have the opportunity to …More

4.9 (1,140)

Aruba Snorkel Cruise with Open Bar and Lunch

Sail, snorkel, swim and swing in Aruba aboard an impressive 85-foot teak Schooner. Snorkel and Swim at three sites: You will have the opportunity to...

4 hours

4.9 (1,140)

from
$108

Restless Native Catamaran Sail and Snorkel Tour

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain makes for a fun guide as …More

4.9 (1,083)

Restless Native Catamaran Sail and Snorkel Tour

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain makes for a fun guide as...

3 hours 30 minutes Free Cancellation

4.9 (1,083)

from
$110

Party Boat: Drinks & Snorkeling in Punta Cana

Enjoy a half day on board of a catamaran along the coast of Punta Cana. an unforgettable day at the beach on the paradisiacal coasts …More

Punta Cana, Dominican Republic

4.8 (4)

Party Boat: Drinks & Snorkeling in Punta Cana

Enjoy a half day on board of a catamaran along the coast of Punta Cana. an unforgettable day at the beach on the paradisiacal coasts...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (4)

from
$110

Good Vibration Catamaran Sail Swim Snorkel

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sailing, swimming, lounging and snorkeling along the shoreline. …More

4.8 (48)

Good Vibration Catamaran Sail Swim Snorkel

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sailing, swimming, lounging and snorkeling along the shoreline....

3 hours Free Cancellation

4.8 (48)

from
$111