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) San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Small-Group El Yunque Waterfall & Waterslides with Pickup 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 →

We are a boutique catamaran specializing in private trips for families and small groups looking for a special day on vacation, We avoid the crowds …More

5.0 (30)

Private catamaran sail & snorkel cruise

We are a boutique catamaran specializing in private trips for families and small groups looking for a special day on vacation, We avoid the crowds...

3 hours Free Cancellation

5.0 (30)

from
$500

Sunset Sail with Cocktails and Appetizers

**A Beautiful Sunset Sail** What better way to experience the Caribbean Sunset than aboard 'The VI Cat' for a beautiful 2-hour sunset cruise with appetizers …More

4.8 (685)

Sunset Sail with Cocktails and Appetizers

**A Beautiful Sunset Sail** What better way to experience the Caribbean Sunset than aboard 'The VI Cat' for a beautiful 2-hour sunset cruise with appetizers...

2 hours Free Cancellation

4.8 (685)

from
$95

Aruba Natural Pool & Cave Safari: North Shore Adventure Tour

Discover the hidden treasures of Aruba’s south side on our exciting 4x4 Jeep Safari—where adventure, culture, and natural beauty come together in one unforgettable experience. …More

Palm - Eagle Beach, Aruba

4.9 (530)

Aruba Natural Pool & Cave Safari: North Shore Adventure Tour

Discover the hidden treasures of Aruba’s south side on our exciting 4x4 Jeep Safari—where adventure, culture, and natural beauty come together in one unforgettable experience....

6 hours Hotel pickup offered Free Cancellation

4.9 (530)

from
$117

El Yunque Off the Beaten Path Tour with Transportation

Feeling adventurous? Dare to explore a different zone of El Yunque, while enjoying in a safe and guided way, the different water activities this natural …More

4.8 (614)

El Yunque Off the Beaten Path Tour with Transportation

Feeling adventurous? Dare to explore a different zone of El Yunque, while enjoying in a safe and guided way, the different water activities this natural...

8 hours Hotel pickup offered Free Cancellation

4.8 (614)

from
$57

Small-Group Cruising and Snorkeling Catamaran Tour

This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limited size sets this tour apart from others. With us, …More

Punta Cana, Dominican Republic

4.9 (2,563)

Small-Group Cruising and Snorkeling Catamaran Tour

This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limited size sets this tour apart from others. With us,...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (2,563)

from
$99

3 Islands Tour, Swim with Pigs, Turtles, Snorkelling & lunch

Embark on an all-inclusive, exhilarating island-hopping adventure with us. Discover four stunning islands in one seamless, fun-filled day. Cruise past Atlantis on Paradise Island, sight …More

4.9 (991)

3 Islands Tour, Swim with Pigs, Turtles, Snorkelling & lunch

Embark on an all-inclusive, exhilarating island-hopping adventure with us. Discover four stunning islands in one seamless, fun-filled day. Cruise past Atlantis on Paradise Island, sight...

4 hours Free Cancellation

4.9 (991)

from
$175

Half-Day Snorkel Sail Tour with Caribbean Lunch

Who doesn't want to spend half the day on Aruba's gorgeous turquoise waters? This 4-hour sail includes snorkel gear and visits to three snorkel spots: …More

4.8 (828)

Half-Day Snorkel Sail Tour with Caribbean Lunch

Who doesn't want to spend half the day on Aruba's gorgeous turquoise waters? This 4-hour sail includes snorkel gear and visits to three snorkel spots:...

4 hours Free Cancellation

4.8 (828)

from
$107

Stingray City Experience Plus One Snorkeling Stop

This tour takes you to the famous Stingray City sandbar, where the wild stingrays swim around you in shallow water. The crew will show you …More

Seven Mile Beach, Cayman Islands

5.0 (573)

Stingray City Experience Plus One Snorkeling Stop

This tour takes you to the famous Stingray City sandbar, where the wild stingrays swim around you in shallow water. The crew will show you...

2 hours 45 minutes Hotel pickup offered Free Cancellation

5.0 (573)

from
$75

Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point

Our Business is family-owned and operated. Our two stop tour Stingray Sandbar & Coral Gardens Snorkeling Tour kicks off from the Royal Watler Cruise Ship …More

Seven Mile Beach, Cayman Islands

4.8 (678)

Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point

Our Business is family-owned and operated. Our two stop tour Stingray Sandbar & Coral Gardens Snorkeling Tour kicks off from the Royal Watler Cruise Ship...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (678)

from
$55

The west side of the island is known for its nature, history and incredible beaches! Along the way, our knowledgeable tour guide will tell you …More

Willemstad, Curacao

4.8 (597)

All West Beach Hopping Tour

The west side of the island is known for its nature, history and incredible beaches! Along the way, our knowledgeable tour guide will tell you...

