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 →

Boat Tour to Bibijagua Beach from Punta Cana

Our tour is special because we have a live DJ, we have a dance instructor and we have a live show. Cancel …More

5.0 (12)

Boat Tour to Bibijagua Beach from Punta Cana

Our tour is special because we have a live DJ, we have a dance instructor and we have a live show. Cancel...

3 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$65

Private Charter Around St Maarten-St.Martin

Private charter on our very comfortable Speed Boats .St.Maarten- St.martin, unique beaches, special atmosphere. we guarantee smooth ride and possibility go closest possible to your …More

5.0 (3)

Private Charter Around St Maarten-St.Martin

Private charter on our very comfortable Speed Boats .St.Maarten- St.martin, unique beaches, special atmosphere. we guarantee smooth ride and possibility go closest possible to your...

5 to 7 hours Free Cancellation

5.0 (3)

from
$1,500

Bamboo Rafting and Boston Jerk Centre Tour in Portland Jamaica

Experience the beauty and adventure of Jamaica's Rio Grande on a bamboo rafting tour. Embark on a peaceful journey through lush greenery and scenic landscapes …More

Kingston, Jamaica

5.0 (10)

Bamboo Rafting and Boston Jerk Centre Tour in Portland Jamaica

Experience the beauty and adventure of Jamaica's Rio Grande on a bamboo rafting tour. Embark on a peaceful journey through lush greenery and scenic landscapes...

4 hours Free Cancellation

5.0 (10)

from
$150

Private Meet your Guide El Yunque and Waterslides Adventure

Connect with nature and breathe in the fresh air on this exhilarating tour to Las Tinajas in Ceiba, Puerto Rico. The clear trails make this …More

Fajardo, Puerto Rico

5.0 (10)

Private Meet your Guide El Yunque and Waterslides Adventure

Connect with nature and breathe in the fresh air on this exhilarating tour to Las Tinajas in Ceiba, Puerto Rico. The clear trails make this...

5 hours 30 minutes Free Cancellation

5.0 (10)

from
$600

Reggae Family Catamaran Cruise From Montego Bay

Take in the wonders of the island from the best seat in the house on board the Island Routes Reggae Family Catamaran Cruise. Get ready …More

Montego Bay, Jamaica

4.8 (16)

Reggae Family Catamaran Cruise From Montego Bay

Take in the wonders of the island from the best seat in the house on board the Island Routes Reggae Family Catamaran Cruise. Get ready...

3 hours Hotel pickup offered Free Cancellation

4.8 (16)

from
$125

St. Lucia: Hotel Chocolat, Catamaran Cruise, Sulphur Springs

This decadent journey is a chocolate lover's dream, beginning aboard a luxurious catamaran cruise to Soufriere to visit the renowned Hotel Chocolat. This bean to …More

Choc, St Lucia

4.9 (15)

St. Lucia: Hotel Chocolat, Catamaran Cruise, Sulphur Springs

This decadent journey is a chocolate lover's dream, beginning aboard a luxurious catamaran cruise to Soufriere to visit the renowned Hotel Chocolat. This bean to...

10 hours Hotel pickup offered

4.9 (15)

from
$287

Montego Bay Bamboo Rafting Tour with Clear Kayak Photoshoot

Bamboo Rafting with Limestone Foot massage & Clear Kayak Photo shoot is two of montego Bay’s Top Rated Activities and this combination package is perfect …More

Montego Bay, Jamaica

5.0 (6)

Montego Bay Bamboo Rafting Tour with Clear Kayak Photoshoot

Bamboo Rafting with Limestone Foot massage & Clear Kayak Photo shoot is two of montego Bay’s Top Rated Activities and this combination package is perfect...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$120

…experience Grenada by sea and land. Sail up the west coast of Grenada to Black Bay where you will disembark to start our guided hike …More

5.0 (5)

Private “Sail & Hike” Tour of Grenada

…experience Grenada by sea and land. Sail up the west coast of Grenada to Black Bay where you will disembark to start our guided hike...

8 hours Free Cancellation

5.0 (5)

from
$302

River Tubing with Private Transportation from Montego Bay

Basically this tour will leave travelers with lots of great memories that will last a lifetime. Go river tubing down Jamaica's Rio Bueno on this …More

Montego Bay, Jamaica

5.0 (5)

River Tubing with Private Transportation from Montego Bay

Basically this tour will leave travelers with lots of great memories that will last a lifetime. Go river tubing down Jamaica's Rio Bueno on this...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$80

Bamboo Rafting & Horseback Ride n Swim Guided Tour In Montego Bay

Bamboo rafting and Horseback ride are two of the top things to do while on vacation in Jamaica. Escape the confines of your hotel resort …More

Montego Bay, Jamaica

4.8 (16)

Bamboo Rafting & Horseback Ride n Swim Guided Tour In Montego Bay

Bamboo rafting and Horseback ride are two of the top things to do while on vacation in Jamaica. Escape the confines of your hotel resort...

