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 →

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a …More

5.0 (51)

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a...

3 hours Free Cancellation

5.0 (51)

from
$166

Ocho Rios Powerboat & Dunn’s River Falls Adventure

Feel the warm tropical breeze kiss your skin as you soar along Jamaica's stunning North Coast on a high-speed powerboat adventure. Pass by iconic sites …More

Ocho Rios, Jamaica

5.0 (43)

Ocho Rios Powerboat & Dunn’s River Falls Adventure

Feel the warm tropical breeze kiss your skin as you soar along Jamaica's stunning North Coast on a high-speed powerboat adventure. Pass by iconic sites...

6 hours Hotel pickup offered Free Cancellation

5.0 (43)

from
$240

Full-Day Catalina Island Snorkeling Tour from La Romana

Welcome aboard and snorkel the most beautiful underwater ecosystem of the Dominican Republic, with a full-day all inclusive tour to Catalina Island. Experience clear turquoise …More

Punta Cana, Dominican Republic

3.6 (92)

Full-Day Catalina Island Snorkeling Tour from La Romana

Welcome aboard and snorkel the most beautiful underwater ecosystem of the Dominican Republic, with a full-day all inclusive tour to Catalina Island. Experience clear turquoise...

9 hours Hotel pickup offered Free Cancellation

3.6 (92)

from
$80

Full-day Private Tour in Turks and Caicos in a Luxury Axopar

Hop aboard and relax on the sundeck of one of our stylish Axopar 37′ while your captain navigates you through the emerald waters of Grace …More

5.0 (7)

Full-day Private Tour in Turks and Caicos in a Luxury Axopar

Hop aboard and relax on the sundeck of one of our stylish Axopar 37′ while your captain navigates you through the emerald waters of Grace...

8 hours Free Cancellation

5.0 (7)

from
$2,995

Nevis Panoramic Drive, Power Catamaran & Beach Experience

Experience a panoramic drive as you tour Nevis learning about its rich history. A photo moment is given at the birth place of Alexander Hamilton …More

4.1 (8)

Nevis Panoramic Drive, Power Catamaran & Beach Experience

Experience a panoramic drive as you tour Nevis learning about its rich history. A photo moment is given at the birth place of Alexander Hamilton...

5 hours Free Cancellation

4.1 (8)

from
$162

VIP Yacht Negril Caves Swimming & Ricks Cafe 15 persons

Welcome to SUN Queen, your VIP Luxury Yacht BOOKING COST INCLUDES UP TO 15 PERSONS ... she's a full 58' Azimut Flybridge Yacht, the only …More

Lucea, Jamaica

5.0 (4)

VIP Yacht Negril Caves Swimming & Ricks Cafe 15 persons

Welcome to SUN Queen, your VIP Luxury Yacht BOOKING COST INCLUDES UP TO 15 PERSONS ... she's a full 58' Azimut Flybridge Yacht, the only...

3 hours 30 minutes Hotel pickup offered

5.0 (4)

from
$4,450

Private Whale and Dolphin Whale Watching Boat Tour

Whale and dolphin watching in Dominica is an exhilarating experience for nature and animal enthusiasts. Our tours are typically conducted on smaller vessels, either 25, …More

4.6 (28)

Private Whale and Dolphin Whale Watching Boat Tour

Whale and dolphin watching in Dominica is an exhilarating experience for nature and animal enthusiasts. Our tours are typically conducted on smaller vessels, either 25,...

3 hours Hotel pickup offered

4.6 (28)

from
$2,300

This is Punta Cana like you’ve never imagined. Parasailing is a thrilling activity that’ll have you whooping over the Caribbean. After pick-up, head to Corales …More

Punta Cana, Dominican Republic

4.8 (25)

Parasailing in Bavaro

This is Punta Cana like you’ve never imagined. Parasailing is a thrilling activity that’ll have you whooping over the Caribbean. After pick-up, head to Corales...

2 hours Hotel pickup offered Free Cancellation

4.8 (25)

from
$57

The very best in deep sea sport fishing beckons off the coast of Jamaica. Imagine heading out onto the open waters off the coast, renowned …More

Montego Bay, Jamaica

4.1 (15)

Deep Sea Sport Fishing From Montego Bay

The very best in deep sea sport fishing beckons off the coast of Jamaica. Imagine heading out onto the open waters off the coast, renowned...

4 hours Hotel pickup offered Free Cancellation

4.1 (15)

from
$270

2-Hour Luxury Axopar Private Charter! Explore the Turks in style!

Relax on the sundeck of our stylish Axopar while your private Captain navigates you through the emerald waters of Grace Bay. Snorkel at the 3rd …More

5.0 (8)

2-Hour Luxury Axopar Private Charter! Explore the Turks in style!

Relax on the sundeck of our stylish Axopar while your private Captain navigates you through the emerald waters of Grace Bay. Snorkel at the 3rd...

