Top Caribbean Cruises, Sailing & Water Tours

Q: Which Caribbean Cruises, Sailing & Water Tours have Instant Confirmation?

Caribbean Cruises, Sailing & Water Tours with Instant Confirmation include: 2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Nassau Swimming Pigs: Snorkeling, Lunch & Private Beach Club View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Caribbean Cruises, Sailing & Water Tours include Hotel Pickup: 2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Small-Group El Yunque Waterfall & Waterslides with Pickup Aruba North Coast ATV Desert Adventure 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 →

Captain's Most Popular Snorkeling and Beach Day with Lunch

Cruising along the Caribbean coast of Dominica is as fun and picturesque as one can imagine. Visit famous spots such as Champagne Reef, Scotts Head …More

5.0 (5)

Captain's Most Popular Snorkeling and Beach Day with Lunch

Cruising along the Caribbean coast of Dominica is as fun and picturesque as one can imagine. Visit famous spots such as Champagne Reef, Scotts Head...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (5)

from
$250

Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a …More

5.0 (11)

Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a...

9 hours 30 minutes Free Cancellation

5.0 (11)

from
$397

Spend 3 hours on a Private relaxing catamaran cruise with this excursion from Punta Cana. Unwind in comfortable transport as you make your way from …More

4.3 (18)

Enjoy Punta Cana in Private Yacht

Spend 3 hours on a Private relaxing catamaran cruise with this excursion from Punta Cana. Unwind in comfortable transport as you make your way from...

4 hours Hotel pickup offered Free Cancellation

4.3 (18)

from
$560

6h Bucket List Tour: Stingray City, Beach & Local Lunch

Meet Antigua's famous southern stingrays in crystal-clear Caribbean waters. Enjoy a stress-free experience with hotel pickup, a local guide and assistance throughout the tour. WHY …More

Five Islands Village, Antigua and Barbuda

5.0 (23)

6h Bucket List Tour: Stingray City, Beach & Local Lunch

Meet Antigua's famous southern stingrays in crystal-clear Caribbean waters. Enjoy a stress-free experience with hotel pickup, a local guide and assistance throughout the tour. WHY...

6 hours 10 minutes Hotel pickup offered Free Cancellation

5.0 (23)

from
$195

Private Snorkel Tour with Captain & Guide Bonaire Marine Park 4hr

Embark on an exclusive journey through the crystal-clear waters of Bonaire and Klein Bonaire with a private boat snorkel tour. This personalized adventure offers an …More

5.0 (11)

Private Snorkel Tour with Captain & Guide Bonaire Marine Park 4hr

Embark on an exclusive journey through the crystal-clear waters of Bonaire and Klein Bonaire with a private boat snorkel tour. This personalized adventure offers an...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$645

Sailing Discovery Day Tour in Martinique

Live a day dream on a legendary sailing boat, a trimaran. Discover the wonderland coasts of one of the most beautiful Caribbean island. • From …More

4.9 (63)

Sailing Discovery Day Tour in Martinique

Live a day dream on a legendary sailing boat, a trimaran. Discover the wonderland coasts of one of the most beautiful Caribbean island. • From...

7 hours 45 minutes Free Cancellation

4.9 (63)

from
$126

An Evening on the Lagoon: Martha Rafting, Luminous Lagoon and Falmouth Highlight

One of Jamaica's top tour, An Evening on the Lagoon is a must see. This exciting tour Combines rafting down the famous Martha Brae River. …More

Lucea, Jamaica

4.7 (13)

An Evening on the Lagoon: Martha Rafting, Luminous Lagoon and Falmouth Highlight

One of Jamaica's top tour, An Evening on the Lagoon is a must see. This exciting tour Combines rafting down the famous Martha Brae River....

6 hours Hotel pickup offered Free Cancellation

4.7 (13)

from
$280

Ultimate Adult only Party boat with open bar

Welcome to the ultimate HipHop Party Boat experience in Punta Cana where crystal-clear Caribbean waters meet nonstop beats, vibes,and unforgettable energy! it’s a floating celebration. …More

Punta Cana, Dominican Republic

4.9 (69)

Ultimate Adult only Party boat with open bar

Welcome to the ultimate HipHop Party Boat experience in Punta Cana where crystal-clear Caribbean waters meet nonstop beats, vibes,and unforgettable energy! it’s a floating celebration....

3 hours Hotel pickup offered Free Cancellation

4.9 (69)

from
$70

Island Hopping Adventure in the British Virgin Islands!

Start your day with a captivating Hike at The Baths, this natural wonder is characterized by massive graite boulders scattered along the beach, forming picturesque …More

5.0 (14)

Island Hopping Adventure in the British Virgin Islands!

Start your day with a captivating Hike at The Baths, this natural wonder is characterized by massive graite boulders scattered along the beach, forming picturesque...

