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 →

Bamboo River Rafting with Limestone Foot Massage

With Brooks Tours Ja, you can experience the thrills of rafting on the Great River at Lethe while also enjoying a well-deserved foot massage. Rafting …More

Montego Bay, Jamaica

5.0 (18)

Bamboo River Rafting with Limestone Foot Massage

With Brooks Tours Ja, you can experience the thrills of rafting on the Great River at Lethe while also enjoying a well-deserved foot massage. Rafting...

4 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$129

Montego Bay: Rafting, ATVing, and Ricks Cafe Tour with Transfers

This is an adrenaline-filled day that lasts anywhere Between 6-8 hours. Travelers will be picked up and transported to the bamboo rafting for their first …More

Montego Bay, Jamaica

4.8 (15)

Montego Bay: Rafting, ATVing, and Ricks Cafe Tour with Transfers

This is an adrenaline-filled day that lasts anywhere Between 6-8 hours. Travelers will be picked up and transported to the bamboo rafting for their first...

5 hours Hotel pickup offered Free Cancellation

4.8 (15)

from
$160

Montego Bay: Negril Catamaran Cruise & Rick's

Join us for an unforgettable day trip to Negril, Jamaica! Start your day with a guided scenic bus ride on Jamaica's North Coast to Negril, …More

Montego Bay, Jamaica

4.2 (299)

Montego Bay: Negril Catamaran Cruise & Rick's

Join us for an unforgettable day trip to Negril, Jamaica! Start your day with a guided scenic bus ride on Jamaica's North Coast to Negril,...

4 to 12 hours Hotel pickup offered Free Cancellation

4.2 (299)

from
$90

Amazing Paradise Island + Snorkeling-Mangrove Tour & Locale Food.

Cayo Arena Paradise Island Tour is the Best Way to Explore and Experience the Most Beautiful Place at Puerto Plata, where you will see our …More

Cabarete, Dominican Republic

4.4 (39)

Amazing Paradise Island + Snorkeling-Mangrove Tour & Locale Food.

Cayo Arena Paradise Island Tour is the Best Way to Explore and Experience the Most Beautiful Place at Puerto Plata, where you will see our...

7 to 8 hours Hotel pickup offered Free Cancellation

4.4 (39)

from
$70

Private Northern Boat Tour- Castries To Rodney Bay or Rodney Bay to Marigot Bay

If you are looking for a shore excursion in St Lucia, which is Certified COVID-19 compliant, where you may tour the North of St. Lucia …More

Marigot Bay, St Lucia

4.5 (15)

Private Northern Boat Tour- Castries To Rodney Bay or Rodney Bay to Marigot Bay

If you are looking for a shore excursion in St Lucia, which is Certified COVID-19 compliant, where you may tour the North of St. Lucia...

2 to 5 hours Hotel pickup offered Free Cancellation

4.5 (15)

from
$120

St. Lucia Private Sunset Cruise - Marigot Bay and Rodney Bay

Romantic Private Sunset Cruise in St. Lucia. The Perfect End to Your Day! Imagine a serene evening on the tranquil Caribbean Sea, sailing along St. …More

Marigot Bay, St Lucia

5.0 (12)

St. Lucia Private Sunset Cruise - Marigot Bay and Rodney Bay

Romantic Private Sunset Cruise in St. Lucia. The Perfect End to Your Day! Imagine a serene evening on the tranquil Caribbean Sea, sailing along St....

2 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$97

Head out with us locals on a private charter that would take you around the Stingrays, Corals, and Starfish. If you wish we can include …More

Seven Mile Beach, Cayman Islands

4.7 (21)

Grand Cayman Half-Day Private Charter

Head out with us locals on a private charter that would take you around the Stingrays, Corals, and Starfish. If you wish we can include...

4 hours Hotel pickup offered Free Cancellation

4.7 (21)

from
$2,100

One hour private jet ski tour in Saint Martin with free passenger

An excursion that will make you discover beautiful spots on the island. On board our brand new 2024 jet skis. It is an excursion suitable …More

4.7 (21)

One hour private jet ski tour in Saint Martin with free passenger

An excursion that will make you discover beautiful spots on the island. On board our brand new 2024 jet skis. It is an excursion suitable...

1 hour Free Cancellation

4.7 (21)

from
$148

Private charter on Casador a classic 68ft sailing yacht.cruiseship possible

This is a private tour so get the whole boat to yourselves! up to 30 people and we are not set on a timetable or …More

4.6 (39)

Private charter on Casador a classic 68ft sailing yacht.cruiseship possible

This is a private tour so get the whole boat to yourselves! up to 30 people and we are not set on a timetable or...

6 to 8 hours Free Cancellation

4.6 (39)

from
$130

Full-Day Private Luxury Yacht Tour in Anguilla

Anguilla is a different island with a different culture. This is a must-do when you come to St Maarten. The good news is that it …More

5.0 (17)

Full-Day Private Luxury Yacht Tour in Anguilla

Anguilla is a different island with a different culture. This is a must-do when you come to St Maarten. The good news is that it...

