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 →

Private FullDay Stingray City, Snorkeling, Kaibo Bar & Grill and Starfish Beach

Avoid the crowds and join us for 4 1/2 hours on your own private boat and crew to get the experience of a life time …More

Grand Cayman, Cayman Islands

5.0 (32)

Private FullDay Stingray City, Snorkeling, Kaibo Bar & Grill and Starfish Beach

Avoid the crowds and join us for 4 1/2 hours on your own private boat and crew to get the experience of a life time...

5 hours Free Cancellation

5.0 (32)

from
$1,200

Explore central Bermuda by land and sea. Enjoy a narrated sightseeing cruise from Royal Naval Dockyard to Bermuda's Capital City - Hamilton. With two hours …More

4.5 (10)

Hamilton Shopping & Sightseeing

Explore central Bermuda by land and sea. Enjoy a narrated sightseeing cruise from Royal Naval Dockyard to Bermuda's Capital City - Hamilton. With two hours...

3 hours 30 minutes Free Cancellation

4.5 (10)

from
$100

Don't miss out on a day on Tip Top Catamaran! It's a beautiful day on the ocean. We do two different snorkeling spots, lunch on …More

Cabarete, Dominican Republic

4.4 (7)

Sosua Catamaran Excursion

Don't miss out on a day on Tip Top Catamaran! It's a beautiful day on the ocean. We do two different snorkeling spots, lunch on...

6 to 7 hours Hotel pickup offered Free Cancellation

4.4 (7)

from
$84

Private Luxury Catamaran Champagne Sunset Cruise

Avoid the crowds. Step on to your fully customizable private sunset cruise with your friends and family. Our attentive office staff will help make your …More

5.0 (4)

Private Luxury Catamaran Champagne Sunset Cruise

Avoid the crowds. Step on to your fully customizable private sunset cruise with your friends and family. Our attentive office staff will help make your...

2 hours Free Cancellation

5.0 (4)

from
$1,095

Visit one of the most beautiful islands on the North Coast. Paradise Island will welcome you with turquoise water, white sand and colorful reef. Visit …More

Cabarete, Dominican Republic

4.3 (53)

Cayo Arena, Paradise Island Tour

Visit one of the most beautiful islands on the North Coast. Paradise Island will welcome you with turquoise water, white sand and colorful reef. Visit...

9 to 10 hours Hotel pickup offered Free Cancellation

4.3 (53)

from
$89

3-Hour Private Charter w/ Open Bar & Snorkeling (Max 26 Persons)

Magic Time is Unique she offers comfort and speed. She is a Catamaran and rides the waves, no more crashing on the waves just rides …More

4.9 (29)

3-Hour Private Charter w/ Open Bar & Snorkeling (Max 26 Persons)

Magic Time is Unique she offers comfort and speed. She is a Catamaran and rides the waves, no more crashing on the waves just rides...

3 hours Free Cancellation

4.9 (29)

from
$800

Saona Island is paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees. This environment invites you to relax. …More

Punta Cana, Dominican Republic

3.9 (88)

Saona Island Tour with Lunch and Pickup

Saona Island is paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees. This environment invites you to relax....

10 hours Hotel pickup offered Free Cancellation

3.9 (88)

from
$64

Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to …More

5.0 (6)

Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to...

2 hours Free Cancellation

5.0 (6)

from
$1,345

Private Stingray City Snorkeling and BioBay Charter for 10 Guests

This private 6 hour afternoon & evening adventure is a wonderful combination of daytime fun, sunset dining and BioBay magic. Your 2-person crew including experienced …More

Grand Cayman, Cayman Islands

5.0 (7)

Private Stingray City Snorkeling and BioBay Charter for 10 Guests

This private 6 hour afternoon & evening adventure is a wonderful combination of daytime fun, sunset dining and BioBay magic. Your 2-person crew including experienced...

6 hours

5.0 (7)

from
$2,000

Private Sunset Catamaran Cruise Turks and Caicos Islands

A Caribbean vacation can't be complete without a private sunset Catamaran cruise. Romantic moment or festive moment with friends, you decide! Sip champagne in front …More

4.6 (9)

Private Sunset Catamaran Cruise Turks and Caicos Islands

A Caribbean vacation can't be complete without a private sunset Catamaran cruise. Romantic moment or festive moment with friends, you decide! Sip champagne in front...

1 hour 30 minutes Free Cancellation

4.6 (9)

from
$1,190

Full-Day Private Catamaran, Turks and Caicos Cruise

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

4.5 (8)

Full-Day Private Catamaran, Turks and Caicos Cruise

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

7 hours Free Cancellation

4.5 (8)

from
$2,690

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

Punta Cana, Dominican Republic

4.1 (9)

Punta Cana : Saona Island Day Tour

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

8 hours Hotel pickup offered Free Cancellation

4.1 (9)

from
$80

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta Cana. Get up close and personal with …More

Punta Cana, Dominican Republic

4.4 (78)

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta Cana. Get up close and personal with...

3 hours Hotel pickup offered Free Cancellation

4.4 (78)

from
$100

No1Sxm Private Intimate Day Sail in St. Maarten

Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west …More

4.8 (5)

No1Sxm Private Intimate Day Sail in St. Maarten

Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west...

5 hours 30 minutes Free Cancellation

4.8 (5)

from
$124

Prepare for an exciting adventure on the beaches of Punta Cana. This experience includes an adrenaline trip on a speedboat and snorkel equipment rental as …More

4.3 (6)

Speed Boat Adventure In Punta Cana

Prepare for an exciting adventure on the beaches of Punta Cana. This experience includes an adrenaline trip on a speedboat and snorkel equipment rental as...

2 hours Free Cancellation

4.3 (6)

from
$75

St Martin Gd-Case: Private day in all inclusive catamaran

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure. …More

5.0 (14)

St Martin Gd-Case: Private day in all inclusive catamaran

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure....

8 hours

5.0 (14)

from
$2,700

Visit one of the most beautiful islands on the North Coast. Paradise Island will welcome you with turquoise water, white sand and colorful reef. Visit …More

Cabarete, Dominican Republic

4.2 (47)

Paradise Island & Mangroves Tour

Visit one of the most beautiful islands on the North Coast. Paradise Island will welcome you with turquoise water, white sand and colorful reef. Visit...

9 to 11 hours Hotel pickup offered Free Cancellation

4.2 (47)

from
$89

Small-Group St Maarten Snorkel Cruise (3H)

Step aboard our spacious catamaran, and begin your 3-hour sightseeing and snorkel cruise! Relax as we cruise along the coast with party music playing, and …More

4.9 (13)

Small-Group St Maarten Snorkel Cruise (3H)

Step aboard our spacious catamaran, and begin your 3-hour sightseeing and snorkel cruise! Relax as we cruise along the coast with party music playing, and...

3 hours Free Cancellation

4.9 (13)

from
$109

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

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can …More

5.0 (16)

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

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can...

8 hours Free Cancellation

5.0 (16)

from
$235

Private Full Day Baths and Beyond Tour in Tortola BVI

Antilles Power Boats will take you on a breathtaking adventure to see all the best of the BVI and give you a day to remember. …More

Tortola, British Virgin Islands

5.0 (21)

Private Full Day Baths and Beyond Tour in Tortola BVI

Antilles Power Boats will take you on a breathtaking adventure to see all the best of the BVI and give you a day to remember....

7 hours Free Cancellation

5.0 (21)

from
$1,650

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?