3 to 4 hours Hotel pickup offered Free Cancellation

4.8 (16)

from
$145

Luminous Lagoon Glistening Waters Tour from Montego Bay Jamaica

Explore the bioluminescence in the luminous lagoon one of Jamaica’s most magical natural attractions, where millions of microscopic organisms create a breathtaking blue-green glow in …More

Trelawny, Jamaica

5.0 (6)

Luminous Lagoon Glistening Waters Tour from Montego Bay Jamaica

Explore the bioluminescence in the luminous lagoon one of Jamaica’s most magical natural attractions, where millions of microscopic organisms create a breathtaking blue-green glow in...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$55

Samana Full-Day Tour with Whale Watching and Horse Riding

Visits for Sanctuary of the Humpback Whales in Samana is free. It is available only during the period from January 15, to March 30 of …More

Punta Cana, Dominican Republic

4.2 (11)

Samana Full-Day Tour with Whale Watching and Horse Riding

Visits for Sanctuary of the Humpback Whales in Samana is free. It is available only during the period from January 15, to March 30 of...

11 hours Hotel pickup offered Free Cancellation

4.2 (11)

from
$145

Punta Cana Catamaran Party: Music, Drinks & Tropical Fun

Hop on the funniest Party Boat in the Caribbean! Looking for unlimited party, sea and fun? Then our Party Boat Tour is for you! From …More

Punta Cana, Dominican Republic

5.0 (15)

Punta Cana Catamaran Party: Music, Drinks & Tropical Fun

Hop on the funniest Party Boat in the Caribbean! Looking for unlimited party, sea and fun? Then our Party Boat Tour is for you! From...

4 hours Hotel pickup offered Free Cancellation

5.0 (15)

from
$69

Half-Day Private Martha Brae Rafting Tour from Montego Bay

Your driver will pick you up at your hotel or cruise ship port. Enjoy a comfortable ride in our air conditioned vehicle on this 40 …More

Montego Bay, Jamaica

5.0 (10)

Half-Day Private Martha Brae Rafting Tour from Montego Bay

Your driver will pick you up at your hotel or cruise ship port. Enjoy a comfortable ride in our air conditioned vehicle on this 40...

4 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$130

Embark with Access Evasion, live an exciting and exhilarating experience aboard Il Vagabondo and its captain "Pinn’ Sparrow ". Conscientious and attentive to your needs, …More

5.0 (2)

White Background Boat Tour

Embark with Access Evasion, live an exciting and exhilarating experience aboard Il Vagabondo and its captain "Pinn’ Sparrow ". Conscientious and attentive to your needs,...

4 to 8 hours Free Cancellation

5.0 (2)

from
$102

Enjoy a comfortable 20-minute drive in our air-conditioned van to board our 34-40 ft fishing boats. Led by a professional crew, you'll experience 4 hours …More

Punta Cana, Dominican Republic

4.1 (16)

Deep Sea Fishing Tour

Enjoy a comfortable 20-minute drive in our air-conditioned van to board our 34-40 ft fishing boats. Led by a professional crew, you'll experience 4 hours...

5 hours Hotel pickup offered Free Cancellation

4.1 (16)

from
$90

Fun tour for kids with River tubing and Konoko Falls

This tour allow you to enjoy Jamaica and also allow your kids to enjoy Jamaica and be safe at the same time. It is often …More

Runaway Bay, Jamaica

5.0 (11)

Fun tour for kids with River tubing and Konoko Falls

This tour allow you to enjoy Jamaica and also allow your kids to enjoy Jamaica and be safe at the same time. It is often...

3 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$124

Private charter,4 hours,Spanish waters,fuik bay bbq and snorkel.

Escape the crowds and join us on our classic 68 ft motor sailing yacht for an amazing trip out on the Caribbean sea. We are …More

5.0 (10)

Private charter,4 hours,Spanish waters,fuik bay bbq and snorkel.

Escape the crowds and join us on our classic 68 ft motor sailing yacht for an amazing trip out on the Caribbean sea. We are...

4 hours Free Cancellation

5.0 (10)

from
$120

Grand Cayman Stingray City & Reef Snorkeling Adventure

Experience two of Grand Cayman’s signature marine adventures in one easy morning on the water. Step into the shallow, crystal-clear waters of Stingray City and …More

Grand Cayman, Cayman Islands

5.0 (6)

Grand Cayman Stingray City & Reef Snorkeling Adventure

Experience two of Grand Cayman’s signature marine adventures in one easy morning on the water. Step into the shallow, crystal-clear waters of Stingray City and...

3 hours

5.0 (6)

from
$139

* Desde Santo Domingo: Isla Saona con almuerzo y transporte

make this excursion to this paradise island on board of speed boat, and catamarán visiting mangrove, and natural swimming pool just for you, special lunch …More

4.3 (30)

* Desde Santo Domingo: Isla Saona con almuerzo y transporte

make this excursion to this paradise island on board of speed boat, and catamarán visiting mangrove, and natural swimming pool just for you, special lunch...

8 hours Free Cancellation

4.3 (30)

from
$90

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?