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 →

Let’s get out of the crowds and enjoy of the attractions of the Dominican Republic by doing it privately. Say goodbye to making big lines …More

Punta Cana, Dominican Republic

4.7 (50)

Private Saona Island Excursion

Let’s get out of the crowds and enjoy of the attractions of the Dominican Republic by doing it privately. Say goodbye to making big lines...

8 to 9 hours Hotel pickup offered Free Cancellation

4.7 (50)

from
$990

Private Yacht in Punta Cana, Unlimited Drinks and HipHop Music

Our 37 foot yacht is the ONLY one in Bavaro, Punta Cana. As you can expect, Picaflor comes equipped with air conditioner, plasma TV, bathroom, …More

Punta Cana, Dominican Republic

4.9 (21)

Private Yacht in Punta Cana, Unlimited Drinks and HipHop Music

Our 37 foot yacht is the ONLY one in Bavaro, Punta Cana. As you can expect, Picaflor comes equipped with air conditioner, plasma TV, bathroom,...

3 hours Free Cancellation

4.9 (21)

from
$1,150

Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica

This is one of the many wonders of the world. A beautiful night swim activity that all travelers to Jamaica must experience at-lease once. …More

Montego Bay, Jamaica

4.6 (58)

Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica

This is one of the many wonders of the world. A beautiful night swim activity that all travelers to Jamaica must experience at-lease once....

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.6 (58)

from
$80

This nature tour takes you in an open flat-bottomed boat into the famous Caroni Wetlands with open lagoons and waterways and a beautiful scenery of …More

4.7 (50)

Sunset Boat Tour into Caroni Wetlands

This nature tour takes you in an open flat-bottomed boat into the famous Caroni Wetlands with open lagoons and waterways and a beautiful scenery of...

4 hours Hotel pickup offered Free Cancellation

4.7 (50)

from
$67

Yacht YES DARLING - Private Boat St Martin, St Barth & Anguilla

Discover YES DARLING, a 20m open yacht with a unique Italian style, decorated with a legendary Porsche 917 theme, and experience an exceptional private experience …More

4.9 (34)

Yacht YES DARLING - Private Boat St Martin, St Barth & Anguilla

Discover YES DARLING, a 20m open yacht with a unique Italian style, decorated with a legendary Porsche 917 theme, and experience an exceptional private experience...

4 to 8 hours Free Cancellation

4.9 (34)

from
$6,163

Private Bamboo Rafting and Limestone Massage In Montego Bay

Escape the confines of your hotel resort and come experience the true beauty and uniqueness of the island of Jamaica. This is a must do …More

Lucea, Jamaica

4.9 (29)

Private Bamboo Rafting and Limestone Massage In Montego Bay

Escape the confines of your hotel resort and come experience the true beauty and uniqueness of the island of Jamaica. This is a must do...

1 to 4 hours Hotel pickup offered Free Cancellation

4.9 (29)

from
$55

Tropical Experience Boat Party with Snorkeling and Natural Pool

Enjoy an unforgettable experience aboard a Party Boat in Punta Cana, where the fun never stops. Sail through the crystal-clear waters of the Caribbean while …More

Punta Cana, Dominican Republic

5.0 (23)

Tropical Experience Boat Party with Snorkeling and Natural Pool

Enjoy an unforgettable experience aboard a Party Boat in Punta Cana, where the fun never stops. Sail through the crystal-clear waters of the Caribbean while...

4 hours Hotel pickup offered Free Cancellation

5.0 (23)

from
$80

ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar

Discover the best of Punta Cana by land and sea with our unforgettable 2-day adventure package! This experience combines adrenaline, nature, culture, and celebration for …More

Punta Cana, Dominican Republic

5.0 (31)

ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar

Discover the best of Punta Cana by land and sea with our unforgettable 2-day adventure package! This experience combines adrenaline, nature, culture, and celebration for...

2 days Hotel pickup offered Free Cancellation

5.0 (31)

from
$69

Soufriere Volcano, Waterfall and Snorkeling Tour by speedboat

Experience the best in Saint Lucia on this small group land and sea adventure to Soufriere, designed for comfort, personal attention, and authentic local experiences. …More

Cap Estate, St Lucia

5.0 (33)

Soufriere Volcano, Waterfall and Snorkeling Tour by speedboat

Experience the best in Saint Lucia on this small group land and sea adventure to Soufriere, designed for comfort, personal attention, and authentic local experiences....

5 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$160

Small Group 7 Mile Beach Stingray City and Coral Gardens Tour

See the Best of the Islands Hottest Spot wrap up in a Five Hour Tour You will enjoy and experience the warmth of the Famous …More

Seven Mile Beach, Cayman Islands

4.6 (21)

Small Group 7 Mile Beach Stingray City and Coral Gardens Tour

See the Best of the Islands Hottest Spot wrap up in a Five Hour Tour You will enjoy and experience the warmth of the Famous...

