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

Hip Hop Party boat booze cruise w Open Bar (adults only)

Enjoy a fun party atmosphere in our 3 hour all you can drink hip hop party boat cruise. A quick stop for snorkeling, drinks in …More

5.0 (4)

Hip Hop Party boat booze cruise w Open Bar (adults only)

Enjoy a fun party atmosphere in our 3 hour all you can drink hip hop party boat cruise. A quick stop for snorkeling, drinks in...

3 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$65

Montego Bay Highlights Tour with Shopping & Bamboo River Rafting

This is the ultimate authentic Jamaican experience. You will be greeted by your professional raft captain who aims to provide you with the best river …More

Montego Bay, Jamaica

4.6 (5)

Montego Bay Highlights Tour with Shopping & Bamboo River Rafting

This is the ultimate authentic Jamaican experience. You will be greeted by your professional raft captain who aims to provide you with the best river...

5 to 6 hours Hotel pickup offered Free Cancellation

4.6 (5)

from
$160

Three Beach Hopping Family Motorboat day

Cruise the coastline of both Dutch and French St. Maarten on a three-beach multigenerational, family adventure by intimate Motorboat for your private group. Listen to …More

Grand Case, St Maarten

5.0 (1)

Three Beach Hopping Family Motorboat day

Cruise the coastline of both Dutch and French St. Maarten on a three-beach multigenerational, family adventure by intimate Motorboat for your private group. Listen to...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$3,500

Athol Island Swimming Pigs Half-Day Boat Tour with Lunch

Visit Pearl Island for snorkeling with beautiful fish on a coral reef. Then onto Green Cay for snorkeling with turtles. Visit Gilligan's Island to find …More

Nassau, Bahamas

4.3 (8)

Athol Island Swimming Pigs Half-Day Boat Tour with Lunch

Visit Pearl Island for snorkeling with beautiful fish on a coral reef. Then onto Green Cay for snorkeling with turtles. Visit Gilligan's Island to find...

4 hours Hotel pickup offered Free Cancellation

4.3 (8)

from
$350

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

5.0 (1)

SPECIAL - All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours

5.0 (1)

from
$1,550

Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty …More

5.0 (1)

Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty...

5 hours Free Cancellation

5.0 (1)

from
$1,300

Snorkeling at Catalina Island & Altos de Chavón Full Day Tour

Discover the Best of the Dominican Republic with Our Catalina Island & Altos de Chavón Full-Day Caribbean Adventure! Immerse yourself in the natural beauty and …More

La Romana, Dominican Republic

4.5 (2)

Snorkeling at Catalina Island & Altos de Chavón Full Day Tour

Discover the Best of the Dominican Republic with Our Catalina Island & Altos de Chavón Full-Day Caribbean Adventure! Immerse yourself in the natural beauty and...

8 hours Hotel pickup offered Free Cancellation

4.5 (2)

from
$129

Grand Turk Eco-Tourism Clear Kayak Tour!

Indulge on a breathtaking experience through the vibrant mangrove eco system in north creek which is considered the largest natural inlet in the Caribbean! , …More

3.4 (13)

Grand Turk Eco-Tourism Clear Kayak Tour!

Indulge on a breathtaking experience through the vibrant mangrove eco system in north creek which is considered the largest natural inlet in the Caribbean! ,...

1 hour 20 minutes Free Cancellation

3.4 (13)

from
$98

Zipline, YS Falls & Pelican Bar Private Tour From Montego Bay

The many attractions on the South Coast of Jamaica are demurely tucked away in the sleepy countryside towns of Westmoreland and St. Elizabeth. This is …More

Black River, Jamaica

5.0 (1)

Zipline, YS Falls & Pelican Bar Private Tour From Montego Bay

The many attractions on the South Coast of Jamaica are demurely tucked away in the sleepy countryside towns of Westmoreland and St. Elizabeth. This is...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$133

Relax as you get picked up from your resort and driven to Bibi Agua Plaza on the beach of Bavaro. You'll embark to the Malibu …More

Punta Cana, Dominican Republic

5.0 (1)

Malibu Party Boat with DJ

Relax as you get picked up from your resort and driven to Bibi Agua Plaza on the beach of Bavaro. You'll embark to the Malibu...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$5,845

Samana Full Day Waterfall, Safari and Beach

Samana, a treasure on the northeast coast of the Dominican Republic, stands out as a truly unique destination. Its white sand beaches, surrounded by crystal-clear …More

Punta Cana, Dominican Republic

3.9 (7)

Samana Full Day Waterfall, Safari and Beach

Samana, a treasure on the northeast coast of the Dominican Republic, stands out as a truly unique destination. Its white sand beaches, surrounded by crystal-clear...

