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 →

Sunset Yacht Cruise Along Trinidad North West Coast

We cruise the beautiful waters along the North West Coast and Gulf of Paria, listen to the sounds of the sea and typical local music …More

5.0 (1)

Sunset Yacht Cruise Along Trinidad North West Coast

We cruise the beautiful waters along the North West Coast and Gulf of Paria, listen to the sounds of the sea and typical local music...

3 hours Free Cancellation

5.0 (1)

from
$227

Half Moon Bay Jet Ski Tour & Snorkeling the La Famille Shipwreck

Start your tour exploring the La Famille Shipwreck and snorkeling the crystal-clear waters of the Caicos Banks. The La Famille Express became firmly planted in …More

4.7 (3)

Half Moon Bay Jet Ski Tour & Snorkeling the La Famille Shipwreck

Start your tour exploring the La Famille Shipwreck and snorkeling the crystal-clear waters of the Caicos Banks. The La Famille Express became firmly planted in...

2 hours Free Cancellation

4.7 (3)

from
$490

Catamaran Cruise with Snorkeling and lunch on board!

Spend a beautiful day on the ocean , cruising along the coast line and enjoy an amazing scenery. Visit two different snorkeling spots. Enjoy the …More

Cabarete, Dominican Republic

3.9 (9)

Catamaran Cruise with Snorkeling and lunch on board!

Spend a beautiful day on the ocean , cruising along the coast line and enjoy an amazing scenery. Visit two different snorkeling spots. Enjoy the...

5 hours 15 minutes Hotel pickup offered Free Cancellation

3.9 (9)

from
$76

Full-Day Excursion to Discover Catalina Island with Lunch Option

Discover the unparalleled beauty of Catalina Island and the Chavon River with our exclusive adventure, designed for adventure seekers, families, and nature enthusiasts. Dive into the best …More

Punta Cana, Dominican Republic

5.0 (1)

Full-Day Excursion to Discover Catalina Island with Lunch Option

Discover the unparalleled beauty of Catalina Island and the Chavon River with our exclusive adventure, designed for adventure seekers, families, and nature enthusiasts. Dive into the best...

9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$149

Punta Cana Terra Country 4x4 Tour with Tasting Experience

Ready for an unforgettable adventure in the heart of the Dominican countryside? This tour promises to be as thrilling as it is enlightening. As you …More

Punta Cana, Dominican Republic

5.0 (1)

Punta Cana Terra Country 4x4 Tour with Tasting Experience

Ready for an unforgettable adventure in the heart of the Dominican countryside? This tour promises to be as thrilling as it is enlightening. As you...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$109

Dive into a magical night with the Luminous Lagoon Boat Tour in Falmouth Jamaica! Set off at sunset or a little after sunset for a …More

Montego Bay, Jamaica

4.0 (6)

Magical Luminous Lagoon

Dive into a magical night with the Luminous Lagoon Boat Tour in Falmouth Jamaica! Set off at sunset or a little after sunset for a...

2 to 3 hours Hotel pickup offered Free Cancellation

4.0 (6)

from
$80

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 (1)

Private Lethe Bamboo River Rafting Adventure Montego Bay Jamaica

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...

90 to 120 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$140

Private Exclusive Saona Island VIP Tours

Experience the idyllic Saona Island on this full-day tour from the mainland via speedboat and catamaran. Zip out to the island on a fast boat, …More

Punta Cana, Dominican Republic

5.0 (1)

Private Exclusive Saona Island VIP Tours

Experience the idyllic Saona Island on this full-day tour from the mainland via speedboat and catamaran. Zip out to the island on a fast boat,...

8 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,511

Grand Cayman Stingray City and Reef Snorkeling Combo Tour

Prepare for an unforgettable day exploring Grand Cayman! Climb aboard a comfortable cabin cruiser with a friendly captain and crew, and set sail for a …More

Grand Cayman, Cayman Islands

4.7 (3)

Grand Cayman Stingray City and Reef Snorkeling Combo Tour

Prepare for an unforgettable day exploring Grand Cayman! Climb aboard a comfortable cabin cruiser with a friendly captain and crew, and set sail for a...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (3)

from
$89

RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica …More

Falmouth, Jamaica

4.7 (3)

RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica...

7 to 8 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$145

Half-Day Private Catamaran Tour in Puerto Plata

Have a blast on the water! Take a 38 feet catamaran, ride along the coast and have a party of your life, while dancing, sipping …More

Cabarete, Dominican Republic

5.0 (1)

Half-Day Private Catamaran Tour in Puerto Plata

Have a blast on the water! Take a 38 feet catamaran, ride along the coast and have a party of your life, while dancing, sipping...