7 hours 30 minutes Free Cancellation

5.0 (17)

from
$1,900

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

5.0 (18)

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

5.0 (18)

from
$119

Private Sunset Catamaran Adventure Cruise with Open Bar

This sunset cruise is the perfect combination of a relaxing and exiting experience. You will be able to adjust the cruise to your personal preference …More

5.0 (22)

Private Sunset Catamaran Adventure Cruise with Open Bar

This sunset cruise is the perfect combination of a relaxing and exiting experience. You will be able to adjust the cruise to your personal preference...

2 hours

5.0 (22)

from
$1,800

Rose Island Swimming with the Pigs Lunch and Private Beach

Our first stop is an amazing snorkeling experience at Rainbow Reef, second stop observing turtles at the sanctuary at Green Cay, our final stop is …More

4.5 (76)

Rose Island Swimming with the Pigs Lunch and Private Beach

Our first stop is an amazing snorkeling experience at Rainbow Reef, second stop observing turtles at the sanctuary at Green Cay, our final stop is...

4 to 5 hours Free Cancellation

4.5 (76)

from
$118

Punta Cana Caribbean Party Boat: Snorkeling, Natural Pool & Bar

Enjoy a relaxing and fun day on the water on this half-day cruise off the coast of Punta Cana. Snorkel a coral reef teeming with …More

5.0 (11)

Punta Cana Caribbean Party Boat: Snorkeling, Natural Pool & Bar

Enjoy a relaxing and fun day on the water on this half-day cruise off the coast of Punta Cana. Snorkel a coral reef teeming with...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$69

Join us for our newest trip while we sail down St Maarten's Golden Coast on one of our 65 foot sail catamarans. Relax on the …More

4.9 (64)

Bubbly Sunset Cruise

Join us for our newest trip while we sail down St Maarten's Golden Coast on one of our 65 foot sail catamarans. Relax on the...

2 hours Free Cancellation

4.9 (64)

from
$65

Seeking a romantic evening for two, a serene escape from the bustling city, or simply a moment of tranquillity amidst nature's splendor, our Private Sunset …More

Marigot Bay, St Lucia

5.0 (16)

Private Sunset and Snorkel Cruise

Seeking a romantic evening for two, a serene escape from the bustling city, or simply a moment of tranquillity amidst nature's splendor, our Private Sunset...

2 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$150

3HR Jetski Tour Stingray City Starfish Point Snorkel Rumpoint

EXPERIENCE THE CAYMAN ISLANDS’ MUST-SEE STOPS IN ONE UNFORGETTABLE GUIDED JET SKI TOUR! Get ready for 3 hours of adventure, crystal-clear water, and true Cayman …More

Seven Mile Beach, Cayman Islands

4.9 (87)

3HR Jetski Tour Stingray City Starfish Point Snorkel Rumpoint

EXPERIENCE THE CAYMAN ISLANDS’ MUST-SEE STOPS IN ONE UNFORGETTABLE GUIDED JET SKI TOUR! Get ready for 3 hours of adventure, crystal-clear water, and true Cayman...

3 hours Hotel pickup offered Free Cancellation

4.9 (87)

from
$395

Bamboo Rafting and Catamaran Party Cruise and Ricks Cafe

1. Bamboo Rafting & Limestone Massage: This tour combines relaxation, adventure, and entertainment all in one seamless experience. You will enjoy a scenic bamboo rafting …More

Lucea, Jamaica

4.7 (28)

Bamboo Rafting and Catamaran Party Cruise and Ricks Cafe

1. Bamboo Rafting & Limestone Massage: This tour combines relaxation, adventure, and entertainment all in one seamless experience. You will enjoy a scenic bamboo rafting...

7 to 9 hours Hotel pickup offered Free Cancellation

4.7 (28)

from
$110

Bamboo Rafting, Catamaran Party Cruise and Snorkeling in Jamaica

The tour combining stands out as unique due to its diverse blend of serene, lively, and adventurous experiences. The combination of these three activities ensures …More

Falmouth, Jamaica

5.0 (15)

Bamboo Rafting, Catamaran Party Cruise and Snorkeling in Jamaica

The tour combining stands out as unique due to its diverse blend of serene, lively, and adventurous experiences. The combination of these three activities ensures...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (15)

from
$110

Whale and Dolphin Watching Cruise in St Lucia

Experience the once-in-a-lifetime sight of wild whales and dolphins in their natural environment. Enjoy magnificent views of the West Coast of St Lucia and sip …More

4.6 (189)

Whale and Dolphin Watching Cruise in St Lucia

Experience the once-in-a-lifetime sight of wild whales and dolphins in their natural environment. Enjoy magnificent views of the West Coast of St Lucia and sip...

3 hours 30 minutes Free Cancellation

4.6 (189)

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?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Cruises, Sailing & Water Tours are:

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?