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 →

This vessel is fully equiprt for a luxury day on the water. See some of the best beaches and coves around the island. Our experienced …More

St John's, Antigua and Barbuda

4.8 (6)

Luxury Private Yacht Rafnar Cruise

This vessel is fully equiprt for a luxury day on the water. See some of the best beaches and coves around the island. Our experienced...

7 hours Free Cancellation

4.8 (6)

from
$2,300

2H Private Boat Tour in Spanish Waters with Swim Stop

We can take groups up to 8 people. Craft a unique Curacao memory with a private boat tour, where the beauty of Spanish Waters unfolds …More

5.0 (2)

2H Private Boat Tour in Spanish Waters with Swim Stop

We can take groups up to 8 people. Craft a unique Curacao memory with a private boat tour, where the beauty of Spanish Waters unfolds...

2 hours Free Cancellation

5.0 (2)

from
$500

Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to …More

Lucea, Jamaica

4.3 (18)

Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to...

8 hours Hotel pickup offered Free Cancellation

4.3 (18)

from
$87

Saona Island Sailing Tour - All Inclusive

Saona Island is one of the most visited places in the Dominican Republic due to its stunning natural beauty and its various and sundry activities. …More

Punta Cana, Dominican Republic

3.8 (21)

Saona Island Sailing Tour - All Inclusive

Saona Island is one of the most visited places in the Dominican Republic due to its stunning natural beauty and its various and sundry activities....

8 hours Hotel pickup offered Free Cancellation

3.8 (21)

from
$70

Enjoy a day in Paradise!! in a private boat, away from the crowd. On our Full Day Tour you will be able to enjoy up …More

5.0 (15)

Full Day Private Boat Tour To Culebra

Enjoy a day in Paradise!! in a private boat, away from the crowd. On our Full Day Tour you will be able to enjoy up...

7 hours Free Cancellation

5.0 (15)

from
$1,650

Adult-only tour dedicated to take groups to Noah’s Ark on Sundays afternoon. Noah’s Ark is a floating beach club build on the aquamarine waters of …More

4.3 (37)

Noahs Ark Catamaran Trip

Adult-only tour dedicated to take groups to Noah’s Ark on Sundays afternoon. Noah’s Ark is a floating beach club build on the aquamarine waters of...

4 hours Hotel pickup offered Free Cancellation

4.3 (37)

from
$120

Full Day ECO Snorkeling with Turtles & BBQ Lunch

Explore the stunning coastlines of St Maarten and St Martin on a thrilling 7-hour powerboat tour. Visit premier snorkeling spots like Tintamarre Island and Creole …More

5.0 (3)

Full Day ECO Snorkeling with Turtles & BBQ Lunch

Explore the stunning coastlines of St Maarten and St Martin on a thrilling 7-hour powerboat tour. Visit premier snorkeling spots like Tintamarre Island and Creole...

7 hours Free Cancellation

5.0 (3)

from
$149

Experience the thrill of snuba, a unique blend of snorkeling and scuba diving, at the stunning Emerald Reef. Breathe comfortably through a regulator connected to …More

5.0 (3)

Snuba Adventure at Emerald Reef

Experience the thrill of snuba, a unique blend of snorkeling and scuba diving, at the stunning Emerald Reef. Breathe comfortably through a regulator connected to...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$112

Punta Cana: Saona Island, Natural Pool, Catamaran and Lunch

Live the Isla Saona experience as it should be! We distinguish ourselves by our personalized attention and a service of excellence from the first minute. …More

Punta Cana, Dominican Republic

3.9 (58)

Punta Cana: Saona Island, Natural Pool, Catamaran and Lunch

Live the Isla Saona experience as it should be! We distinguish ourselves by our personalized attention and a service of excellence from the first minute....

7 to 8 hours Hotel pickup offered Free Cancellation

3.9 (58)

from
$75

Excursión de un día a la Isla Saona desde Punta Cana con almuerzo

Discover a dynamic way of getting to know Isla Saona on an excursion sailing the sea by catamaran and speedboat while enjoying the sun and …More

Punta Cana, Dominican Republic

3.9 (31)

Excursión de un día a la Isla Saona desde Punta Cana con almuerzo

Discover a dynamic way of getting to know Isla Saona on an excursion sailing the sea by catamaran and speedboat while enjoying the sun and...

10 hours 30 minutes Hotel pickup offered Free Cancellation

3.9 (31)

from
$75

Bioluminescent Bay Adventure in Grand Cayman

Join us for an unforgettable evening as you witness millions of tiny plankton illuminating the waters at night. This unique boat tour gives you the …More

Grand Cayman, Cayman Islands

4.1 (28)

Bioluminescent Bay Adventure in Grand Cayman

Join us for an unforgettable evening as you witness millions of tiny plankton illuminating the waters at night. This unique boat tour gives you the...

