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 →

3 hours Bamboo Rafting Activity in Lethe Jamaica

My tour is a private tour. I normally let travelers tell me their interests so I can guide them on the activities that they like …More

Trelawny, Jamaica

5.0 (1)

3 hours Bamboo Rafting Activity in Lethe Jamaica

My tour is a private tour. I normally let travelers tell me their interests so I can guide them on the activities that they like...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$100

Private Afternoon Half Day Bottom Fishing Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! Catch grouper, …More

5.0 (1)

Private Afternoon Half Day Bottom Fishing Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! Catch grouper,...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,951

For Cruise Passengers: 4 Hour Boat Tour of St Maarten/St Martin

Are you traveling to Sint Maarten on a cruise this year? Well this package was made just for you! Enjoy the day in the ocean swimming, …More

5.0 (1)

For Cruise Passengers: 4 Hour Boat Tour of St Maarten/St Martin

Are you traveling to Sint Maarten on a cruise this year? Well this package was made just for you! Enjoy the day in the ocean swimming,...

4 hours Free Cancellation

5.0 (1)

from
$175

Rose Island Swimming Pigs & Beach Snorkeling Experience Nassau

Visiting the Bahamas without meeting the famous swimming pigs? That’s a sure miss! Perfect for travelers looking to soak in the natural beauty of the …More

3.8 (4)

Rose Island Swimming Pigs & Beach Snorkeling Experience Nassau

Visiting the Bahamas without meeting the famous swimming pigs? That’s a sure miss! Perfect for travelers looking to soak in the natural beauty of the...

3 hours 30 minutes Free Cancellation

3.8 (4)

from
$89

Bamboo Rafting Tour in Montego Bay with Limestone Foot Massage

Purely Majestic Operators’ bamboo rafting tour stands out by combining breathtaking natural beauty with exceptional service and safety. Unlike typical tours, our experience emphasizes a …More

Montego Bay, Jamaica

5.0 (1)

Bamboo Rafting Tour in Montego Bay with Limestone Foot Massage

Purely Majestic Operators’ bamboo rafting tour stands out by combining breathtaking natural beauty with exceptional service and safety. Unlike typical tours, our experience emphasizes a...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$110

Jetskii & Bamboo River Rafting Tour from Montego Bay

Purely Majestic Operators’ jet ski and bamboo rafting tours stand out by offering a seamless blend of thrilling adventure and serene relaxation, all guided by …More

Montego Bay, Jamaica

5.0 (1)

Jetskii & Bamboo River Rafting Tour from Montego Bay

Purely Majestic Operators’ jet ski and bamboo rafting tours stand out by offering a seamless blend of thrilling adventure and serene relaxation, all guided by...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$240

Barbados Carlisle Bay Shipwreck Snorkeling Tour

Shipwrecks in Barbados serve as artificial reefs, attracting a stunning variety of fish, coral, and other sea creatures. This creates a vibrant underwater ecosystem perfect …More

5.0 (1)

Barbados Carlisle Bay Shipwreck Snorkeling Tour

Shipwrecks in Barbados serve as artificial reefs, attracting a stunning variety of fish, coral, and other sea creatures. This creates a vibrant underwater ecosystem perfect...

1 hour Free Cancellation

5.0 (1)

from
$40

Experience the ultimate Caribbean adventure with the Caribbean Sea and Blue Lagoon Tour. What makes this tour truly unique is its access to the only …More

Punta Cana, Dominican Republic

5.0 (1)

Caribbean Sea and Blue Lagoon

Experience the ultimate Caribbean adventure with the Caribbean Sea and Blue Lagoon Tour. What makes this tour truly unique is its access to the only...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$139

Snorkel And Beach Hopping Private Boat Tour from Ocho Rios

The Ultimate Private Snorkel and Beach Hopping Ocho Rios,Jamaica Cruise shore Excursions and Day Tour Private Snorkel is the exclusive boat charter for up to 6 …More

Ocho Rios, Jamaica

5.0 (1)

Snorkel And Beach Hopping Private Boat Tour from Ocho Rios

The Ultimate Private Snorkel and Beach Hopping Ocho Rios,Jamaica Cruise shore Excursions and Day Tour Private Snorkel is the exclusive boat charter for up to 6...

