Top Caribbean Cruises, Sailing & Water Tours

Grand Cayman Private Custom Boating Adventure

We provide a variety of tour options accommodating guests that'd like to make one stop or see it all. Our team are all born and …More

Likely to Sell Out
Likely to Sell Out
Grand Cayman, Cayman Islands

We provide a variety of tour options accommodating guests that'd like to make one stop or see it all. Our team are all born and...

2 to 6 hours Free Cancellation
5.0 (10)
from
$599
Be Happy - Full Day Private Catamaran Cruise - St Maarten

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

Likely to Sell Out
Likely to Sell Out

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

8 hours Free Cancellation
5.0 (9)
from
$235
Taiguey Emotion Show

Taigüey Emotion Show, a unique and unforgettable experience. Enjoy sailing through the amazing crystal clear coast of Punta Cana, with a stop at the magnificent …More

Punta Cana, Dominican Republic

Taigüey Emotion Show, a unique and unforgettable experience. Enjoy sailing through the amazing crystal clear coast of Punta Cana, with a stop at the magnificent...

4 hours Hotel pickup offered Free Cancellation
4.6 (97)
from
$67
PARTY BOAT - Private Sailing Catamaran

Enjoy and incredible 75 passenger Sailing Catamaran just for your family or friends. Focused on customers who want to enjoy a cruise along the coast …More

Enjoy and incredible 75 passenger Sailing Catamaran just for your family or friends. Focused on customers who want to enjoy a cruise along the coast...

3 hours Hotel pickup offered Free Cancellation
5.0 (70)
from
$750
Brunch & Snorkel Catamaran Tour

An unique experience on the water for young and old! Enjoy an unforgettable morning on our sailing catamaran, cruising along the coasts of Bonaire and …More

An unique experience on the water for young and old! Enjoy an unforgettable morning on our sailing catamaran, cruising along the coasts of Bonaire and...

4 hours 30 minutes
5.0 (77)
from
$130
Private Aruba Kayak & Snorkeling Tour + Transortation

If you love the Ocean and adventure, Kayak is one of the best options to explore Aruba's untouched Southside coastline and enjoy its beautiful Coral …More

Likely to Sell Out
Likely to Sell Out
Paradera, Aruba

If you love the Ocean and adventure, Kayak is one of the best options to explore Aruba's untouched Southside coastline and enjoy its beautiful Coral...

2 to 3 hours Hotel pickup offered Free Cancellation
4.8 (12)
from
$155
Tobago Buccoo Reef Glass Bottom Boat Tour

Explore the underwater world of Buccoo Reef! Sea grass, exotic fish, coral garden – it's all viewable from your large covered glass bottom boat (Dry or …More

Explore the underwater world of Buccoo Reef! Sea grass, exotic fish, coral garden – it's all viewable from your large covered glass bottom boat (Dry or...

3 hours 30 minutes Hotel pickup offered Free Cancellation
4.3 (75)
from
$78
Bamboo Rafting and Limestone Massage in Montego Bay

Escape your hotel resort and discover the true beauty of Jamaica with an unforgettable bamboo rafting experience. Glide through lush rainforests on a traditional bamboo …More

Montego Bay, Jamaica

Escape your hotel resort and discover the true beauty of Jamaica with an unforgettable bamboo rafting experience. Glide through lush rainforests on a traditional bamboo...

2 to 3 hours Hotel pickup offered Free Cancellation
4.5 (16)
from
$69
Lethe Bamboo Rafting with Limestone Massage Montego Bay Jamaica

This experience offers a perfect blend of relaxation, culture, and natural beauty, making it one of the most unique and peaceful tours in Montego Bay. …More

Montego Bay, Jamaica

This experience offers a perfect blend of relaxation, culture, and natural beauty, making it one of the most unique and peaceful tours in Montego Bay....

2 to 3 hours Hotel pickup offered Free Cancellation
4.6 (19)
from
$56
Antigua Sunset Catamaran Cruise From St. John's

Set sail on a one-of-a-kind tropical sunset cruise to experience the spectacular Antiguan sunset. Once aboard the catamaran enjoy a welcome cocktail as you take …More

Set sail on a one-of-a-kind tropical sunset cruise to experience the spectacular Antiguan sunset. Once aboard the catamaran enjoy a welcome cocktail as you take...

2 hours 30 minutes Hotel pickup offered
4.6 (85)
from
$141
Private Morning Half-Day Snorkeling Trip

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy …More

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy...

2 to 4 hours
5.0 (27)
from
$2,540
Private 4 hour Catamaran Tour

Are you and your group seeking a private catamaran experience, tailored to your preferences, without sharing it with other guests? Look no further – our …More

Grand Cayman, Cayman Islands

Are you and your group seeking a private catamaran experience, tailored to your preferences, without sharing it with other guests? Look no further – our...

4 hours Hotel pickup offered Free Cancellation
4.7 (18)
from
$1,499
Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some …More

Likely to Sell Out
Likely to Sell Out

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some...

6 hours Free Cancellation
5.0 (16)
from
$1,650
Private, Skippered Catamaran Day Trip in Grenada

With this 7-hour Day Trip, you will enjoy the most beautiful sights of the south coast of Grenada onboard our luxury catamaran. The boat is …More

With this 7-hour Day Trip, you will enjoy the most beautiful sights of the south coast of Grenada onboard our luxury catamaran. The boat is...

7 hours
4.9 (74)
from
$1,350
Experience Full Day Tour of Tropical Bliss at Isla Saona

Experience Paradise at Isla Saona! If you’re looking for a unique Caribbean adventure, our Isla Saona excursion is the perfect choice. Set sail on a …More

Punta Cana, Dominican Republic

Experience Paradise at Isla Saona! If you’re looking for a unique Caribbean adventure, our Isla Saona excursion is the perfect choice. Set sail on a...

6 hours Hotel pickup offered Free Cancellation
4.3 (18)
from
$89
Sail and Snorkel at Cades Reef

Enjoy the majestic views as you travel down the southern coast of the island. A stop will be made at Cades Reef for the opportunity to snorkel …More

Enjoy the majestic views as you travel down the southern coast of the island. A stop will be made at Cades Reef for the opportunity to snorkel...

6 hours Free Cancellation
4.5 (74)
from
$115
Saona Island Catamaran Adventure with Free Food and Transportation

You will take the experience of a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment …More

Punta Cana, Dominican Republic

You will take the experience of a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment...

9 hours Hotel pickup offered Free Cancellation
3.8 (32)
from
$75
Jungle River Safari Shore Excursion | Taino Bay & Amber Cove

What makes this guided tour special is the opportunity to experience the natural beauty of Cabarete from a different perspective, traveling by boat through the …More

Cabarete, Dominican Republic

What makes this guided tour special is the opportunity to experience the natural beauty of Cabarete from a different perspective, traveling by boat through the...

4 hours Hotel pickup offered Free Cancellation
4.6 (19)
from
$95
Saona Island Tour Catamaran Buffet Lunch & Full Day Trip

Isla Saona is not only a beautiful natural place, but it also has a very interesting history. For the Taínos, indigenous inhabitants of the island, …More

Punta Cana, Dominican Republic

Isla Saona is not only a beautiful natural place, but it also has a very interesting history. For the Taínos, indigenous inhabitants of the island,...

8 hours Hotel pickup offered Free Cancellation
3.9 (13)
from
$75
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

Likely to Sell Out
Likely to Sell Out

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

Frequently Asked Questions

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

Recent tour reviews
Activity name

Discover Caribbean