7 hours Free Cancellation

5.0 (14)

from
$2,570

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

Your very popular day trip is packed with everything you need. Offering a chance to explore and experience the natural beauty of this one of …More

Punta Cana, Dominican Republic

4.5 (15)

Beautiful Saona Island

Your very popular day trip is packed with everything you need. Offering a chance to explore and experience the natural beauty of this one of...

6 hours Hotel pickup offered Free Cancellation

4.5 (15)

from
$105

If you are looking for a small group experience to kayak and snorkel at two great snorkel spots away from the crowds - this is …More

5.0 (3)

Coral Reef and Turtle Kayak Excursion

If you are looking for a small group experience to kayak and snorkel at two great snorkel spots away from the crowds - this is...

5 hours Free Cancellation

5.0 (3)

from
$159

Experience a Virgin Islands tour unlike any other - without the crowds! Take an adventurous kayak over crystal clear waters and snorkel over a healthy …More

5.0 (3)

Coral Reef and Turtle Discovery Tour

Experience a Virgin Islands tour unlike any other - without the crowds! Take an adventurous kayak over crystal clear waters and snorkel over a healthy...

5 hours Free Cancellation

5.0 (3)

from
$159

Private Full Day Charter to Jost Van Dyke from US Virgin Islands

Sleep in, take it slow, and still have an incredible day exploring Jost Van Dyke. With a late departure at 11 AM and a return …More

5.0 (6)

Private Full Day Charter to Jost Van Dyke from US Virgin Islands

Sleep in, take it slow, and still have an incredible day exploring Jost Van Dyke. With a late departure at 11 AM and a return...

6 hours 30 minutes Free Cancellation

5.0 (6)

from
$1,495

Punta Cana Party Boat Snorkeling with Music DJ and Open Bar

A real party boat Snorkeing cruise with everything included: Transportation, Snorkeling Equipment, Nachos with hot sauce, fresh fruits, coke, sprite, rum, beer, WIFI, and you …More

Punta Cana, Dominican Republic

3.4 (165)

Punta Cana Party Boat Snorkeling with Music DJ and Open Bar

A real party boat Snorkeing cruise with everything included: Transportation, Snorkeling Equipment, Nachos with hot sauce, fresh fruits, coke, sprite, rum, beer, WIFI, and you...

3 hours Hotel pickup offered Free Cancellation

3.4 (165)

from
$61

Private Whale Watching Charter (Grand Turk)

Our tours are done on a purpose built 46' Power Catamaran, powered by twin Yamaha f250hp outboard motors, configured with lots of seating, both sun …More

5.0 (4)

Private Whale Watching Charter (Grand Turk)

Our tours are done on a purpose built 46' Power Catamaran, powered by twin Yamaha f250hp outboard motors, configured with lots of seating, both sun...

3 hours 30 minutes Free Cancellation

5.0 (4)

from
$167

Curaçao: Easy Water Bike Ride with Sea Turtle Viewing & Photos

Discover Curaçao’s stunning marine beauty from one of the most unique seats on the ocean, your own eco-friendly water bike. Join Water Bikes Curaçao for …More

4.8 (55)

Curaçao: Easy Water Bike Ride with Sea Turtle Viewing & Photos

Discover Curaçao’s stunning marine beauty from one of the most unique seats on the ocean, your own eco-friendly water bike. Join Water Bikes Curaçao for...

1 hour Free Cancellation

4.8 (55)

from
$79

Mojito - Full Day Private Catamaran Cruise - St Maarten

Join us on Mojito one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy …More

4.8 (24)

Mojito - Full Day Private Catamaran Cruise - St Maarten

Join us on Mojito one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy...

8 hours Free Cancellation

4.8 (24)

from
$230

All aboard our premium catamaran for a tour of the beautiful town of Soufriere by way of the water! Pass by quaint fishing villages as …More

Castries, St Lucia

4.6 (67)

Soufriere Adventure Cruise

All aboard our premium catamaran for a tour of the beautiful town of Soufriere by way of the water! Pass by quaint fishing villages as...

7 hours Hotel pickup offered

4.6 (67)

from
$153

Barbados Catamaran Snorkel Cruise with Open Bar

Gorgeous smaller catamaran for those looking for fun and relaxed vibe. Avoid the crowds with Super Cats- this boat sails with a maximum of 12 …More

Diamond Valley, Barbados

4.9 (7)

Barbados Catamaran Snorkel Cruise with Open Bar

Gorgeous smaller catamaran for those looking for fun and relaxed vibe. Avoid the crowds with Super Cats- this boat sails with a maximum of 12...

3 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$85

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Caribbean Cruises, Sailing & Water Tours?

What are the best kid-friendly options for Caribbean Cruises, Sailing & Water Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Cruises, Sailing & Water Tours are:

View all kid-friendly Tours →

Which Caribbean Cruises, Sailing & Water Tours have Instant Confirmation?

Which Caribbean Cruises, Sailing & Water Tours have Free Cancellation?

Caribbean Cruises, Sailing & Water Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Caribbean Cruises, Sailing & Water Tours have Hotel Pickup?

Got any more Caribbean trip ideas?

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