5 hours Hotel pickup offered Free Cancellation

4.6 (21)

from
$65

Punta Cana Private Boat Tour with Open Bar and BBQ

Embark in our 3 hour Private Boat Tour with your loved ones in one of the best coastlines of Punta Cana and snorkel in the …More

Punta Cana, Dominican Republic

4.9 (25)

Punta Cana Private Boat Tour with Open Bar and BBQ

Embark in our 3 hour Private Boat Tour with your loved ones in one of the best coastlines of Punta Cana and snorkel in the...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (25)

from
$748

Hip Hop solo para adultos PartyBoat con Bebidas ilimitadas y Bar

Enjoy an unforgettable a Experience Abaord a Party Boat in Punta Cana ,Where the fun never Stops. Sail the Cristal Clear Waters of the Caribbean …More

Punta Cana, Dominican Republic

4.9 (21)

Hip Hop solo para adultos PartyBoat con Bebidas ilimitadas y Bar

Enjoy an unforgettable a Experience Abaord a Party Boat in Punta Cana ,Where the fun never Stops. Sail the Cristal Clear Waters of the Caribbean...

4 hours Hotel pickup offered Free Cancellation

4.9 (21)

from
$63

Key to the Sea Half-Day Private Boat Charter: Sun & Snorkel Tour

Experience the ultimate crowd-free day on the water with our premium half-day private boat charter. Cruising aboard our immaculate 27-foot Sea Ray Sundeck (No-Ah'Genda), your …More

5.0 (38)

Key to the Sea Half-Day Private Boat Charter: Sun & Snorkel Tour

Experience the ultimate crowd-free day on the water with our premium half-day private boat charter. Cruising aboard our immaculate 27-foot Sea Ray Sundeck (No-Ah'Genda), your...

4 hours Free Cancellation

5.0 (38)

from
$1,599

Great River Raft and Full Limestone body Massage In Montego Bay

Located in the hills of Honover Great River is an amazing tour where travelers are piloted on a 30 ft hand crafted bamboo raft. Relax …More

Montego Bay, Jamaica

5.0 (33)

Great River Raft and Full Limestone body Massage In Montego Bay

Located in the hills of Honover Great River is an amazing tour where travelers are piloted on a 30 ft hand crafted bamboo raft. Relax...

1 to 2 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$15

Los Haitises National Park Boat Tour from Punta Cana

Explore Los Haitises National Park on a full-day excursion from Punta Cana featuring a boat journey through mangroves, limestone formations and caves with Taíno rock …More

Punta Cana, Dominican Republic

4.7 (21)

Los Haitises National Park Boat Tour from Punta Cana

Explore Los Haitises National Park on a full-day excursion from Punta Cana featuring a boat journey through mangroves, limestone formations and caves with Taíno rock...

1 day Hotel pickup offered Free Cancellation

4.7 (21)

from
$162

Discover the beauty of Cayo Icacos, Puerto Rico, on a private boat excursion departing from Marina Puerto del Rey in Fajardo. Enjoy crystal-clear turquoise waters, …More

Fajardo, Puerto Rico

5.0 (18)

Fajardo Puerto Rico Private Boat Tour to Cayo Icacos

Discover the beauty of Cayo Icacos, Puerto Rico, on a private boat excursion departing from Marina Puerto del Rey in Fajardo. Enjoy crystal-clear turquoise waters,...

4 hours Free Cancellation

5.0 (18)

from
$850

Full Day Adventure Buggy Ride and Party Boat

Discover the Dominican countryside by ATV, then explore the coastline by double-decker catamaran. There are countless delights on this full-day tour: sample organic products; explore …More

Punta Cana, Dominican Republic

5.0 (12)

Full Day Adventure Buggy Ride and Party Boat

Discover the Dominican countryside by ATV, then explore the coastline by double-decker catamaran. There are countless delights on this full-day tour: sample organic products; explore...

6 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$110

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

4.7 (53)

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 Free Cancellation

4.7 (53)

from
$99

Private Catamaran in Punta Cana with Sonkling Beverages Party and DJ

Experience an unforgettable catamaran adventure in Punta Cana! Looking for a unique experience to share with your family, friends or celebrate a birthday? Our catamaran …More

Punta Cana, Dominican Republic

5.0 (15)

Private Catamaran in Punta Cana with Sonkling Beverages Party and DJ

Experience an unforgettable catamaran adventure in Punta Cana! Looking for a unique experience to share with your family, friends or celebrate a birthday? Our catamaran...

3 hours Hotel pickup offered Free Cancellation

5.0 (15)

from
$770

#1 Rated 4 Hour Private Rose Island Tour Beach Snorkeling Turtles

Explore the stunning waters of the Bahamas aboard a 28 ft Regulator FS Center Console with RiG Charters. Perfect for up to eight guests, this …More

5.0 (31)

#1 Rated 4 Hour Private Rose Island Tour Beach Snorkeling Turtles

Explore the stunning waters of the Bahamas aboard a 28 ft Regulator FS Center Console with RiG Charters. Perfect for up to eight guests, this...

4 hours Free Cancellation

5.0 (31)

from
$1,200

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?