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

Blue Parrot Snorkel Sail with 4 course lunch or dinner in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! What ever your desires, the crew of the …More

Palm - Eagle Beach, Aruba

5.0 (8)

Blue Parrot Snorkel Sail with 4 course lunch or dinner in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! What ever your desires, the crew of the...

4 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$1,919

We offer Sailing based on the wind speed, transportation to and from your hotel, and the all-inclusive bar along, the trip itself is 3 hours …More

Nassau, Bahamas

4.2 (20)

All Inclusive Half Day Sail and Snorkel

We offer Sailing based on the wind speed, transportation to and from your hotel, and the all-inclusive bar along, the trip itself is 3 hours...

5 hours Hotel pickup offered Free Cancellation

4.2 (20)

from
$165

Learn how to operate and sail a Hobie Cat Wave or Hobie Cat Getaway like a true skipper. Your expert teacher will be a certified …More

4.5 (10)

Hobie Cat Sailing Lesson

Learn how to operate and sail a Hobie Cat Wave or Hobie Cat Getaway like a true skipper. Your expert teacher will be a certified...

1 hour 30 minutes Free Cancellation

4.5 (10)

from
$145

Private Stingray City Snorkeling Half Day Charter for 10 Guests

Make lasting memories and avoid the crowds with a completely private, full day boat charter in the crystal blue waters of Grand Cayman. Your 2-person …More

Grand Cayman, Cayman Islands

5.0 (13)

Private Stingray City Snorkeling Half Day Charter for 10 Guests

Make lasting memories and avoid the crowds with a completely private, full day boat charter in the crystal blue waters of Grand Cayman. Your 2-person...

4 hours

5.0 (13)

from
$1,200

Starfish Encounter & Mangrove Exploration in Grand Cayman

• Our starfish and mangrove tour in Grand Cayman stands out for its unique blend of adventure and ecological discovery. • Navigate through tranquil mangrove …More

Grand Cayman, Cayman Islands

5.0 (2)

Starfish Encounter & Mangrove Exploration in Grand Cayman

• Our starfish and mangrove tour in Grand Cayman stands out for its unique blend of adventure and ecological discovery. • Navigate through tranquil mangrove...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$140

Iguana Island is in the Turks and Caicos Islands, a UK Overseas Territory situated south of the Bahamas in the Caribbean. Managed by the Turks …More

4.8 (38)

Mangrove Cay and Iguana Island Tours

Iguana Island is in the Turks and Caicos Islands, a UK Overseas Territory situated south of the Bahamas in the Caribbean. Managed by the Turks...

3 hours Hotel pickup offered

4.8 (38)

from
$150

4 Hours Party Boat Catamaran Cruise in Negril

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from …More

Montego Bay, Jamaica

5.0 (11)

4 Hours Party Boat Catamaran Cruise in Negril

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$120

Party Boat in Punta Cana with Drinks and Transportation Included

Hop aboard a beautiful catamaran bound for the coast of Bavaria and enjoy this half-day boat tour that includes snorkeling, dancing and alcoholic and non-alcoholic …More

Punta Cana, Dominican Republic

4.3 (4)

Party Boat in Punta Cana with Drinks and Transportation Included

Hop aboard a beautiful catamaran bound for the coast of Bavaria and enjoy this half-day boat tour that includes snorkeling, dancing and alcoholic and non-alcoholic...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.3 (4)

from
$58

PRIVATE: 3in1 - Los Haitises N.P. + Y. Waterfall + Mount. Redonda

PRIVATE TOUR: You're about to live your best and unique experience of a full day trip exploring Los Haitises National Park, hiking its rainforests used …More

Punta Cana, Dominican Republic

4.6 (11)

PRIVATE: 3in1 - Los Haitises N.P. + Y. Waterfall + Mount. Redonda

PRIVATE TOUR: You're about to live your best and unique experience of a full day trip exploring Los Haitises National Park, hiking its rainforests used...

12 to 14 hours Hotel pickup offered Free Cancellation

4.6 (11)

from
$149

Discover the best of the Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or …More

5.0 (7)

Private Morning Tour Fjord 38 Ben

Discover the best of the Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or...

4 hours Free Cancellation

5.0 (7)

from
$1,990

Dunn's River Falls Catamaran Cruise, Ocho Rios from Montego Bay

Step aboard the Chukka Cat and sail away with us along the coast of Ocho Rios. Experience Jamaica at its finest on our sixty-five foot …More

Montego Bay, Jamaica

4.7 (10)

Dunn's River Falls Catamaran Cruise, Ocho Rios from Montego Bay

Step aboard the Chukka Cat and sail away with us along the coast of Ocho Rios. Experience Jamaica at its finest on our sixty-five foot...

