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 →

Sunset Kayak Tour in the Mangrove Lagoon, St Thomas

Golden Hour Kayaking Introduction and brief orientation at Virgin Islands Ecotours’ Marina Board a two-person kayak and paddle with your guide through the mangrove passageways …More

4.9 (140)

Sunset Kayak Tour in the Mangrove Lagoon, St Thomas

Golden Hour Kayaking Introduction and brief orientation at Virgin Islands Ecotours’ Marina Board a two-person kayak and paddle with your guide through the mangrove passageways...

1 hour 30 minutes Free Cancellation

4.9 (140)

from
$59

Marine Park - Private Boat charter with LOCAL Captain/ Guide

We are eager to show you the best Bonaire has to offer. Charter your own boat and discover Bonaire’s hidden gems with a local captain/ …More

5.0 (254)

Marine Park - Private Boat charter with LOCAL Captain/ Guide

We are eager to show you the best Bonaire has to offer. Charter your own boat and discover Bonaire’s hidden gems with a local captain/...

3 hours Free Cancellation

5.0 (254)

from
$550

Negril Glass Bottom Boat Tour Snorkeling and Booby Cay

Come along for an unforgettable glass bottom tour out into the reefs of the beautiful Caribbean Sea in Negril. Snorkel on our healthy reefs with …More

Negril, Jamaica

4.9 (226)

Negril Glass Bottom Boat Tour Snorkeling and Booby Cay

Come along for an unforgettable glass bottom tour out into the reefs of the beautiful Caribbean Sea in Negril. Snorkel on our healthy reefs with...

2 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (226)

from
$65

Have you ever wanted to ride the waves yourself; meanwhile enjoying the nice views of the coastline with its coves and bays, well this is …More

4.5 (256)

Jet Ski Adventure Tour Curacao

Have you ever wanted to ride the waves yourself; meanwhile enjoying the nice views of the coastline with its coves and bays, well this is...

1 to 2 hours Free Cancellation

4.5 (256)

from
$65

Speed Boat & Snorkeling Tour Pinel & Tintamarre Islands for CRUISE SHIP GUESTS

Take to the water on a comprehensive speedboat tour of St Maarten, with several snorkeling stops included in your 6-hour excursion. Snorkel at Creole Rock, …More

4.9 (156)

Speed Boat & Snorkeling Tour Pinel & Tintamarre Islands for CRUISE SHIP GUESTS

Take to the water on a comprehensive speedboat tour of St Maarten, with several snorkeling stops included in your 6-hour excursion. Snorkel at Creole Rock,...

6 hours Free Cancellation

4.9 (156)

from
$149

Bio Bay Tour Vieques – Full Clear Canoes Experience

NOTICE: We are not responsible for ferry delays, cancellations, or any issues related to ferry services. These are completely out of our control. If you …More

Vieques, Puerto Rico

4.5 (279)

Bio Bay Tour Vieques – Full Clear Canoes Experience

NOTICE: We are not responsible for ferry delays, cancellations, or any issues related to ferry services. These are completely out of our control. If you...

1 hour 30 minutes Free Cancellation

4.5 (279)

from
$57

The Ultimate Bahamian Beach Day: Pigs, Jet Ski, Snorkeling & More

Get ready for the ultimate Bahamian escape at Mansa Bay! This all-in-one adventure has it all: swim with friendly pigs, ride jet skis, splash on …More

4.9 (46)

The Ultimate Bahamian Beach Day: Pigs, Jet Ski, Snorkeling & More

Get ready for the ultimate Bahamian escape at Mansa Bay! This all-in-one adventure has it all: swim with friendly pigs, ride jet skis, splash on...

3 hours 30 minutes Free Cancellation

4.9 (46)

from
$199

Best of Mangrove Lagoon Kayak, Hike and Snorkel Adventure with Picnic Lunch

This Kayak, Hike, and Snorkel Adventure is the best way to explore the Mangrove Lagoon in St. Thomas as well as the island of Cas …More

4.9 (352)

Best of Mangrove Lagoon Kayak, Hike and Snorkel Adventure with Picnic Lunch

This Kayak, Hike, and Snorkel Adventure is the best way to explore the Mangrove Lagoon in St. Thomas as well as the island of Cas...

5 hours Free Cancellation

4.9 (352)

from
$159

Private Rose Island Swimming Pigs Snorkeling and Turtles

Come along and explore with us. Within this 4 hour tour you will snorkel with turtles at green Cay, snorkel with fishes at the reefs …More

Nassau, Bahamas

4.8 (233)

Private Rose Island Swimming Pigs Snorkeling and Turtles

Come along and explore with us. Within this 4 hour tour you will snorkel with turtles at green Cay, snorkel with fishes at the reefs...

