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 →

Punta Cana: Adults Only Party Boat,Open Bar & Snorkeling

Get ready for the ultimate Punta Cana Party Boat experience with Jhoraji Tours! This isn't just a boat ride — it's a Caribbean celebration filled …More

Punta Cana, Dominican Republic

3.5 (2)

Punta Cana: Adults Only Party Boat,Open Bar & Snorkeling

Get ready for the ultimate Punta Cana Party Boat experience with Jhoraji Tours! This isn't just a boat ride — it's a Caribbean celebration filled...

6 hours Hotel pickup offered Free Cancellation

3.5 (2)

from
$60

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

Our Horseback Ride & Catamaran Cruise Experience combines the charm of horseback riding with the relaxing beauty of the Caribbean Sea, giving you two unique …More

Lucea, Jamaica

4.0 (1)

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

Our Horseback Ride & Catamaran Cruise Experience combines the charm of horseback riding with the relaxing beauty of the Caribbean Sea, giving you two unique...

5 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$500

Portland Nature and Eco Tour -From Montego Bay, Negril, Ocho Rios

Stop At: Boston Bay, is a stunning coastal town with white sand beaches and turquoise waters. Known for water sports such as swimming, surfing, and …More

Lucea, Jamaica

4.0 (1)

Portland Nature and Eco Tour -From Montego Bay, Negril, Ocho Rios

Stop At: Boston Bay, is a stunning coastal town with white sand beaches and turquoise waters. Known for water sports such as swimming, surfing, and...

10 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$500

Punta Cana Private Catamaran: Open Bar, Snorkeling & Natural Pool

Ready to enjoy a private Punta Cana booze cruise with a small group of your family friends? Our Party Boat offers the best service for …More

4.0 (1)

Punta Cana Private Catamaran: Open Bar, Snorkeling & Natural Pool

Ready to enjoy a private Punta Cana booze cruise with a small group of your family friends? Our Party Boat offers the best service for...

4 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$990

Catamaran Tour in Bavaro, Punta Cana – Snorkeling Experience

Explore the beauty of the Punta Cana coastline during our exclusive Bavaro Catamaran Tour. Enjoy the sounds of the Caribbean, relax, and feel the ocean …More

Punta Cana, Dominican Republic

3.7 (3)

Catamaran Tour in Bavaro, Punta Cana – Snorkeling Experience

Explore the beauty of the Punta Cana coastline during our exclusive Bavaro Catamaran Tour. Enjoy the sounds of the Caribbean, relax, and feel the ocean...

3 hours Hotel pickup offered Free Cancellation

3.7 (3)

from
$125

Enjoy our new catamaran; Caribbean Sea ;. We will visit the Reserve "CENOTE",where we will swim in one of the most beautiful springs of crystalline …More

Punta Cana, Dominican Republic

3.0 (1)

Catamaran Caribbean Paradise

Enjoy our new catamaran; Caribbean Sea ;. We will visit the Reserve "CENOTE",where we will swim in one of the most beautiful springs of crystalline...

5 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$80

Full day excursion to Saona Island from Uvero Alto wih snorkeling

Embark on a full-day adventure to explore the most impressive and hidden corners of Saona Island. Start by admiring Saona Marita Bay in Bayahibe, then …More

Punta Cana, Dominican Republic

4.0 (1)

Full day excursion to Saona Island from Uvero Alto wih snorkeling

Embark on a full-day adventure to explore the most impressive and hidden corners of Saona Island. Start by admiring Saona Marita Bay in Bayahibe, then...

8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$170

Puerto Plata: Waterfalls of Damajagua (SAFARI HALF DAY)

In the municipality of Imbert, we will discover the world-famous “Damajagua Waterfalls”. With the necessary equipment for the adventure, we walk through the Dominican rainforest, …More

Puerto Plata, Dominican Republic

4.0 (1)

Puerto Plata: Waterfalls of Damajagua (SAFARI HALF DAY)

In the municipality of Imbert, we will discover the world-famous “Damajagua Waterfalls”. With the necessary equipment for the adventure, we walk through the Dominican rainforest,...

4 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$69

Adventure in Samaná : El Limón Waterfall

Live an authentic adventure along the eastern coastal plain of the Dominican Republic. Ride to the impressive El Limón Waterfall enjoying the beautiful landscapes and …More

La Romana, Dominican Republic

4.0 (1)

Adventure in Samaná : El Limón Waterfall

Live an authentic adventure along the eastern coastal plain of the Dominican Republic. Ride to the impressive El Limón Waterfall enjoying the beautiful landscapes and...

9 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$300

Full Day Catalina Island Snorkeling Adventure & Altos de Chavon

Catalina Island is recognized as one of the best snorkeling and scuba diving destinations in the Dominican Republic. This amazing day-trip excursion will give you …More

Punta Cana, Dominican Republic

3.5 (2)

Full Day Catalina Island Snorkeling Adventure & Altos de Chavon

Catalina Island is recognized as one of the best snorkeling and scuba diving destinations in the Dominican Republic. This amazing day-trip excursion will give you...

