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) San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Small-Group El Yunque Waterfall & Waterslides with Pickup 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 →

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a …More

4.9 (295)

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a...

5 hours Free Cancellation

4.9 (295)

from
$149

Jolly Pirate Afternoon Sail with Snorkeling

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, Antilla! You can choose to swim …More

4.7 (512)

Jolly Pirate Afternoon Sail with Snorkeling

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, Antilla! You can choose to swim...

3 hours

4.7 (512)

from
$89

Round Trip Transportation: San Juan to the Ceiba Ferry Terminal

**FERRY TICKETS TO CULEBRA OR VIEQUES ARE NOT INCLUDED AND ARE SOLD SEPARATELY** Skip the hassle and cost of getting to and from the Ceiba …More

Isla Verde, Puerto Rico

4.4 (69)

Round Trip Transportation: San Juan to the Ceiba Ferry Terminal

**FERRY TICKETS TO CULEBRA OR VIEQUES ARE NOT INCLUDED AND ARE SOLD SEPARATELY** Skip the hassle and cost of getting to and from the Ceiba...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.4 (69)

from
$45

St Kitts Shore Excursion: Nevis Beach Getaway

Maximize your time in St Kitts-Nevis with this upscale beach transfer. Tantalizingly close, Nevis can be difficult or expensive to reach for cruisers to St …More

4.5 (147)

St Kitts Shore Excursion: Nevis Beach Getaway

Maximize your time in St Kitts-Nevis with this upscale beach transfer. Tantalizingly close, Nevis can be difficult or expensive to reach for cruisers to St...

5 hours Free Cancellation

4.5 (147)

from
$57

This Nassau sunset dinner cruise is a truly unique experience. Relax in a casual atmosphere on a sailing catamaran while sitting on the nets or …More

Nassau, Bahamas

4.4 (436)

Nassau Sunset Dinner Cruise

This Nassau sunset dinner cruise is a truly unique experience. Relax in a casual atmosphere on a sailing catamaran while sitting on the nets or...

2 hours Free Cancellation

4.4 (436)

from
$103

Bioluminescent Boat Tour in Mosquito Bay, Vieques

The Mosquito Bay in Vieques holds the prestigious title of being the brightest among the five bioluminescent bays recognized by The Guinness Book of World …More

Vieques, Puerto Rico

4.7 (232)

Bioluminescent Boat Tour in Mosquito Bay, Vieques

The Mosquito Bay in Vieques holds the prestigious title of being the brightest among the five bioluminescent bays recognized by The Guinness Book of World...

40 minutes Free Cancellation

4.7 (232)

from
$85

Aruba Glass Bottom Kayak Tour through the Mangrove Forest

Mangrove Forest Tour: Embark on a serene journey through pristine waters, where you'll glide above lively coral reefs in search of the sea life gracefully …More

4.7 (213)

Aruba Glass Bottom Kayak Tour through the Mangrove Forest

Mangrove Forest Tour: Embark on a serene journey through pristine waters, where you'll glide above lively coral reefs in search of the sea life gracefully...

90 to 120 minutes Free Cancellation

4.7 (213)

from
$70

Half or Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our 29' or 32' Power Catamaran and explore the very best of …More

5.0 (155)

Half or Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our 29' or 32' Power Catamaran and explore the very best of...

3 hours 30 minutes Free Cancellation

5.0 (155)

from
$895

Full-Day Tour: El Yunque, Luquillo Beach, Bio Bay Night Kayaking

Weight limit is 240 lbs. per person. Our tour guide will meet you at your hotel or location, (contact us for confirmation). Exposition regarding our …More

Luquillo, Puerto Rico

4.5 (93)

Full-Day Tour: El Yunque, Luquillo Beach, Bio Bay Night Kayaking

Weight limit is 240 lbs. per person. Our tour guide will meet you at your hotel or location, (contact us for confirmation). Exposition regarding our...

10 hours Hotel pickup offered Free Cancellation

4.5 (93)

from
$155

Adventure Antigua - The Xtreme Circumnavigation tour

The Xtreme Circumnavigation tour is a full day boat tour on our 45ft powerboat that goes right around the entire coastline of Antigua - make …More

4.9 (1,107)

Adventure Antigua - The Xtreme Circumnavigation tour

The Xtreme Circumnavigation tour is a full day boat tour on our 45ft powerboat that goes right around the entire coastline of Antigua - make...

