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 →

Our Party Boat tour in Punta Cana is special because it combines adventure and fun in a paradisiacal environment. For three hours, you will enjoy …More

Punta Cana, Dominican Republic

5.0 (1)

Open Party Boat in Punta Cana

Our Party Boat tour in Punta Cana is special because it combines adventure and fun in a paradisiacal environment. For three hours, you will enjoy...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$59

Experience grouper fishing with Grand Cayman’s #1 Grouper Fishing Charter Company! Unlike ordinary fishing charters, we specialize in offshore grouper fishing, taking guests on an …More

Grand Cayman, Cayman Islands

5.0 (1)

Offshore Grouper fishing

Experience grouper fishing with Grand Cayman’s #1 Grouper Fishing Charter Company! Unlike ordinary fishing charters, we specialize in offshore grouper fishing, taking guests on an...

5 hours Free Cancellation

5.0 (1)

from
$1,500

Full Day Island Tour in Isla Saona from Punta Cana

Start your day with an exciting journey by catamaran and speedboat to the famous Saona Island. Enjoy panoramic views of the Caribbean Sea as we …More

Punta Cana, Dominican Republic

3.9 (7)

Full Day Island Tour in Isla Saona from Punta Cana

Start your day with an exciting journey by catamaran and speedboat to the famous Saona Island. Enjoy panoramic views of the Caribbean Sea as we...

10 hours Hotel pickup offered Free Cancellation

3.9 (7)

from
$68

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a …More

Ocho Rios, Jamaica

5.0 (1)

All day Tour of Ocho Rios

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a...

2 days Hotel pickup offered

5.0 (1)

from
$250

Saona Island Speedboat Tour with Altos de Chavón from Punta Cana

This activity seeks to offer travelers the combination of fun with culture, since we combine the visit to Altos de Chavón with the excursion to …More

Punta Cana, Dominican Republic

3.3 (11)

Saona Island Speedboat Tour with Altos de Chavón from Punta Cana

This activity seeks to offer travelers the combination of fun with culture, since we combine the visit to Altos de Chavón with the excursion to...

10 hours Hotel pickup offered Free Cancellation

3.3 (11)

from
$99

Half Day Party Boat and Snorkeling in Punta Cana

What makes our experience unique is the perfect mix of Caribbean rhythm, crystal-clear waters, and true Dominican hospitality. Our goal is always your happiness — …More

Punta Cana, Dominican Republic

4.5 (4)

Half Day Party Boat and Snorkeling in Punta Cana

What makes our experience unique is the perfect mix of Caribbean rhythm, crystal-clear waters, and true Dominican hospitality. Our goal is always your happiness —...

4 hours Hotel pickup offered Free Cancellation

4.5 (4)

from
$49

Sunset Cruise in Punta Cana: Private Catamaran w/ BBQ & Open Bar

Savor in romance and relaxation aboard our exclusive private sunset catamaran cruise in Punta Cana, Bávaro. Sail along the scenic coastline as the sun sets, …More

Punta Cana, Dominican Republic

5.0 (1)

Sunset Cruise in Punta Cana: Private Catamaran w/ BBQ & Open Bar

Savor in romance and relaxation aboard our exclusive private sunset catamaran cruise in Punta Cana, Bávaro. Sail along the scenic coastline as the sun sets,...

3 hours 30 minutes Hotel pickup offered

5.0 (1)

from
$169

Bavaro Catamaran: Sail, Snorkel & Party with Drinks and Snacks

Experience the ultimate Bavaro Coast Cruise adventure in Punta Cana! Sail in a comfortable luxury catamaran, enjoy drinks, animation, and snorkeling. Cruise along beautiful Bavaro's …More

Punta Cana, Dominican Republic

5.0 (1)

Bavaro Catamaran: Sail, Snorkel & Party with Drinks and Snacks

Experience the ultimate Bavaro Coast Cruise adventure in Punta Cana! Sail in a comfortable luxury catamaran, enjoy drinks, animation, and snorkeling. Cruise along beautiful Bavaro's...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$105

River Tubing, Dunns River Falls & ZipLine tour from Montego Bay

A river tubing, zip line, and Dunn's River Falls tour is an exciting and adventurous excursion that combines three thrilling activities in one. First, you …More

Montego Bay, Jamaica

5.0 (1)

River Tubing, Dunns River Falls & ZipLine tour from Montego Bay

A river tubing, zip line, and Dunn's River Falls tour is an exciting and adventurous excursion that combines three thrilling activities in one. First, you...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$269

ATV, Bamboo Rafting & Horseback Riding from Montego Bay

Experience the thrill of ATV, bamboo rafting, and horseback riding on our combo tour in Jamaica. Escape your resort and discover the island's beauty. Sit …More

Montego Bay, Jamaica

5.0 (1)

ATV, Bamboo Rafting & Horseback Riding from Montego Bay

Experience the thrill of ATV, bamboo rafting, and horseback riding on our combo tour in Jamaica. Escape your resort and discover the island's beauty. Sit...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$112

Anamuya Mountains Small Group Walking Tour

Take a walk on the wild side with a tour of the Dominican Republic's rugged Anamuya Mountains. See a snapshot of rural life as shown …More

Punta Cana, Dominican Republic

4.0 (3)

Anamuya Mountains Small Group Walking Tour

Take a walk on the wild side with a tour of the Dominican Republic's rugged Anamuya Mountains. See a snapshot of rural life as shown...

