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: 3 Hours Private Sunset Sail and Swim Party Boat: Drinks & Snorkeling in Punta Cana Discovery Package Saona Island & ATV From Punta Cana Half Day Sosua Sunset Cruise with Snorkeling Catalina Island & Snorkeling Paradise From 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 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

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 Luxury Catamaran - Saona or Catalina island

This private day is yours to tailor! Hand pick off track spots and activities for a full personal experience that the crew will help you …More

5.0 (69)

Private Luxury Catamaran - Saona or Catalina island

This private day is yours to tailor! Hand pick off track spots and activities for a full personal experience that the crew will help you...

4 to 8 hours Hotel pickup offered Free Cancellation

5.0 (69)

from
$1,990

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs …More

4.9 (22)

Private Catamaran Charter on Elusive

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs...

3 hours Free Cancellation

4.9 (22)

from
$2,000

Private Sunset Charter on Elusive Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury …More

5.0 (5)

Private Sunset Charter on Elusive Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury...

3 hours Free Cancellation

5.0 (5)

from
$2,000

2 Hour Private Sunset Catamaran Sailing Charter from Grace Bay, Providenciales

There’s no better way to soak up the last rays of the Caribbean sun than with a Private Champagne Sail in Turks and Caicos. Get picked …More

5.0 (9)

2 Hour Private Sunset Catamaran Sailing Charter from Grace Bay, Providenciales

There’s no better way to soak up the last rays of the Caribbean sun than with a Private Champagne Sail in Turks and Caicos. Get picked...

2 hours Free Cancellation

5.0 (9)

from
$2,100

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs …More

5.0 (17)

Private Catamaran Charter on Wyuna

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs...

3 hours Free Cancellation

5.0 (17)

from
$2,120

Experience the magic of an Aruban sunset aboard your own private catamaran. As the sky transforms into breathtaking hues of orange and pink, sip on …More

5.0 (7)

Private Sunset Tour in Aruba

Experience the magic of an Aruban sunset aboard your own private catamaran. As the sky transforms into breathtaking hues of orange and pink, sip on...

2 hours Free Cancellation

5.0 (7)

from
$2,150

Private Sunset Charter on Wyuna Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury …More

5.0 (1)

Private Sunset Charter on Wyuna Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury...

3 hours Free Cancellation

5.0 (1)

from
$2,150

Private St Lucia Full Day Snorkeling Charter for Up to 15 Guests

Hop aboard one of our catamarans for an exciting full day of snorkeling. Choose from a variety of different snorkeling sites offered along the West …More

5.0 (11)

Private St Lucia Full Day Snorkeling Charter for Up to 15 Guests

Hop aboard one of our catamarans for an exciting full day of snorkeling. Choose from a variety of different snorkeling sites offered along the West...

7 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$2,230

Private 1/2 Day Yacht Charter in Bonaire - Customizable!

100% Customizable! Our private charter experience on Bonaire is unmatched. As the only American yacht operators on the island, we understand the importance of personalized …More

5.0 (46)

Private 1/2 Day Yacht Charter in Bonaire - Customizable!

100% Customizable! Our private charter experience on Bonaire is unmatched. As the only American yacht operators on the island, we understand the importance of personalized...

4 hours 30 minutes

5.0 (46)

from
$2,299

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail. …More

5.0 (190)

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail....

4 hours Hotel pickup offered Free Cancellation

5.0 (190)

from
$2,380

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by …More

Fajardo, Puerto Rico

5.0 (16)

Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by...

8 hours Free Cancellation

5.0 (16)

from
$2,395

Montego Bay Private Yacht Tour with Open Bar and Lunch

We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the …More

Montego Bay, Jamaica

4.9 (68)

Montego Bay Private Yacht Tour with Open Bar and Lunch

We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the...

4 hours Free Cancellation

4.9 (68)

from
$2,500

Spend the day in Les Saintes or Guadeloupe or Martinique or Marie Galante (French Islands) relaxing on the beach of just being in the French …More

5.0 (1)

Boat Cruise to the French Islands

Spend the day in Les Saintes or Guadeloupe or Martinique or Marie Galante (French Islands) relaxing on the beach of just being in the French...

8 to 10 hours Hotel pickup offered

5.0 (1)

from
$2,500

St Martin Gd-Case: Private day in all inclusive catamaran

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure. …More

5.0 (14)

St Martin Gd-Case: Private day in all inclusive catamaran

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure....

8 hours

5.0 (14)

from
$2,700

Private Full-Day Catamaran Sailing Charter in St Maarten

Experience some of the finest sailing, swimming and snorkeling in the turquoise waters of St. Maarten. We can alter our trips to meet your needs, …More

5.0 (113)

Private Full-Day Catamaran Sailing Charter in St Maarten

Experience some of the finest sailing, swimming and snorkeling in the turquoise waters of St. Maarten. We can alter our trips to meet your needs,...

8 hours Free Cancellation

5.0 (113)

from
$2,800

2.5hr Private Catamaran Cruise with Snorkeling, Bar, Food

Experience the exclusivity of a private catamaran charter with Aristo Kat Tours Ltd. By booking private, you will create your own vibe - select your …More

5.0 (2)

2.5hr Private Catamaran Cruise with Snorkeling, Bar, Food

Experience the exclusivity of a private catamaran charter with Aristo Kat Tours Ltd. By booking private, you will create your own vibe - select your...

2 hours 30 minutes Free Cancellation

5.0 (2)

from
$2,900

2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night …More

5.0 (2)

2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night...

2 days

5.0 (2)

from
$4,798