Top Caribbean Sailing Trips

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 →

Half Day Sosua Sunset Cruise with Snorkeling

Enjoy the ocean breeze in your hair, the sun on your back and a cocktail in your hand and listen to the soft Caribbean rhythms. …More

Puerto Plata, Dominican Republic

4.4 (9)

Half Day Sosua Sunset Cruise with Snorkeling

Enjoy the ocean breeze in your hair, the sun on your back and a cocktail in your hand and listen to the soft Caribbean rhythms....

4 hours Hotel pickup offered Free Cancellation

4.4 (9)

from
$80

Highlights - Head to the hidden Saona Island from Bayahibe aboard a thrilling speedboat or a cruising catamaran - Take a dip near a sandbar …More

Punta Cana, Dominican Republic

3.7 (6)

Saona Island by Paradise Travel

Highlights - Head to the hidden Saona Island from Bayahibe aboard a thrilling speedboat or a cruising catamaran - Take a dip near a sandbar...

7 to 8 hours Hotel pickup offered Free Cancellation

3.7 (6)

from
$80

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Explore the remarkable Altos de Chavon and dig your toes in the sand of Saona Island during this full-day excursion from Punta Cana, available every …More

Punta Cana, Dominican Republic

4.5 (2,648)

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Explore the remarkable Altos de Chavon and dig your toes in the sand of Saona Island during this full-day excursion from Punta Cana, available every...

9 hours Hotel pickup offered Free Cancellation

4.5 (2,648)

from
$82

Private, All Inclusive, Double-Decker Catamaran in Punta Cana

Our Catamaran Party Boat Tour is a MUST when it comes to Punta Cana experiences. This booze cruise takes you along the Coast of Bavaro …More

Punta Cana, Dominican Republic

5.0 (37)

Private, All Inclusive, Double-Decker Catamaran in Punta Cana

Our Catamaran Party Boat Tour is a MUST when it comes to Punta Cana experiences. This booze cruise takes you along the Coast of Bavaro...

3 hours Hotel pickup offered Free Cancellation

5.0 (37)

from
$83

Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the …More

4.7 (515)

Tango Caribbean Dinner Cruise

Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the...

3 hours Free Cancellation

4.7 (515)

from
$85

Morning Snorkel Sail with Premium Champagne Brunch

Start your day with a relaxed catamaran sail along Aruba’s turquoise coast, paired with a fresh mimosa brunch on board. With multiple snorkeling stops at …More

4.7 (2,136)

Morning Snorkel Sail with Premium Champagne Brunch

Start your day with a relaxed catamaran sail along Aruba’s turquoise coast, paired with a fresh mimosa brunch on board. With multiple snorkeling stops at...

4 hours Free Cancellation

4.7 (2,136)

from
$85

Restless Native Catamaran Sunset & Swizzle Cruise

Start a night out in Bermuda the right way with a 1.5-hour sunset cocktail cruise aboard a 50-foot catamaran. Sunsets in paradise are always great, …More

4.8 (363)

Restless Native Catamaran Sunset & Swizzle Cruise

Start a night out in Bermuda the right way with a 1.5-hour sunset cocktail cruise aboard a 50-foot catamaran. Sunsets in paradise are always great,...

1 hour 30 minutes Free Cancellation

4.8 (363)

from
$85

Sunset & Champagne Cruise on a Classic Schooner with boat dogs

...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a glass of champagne, fresh Appetizers from the onboard …More

4.9 (213)

Sunset & Champagne Cruise on a Classic Schooner with boat dogs

...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a glass of champagne, fresh Appetizers from the onboard...

2 hours 30 minutes Free Cancellation

4.9 (213)

from
$85

Barbados Snorkeling and Sailing Adventure for Small Groups

Our team knows how to blend adventure and relaxation perfectly. From snorkeling with sea turtles and exploring shipwrecks to sipping rum punch as you sail …More

4.8 (51)

Barbados Snorkeling and Sailing Adventure for Small Groups

Our team knows how to blend adventure and relaxation perfectly. From snorkeling with sea turtles and exploring shipwrecks to sipping rum punch as you sail...