4 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$49

Blue Waterfalls (Bassin Bleu) adventures from Jacmel, Haiti

Get ready for the thrill of a lifetime! Nestled in the hills of the Southern of Haiti lies a treasure you won’t likely find anywhere …More

4.5 (2)

Blue Waterfalls (Bassin Bleu) adventures from Jacmel, Haiti

Get ready for the thrill of a lifetime! Nestled in the hills of the Southern of Haiti lies a treasure you won’t likely find anywhere...

6 hours Free Cancellation

4.5 (2)

from
$60

Grand Cayman: Stingray City and Snorkeling with Beach Lunch

One incredible half-day. Different sides of Grand Cayman. One unforgettable Caribbean adventure. Step into the warm, crystal-clear shallows of Stingray City, where majestic southern stingrays …More

Grand Cayman, Cayman Islands

5.0 (1)

Grand Cayman: Stingray City and Snorkeling with Beach Lunch

One incredible half-day. Different sides of Grand Cayman. One unforgettable Caribbean adventure. Step into the warm, crystal-clear shallows of Stingray City, where majestic southern stingrays...

5 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$189

Yacht Charter/Excursion Party Boat with Open Bar in Punta Cana

PICAFLOR is a 37 foot yatch, will all the comforts including aircondioning, bathroom, two showers (hot & cold water), two beds, kitchen, barb b que. …More

Punta Cana, Dominican Republic

5.0 (1)

Yacht Charter/Excursion Party Boat with Open Bar in Punta Cana

PICAFLOR is a 37 foot yatch, will all the comforts including aircondioning, bathroom, two showers (hot & cold water), two beds, kitchen, barb b que....

3 hours Free Cancellation

5.0 (1)

from
$1,350

Dunns River and Blue Hole Day trip from Montego Bay

For One-4 person One of our professional and knowledgeable drivers will pick you up from your Hotel/Airbnb and take you to Dunns’ River fall and …More

5.0 (1)

Dunns River and Blue Hole Day trip from Montego Bay

For One-4 person One of our professional and knowledgeable drivers will pick you up from your Hotel/Airbnb and take you to Dunns’ River fall and...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$225

Private Tour to Paradise Island with Snorkel & Manatee Sanctuary

Paradise Island is one of the best places to visit in northern part of the Dominican Republic. If you like sun, azur water and white …More

Puerto Plata, Dominican Republic

5.0 (1)

Private Tour to Paradise Island with Snorkel & Manatee Sanctuary

Paradise Island is one of the best places to visit in northern part of the Dominican Republic. If you like sun, azur water and white...

9 to 10 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$109

Calypso Rafting Blue Hole and Scotchies Ocho Rios

We provide the best experience for visitors to Jamaica. With our passion, we can help you get the most out of your vacation. You’ll get …More

Ocho Rios, Jamaica

5.0 (1)

Calypso Rafting Blue Hole and Scotchies Ocho Rios

We provide the best experience for visitors to Jamaica. With our passion, we can help you get the most out of your vacation. You’ll get...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$170

Enjoy views of the Dominican Republic's east coast aboard a catamaran cruise from Punta Cana. Relax on board the boat and sip drinks from the …More

Punta Cana, Dominican Republic

5.0 (1)

Fiesta en el Mar: Party Boat Punta Cana

Enjoy views of the Dominican Republic's east coast aboard a catamaran cruise from Punta Cana. Relax on board the boat and sip drinks from the...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$45

Bamboo Rafting & Horseback -dunns river Transfer not included

Enjoy an authentic Bamboo Rafting with Limestone Massage Jamaica and create "Jungle Socks" that leave your skin feeling silky, smooth, and rejuvenated long after washing. …More

Montego Bay, Jamaica

4.2 (5)

Bamboo Rafting & Horseback -dunns river Transfer not included

Enjoy an authentic Bamboo Rafting with Limestone Massage Jamaica and create "Jungle Socks" that leave your skin feeling silky, smooth, and rejuvenated long after washing....

6 hours Hotel pickup offered Free Cancellation

4.2 (5)

from
$165

Saona Island Day Trip + Lobsters Included

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) …More

Punta Cana, Dominican Republic

4.2 (5)

Saona Island Day Trip + Lobsters Included

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve)...

8 hours Hotel pickup offered Free Cancellation

4.2 (5)

from
$225

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?