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 →

Private Full Day or Half Day Charter - 37' Midnight Express

Experience dual-country boat trips, explore numerous popular destinations with our 37' Midnight Express – a distinctive blue and white vessel powered by 3x 300HP outboards. …More

Cruz Bay, US Virgin Islands

5.0 (3)

Private Full Day or Half Day Charter - 37' Midnight Express

Experience dual-country boat trips, explore numerous popular destinations with our 37' Midnight Express – a distinctive blue and white vessel powered by 3x 300HP outboards....

4 to 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,000

Swimming Pigs, turtles, snorkeling rose island reef.

It's more than a tour, it’s an adventure! Discover the extraordinary! Unlike other tour companies, we redefine exploration by offering a unique 3-island journey. Start …More

Nassau, Bahamas

5.0 (12)

Swimming Pigs, turtles, snorkeling rose island reef.

It's more than a tour, it’s an adventure! Discover the extraordinary! Unlike other tour companies, we redefine exploration by offering a unique 3-island journey. Start...

4 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$215

Crystal Bay Exuma Private Boat Tours & Fishing Charters

Our services are the private boat tour and fishing charter which allows the comfort and bliss of knowing you can enjoy your dream vacation in …More

Great Exuma, Bahamas

5.0 (12)

Crystal Bay Exuma Private Boat Tours & Fishing Charters

Our services are the private boat tour and fishing charter which allows the comfort and bliss of knowing you can enjoy your dream vacation in...

4 to 8 hours Free Cancellation

5.0 (12)

from
$266

Bioluminescent Night Kayaking with Transport from San Juan 4pm

Feel the anticipation of exploring a new place, will escort you on a memorable journey to the mangrove forest of Laguna Grande where you will …More

Isla Verde, Puerto Rico

4.4 (31)

Bioluminescent Night Kayaking with Transport from San Juan 4pm

Feel the anticipation of exploring a new place, will escort you on a memorable journey to the mangrove forest of Laguna Grande where you will...

2 hours Hotel pickup offered Free Cancellation

4.4 (31)

from
$115

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private …More

Cruz Bay, US Virgin Islands

5.0 (13)

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private...

2 to 3 hours Free Cancellation

5.0 (13)

from
$1,000

Get ready for the most exciting experience of your life! Cayo Arena, whose real name is Cayo Paraiso is a coral island situated to the …More

Cabarete, Dominican Republic

4.4 (11)

Cayo Arena Day Trip from Puerto Plata

Get ready for the most exciting experience of your life! Cayo Arena, whose real name is Cayo Paraiso is a coral island situated to the...

10 hours Hotel pickup offered Free Cancellation

4.4 (11)

from
$95

Bamboo Rafting With Limestone Foot Massage

Are you ready to immerse yourself in nature's tranquility while indulging in an unforgettable adventure? Look no further than Premier Transfers and Tours for the …More

Montego Bay, Jamaica

5.0 (14)

Bamboo Rafting With Limestone Foot Massage

Are you ready to immerse yourself in nature's tranquility while indulging in an unforgettable adventure? Look no further than Premier Transfers and Tours for the...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (14)

from
$115

Lunch Seafari to pristine cays, shipwreck and lunch at TIKI BAR

The thee hour Jet ski excursion will allow you to visit the La famille express a general Cargo ship that run a ground in 2004, …More

4.8 (5)

Lunch Seafari to pristine cays, shipwreck and lunch at TIKI BAR

The thee hour Jet ski excursion will allow you to visit the La famille express a general Cargo ship that run a ground in 2004,...

3 hours Free Cancellation

4.8 (5)

from
$534

All Inclusive Saône Island, Lunch + Drinks + Transportation

Live an unforgettable day in the Caribbean. From your hotel, you will travel by bus to Bayahibe, where you will board a catamaran with music …More

Punta Cana, Dominican Republic

4.7 (22)

All Inclusive Saône Island, Lunch + Drinks + Transportation

Live an unforgettable day in the Caribbean. From your hotel, you will travel by bus to Bayahibe, where you will board a catamaran with music...

6 to 8 hours Hotel pickup offered Free Cancellation

4.7 (22)

from
$71

Samana Full-Day Tour from Punta Cana: Waterfall & Bacardi Beach

Discover the natural beauty of the Samaná Peninsula on a full-day adventure from Punta Cana combining tropical landscapes, local culture, and some of the Dominican …More

Punta Cana, Dominican Republic

4.4 (22)

Samana Full-Day Tour from Punta Cana: Waterfall & Bacardi Beach

Discover the natural beauty of the Samaná Peninsula on a full-day adventure from Punta Cana combining tropical landscapes, local culture, and some of the Dominican...