5 hours Hotel pickup offered

5.0 (1)

from
$1,650

Discover paradise on Saona Island, where white sandy beaches, clear turquoise waters, and countless palm trees provide an unspoiled environment that vacation dreams are made …More

Punta Cana, Dominican Republic

4.7 (3)

Saona Island Summer

Discover paradise on Saona Island, where white sandy beaches, clear turquoise waters, and countless palm trees provide an unspoiled environment that vacation dreams are made...

8 to 9 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$95

Whale Watching Tour in Samana Bay from Las Terrenas

Embark on an adventure that will leave you breathless! Enjoy the stunning view of Samaná Bay and witness a unique whale show. Observe these majestic …More

4.1 (7)

Whale Watching Tour in Samana Bay from Las Terrenas

Embark on an adventure that will leave you breathless! Enjoy the stunning view of Samaná Bay and witness a unique whale show. Observe these majestic...

6 hours Hotel pickup offered Free Cancellation

4.1 (7)

from
$125

Private Luxury Catamaran to Saona or Catalina Island

Our Private Luxury Catamaran Tour stands out with its exclusivity and personalized service. Unlike crowded group tours, you’ll enjoy private round-trip transportation from Punta Cana, …More

Punta Cana, Dominican Republic

5.0 (1)

Private Luxury Catamaran to Saona or Catalina Island

Our Private Luxury Catamaran Tour stands out with its exclusivity and personalized service. Unlike crowded group tours, you’ll enjoy private round-trip transportation from Punta Cana,...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$282

Full-Day Saona Island Tours All Inclusive

Explore the breathtaking Saona Island, a true Caribbean gem located within Cotubanamá National Park. Spend an unforgettable day surrounded by white-sand beaches, crystal-clear waters, and …More

Punta Cana, Dominican Republic

4.3 (8)

Full-Day Saona Island Tours All Inclusive

Explore the breathtaking Saona Island, a true Caribbean gem located within Cotubanamá National Park. Spend an unforgettable day surrounded by white-sand beaches, crystal-clear waters, and...

9 to 10 hours Hotel pickup offered Free Cancellation

4.3 (8)

from
$89

Private Catamaran with crew lunch drinks music for up to 15 pax

Gather your friends and get ready for an unforgettable day on the crystal-clear waters of Sosua Beach! This vibrant catamaran boat excursion is designed specifically …More

Cabarete, Dominican Republic

4.5 (4)

Private Catamaran with crew lunch drinks music for up to 15 pax

Gather your friends and get ready for an unforgettable day on the crystal-clear waters of Sosua Beach! This vibrant catamaran boat excursion is designed specifically...

3 to 4 hours Hotel pickup offered Free Cancellation

4.5 (4)

from
$1,599

Luminous Lagoon Small Group Tour from Montego Bay

Located in Falmouth, Trelawny the Luminous Lagoon (Glistening Waters) is a natural wonder, it is a phosphorescent lagoon where guests are taken on a beautiful …More

Montego Bay, Jamaica

3.8 (5)

Luminous Lagoon Small Group Tour from Montego Bay

Located in Falmouth, Trelawny the Luminous Lagoon (Glistening Waters) is a natural wonder, it is a phosphorescent lagoon where guests are taken on a beautiful...

45 minutes Hotel pickup offered Free Cancellation

3.8 (5)

from
$250

Private Group Negril Catamarans Sailing and Snorkel Boat tours offer fun and excitement in Negril Jamaica . Sail and snorkel at excellent Sand reefs and …More

Negril, Jamaica

5.0 (1)

Private Catamaran Negril Jamaica Sail -Open Bar

Private Group Negril Catamarans Sailing and Snorkel Boat tours offer fun and excitement in Negril Jamaica . Sail and snorkel at excellent Sand reefs and...

3 hours Hotel pickup offered

5.0 (1)

from
$2,900

Stingray City & Two Reef Snorkeling Adventure in Grand Cayman

Experience three of Grand Cayman’s signature marine adventures in one incredible morning on the water. Meet the famous southern stingrays in the shallow, crystal-clear waters …More

Grand Cayman, Cayman Islands

5.0 (1)

Stingray City & Two Reef Snorkeling Adventure in Grand Cayman

Experience three of Grand Cayman’s signature marine adventures in one incredible morning on the water. Meet the famous southern stingrays in the shallow, crystal-clear waters...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$119

ATV Blue Hole Rafting and Horseback Ride from Montego Bay 4in1

Choose our ATV, horseback riding, bamboo rafting, and Blue Hole Adventure tours for an affordable, reliable, and trustworthy experience that combines the best of Jamaica’s …More

Montego Bay, Jamaica

5.0 (1)

ATV Blue Hole Rafting and Horseback Ride from Montego Bay 4in1

Choose our ATV, horseback riding, bamboo rafting, and Blue Hole Adventure tours for an affordable, reliable, and trustworthy experience that combines the best of Jamaica’s...

5 to 6 hours Free Cancellation

5.0 (1)

from
$150

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?