10 to 12 hours Hotel pickup offered Free Cancellation

3.5 (2)

from
$135

Cayman Combo Tour Stingray City, Starfish Point & Reef Snorkeling

Get ready for an unforgettable Caribbean adventure through three of Grand Cayman’s most iconic marine experiences! Set out by boat to discover Stingray City, Starfish …More

Grand Cayman, Cayman Islands

4.0 (1)

Cayman Combo Tour Stingray City, Starfish Point & Reef Snorkeling

Get ready for an unforgettable Caribbean adventure through three of Grand Cayman’s most iconic marine experiences! Set out by boat to discover Stingray City, Starfish...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.0 (1)

from
$119

Come and not only dream of a paradise, give yourself the opportunity to live in it. The enchanting Isla Saona is your dream come true. …More

Punta Cana, Dominican Republic

3.7 (3)

Full day - Saona Island from punta cana

Come and not only dream of a paradise, give yourself the opportunity to live in it. The enchanting Isla Saona is your dream come true....

8 hours 30 minutes Free Cancellation

3.7 (3)

from
$75

Bamboo Rafting and Catamaran Cruise Party Boat Tour Montego Bay

Experience the best of Jamaica with our Bamboo Rafting and Catamaran Party Boat adventure in Montego Bay! This unforgettable combination of relaxation and excitement offers …More

Montego Bay, Jamaica

4.0 (1)

Bamboo Rafting and Catamaran Cruise Party Boat Tour Montego Bay

Experience the best of Jamaica with our Bamboo Rafting and Catamaran Party Boat adventure in Montego Bay! This unforgettable combination of relaxation and excitement offers...

6 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$85

Private Trip to Los Haitises from Sabana De La Mar

This is a private tour with locals tours guides. You will learn the original information about the culture of Los haitises national park. Locals know …More

3.5 (2)

Private Trip to Los Haitises from Sabana De La Mar

This is a private tour with locals tours guides. You will learn the original information about the culture of Los haitises national park. Locals know...

3 to 4 hours

3.5 (2)

from
$95

Whale Watching in Punta Cana to Samana and Bacardi Island

From the Punta Cana hotels, we’ll enjoy the beautiful landscapes of the Oriental Mountain Range as we drive north of Punta Cana before arriving in …More

3.3 (3)

Whale Watching in Punta Cana to Samana and Bacardi Island

From the Punta Cana hotels, we’ll enjoy the beautiful landscapes of the Oriental Mountain Range as we drive north of Punta Cana before arriving in...

10 hours 30 minutes Hotel pickup offered

3.3 (3)

from
$135

Beach Buggy Excursion in Punta Cana Bavaro

It is a short activity of only 4 hours so you will have the whole day to enjoy your hotel once finished. You can choose …More

Punta Cana, Dominican Republic

4.0 (1)

Beach Buggy Excursion in Punta Cana Bavaro

It is a short activity of only 4 hours so you will have the whole day to enjoy your hotel once finished. You can choose...

4 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$54

f you are looking for parties at sunrise or sunset on a boat where alcohol flows freely and the music pumped, then climb aboard the …More

Punta Cana, Dominican Republic

3.0 (2)

Party Boat in Punta Cana - Booze Cruse

f you are looking for parties at sunrise or sunset on a boat where alcohol flows freely and the music pumped, then climb aboard the...

3 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$75

Saona Island Adventure: Natural Pool & All-Inclusive Drinks

Experience Paradise at Isla Saona! If you’re looking for a unique Caribbean adventure, our Isla Saona excursion is the perfect choice. Set sail on a …More

Punta Cana, Dominican Republic

2.8 (4)

Saona Island Adventure: Natural Pool & All-Inclusive Drinks

Experience Paradise at Isla Saona! If you’re looking for a unique Caribbean adventure, our Isla Saona excursion is the perfect choice. Set sail on a...

6 hours Hotel pickup offered Free Cancellation

2.8 (4)

from
$79

Full-Day Tour of Saona Island from Punta Cana

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) …More

Punta Cana, Dominican Republic

3.0 (1)

Full-Day Tour of Saona Island from Punta Cana

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve)...

10 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$85

Full-day Whale watching Tour in Samana Bay from Punta Cana

Embark on a 5-in-1 adventure that will take your breath away! Enjoy the impressive view of Samaná Bay and witness a unique whale show. Observe …More

Samaná, Dominican Republic

3.0 (2)

Full-day Whale watching Tour in Samana Bay from Punta Cana

Embark on a 5-in-1 adventure that will take your breath away! Enjoy the impressive view of Samaná Bay and witness a unique whale show. Observe...

8 hours Hotel pickup offered Free Cancellation

3.0 (2)

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?