7 hours Hotel pickup offered Free Cancellation

4.8 (597)

from
$85

Punta Cana Hip Hop Party Boat Adults Only Live DJ & Open Bar

Dance and celebrate off the coast of the Dominican Republic on this party boat package. Designed for adults only, board a catamaran and set off …More

Punta Cana, Dominican Republic

4.9 (1,429)

Punta Cana Hip Hop Party Boat Adults Only Live DJ & Open Bar

Dance and celebrate off the coast of the Dominican Republic on this party boat package. Designed for adults only, board a catamaran and set off...

3 hours 20 minutes Hotel pickup offered Free Cancellation

4.9 (1,429)

from
$65

Private Catamaran Cruise with Slide & unlimited drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip, you …More

La Romana, Dominican Republic

4.9 (769)

Private Catamaran Cruise with Slide & unlimited drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip, you...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (769)

from
$795

Nassau 3 Island Tour Swimming Pigs Turtles Snorkeling Beach Club

Embark on an all-inclusive, exhilarating island-hopping adventure with us. Discover four stunning islands in one seamless, fun-filled day. Cruise past Atlantis on Paradise Island, sight …More

4.8 (509)

Nassau 3 Island Tour Swimming Pigs Turtles Snorkeling Beach Club

Embark on an all-inclusive, exhilarating island-hopping adventure with us. Discover four stunning islands in one seamless, fun-filled day. Cruise past Atlantis on Paradise Island, sight...

4 hours Free Cancellation

4.8 (509)

from
$140

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove

Be sure to come hungry for The VI Cat's Harbor Lights Dinner Sail! This catamaran's dinner has offerings for all palettes in front of an …More

4.8 (1,331)

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove

Be sure to come hungry for The VI Cat's Harbor Lights Dinner Sail! This catamaran's dinner has offerings for all palettes in front of an...

2 hours Free Cancellation

4.8 (1,331)

from
$119

50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select …More

5.0 (681)

50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select...

4 to 7 hours Free Cancellation

5.0 (681)

from
$1,441

Iconic Aruba Sail and Snorkel Experience

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck. …More

4.8 (511)

Iconic Aruba Sail and Snorkel Experience

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck....

2 hours 30 minutes Free Cancellation

4.8 (511)

from
$67

Cocktail Sunset Cruise from Sapphire Beach Resort

Experience the magic of a Caribbean sunset aboard the Breakaway yacht for a Cocktail Sunset Cruise from 5:00 PM to 7:00 PM. Glide along the …More

4.9 (771)

Cocktail Sunset Cruise from Sapphire Beach Resort

Experience the magic of a Caribbean sunset aboard the Breakaway yacht for a Cocktail Sunset Cruise from 5:00 PM to 7:00 PM. Glide along the...

2 hours Free Cancellation

4.9 (771)

from
$110

Starfish Point, Stingray City & Coral Garden (3-STOP Adventure)

A Family-Business Owned Operated Company providing numerous excursions in the Cayman Islands for over two decades. We provide FREE Courtesy pick up for our Cruise …More

George Town, Cayman Islands

4.8 (1,208)

Starfish Point, Stingray City & Coral Garden (3-STOP Adventure)

A Family-Business Owned Operated Company providing numerous excursions in the Cayman Islands for over two decades. We provide FREE Courtesy pick up for our Cruise...

3 hours 30 minutes Free Cancellation

4.8 (1,208)

from
$80

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Explore the remarkable Altos de Chavon and dig your toes in the sand of Saona Island during this full-day excursion from Punta Cana, available every …More

Punta Cana, Dominican Republic

4.5 (2,648)

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Explore the remarkable Altos de Chavon and dig your toes in the sand of Saona Island during this full-day excursion from Punta Cana, available every...

9 hours Hotel pickup offered Free Cancellation

4.5 (2,648)

from
$82

Parasailing, Snorkel Cruise & Virgen Beach from Punta Cana

Relax and enjoy with these impressive attractions in an unforgettable adventure in Punta Cana. While parasailing, observe from 500 feet in the air the beauty …More

Punta Cana, Dominican Republic

4.9 (528)

Parasailing, Snorkel Cruise & Virgen Beach from Punta Cana

Relax and enjoy with these impressive attractions in an unforgettable adventure in Punta Cana. While parasailing, observe from 500 feet in the air the beauty...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (528)

from
$159

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?