13 hours Hotel pickup offered Free Cancellation

3.9 (7)

from
$105

Catalina Island and Snorkeling - Full-day Trip

Discover Catalina Island like never before! Sail along the turquoise Caribbean waters aboard a comfortable catamaran or speedboat, enjoying the stunning coastal views along the …More

4.5 (4)

Catalina Island and Snorkeling - Full-day Trip

Discover Catalina Island like never before! Sail along the turquoise Caribbean waters aboard a comfortable catamaran or speedboat, enjoying the stunning coastal views along the...

8 to 9 hours Hotel pickup offered Free Cancellation

4.5 (4)

from
$85

Every Friday Evening sailing from Ribbiz Ocean Lounge located on the waterfront at Victoria Pier Downtown in Kingston. Come aboard a 69ft Power Catamaran for …More

Lucea, Jamaica

5.0 (1)

Experience Kingston From The Water

Every Friday Evening sailing from Ribbiz Ocean Lounge located on the waterfront at Victoria Pier Downtown in Kingston. Come aboard a 69ft Power Catamaran for...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$450

Zipline, Horseback & Catamaran Cruise-From MoBay Negril Ocho Rios

Guests can experience the island from above, on land, and from the Caribbean Sea—all in one exciting outing. Soar Above Jamaica Feel the adrenaline of …More

Lucea, Jamaica

5.0 (1)

Zipline, Horseback & Catamaran Cruise-From MoBay Negril Ocho Rios

Guests can experience the island from above, on land, and from the Caribbean Sea—all in one exciting outing. Soar Above Jamaica Feel the adrenaline of...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$550

Exclusive Deep Sea Fishing in Montego Bay: A Private Adventure

Experience the advantage of Montego Bay's unique geography, where the deep sea meets the shore. Our expert captains will take you to the prime fishing …More

Montego Bay, Jamaica

5.0 (1)

Exclusive Deep Sea Fishing in Montego Bay: A Private Adventure

Experience the advantage of Montego Bay's unique geography, where the deep sea meets the shore. Our expert captains will take you to the prime fishing...

4 hours Free Cancellation

5.0 (1)

from
$200

Exclusive Catch: Private Guided Reef Fishing in Montego Bay

Immerse yourself in an unforgettable bottom fishing adventure in Montego Bay, where the thrill of reeling in prized catches like snapper, grouper, and jacks awaits! …More

Montego Bay, Jamaica

5.0 (1)

Exclusive Catch: Private Guided Reef Fishing in Montego Bay

Immerse yourself in an unforgettable bottom fishing adventure in Montego Bay, where the thrill of reeling in prized catches like snapper, grouper, and jacks awaits!...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$122

Private Glass Bottom Boat Sight Seeing Tour Jamaica

Climb aboard a glass bottom boat where you are present with the windows into the underwater world, and experience the unique marine landscape filled with …More

Negril, Jamaica

5.0 (1)

Private Glass Bottom Boat Sight Seeing Tour Jamaica

Climb aboard a glass bottom boat where you are present with the windows into the underwater world, and experience the unique marine landscape filled with...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$88

Our tour to Samaná unique is the perfect combination of adventure, natural beauty, and moments of relaxation, all in a single day. From a delightful …More

Samaná, Dominican Republic

4.0 (1)

Samana Full Day From Punta Cana

Our tour to Samaná unique is the perfect combination of adventure, natural beauty, and moments of relaxation, all in a single day. From a delightful...

10 hours Free Cancellation

4.0 (1)

from
$170

Private Luminous Lagoon Night Cruise from Montego Bay

Meet your guide during pickup at your hotel. Depart on your evening ride to the Luminous Lagoon, in the Trelawny Parish on Jamaica’s north coast. …More

Montego Bay, Jamaica

5.0 (1)

Private Luminous Lagoon Night Cruise from Montego Bay

Meet your guide during pickup at your hotel. Depart on your evening ride to the Luminous Lagoon, in the Trelawny Parish on Jamaica’s north coast....

1 hour Hotel pickup offered Free Cancellation

5.0 (1)

from
$80

Ecological Park & Boat ride on the River

Enjoy the Dominican flora and fauna. The ecological park where all native trees, plants, flowers and fruits grow, can be admired and also the fruit …More

Cabarete, Dominican Republic

5.0 (1)

Ecological Park & Boat ride on the River

Enjoy the Dominican flora and fauna. The ecological park where all native trees, plants, flowers and fruits grow, can be admired and also the fruit...

6 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$79

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?