3 hours Hotel pickup offered Free Cancellation

4.1 (28)

from
$139

Experience a unique side of Barbados’ night life on an Atlantis Submarine Night Tour. A short boat ride and transfer to the submarine then, Dive! …More

Speightstown, Barbados

4.1 (37)

Atlantis Submarines Night Tour

Experience a unique side of Barbados’ night life on an Atlantis Submarine Night Tour. A short boat ride and transfer to the submarine then, Dive!...

2 hours Hotel pickup offered Free Cancellation

4.1 (37)

from
$130

Exuma Swimming Pigs and Sharks Tour by Plane

Experience the highlights of the Exuma Islands on this Half-Day adventure from Nassau, with the opportunity to visit seven or more islands in one day! …More

Nassau, Bahamas

5.0 (6)

Exuma Swimming Pigs and Sharks Tour by Plane

Experience the highlights of the Exuma Islands on this Half-Day adventure from Nassau, with the opportunity to visit seven or more islands in one day!...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$4,000

Private 4 hour Rose Island tour snorkeling fishing

Fun all day boating experience with a friendly staff who is will to go above and beyond to make your vacation one to remember. From …More

5.0 (6)

Private 4 hour Rose Island tour snorkeling fishing

Fun all day boating experience with a friendly staff who is will to go above and beyond to make your vacation one to remember. From...

4 hours Free Cancellation

5.0 (6)

from
$700

Private Swim With Pigs and Snorkeling in Paradise Tour

A scenic boat ride on turquoise Bahamian seas takes you on this unbeatable excursion where you get to splash, swim and feed pigs in paradise, …More

5.0 (9)

Private Swim With Pigs and Snorkeling in Paradise Tour

A scenic boat ride on turquoise Bahamian seas takes you on this unbeatable excursion where you get to splash, swim and feed pigs in paradise,...

4 hours Free Cancellation

5.0 (9)

from
$850

27ft Dream Life Private Charter in Nassau

With this private tour you have the flexibility to experience The Bahamas your way without being grouped together with strangers. …More

5.0 (6)

27ft Dream Life Private Charter in Nassau

With this private tour you have the flexibility to experience The Bahamas your way without being grouped together with strangers....

4 hours Free Cancellation

5.0 (6)

from
$890

Private Sightseeing Tour in Nassau with Lunch

Prepare for an unforgettable half-day adventure aboard our private charter, exploring the stunning surroundings of Nassau and creating memories with the coolest pigs in the …More

Nassau, Bahamas

5.0 (2)

Private Sightseeing Tour in Nassau with Lunch

Prepare for an unforgettable half-day adventure aboard our private charter, exploring the stunning surroundings of Nassau and creating memories with the coolest pigs in the...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$283

Combo El Yunque and Snorkeling Small-Group Tour from San Juan

Immerse yourself in an unforgettable adventure with our El Yunque rainforest and Puerto Rico Caribbean San Juan snorkeling combo tour! Delve into the lush wonders …More

Isla Verde, Puerto Rico

4.7 (10)

Combo El Yunque and Snorkeling Small-Group Tour from San Juan

Immerse yourself in an unforgettable adventure with our El Yunque rainforest and Puerto Rico Caribbean San Juan snorkeling combo tour! Delve into the lush wonders...

8 hours Hotel pickup offered Free Cancellation

4.7 (10)

from
$175

Bio Bay Night Kayaking with Transport from San Juan

Paddle through the mangrove forest on your way to the unique Bioluminescent Bay of Laguna Grande in Fajardo, Puerto Rico! Savor your surroundings while the …More

Luquillo, Puerto Rico

4.2 (29)

Bio Bay Night Kayaking with Transport from San Juan

Paddle through the mangrove forest on your way to the unique Bioluminescent Bay of Laguna Grande in Fajardo, Puerto Rico! Savor your surroundings while the...

2 hours Hotel pickup offered Free Cancellation

4.2 (29)

from
$125

St Maarten Boat Tour with Lunch, Drinks, & Snorkeling Gear

Looking to spend the day in the ocean breeze and explore all the secrets of the amazing Sint Maarten/Saint Martin island? Then this is the …More

5.0 (7)

St Maarten Boat Tour with Lunch, Drinks, & Snorkeling Gear

Looking to spend the day in the ocean breeze and explore all the secrets of the amazing Sint Maarten/Saint Martin island? Then this is the...

4 hours Free Cancellation

5.0 (7)

from
$175

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?