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 →

Party Cruise with Snorkeling & Parasailing

Enjoy the luxury and comfort on a half-day party cruise on the newest sailing catamaran of Punta Cana, with two of the most popular water …More

4.9 (159)

Party Cruise with Snorkeling & Parasailing

Enjoy the luxury and comfort on a half-day party cruise on the newest sailing catamaran of Punta Cana, with two of the most popular water...

4 hours Hotel pickup offered Free Cancellation

4.9 (159)

from
$125

Punta Cana Private Cruise Up To 10 Snorkeling & Seafood lunch

Only company with a floating kitchen and large floating bar Our menu options cater to all tastes—including seafood, meat, surf and turf, vegetarian, and more. …More

Punta Cana, Dominican Republic

5.0 (179)

Punta Cana Private Cruise Up To 10 Snorkeling & Seafood lunch

Only company with a floating kitchen and large floating bar Our menu options cater to all tastes—including seafood, meat, surf and turf, vegetarian, and more....

4 hours Hotel pickup offered Free Cancellation

5.0 (179)

from
$1,063

ATV Adventure & Bamboo Rafting with Limestone Massage

Our Bamboo River Rafting and ATV riding COMBO tour is the perfect and adventurous way to explore the natural beauty and local culture of Jamaica. …More

Lucea, Jamaica

5.0 (25)

ATV Adventure & Bamboo Rafting with Limestone Massage

Our Bamboo River Rafting and ATV riding COMBO tour is the perfect and adventurous way to explore the natural beauty and local culture of Jamaica....

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$126

Public Paradise in Saona Relaxation and Adventure on Dream Beaches

Embark on an authentic getaway to Saona, far from the hustle and bustle of mass tourism. Our excursion offers you total immersion in a preserved …More

Punta Cana, Dominican Republic

4.9 (168)

Public Paradise in Saona Relaxation and Adventure on Dream Beaches

Embark on an authentic getaway to Saona, far from the hustle and bustle of mass tourism. Our excursion offers you total immersion in a preserved...

8 hours Hotel pickup offered Free Cancellation

4.9 (168)

from
$140

Private Half-Day Catamaran Cruise, Turks and Caicos Islands

Private catamaran cruise with Captain Ben, smiling, funny and who knows the islands by heart. You will spend an unforgettable half day in the most …More

4.8 (35)

Private Half-Day Catamaran Cruise, Turks and Caicos Islands

Private catamaran cruise with Captain Ben, smiling, funny and who knows the islands by heart. You will spend an unforgettable half day in the most...

4 hours Free Cancellation

4.8 (35)

from
$1,990

Discover the best of the Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or …More

4.8 (19)

Private Afternoon Tour Fjord 38 Ben

Discover the best of the Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or...

4 hours Free Cancellation

4.8 (19)

from
$2,490

LUXURY REEF & NYLON POOL ADVENTURE Cruise • Snorkel • Sip • Relax Experience Tobago from the water with Fish Tobago Tours on our Luxury …More

4.9 (156)

Luxury Reef and Nylon Pool Adventure

LUXURY REEF & NYLON POOL ADVENTURE Cruise • Snorkel • Sip • Relax Experience Tobago from the water with Fish Tobago Tours on our Luxury...

3 hours

4.9 (156)

from
$230

Private Jet Car or Jet Ski Experience in Montego Bay

Take a splash into Montego Bay’s crystal Blue waters like never before on this exciting Jet Car Tour. This is a unique exciting and exhilarating …More

Montego Bay, Jamaica

5.0 (15)

Private Jet Car or Jet Ski Experience in Montego Bay

Take a splash into Montego Bay’s crystal Blue waters like never before on this exciting Jet Car Tour. This is a unique exciting and exhilarating...

1 hour 20 minutes Hotel pickup offered Free Cancellation

5.0 (15)

from
$98

Private Full Day Snorkel Soufriere Charter

Escape your day to day life and discover serenity aboard our vessel,Wild Dreams. Our private snorkeling trip combines an exploration of the stunningly abundant alive …More

Anse La Raye, St Lucia

5.0 (19)

Private Full Day Snorkel Soufriere Charter

Escape your day to day life and discover serenity aboard our vessel,Wild Dreams. Our private snorkeling trip combines an exploration of the stunningly abundant alive...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (19)

from
$265

Saona Island Tour: Small Group Trip on Trimaran Motorise

Come and enjoy a day on the island of Saona in a small group, far from the tourist hordes. On a comfortable motorized trimaran suitable …More

5.0 (47)

Saona Island Tour: Small Group Trip on Trimaran Motorise

Come and enjoy a day on the island of Saona in a small group, far from the tourist hordes. On a comfortable motorized trimaran suitable...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (47)

from
$110

Icacos or Palomino Private Sunset Boat Tour from Fajardo PR

You want to do something different? Enjoy a private boat sunset experience on a private island from the east coast of Puerto Rico. This is …More

Fajardo, Puerto Rico

4.8 (18)

Icacos or Palomino Private Sunset Boat Tour from Fajardo PR

You want to do something different? Enjoy a private boat sunset experience on a private island from the east coast of Puerto Rico. This is...

