Top Caribbean Sailing Trips

Q: Which Caribbean Sailing Trips have Instant Confirmation?

Caribbean Sailing Trips with Instant Confirmation include: Exclusive Hip Hop Punta Cana Party Boat with Open Bar *Only Adult 7 Hour Private Catamaran Sail, Snorkel and Beach BBQ Grace Bay, Providenciales 2 days 1 night by private catamaran from St Martin to St Barth 2.5hr Private Catamaran Cruise with Snorkeling, Bar, Food St Martin Gd-Case: Private day in all inclusive catamaran View all Tours with Instant Confirmation →

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 →

Full Day Private Charter, Snorkel St. John (12 guests, 55’ yacht)

Explore the Virgin Islands in style and luxury aboard this beautiful 54 foot sailing yacht for an amazing full day (10am - 4pm) sailing excursion. …More

5.0 (102)

Full Day Private Charter, Snorkel St. John (12 guests, 55’ yacht)

Explore the Virgin Islands in style and luxury aboard this beautiful 54 foot sailing yacht for an amazing full day (10am - 4pm) sailing excursion....

6 hours Free Cancellation

5.0 (102)

from
$1,985

Private Full Day Sail/ Snorkel Experience USVI (Sapphire Marina, STT pick up)

This is a private personal sailing experience for up to six guest. Avoid the crowds and choose how you want to spend the best day …More

5.0 (18)

Private Full Day Sail/ Snorkel Experience USVI (Sapphire Marina, STT pick up)

This is a private personal sailing experience for up to six guest. Avoid the crowds and choose how you want to spend the best day...

7 hours Free Cancellation

5.0 (18)

from
$1,975

Blue Parrot Snorkel Sail with 4 course lunch or dinner in Aruba

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

Palm - Eagle Beach, Aruba

5.0 (8)

Blue Parrot Snorkel Sail with 4 course lunch or dinner in Aruba

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

4 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$1,919

Sail Away in Montego Bay on a Private Catamaran

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the …More

Montego Bay, Jamaica

5.0 (20)

Sail Away in Montego Bay on a Private Catamaran

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the...

3 hours Free Cancellation

5.0 (20)

from
$1,850

Private St. Maarten Cruise - Hakuna Matata Catamaran

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you …More

5.0 (71)

Private St. Maarten Cruise - Hakuna Matata Catamaran

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you...

7 hours

5.0 (71)

from
$1,830

Take a look at the pictures this is a steal of a deal . in addition the vibes with the crew is priceless.. I hope …More

Five Islands Village, Antigua and Barbuda

4.9 (12)

Catamaran private charter

Take a look at the pictures this is a steal of a deal . in addition the vibes with the crew is priceless.. I hope...

5 hours Hotel pickup offered Free Cancellation

4.9 (12)

from
$1,800

Full-Day Private Boat Charter Caribbean adventure

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Decks DE stern and …More

5.0 (2)

Full-Day Private Boat Charter Caribbean adventure

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Decks DE stern and...

6 hours Free Cancellation

5.0 (2)

from
$1,779

Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing stories and will keep you entertained with …More

5.0 (498)

Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing stories and will keep you entertained with...

6 hours Free Cancellation

5.0 (498)

from
$1,750

St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran …More

5.0 (114)

St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran...

6 hours 30 minutes Free Cancellation

5.0 (114)

from
$1,650

Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some …More

5.0 (16)

Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some...

6 hours Free Cancellation

5.0 (16)

from
$1,650

Private catamaran for groups up to 15 people and Lunch on board

Live a unique experience aboard a catamaran in Puerto Plata! Embark on an exclusive journey through the crystal-clear Caribbean waters, enjoying breathtaking landscapes and hidden …More

Puerto Plata, Dominican Republic

Private catamaran for groups up to 15 people and Lunch on board

Live a unique experience aboard a catamaran in Puerto Plata! Embark on an exclusive journey through the crystal-clear Caribbean waters, enjoying breathtaking landscapes and hidden...

4 hours Hotel pickup offered Free Cancellation

from
$1,599

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 (1)

SPECIAL - 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 (1)

from
$1,550

Half-Day The Soul Of Pirates Private Boat Trip Adventure Caribbean Charter SXM

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Things to do: snorkel, …More

5.0 (7)

Half-Day The Soul Of Pirates Private Boat Trip Adventure Caribbean Charter SXM

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Things to do: snorkel,...

3 hours 30 minutes Free Cancellation

5.0 (7)

from
$1,538

Are you and your group seeking a private catamaran experience, tailored to your preferences, without sharing it with other guests? Look no further – our …More

Grand Cayman, Cayman Islands

4.7 (18)

Private 4 hour Catamaran Tour

Are you and your group seeking a private catamaran experience, tailored to your preferences, without sharing it with other guests? Look no further – our...

4 hours Hotel pickup offered Free Cancellation

4.7 (18)

from
$1,499

Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 guest max

A Private Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

5.0 (122)

Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 guest max

A Private Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

6 hours 30 minutes Free Cancellation

5.0 (122)

from
$1,495

Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early …More

5.0 (2)

Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early...

2 hours Free Cancellation

5.0 (2)

from
$1,495

Miches Private Sailing Tour in Punta Cana Natural Reserve

Unique opportunity of Sailing and cruising in the Punta Cana and Cape Engaño crystal clear shallow waters, with 2 nets to relax that will be …More

La Romana, Dominican Republic

Miches Private Sailing Tour in Punta Cana Natural Reserve

Unique opportunity of Sailing and cruising in the Punta Cana and Cape Engaño crystal clear shallow waters, with 2 nets to relax that will be...

5 hours 30 minutes Hotel pickup offered Free Cancellation

from
$1,489

50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select …More

5.0 (681)

50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select...

4 to 7 hours Free Cancellation

5.0 (681)

from
$1,441

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy …More

5.0 (70)