4 hours Free Cancellation

5.0 (1)

from
$1,555

Punta Cana Private Yacht to Saona Island, Snorkel & Natural Pool

Enjoy an 8-hour private yacht tour to Saona or Catalina Island. Snorkel, relax with premium amenities, and customize your experience. Perfect for up to 15 …More

Punta Cana, Dominican Republic

5.0 (1)

Punta Cana Private Yacht to Saona Island, Snorkel & Natural Pool

Enjoy an 8-hour private yacht tour to Saona or Catalina Island. Snorkel, relax with premium amenities, and customize your experience. Perfect for up to 15...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,400

South Coast Tour Black River & YS Waterfalls

Ready for an unforgettable Jamaican adventure? Cruise through lush hills and villages en route to the South Coast! Start with a thrilling Black River safari, …More

Montego Bay, Jamaica

5.0 (1)

South Coast Tour Black River & YS Waterfalls

Ready for an unforgettable Jamaican adventure? Cruise through lush hills and villages en route to the South Coast! Start with a thrilling Black River safari,...

6 to 12 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$150

Rockland Birds Sanctuary & Bamboo Rafting With Limestone Massage

Booking a bird sanctuary and bamboo rafting combo tour offers a unique blend of tranquility, natural beauty, and adventure, making it an unforgettable experience for …More

Lucea, Jamaica

5.0 (1)

Rockland Birds Sanctuary & Bamboo Rafting With Limestone Massage

Booking a bird sanctuary and bamboo rafting combo tour offers a unique blend of tranquility, natural beauty, and adventure, making it an unforgettable experience for...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$162

Luminous Lagoon & River Tubing Falmouth from Montego Bay/Falmouth

Mystic Lagoon Tours is situated along the banks of The Luminous Lagoon, considered one of the most spectacular natural phenomena in the world. The Lagoon …More

Montego Bay, Jamaica

4.2 (5)

Luminous Lagoon & River Tubing Falmouth from Montego Bay/Falmouth

Mystic Lagoon Tours is situated along the banks of The Luminous Lagoon, considered one of the most spectacular natural phenomena in the world. The Lagoon...

5 to 6 hours Hotel pickup offered Free Cancellation

4.2 (5)

from
$29

Private Luxury Dinner Cruise “Sail & Dine”

Different to other tour operators the Corsair is an able sailing ship – Sails will be set according to the wind situation. Included on your …More

4.0 (1)

Private Luxury Dinner Cruise “Sail & Dine”

Different to other tour operators the Corsair is an able sailing ship – Sails will be set according to the wind situation. Included on your...

4 hours Free Cancellation

4.0 (1)

from
$950

Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds, …More

Ocho Rios, Jamaica

5.0 (1)

Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds,...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$99

Will give you an excellent opportunity to experience the fascinating nature of this country doing 3 excursion in one day for the best deal Experience …More

Punta Cana, Dominican Republic

4.5 (4)

Trial Pack Punta Cana

Will give you an excellent opportunity to experience the fascinating nature of this country doing 3 excursion in one day for the best deal Experience...

6 hours 30 minutes Hotel pickup offered Free Cancellation

4.5 (4)

from
$145

Dominican Republic: See Almost it ALL in 6 Days, 1st Class Custom Tours

You absolutely will not find another tour out there as packed with activities and attractions as this one, provided by CharlieTheTraveler. You will also not …More

Punta Cana, Dominican Republic

5.0 (1)

Dominican Republic: See Almost it ALL in 6 Days, 1st Class Custom Tours

You absolutely will not find another tour out there as packed with activities and attractions as this one, provided by CharlieTheTraveler. You will also not...

6 days

5.0 (1)

from
$2,963

BBQ and Slide on a Private Catamaran with Unlimited Drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip you …More

Punta Cana, Dominican Republic

4.7 (3)

BBQ and Slide on a Private Catamaran with Unlimited Drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip you...

4 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$1,100

Tour with Whale Watching in Samaná, Beach and Waterfall

The whale season only occurs once a year, in the winter time. For this reason it is important that tourists who are in the country …More

Punta Cana, Dominican Republic

5.0 (1)

Tour with Whale Watching in Samaná, Beach and Waterfall

The whale season only occurs once a year, in the winter time. For this reason it is important that tourists who are in the country...

12 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$115

AIDAperla, AIDAbella & AIDAdiva: Saona Island Shore Excursion

Created for AIDA cruise passengers calling at La Romana, this small-group shore excursion is timed to your ship's schedule. Whether you arrive aboard AIDAdiva, AIDAbella …More

4.7 (3)

AIDAperla, AIDAbella & AIDAdiva: Saona Island Shore Excursion

Created for AIDA cruise passengers calling at La Romana, this small-group shore excursion is timed to your ship's schedule. Whether you arrive aboard AIDAdiva, AIDAbella...

8 hours Free Cancellation

4.7 (3)

from
$139

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?

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

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?