3 hours Hotel pickup offered Free Cancellation

4.8 (51)

from
$85

Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada to make our way to the iconic …More

5.0 (44)

Half Day Snorkeling Trip in Grenada

Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada to make our way to the iconic...

4 hours Free Cancellation

5.0 (44)

from
$85

Stroll and Initiation to Sailing in the Baie des Saintes

I invite you to come and share my passion for sailing and navigation in one of the most beautiful bays in the world! I am …More

5.0 (31)

Stroll and Initiation to Sailing in the Baie des Saintes

I invite you to come and share my passion for sailing and navigation in one of the most beautiful bays in the world! I am...

3 hours Free Cancellation

5.0 (31)

from
$86

Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to …More

Lucea, Jamaica

4.3 (18)

Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to...

8 hours Hotel pickup offered Free Cancellation

4.3 (18)

from
$87

Jolly Pirate Afternoon Sail with Snorkeling

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, Antilla! You can choose to swim …More

4.7 (512)

Jolly Pirate Afternoon Sail with Snorkeling

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, Antilla! You can choose to swim...

3 hours

4.7 (512)

from
$89

Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under …More

4.6 (78)

Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under...

1 hour 30 minutes Free Cancellation

4.6 (78)

from
$89

4-hour snorkel cruise to Underwater Sculptures with boat dogs

This tour is offered in different options for different budgets, please be sure to pick the right one!!! Sail to the world-famous Underwater Sculpture Park …More

4.8 (464)

4-hour snorkel cruise to Underwater Sculptures with boat dogs

This tour is offered in different options for different budgets, please be sure to pick the right one!!! Sail to the world-famous Underwater Sculpture Park...

4 hours Free Cancellation

4.8 (464)

from
$89

Catamaran Booze Cruise, Snorkeling & Punta Cana Coast View

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Have a flavorful typical Dominican lunch at an …More

4.9 (140)

Catamaran Booze Cruise, Snorkeling & Punta Cana Coast View

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Have a flavorful typical Dominican lunch at an...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (140)

from
$89

Sail the coastline of the tropical island paradise of St. Lucia, watching the sunset and sipping champagne. Let yourself be swept away by the romance …More

Choc, St Lucia

4.4 (79)

Cruise Sunset Party in Castries

Sail the coastline of the tropical island paradise of St. Lucia, watching the sunset and sipping champagne. Let yourself be swept away by the romance...

2 hours Hotel pickup offered Free Cancellation

4.4 (79)

from
$89

An Astronomical Moment: Aruba Celestial Sunset Cruise

A celestial sunset is the astronomical moment the sun disappears below the horizon, followed by three stages of twilight—civil, nautical, and astronomical—driven by the sun's …More

4.7 (6)

An Astronomical Moment: Aruba Celestial Sunset Cruise

A celestial sunset is the astronomical moment the sun disappears below the horizon, followed by three stages of twilight—civil, nautical, and astronomical—driven by the sun's...

2 hours 30 minutes Free Cancellation

4.7 (6)

from
$89

Catalina Island & Snorkeling Paradise From Punta Cana

We enjoy a catamaran tour across crystal clear waters to Catalina Island, the best-known area for snorkeling in the Dominican Republic.Your day begins with a …More

4.7 (3)

Catalina Island & Snorkeling Paradise From Punta Cana

We enjoy a catamaran tour across crystal clear waters to Catalina Island, the best-known area for snorkeling in the Dominican Republic.Your day begins with a...

9 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$89

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at two spectacular locations. A friendly crew will take you …More

4.7 (318)

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at two spectacular locations. A friendly crew will take you...

3 hours Free Cancellation

4.7 (318)

from
$90