330 to 360 minutes Free Cancellation

4.9 (1,107)

from
$248

San Juan Snorkeling Tour with Fish & Turtles - Best Facilities

Discover the underwater treasures of San Juan with Scuba Dogs at Escambrón Marine Park! Explore a vibrant Caribbean ecosystem filled with tropical fish, fascinating underwater …More

4.8 (206)

San Juan Snorkeling Tour with Fish & Turtles - Best Facilities

Discover the underwater treasures of San Juan with Scuba Dogs at Escambrón Marine Park! Explore a vibrant Caribbean ecosystem filled with tropical fish, fascinating underwater...

2 hours Free Cancellation

4.8 (206)

from
$45

Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under …More

4.6 (78)

Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under...

1 hour 30 minutes Free Cancellation

4.6 (78)

from
$89

Che’s snorkel catamaran! turtles, wrecks & pickup (small group)

(Semi private) We are the only cruise that sails early to avoid the crowds of commercial tours. That’s our niche! Che’s snorkel focused trip has …More

5.0 (570)

Che’s snorkel catamaran! turtles, wrecks & pickup (small group)

(Semi private) We are the only cruise that sails early to avoid the crowds of commercial tours. That’s our niche! Che’s snorkel focused trip has...

3 hours Hotel pickup offered Free Cancellation

5.0 (570)

from
$70

Culebra Snorkel and Beach Day with Lunch and Drinks

Come aboard a 46-ft boat for a fantastic beach and snorkeling day trip to the best beaches and snorkeling spots in the clear waters of …More

Fajardo, Puerto Rico

4.8 (400)

Culebra Snorkel and Beach Day with Lunch and Drinks

Come aboard a 46-ft boat for a fantastic beach and snorkeling day trip to the best beaches and snorkeling spots in the clear waters of...

7 hours Free Cancellation

4.8 (400)

from
$162

Group Reef, Beach and Sandbar Tour from Providenciales

Embark on an unforgettable journey on a captivating coastal cruise along Providenciales stunning north shore. Dive into the crystal-clear waters of the barrier reef for …More

4.9 (202)

Group Reef, Beach and Sandbar Tour from Providenciales

Embark on an unforgettable journey on a captivating coastal cruise along Providenciales stunning north shore. Dive into the crystal-clear waters of the barrier reef for...

4 hours Hotel pickup offered Free Cancellation

4.9 (202)

from
$146

Deluxe Half-Day Snorkel Sail on Luxury Catamaran

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, home to some of the best snorkeling in …More

4.9 (445)

Deluxe Half-Day Snorkel Sail on Luxury Catamaran

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, home to some of the best snorkeling in...

4 hours 30 minutes Free Cancellation

4.9 (445)

from
$159

Private San Juan Bay Boat Sunset-Night Cruise

Enjoy an unforgettable experience in our unique private boat ride at the bay of San Juan. You will have the opportunity to know some history …More

5.0 (81)

Private San Juan Bay Boat Sunset-Night Cruise

Enjoy an unforgettable experience in our unique private boat ride at the bay of San Juan. You will have the opportunity to know some history...

1 hour 30 minutes Free Cancellation

5.0 (81)

from
$389

Billy Bones Snorkeling with Turtles for CRUISE SHIP GUESTS

Visit Tintamarre Island ,Creole Rock and Pinel Island on the same day. Snorkel with turtles and tropical fish, enjoy to sip rum punch on the …More

4.9 (175)

Billy Bones Snorkeling with Turtles for CRUISE SHIP GUESTS

Visit Tintamarre Island ,Creole Rock and Pinel Island on the same day. Snorkel with turtles and tropical fish, enjoy to sip rum punch on the...

6 hours Free Cancellation

4.9 (175)

from
$145

007 Private Beach Club Swimming Pigs Snorkeling Lunch Drinks

Our first stop is an amazing snorkeling experience at Rainbow Reef, second stop observing turtles at the sanctuary at Green Cay, our final stop is …More

4.6 (205)

007 Private Beach Club Swimming Pigs Snorkeling Lunch Drinks

Our first stop is an amazing snorkeling experience at Rainbow Reef, second stop observing turtles at the sanctuary at Green Cay, our final stop is...

4 hours Free Cancellation

4.6 (205)

from
$118

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at …More

4.9 (350)

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at...

6 hours 30 minutes Free Cancellation

4.9 (350)

from
$149

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?