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) Nassau Swimming Pigs: Snorkeling, Lunch & Private Beach Club San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour 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 →

Punta Cana Parasailing & Snorkeling Cruise Experience

Surprise yourself in this combination of two great excursions. While the clear water splashes your feet, fly 500 feet high and enjoy a spectacular panoramic …More

Punta Cana, Dominican Republic

4.8 (620)

Punta Cana Parasailing & Snorkeling Cruise Experience

Surprise yourself in this combination of two great excursions. While the clear water splashes your feet, fly 500 feet high and enjoy a spectacular panoramic...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (620)

from
$140

Puerto Rico Sunset Magic: Bio Bay Kayaking Tour from Fajardo

Over 17 years in the industry & the only company that features professional guide & Marine Biologist as your lead guide, rest assure that we …More

Fajardo, Puerto Rico

4.8 (242)

Puerto Rico Sunset Magic: Bio Bay Kayaking Tour from Fajardo

Over 17 years in the industry & the only company that features professional guide & Marine Biologist as your lead guide, rest assure that we...

2 hours Free Cancellation

4.8 (242)

from
$69

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. John’s National Park and a remote, uninhabited …More

4.9 (1,058)

Snorkel Cat All Inclusive Adventure

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. John’s National Park and a remote, uninhabited...

5 hours Free Cancellation

4.9 (1,058)

from
$150

Champagne Sunset Sail from Margaritaville

Climb aboard our brand-new catamaran, Snorkel Cat, and immerse yourself in the breathtaking beauty of a Caribbean sunset. Departing from 5:00 pm to 7:00 pm, …More

4.8 (851)

Champagne Sunset Sail from Margaritaville

Climb aboard our brand-new catamaran, Snorkel Cat, and immerse yourself in the breathtaking beauty of a Caribbean sunset. Departing from 5:00 pm to 7:00 pm,...

2 hours Free Cancellation

4.8 (851)

from
$110

Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

We offer a semi private setting with a maximum of 6 guest and a personalized experience. The sailboat Cosmos Mariner is stable, sea kindly, and …More

5.0 (257)

Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

We offer a semi private setting with a maximum of 6 guest and a personalized experience. The sailboat Cosmos Mariner is stable, sea kindly, and...

3 hours Free Cancellation

5.0 (257)

from
$159

San Juan: VIP Snorkeling with Turtles Tour

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in …More

5.0 (329)

San Juan: VIP Snorkeling with Turtles Tour

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in...

1 hour 30 minutes Free Cancellation

5.0 (329)

from
$70

Enjoy an awesome and interactive underwater eco-tour wearing Hartley diving helmets. One's head stays dry. Glasses, contacts, make-up, and big hair are fine. Just walk, …More

4.9 (500)

Hartley Helmet Diving in Bermuda

Enjoy an awesome and interactive underwater eco-tour wearing Hartley diving helmets. One's head stays dry. Glasses, contacts, make-up, and big hair are fine. Just walk,...

3 hours 30 minutes Free Cancellation

4.9 (500)

from
$155

Private, luxury, custom charters to Stingray City, Snorkeling & More

Luxury, knowledge & value - these are the values of Cobalt Custom Charters. Whether doing a morning, afternoon, or biobay charter, you will have the experience …More

Grand Cayman, Cayman Islands

5.0 (514)

Private, luxury, custom charters to Stingray City, Snorkeling & More

Luxury, knowledge & value - these are the values of Cobalt Custom Charters. Whether doing a morning, afternoon, or biobay charter, you will have the experience...

2 to 4 hours Free Cancellation

5.0 (514)

from
$610

Coral Quest: A Marine Conservation Experience (All Ages)

Discover the Caribbean Beneath the Surface. Coral Quest is more than a catamaran tour, it's an unforgettable marine conservation adventure for families and ocean lovers …More

Punta Cana, Dominican Republic

5.0 (569)

Coral Quest: A Marine Conservation Experience (All Ages)

Discover the Caribbean Beneath the Surface. Coral Quest is more than a catamaran tour, it's an unforgettable marine conservation adventure for families and ocean lovers...

4 hours Hotel pickup offered Free Cancellation

5.0 (569)

from
$114

Caribbean Escape: An Adults-Only Ocean Experience (15+) Premium

Escape the crowds on this premium catamaran experience in Punta Cana, limited to just 35% of the boat's capacity for maximum comfort and personalized service. …More

Punta Cana, Dominican Republic

4.9 (1,767)

Caribbean Escape: An Adults-Only Ocean Experience (15+) Premium

Escape the crowds on this premium catamaran experience in Punta Cana, limited to just 35% of the boat's capacity for maximum comfort and personalized service....

4 hours Hotel pickup offered Free Cancellation

4.9 (1,767)

from
$114

Caribbean Escape: An Adults-Only Ocean Experience (15+) Light

Escape the crowds on this premium catamaran experience in Punta Cana, limited to just 35% of the boat's capacity for maximum comfort and personalized service. …More

Punta Cana, Dominican Republic

4.9 (520)

Caribbean Escape: An Adults-Only Ocean Experience (15+) Light

Escape the crowds on this premium catamaran experience in Punta Cana, limited to just 35% of the boat's capacity for maximum comfort and personalized service....