2 hours Free Cancellation

4.8 (18)

from
$399

Island Hopper Adventure in Providenciales

Our Island Hoppers Adventure is one of our signature adventure and offered daily from 9 am till 3:00 pm. This Adventure is 2 Hours and …More

4.7 (28)

Island Hopper Adventure in Providenciales

Our Island Hoppers Adventure is one of our signature adventure and offered daily from 9 am till 3:00 pm. This Adventure is 2 Hours and...

2 hours Free Cancellation

4.7 (28)

from
$430

Private Charter 37' Axopar in US Virgin Islands

Stormy Pirates Boat Charters is a family owned and operated company serving both St.Thomas and St. John. This private trip is completely customizable for your …More

5.0 (85)

Private Charter 37' Axopar in US Virgin Islands

Stormy Pirates Boat Charters is a family owned and operated company serving both St.Thomas and St. John. This private trip is completely customizable for your...

6 hours

5.0 (85)

from
$1,695

Trinidad Northern Eco-Cultural Full-Day Highlights Tour from Port of Spain

This day trip will start with a brief city tour in the bustling heart of Port of Spain, Trinidad’s capital. Enjoy the scenic North Coast …More

4.9 (35)

Trinidad Northern Eco-Cultural Full-Day Highlights Tour from Port of Spain

This day trip will start with a brief city tour in the bustling heart of Port of Spain, Trinidad’s capital. Enjoy the scenic North Coast...

8 hours Hotel pickup offered Free Cancellation

4.9 (35)

from
$135

Private Luxury Catamaran Cruise in St. Lucia

Experience luxury on board our impressive 50ft Power Catamaran, complete with all the amenities. Our crew is dedicated to providing personalized trips that cater to …More

4.9 (119)

Private Luxury Catamaran Cruise in St. Lucia

Experience luxury on board our impressive 50ft Power Catamaran, complete with all the amenities. Our crew is dedicated to providing personalized trips that cater to...

4 to 8 hours Free Cancellation

4.9 (119)

from
$2,000

Adults Only Jolly Pirate Sunset Grub and Grog Dinner Sail

Join the Jolly Crew aboard Aruba's liveliest sunset party cruise with an opportunity to swing from the Jolly Pirate yard arm. There's a DJ aboard …More

4.9 (61)

Adults Only Jolly Pirate Sunset Grub and Grog Dinner Sail

Join the Jolly Crew aboard Aruba's liveliest sunset party cruise with an opportunity to swing from the Jolly Pirate yard arm. There's a DJ aboard...

3 hours

4.9 (61)

from
$125

Venture to Mangrove Cay and explore its estuaries. Be ready to sight juvenile turtles, sharks, jellyfish, and conch and learn about the mangrove ecosystem. …More

4.9 (131)

Mangrove Cay Tour

Venture to Mangrove Cay and explore its estuaries. Be ready to sight juvenile turtles, sharks, jellyfish, and conch and learn about the mangrove ecosystem....

2 hours Hotel pickup offered

4.9 (131)

from
$105

Discover Le François and its treasures! Go on a boat trip for a whole day! Visit the famous “White Funds” and the “Josephine’s Bathtub”! Islet …More

4.8 (77)

White Funds Day Le François

Discover Le François and its treasures! Go on a boat trip for a whole day! Visit the famous “White Funds” and the “Josephine’s Bathtub”! Islet...

7 hours Free Cancellation

4.8 (77)

from
$97

El Yunque Rainforest, Waterslides & Beach Tour from San Juan

Experience the Best of Puerto Rico on This Unforgettable Full-Day Tour! Embark on an exciting adventure through the breathtaking El Yunque Rainforest, where you’ll explore …More

Isla Verde, Puerto Rico

5.0 (29)

El Yunque Rainforest, Waterslides & Beach Tour from San Juan

Experience the Best of Puerto Rico on This Unforgettable Full-Day Tour! Embark on an exciting adventure through the breathtaking El Yunque Rainforest, where you’ll explore...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$95

Samana + Baracardi Island Tour And Lemon Jump From Puntacana

If it is about beautiful beaches and exuberant nature, you cannot stay without visiting the Samana peninsula. Starting this excursion with the beautiful views of …More

Punta Cana, Dominican Republic

4.9 (20)

Samana + Baracardi Island Tour And Lemon Jump From Puntacana

If it is about beautiful beaches and exuberant nature, you cannot stay without visiting the Samana peninsula. Starting this excursion with the beautiful views of...

7 to 8 hours Hotel pickup offered Free Cancellation

4.9 (20)

from
$130

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?