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: National Park & Surrounding Cays Sunset Sail 4 Hours Party Boat Catamaran Cruise in Negril Half-Day Sailing Boat Adventure Glass Bottom Boat in Punta Cana Experience a Submarine Scooter with ScubaDoo Punta Cana

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 →

Private Catamaran wonderful Snorqueling slide & entartaiment team

Step aboard a catamaran with friends and family for a private cruise up the coast of the Dominican Republic. You'll be received by a captain …More

Punta Cana, Dominican Republic

4.9 (210)

Private Catamaran wonderful Snorqueling slide & entartaiment team

Step aboard a catamaran with friends and family for a private cruise up the coast of the Dominican Republic. You'll be received by a captain...

4 hours Hotel pickup offered Free Cancellation

4.9 (210)

from
$702

Private Angelfish Snorkeling with Brunch in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical …More

Palm - Eagle Beach, Aruba

5.0 (3)

Private Angelfish Snorkeling with Brunch in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical...

3 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$707

Private Party Boat Cruise: Sound System, Open Bar, Natural Pool

Set sail aboard a double-decker catamaran in the Caribbean Sea, beginning with hotel pickup in Punta Cana in the morning or afternoon. Snorkel in crystal …More

Punta Cana, Dominican Republic

5.0 (97)

Private Party Boat Cruise: Sound System, Open Bar, Natural Pool

Set sail aboard a double-decker catamaran in the Caribbean Sea, beginning with hotel pickup in Punta Cana in the morning or afternoon. Snorkel in crystal...

3 hours Hotel pickup offered Free Cancellation

5.0 (97)

from
$745

Private Catamaran Cruise with Slide & unlimited drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip, you …More

La Romana, Dominican Republic

4.9 (765)

Private Catamaran Cruise with Slide & unlimited drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip, you...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (765)

from
$795

Private Sunset Sailor's Delight from Sapphire Marina

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones …More

5.0 (15)

Private Sunset Sailor's Delight from Sapphire Marina

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones...

2 hours Free Cancellation

5.0 (15)

from
$795

Simply Sailing Private Sail from Sapphire Marina

This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry" …More

5.0 (19)

Simply Sailing Private Sail from Sapphire Marina

This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry"...

3 hours Free Cancellation

5.0 (19)

from
$799

I Like Turtles Private Sailing and Snorkeling from Sapphire

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the …More

5.0 (3)

I Like Turtles Private Sailing and Snorkeling from Sapphire

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the...

3 hours Free Cancellation

5.0 (3)

from
$799

Coral Sunset Sail with 3 Course Dinner in Aruba

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer …More

Palm - Eagle Beach, Aruba

4.8 (13)

Coral Sunset Sail with 3 Course Dinner in Aruba

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer...

3 hours Hotel pickup offered Free Cancellation

4.8 (13)

from
$859

Sail and cruise in the Caribbean sea on your own private Boat, Snorkel in a natural reserve, try Paddle Boarding, enjoy landscapes of virgin beaches, …More

5.0 (7)

Punta Cana Private Sailing Experience

Sail and cruise in the Caribbean sea on your own private Boat, Snorkel in a natural reserve, try Paddle Boarding, enjoy landscapes of virgin beaches,...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (7)

from
$889

Punta Cana Private Party Catamaran with Open Bar

The first stop is at the reef of Cabeza de Toro beach for an unforgettable snorkeling experience. All necessary and disinfected snorkeling equipment will be …More

Punta Cana, Dominican Republic

5.0 (17)

Punta Cana Private Party Catamaran with Open Bar

The first stop is at the reef of Cabeza de Toro beach for an unforgettable snorkeling experience. All necessary and disinfected snorkeling equipment will be...

4 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$890

This excursion will allow you to enjoy the ocean on your own terms. You will be able to snorkel, drink, dance, swim, enjoy the lovely …More

Punta Cana, Dominican Republic

5.0 (62)

Private Snorkeling in Punta Cana

This excursion will allow you to enjoy the ocean on your own terms. You will be able to snorkel, drink, dance, swim, enjoy the lovely...

3 hours Hotel pickup offered Free Cancellation

5.0 (62)

from
$920

Private Luxury Dinner Cruise “Sail & Dine”

Different to other tour operators the Corsair is an able sailing ship – Sails will be set according to the wind situation. Included on your …More

4.0 (1)

Private Luxury Dinner Cruise “Sail & Dine”

Different to other tour operators the Corsair is an able sailing ship – Sails will be set according to the wind situation. Included on your...

4 hours Free Cancellation

4.0 (1)

from
$950

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran …More

5.0 (301)

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran...

3 hours Free Cancellation

5.0 (301)

from
$999

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private …More

Cruz Bay, US Virgin Islands

5.0 (13)

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private...

2 to 3 hours Free Cancellation

5.0 (13)

from
$1,000

With the assistance of expert ecotour guide, our experienced USCG Captain and crew you will enjoy a day of great sailing and learning history of …More

Historic / Educational Private Day Sail - South Coast of Puerto Rico

With the assistance of expert ecotour guide, our experienced USCG Captain and crew you will enjoy a day of great sailing and learning history of...

6 hours Free Cancellation

from
$1,050

Punta Cana Private Cruise Up To 10 Snorkeling & Seafood lunch

Only company with a floating kitchen and large floating bar Our menu options cater to all tastes—including seafood, meat, surf and turf, vegetarian, and more. …More

Punta Cana, Dominican Republic

5.0 (179)

Punta Cana Private Cruise Up To 10 Snorkeling & Seafood lunch

Only company with a floating kitchen and large floating bar Our menu options cater to all tastes—including seafood, meat, surf and turf, vegetarian, and more....

4 hours Hotel pickup offered Free Cancellation

5.0 (179)

from
$1,063

Private Caribbean Snorkeling Cruise At Punta Cana & Sharks, Stingray Encounter

Perfect for both small and large groups. Explore the beauty of Punta Cana's white sands and turquoise blue clear waters in your own upgraded private …More

5.0 (45)

Private Caribbean Snorkeling Cruise At Punta Cana & Sharks, Stingray Encounter

Perfect for both small and large groups. Explore the beauty of Punta Cana's white sands and turquoise blue clear waters in your own upgraded private...

4 hours Hotel pickup offered Free Cancellation

5.0 (45)

from
$1,295

Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty …More

5.0 (1)

Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty...

5 hours Free Cancellation

5.0 (1)

from
$1,300

Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to …More

5.0 (6)

Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to...

2 hours Free Cancellation

5.0 (6)

from
$1,345

SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

5.0 (3)

SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours

5.0 (3)

from
$1,347