4 hours Hotel pickup offered Free Cancellation

4.8 (233)

from
$775

Rose Island: Private Snorkeling, Fishing, and Swimming with Pigs

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

4.8 (36)

Rose Island: Private Snorkeling, Fishing, and Swimming with Pigs

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

4.8 (36)

from
$850

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at two spectacular locations. A friendly crew will take you …More

4.7 (318)

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at two spectacular locations. A friendly crew will take you...

3 hours Free Cancellation

4.7 (318)

from
$90

Bio Bay Night Kayaking with Transport from San Juan Area

Weight limit is 240 lbs. per person. Pregnant women are not allowed to participate in the kayaking tour Paddle through the mangrove forest on your …More

Luquillo, Puerto Rico

4.4 (150)

Bio Bay Night Kayaking with Transport from San Juan Area

Weight limit is 240 lbs. per person. Pregnant women are not allowed to participate in the kayaking tour Paddle through the mangrove forest on your...

5 hours Hotel pickup offered Free Cancellation

4.4 (150)

from
$125

NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe ALL HOTELS

Lets set sail.. ! Your crew awaits. On Negril's Sweetheart Catamaran, SUNSHINE of the Seas, our staff are there to take care of you, as …More

Lucea, Jamaica

4.2 (359)

NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe ALL HOTELS

Lets set sail.. ! Your crew awaits. On Negril's Sweetheart Catamaran, SUNSHINE of the Seas, our staff are there to take care of you, as...

8 hours Hotel pickup offered Free Cancellation

4.2 (359)

from
$87

Swimming with Pigs in Nassau, Transportation Included

You will be transported via the scenic route to Fort Montague to catch a short 20 min boat ride to Rose Island. Upon arrival at …More

Nassau, Bahamas

4.7 (384)

Swimming with Pigs in Nassau, Transportation Included

You will be transported via the scenic route to Fort Montague to catch a short 20 min boat ride to Rose Island. Upon arrival at...

4 hours Hotel pickup offered Free Cancellation

4.7 (384)

from
$179

Discover The Baths of Virgin Gorda Full Day Adventure - Westin St. John

Join us aboard our 45' express cruiser for an unforgettable tour of the British Virgin Islands, and one of the most famous destinations in the …More

4.6 (109)

Discover The Baths of Virgin Gorda Full Day Adventure - Westin St. John

Join us aboard our 45' express cruiser for an unforgettable tour of the British Virgin Islands, and one of the most famous destinations in the...

9 hours Free Cancellation

4.6 (109)

from
$329

Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no …More

4.7 (725)

Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no...

2 hours Free Cancellation

4.7 (725)

from
$119

Private Sunset Cruise in Caribbean in St. Lucia

Private sunset cruise where customers can enjoy on of the many breathtaking sunsets St. Lucia is known for. We have the most friendly Captain and …More

Marigot Bay, St Lucia

4.7 (83)

Private Sunset Cruise in Caribbean in St. Lucia

Private sunset cruise where customers can enjoy on of the many breathtaking sunsets St. Lucia is known for. We have the most friendly Captain and...

2 hours Hotel pickup offered Free Cancellation

4.7 (83)

from
$73

Experience ultimate luxury with our Catamaran Yacht and create an unforgettable day at Klein Curaçao with our All Inclusive Tour. After one hour of sailing …More

4.4 (153)

Klein Curaçao Tour on a Catamaran Yacht

Experience ultimate luxury with our Catamaran Yacht and create an unforgettable day at Klein Curaçao with our All Inclusive Tour. After one hour of sailing...

8 hours Free Cancellation

4.4 (153)

from
$145

PH Whale Watch & Dolphin Cruise in Dominica

Dominica is the only country in the world where the sperm whale resides all year long. Just a short boat ride brings you into contact …More

4.7 (262)

PH Whale Watch & Dolphin Cruise in Dominica

Dominica is the only country in the world where the sperm whale resides all year long. Just a short boat ride brings you into contact...

3 hours Free Cancellation

4.7 (262)

from
$96

Jamaica Martha Brae River Rafting/Dunn’s River Falls Private Tour

This is a CASHLESS AND HASSLE FREE TOUR that INCLUDES Entrance Fees and transportation fee for the day. We pickup in a clean private and …More

Lucea, Jamaica

5.0 (89)

Jamaica Martha Brae River Rafting/Dunn’s River Falls Private Tour

This is a CASHLESS AND HASSLE FREE TOUR that INCLUDES Entrance Fees and transportation fee for the day. We pickup in a clean private and...

8 hours Hotel pickup offered Free Cancellation

5.0 (89)

from
$317

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?