4 hours Hotel pickup offered Free Cancellation

4.9 (520)

from
$99

St Lucia Full-Day Catamaran Sightseeing Cruise With Snorkeling

Join this full-day catamaran tour, where you cruise down to Soufriere, see the Pitons, and visit Toraille Waterfall, the Sulphur Springs (where you have the …More

Choc, St Lucia

4.7 (672)

St Lucia Full-Day Catamaran Sightseeing Cruise With Snorkeling

Join this full-day catamaran tour, where you cruise down to Soufriere, see the Pitons, and visit Toraille Waterfall, the Sulphur Springs (where you have the...

8 hours Free Cancellation

4.7 (672)

from
$145

Barbados Turtle & Shipwreck Snorkel Adventure

Set sail with Tranquility Cruises on an unforgettable Turtle & Shipwreck Adventure along Barbados’ beautiful coastline. Departing from Carlisle Bay, this 80-minute cruise includes snorkeling …More

Speightstown, Barbados

4.8 (1,040)

Barbados Turtle & Shipwreck Snorkel Adventure

Set sail with Tranquility Cruises on an unforgettable Turtle & Shipwreck Adventure along Barbados’ beautiful coastline. Departing from Carlisle Bay, this 80-minute cruise includes snorkeling...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.8 (1,040)

from
$27

Cave, Waterfall and River Adventure in Charco Azul from San Juan

This is an absolutely unforgettable experience. This day trip has it all: adventure, pristine tropical rivers, waterfalls, cave swimming, beautiful scenery, adrenaline, fun and even …More

5.0 (2,599)

Cave, Waterfall and River Adventure in Charco Azul from San Juan

This is an absolutely unforgettable experience. This day trip has it all: adventure, pristine tropical rivers, waterfalls, cave swimming, beautiful scenery, adrenaline, fun and even...

5 hours Free Cancellation

5.0 (2,599)

from
$125

Margaritaville Hip-Strip and Great River Rafting Private Tour

Your journey begins with a scenic drive to the Lethe Rafting Village, where you'll board a handcrafted 30-foot bamboo raft. Guided by an experienced raft …More

Montego Bay, Jamaica

4.8 (243)

Margaritaville Hip-Strip and Great River Rafting Private Tour

Your journey begins with a scenic drive to the Lethe Rafting Village, where you'll board a handcrafted 30-foot bamboo raft. Guided by an experienced raft...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (243)

from
$20

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 (465)

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 (465)

from
$89

Punta Cana Hip Hop Party Cruise with Live DJ & Unlimited Drinks

Hip Hop Party Catamaran – Adults Only Straight vibes, no limits. Hop on the hottest Caribbean Party Boat where real Hip Hop hits hard, the …More

La Romana, Dominican Republic

4.8 (2,149)

Punta Cana Hip Hop Party Cruise with Live DJ & Unlimited Drinks

Hip Hop Party Catamaran – Adults Only Straight vibes, no limits. Hop on the hottest Caribbean Party Boat where real Hip Hop hits hard, the...

3 hours Hotel pickup offered Free Cancellation

4.8 (2,149)

from
$65

WE PRIDE OURSELVES ON PROVIDING GREAT MEMORIES FOR ALL OUR GUESTS :-) Grenada has some of the Caribbean’s most picturesque coastlines and beaches. Whether you …More

5.0 (40)

Grenada Luxury Private Boat Cruises

WE PRIDE OURSELVES ON PROVIDING GREAT MEMORIES FOR ALL OUR GUESTS :-) Grenada has some of the Caribbean’s most picturesque coastlines and beaches. Whether you...

2 to 8 hours Free Cancellation

5.0 (40)

from
$515

Punta Cana Hip Hop Party Boat: Snorkeling, Open Bar & Adults Only

Why Travelers Love This Tour? • Snorkel in crystal-clear waters • Unlimited drinks & live DJ beats • Stunning Caribbean views Our Party Boat Catamaran …More

4.9 (575)

Punta Cana Hip Hop Party Boat: Snorkeling, Open Bar & Adults Only

Why Travelers Love This Tour? • Snorkel in crystal-clear waters • Unlimited drinks & live DJ beats • Stunning Caribbean views Our Party Boat Catamaran...

3 hours Hotel pickup offered Free Cancellation

4.9 (575)

from
$65

Guided Kayaking Tour of the Mitan Pond and its Mangrove

Embark on a unique exploration of the Mitan Pond, a peaceful stretch of water nestled on the edge of Grande-Anse Beach in Deshaies with a …More

Basse-Terre Island, Guadeloupe

5.0 (31)

Guided Kayaking Tour of the Mitan Pond and its Mangrove

Embark on a unique exploration of the Mitan Pond, a peaceful stretch of water nestled on the edge of Grande-Anse Beach in Deshaies with a...

2 hours 30 minutes Free Cancellation

5.0 (31)

from
$40

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?