2 hours Free Cancellation

5.0 (8)

from
$995

Los Haitises & Cayo Levantado (Lunch included, from Samana in Catamaran or Boat)

This is a Trip with Local tour guides. Focus in Nature and Wildlife of Los Haitises National Park. Our Guides will provide all informations needs …More

3.7 (17)

Los Haitises & Cayo Levantado (Lunch included, from Samana in Catamaran or Boat)

This is a Trip with Local tour guides. Focus in Nature and Wildlife of Los Haitises National Park. Our Guides will provide all informations needs...

6 to 8 hours

3.7 (17)

from
$60

Parasailing Adventure in Punta Cana with Pick Up

Get your adventure cap ready and get ready for breathtaking views. Our high flying team would love to take you on a flight so smooth …More

Punta Cana, Dominican Republic

4.6 (5)

Parasailing Adventure in Punta Cana with Pick Up

Get your adventure cap ready and get ready for breathtaking views. Our high flying team would love to take you on a flight so smooth...

20 minutes Hotel pickup offered Free Cancellation

4.6 (5)

from
$120

Private 7-Hour Catamaran Tour in Turks and Caicos

A truly one of a kind private Catamaran experience of Turks and Caicos beauty. This 7-hour tour, with our 42-foot Island Queen Catamaran, will take …More

5.0 (8)

Private 7-Hour Catamaran Tour in Turks and Caicos

A truly one of a kind private Catamaran experience of Turks and Caicos beauty. This 7-hour tour, with our 42-foot Island Queen Catamaran, will take...

7 hours Free Cancellation

5.0 (8)

from
$3,395

Private Captain's Most Popular Snorkeling and Beach Day with Lunch

Cruising along the Caribbean coast of Dominica is as fun and picturesque as one can imagine. Visit famous spots such as Champagne Reef, Scotts Head …More

5.0 (1)

Private Captain's Most Popular Snorkeling and Beach Day with Lunch

Cruising along the Caribbean coast of Dominica is as fun and picturesque as one can imagine. Visit famous spots such as Champagne Reef, Scotts Head...

4 hours 30 minutes Hotel pickup offered

5.0 (1)

from
$1,200

Shared 2 hours Sosúa Bay Snorkeling with Professional Guide

Join the Dive Cabarete team for a fun, safe and interesting snorkel experience! All our snorkel trips are guided by experienced SCUBA Instructors or Divemasters, …More

4.9 (48)

Shared 2 hours Sosúa Bay Snorkeling with Professional Guide

Join the Dive Cabarete team for a fun, safe and interesting snorkel experience! All our snorkel trips are guided by experienced SCUBA Instructors or Divemasters,...

2 hours Free Cancellation

4.9 (48)

from
$45

Saona Island Full Day Tour with Buffet Lunch, Paella, & Open Bar

Join us for an unforgettable full-day adventure to Saona Island, ideal for families and couples! Your experience begins with convenient hotel pickup in a comfortable …More

Punta Cana, Dominican Republic

4.8 (11)

Saona Island Full Day Tour with Buffet Lunch, Paella, & Open Bar

Join us for an unforgettable full-day adventure to Saona Island, ideal for families and couples! Your experience begins with convenient hotel pickup in a comfortable...

12 hours Hotel pickup offered Free Cancellation

4.8 (11)

from
$76

1. Exclusive Access and Privacy: Unlike larger group tours, a private catamaran offers a tailored experience, ideal for family gatherings, friends, or romantic getaways. 2. …More

Choc, St Lucia

5.0 (7)

Half Day Private Power Cat Charter

1. Exclusive Access and Privacy: Unlike larger group tours, a private catamaran offers a tailored experience, ideal for family gatherings, friends, or romantic getaways. 2....

4 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$2,150

Don't Worry - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Don't Worry, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a …More

5.0 (5)

Don't Worry - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Don't Worry, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a...

4 hours Free Cancellation

5.0 (5)

from
$210

Saona Island: Full-day Catamaran Tour - Small Group

Discover Saona Island, a natural jewel of the Dominican Republic, Known for its white sand beaches, turquoise waters, and endless palm trees, only accessible by …More

La Romana, Dominican Republic

4.8 (32)

Saona Island: Full-day Catamaran Tour - Small Group

Discover Saona Island, a natural jewel of the Dominican Republic, Known for its white sand beaches, turquoise waters, and endless palm trees, only accessible by...

8 hours Hotel pickup offered Free Cancellation

4.8 (32)

from
$135

Sightseeing Boat Trip Spanish Water Curacao

The Spanish water is one of the most popular waters of Curaçao. This is because the water is relatively calm, making it a real attraction …More

4.6 (38)

Sightseeing Boat Trip Spanish Water Curacao

The Spanish water is one of the most popular waters of Curaçao. This is because the water is relatively calm, making it a real attraction...

2 hours Free Cancellation

4.6 (38)

from
$45

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?