7 hours Free Cancellation

4.7 (10)

from
$149

Saona Island Full Day Tour Lunch and Transportation Included

You cannot miss this excursion to paradise, an unforgettable trip Once we are in Bayahibe we will take a speedboat to start the trip to …More

Punta Cana, Dominican Republic

3.3 (6)

Saona Island Full Day Tour Lunch and Transportation Included

You cannot miss this excursion to paradise, an unforgettable trip Once we are in Bayahibe we will take a speedboat to start the trip to...

9 hours Hotel pickup offered Free Cancellation

3.3 (6)

from
$75

Sail and cruise in the Caribbean sea on your own private Boat, Snorkel in a natural reserve, try Paddle Boarding, enjoy landscapes of virgin beaches, …More

5.0 (7)

Punta Cana Private Sailing Experience

Sail and cruise in the Caribbean sea on your own private Boat, Snorkel in a natural reserve, try Paddle Boarding, enjoy landscapes of virgin beaches,...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (7)

from
$889

Full-Day Cruise to Saona Island - Natural Pool and Lunch

Discover a dynamic way of getting to know Isla Saona on an excursion sailing the sea by catamaran and speedboat while enjoying the sun and …More

Punta Cana, Dominican Republic

4.2 (55)

Full-Day Cruise to Saona Island - Natural Pool and Lunch

Discover a dynamic way of getting to know Isla Saona on an excursion sailing the sea by catamaran and speedboat while enjoying the sun and...

10 hours 30 minutes Hotel pickup offered Free Cancellation

4.2 (55)

from
$75

Luxury Catamaran, Snorkel and Dining Experience Barbados

Enjoy a luxury shared catamaran cruise along Barbados’ stunning coast. Create lasting memories on this experience that whisks you away from magnificent Caribbean shores into …More

Saint Joseph Parish, Barbados

4.8 (25)

Luxury Catamaran, Snorkel and Dining Experience Barbados

Enjoy a luxury shared catamaran cruise along Barbados’ stunning coast. Create lasting memories on this experience that whisks you away from magnificent Caribbean shores into...

5 hours Hotel pickup offered

4.8 (25)

from
$316

Sailing has sensation. Come live an unforgettable experience on a sailboat. A timeless adventure aboard our sailboat. Come hoist the sails on the Caribbean Sea …More

5.0 (11)

Half-Day Sailing Boat Adventure

Sailing has sensation. Come live an unforgettable experience on a sailboat. A timeless adventure aboard our sailboat. Come hoist the sails on the Caribbean Sea...

4 hours Free Cancellation

5.0 (11)

from
$124

Discover Sosua's Underwater World & Beach Day

Enjoy the underwater world in Sosua, we will take you out by boat to two different Snorkeling Reefs. We provide with the snorkeling equipment and …More

Cabarete, Dominican Republic

4.8 (13)

Discover Sosua's Underwater World & Beach Day

Enjoy the underwater world in Sosua, we will take you out by boat to two different Snorkeling Reefs. We provide with the snorkeling equipment and...

5 to 6 hours Hotel pickup offered Free Cancellation

4.8 (13)

from
$66

1/2 Day Private Catamaran out of Soufriere

Designed for those who want to move at their own pace and see the West Coast of St. Lucia. This half day coastal cruise allows …More

Soufriere, St Lucia

4.9 (9)

1/2 Day Private Catamaran out of Soufriere

Designed for those who want to move at their own pace and see the West Coast of St. Lucia. This half day coastal cruise allows...

4 hours Hotel pickup offered Free Cancellation

4.9 (9)

from
$2,340

Blue Hole Waterfalls + Bamboo River Rafting Tour from Ocho Rios

This tour is unique because of the guides we use and the way how information is given to the people, also the prices are the …More

Ocho Rios, Jamaica

4.8 (21)

Blue Hole Waterfalls + Bamboo River Rafting Tour from Ocho Rios

This tour is unique because of the guides we use and the way how information is given to the people, also the prices are the...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (21)

from
$94

Private Clear Boat experience in Grace Bay

Come aboard our truly unique 100% Clear Boats. These are NOT your average glass bottom boat but a 100% clear boat. This tour is for …More

5.0 (5)

Private Clear Boat experience in Grace Bay

Come aboard our truly unique 100% Clear Boats. These are NOT your average glass bottom boat but a 100% clear boat. This tour is for...

1 hour 15 minutes Free Cancellation

5.0 (5)

from
$1,299

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?