10 to 11 hours Hotel pickup offered Free Cancellation

4.4 (22)

from
$115

Dunns River Falls & Blue Hole Combo Trip from Montego Bay

Guaranteed to have a fun-filled action-packed day, with the tour combination of the Blue Hole and Dunn's River Falls and Park. At Blue Hole you …More

Montego Bay, Jamaica

5.0 (5)

Dunns River Falls & Blue Hole Combo Trip from Montego Bay

Guaranteed to have a fun-filled action-packed day, with the tour combination of the Blue Hole and Dunn's River Falls and Park. At Blue Hole you...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$118

Private Catamaran Sunset Cruise in Turks and Caicos

Join us on this fully customizable private catamaran sunset cruise in the beautiful Grace Bay in Turks and Caicos. This memorable excursion will depart from …More

4.8 (4)

Private Catamaran Sunset Cruise in Turks and Caicos

Join us on this fully customizable private catamaran sunset cruise in the beautiful Grace Bay in Turks and Caicos. This memorable excursion will depart from...

2 hours Free Cancellation

4.8 (4)

from
$1,650

4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food

This 47 foot catamaran is the luxurious way to experience Montego Bay by sea. Guests can enjoy an indoor, air-conditioned cabin with a full premium …More

5.0 (18)

4hr Private Luxury Yacht with Snorkeling, DJ, Bar, Food

This 47 foot catamaran is the luxurious way to experience Montego Bay by sea. Guests can enjoy an indoor, air-conditioned cabin with a full premium...

4 hours Free Cancellation

5.0 (18)

from
$4,300

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

Outtaheretours is led by a team of Sailors,Divers, Instructors and Seaman with many years working in Aquatic Tourism. We are positive that nothing short of …More

Fajardo, Puerto Rico

5.0 (11)

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

Outtaheretours is led by a team of Sailors,Divers, Instructors and Seaman with many years working in Aquatic Tourism. We are positive that nothing short of...

3 to 5 hours Free Cancellation

5.0 (11)

from
$850

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Take a break from the beaches of Punta Cana and spend an unforgettable day exploring Saona Island, one of the Dominican Republic’s most beautiful natural …More

Punta Cana, Dominican Republic

4.3 (44)

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Take a break from the beaches of Punta Cana and spend an unforgettable day exploring Saona Island, one of the Dominican Republic’s most beautiful natural...

9 hours Hotel pickup offered Free Cancellation

4.3 (44)

from
$78

Bamboo Rafting & Limestone Foot Massage from Montego Bay

This is a very relaxing tour, full of nature and serenity, that will leave you yearning for more, as you cruise down the magnificent “Great …More

Montego Bay, Jamaica

5.0 (12)

Bamboo Rafting & Limestone Foot Massage from Montego Bay

This is a very relaxing tour, full of nature and serenity, that will leave you yearning for more, as you cruise down the magnificent “Great...

1 hour 30 minutes Hotel pickup offered Free Cancellation

5.0 (12)

from
$115

The trip Includes : a snorkel to see the marine life of Punta Cana in the "Sanctuary Reef" and anchor in a sandbar of 3-4 …More

Punta Cana, Dominican Republic

5.0 (16)

Cap Cana Private Family Catamaran

The trip Includes : a snorkel to see the marine life of Punta Cana in the "Sanctuary Reef" and anchor in a sandbar of 3-4...

3 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$950

Catamaran and Snorkeling Cruise At Carlisle Bay

Enjoy a luxurious catamaran cruise in Barbados and sail along the gorgeous crystalline coastline. Swim and snorkel near a shallow shipwreck teeming with brilliantly hued tropical marine …More

Saint Joseph Parish, Barbados

4.6 (32)

Catamaran and Snorkeling Cruise At Carlisle Bay

Enjoy a luxurious catamaran cruise in Barbados and sail along the gorgeous crystalline coastline. Swim and snorkel near a shallow shipwreck teeming with brilliantly hued tropical marine...

5 hours Hotel pickup offered

4.6 (32)

from
$146

Your 4-hours glass bottom boat and reef adventure from Punta Cana begins by meeting your friendly local guide at your hotel in Punta Cana and …More

Punta Cana, Dominican Republic

4.4 (14)

Glass Bottom Boat in Punta Cana

Your 4-hours glass bottom boat and reef adventure from Punta Cana begins by meeting your friendly local guide at your hotel in Punta Cana and...

4 hours Hotel pickup offered Free Cancellation

4.4 (14)

from
$65

Bamboo Rafting, Margaritaville & Sightseeing Tour In Ocho Rios

One of the most calming and relaxing experience you can have in Jamaica is rafting on the White River. Located in the parish of St …More

Ocho Rios, Jamaica

5.0 (7)

Bamboo Rafting, Margaritaville & Sightseeing Tour In Ocho Rios

One of the most calming and relaxing experience you can have in Jamaica is rafting on the White River. Located in the parish of St...

3 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$65

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?