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 →

Private,Turtles, snorkeling, beach stops, pigs, drinks included!”

If swimming with pigs, swimming with turtles, snorkeling at a reef and a shipwreck and relaxing on beautiful beach is on your bucket list look …More

5.0 (13)

Private,Turtles, snorkeling, beach stops, pigs, drinks included!”

If swimming with pigs, swimming with turtles, snorkeling at a reef and a shipwreck and relaxing on beautiful beach is on your bucket list look...

4 hours 25 minutes Free Cancellation

5.0 (13)

from
$800

Private Ultimate Fish, Snorkel & Cruise 3/4 Day on Serendipity

Fish, Snorkel and Cruise Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! …More

5.0 (3)

Private Ultimate Fish, Snorkel & Cruise 3/4 Day on Serendipity

Fish, Snorkel and Cruise Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! ...

6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$5,161

Family Catamaran & Snorkeling Cruise Turks & Caicos

This 3 hour luxurious 65-ft. “Kitty Katt” family catamaran cruise will take you to one of Turks and Caicos' most stunning coral reefs, where you’ll …More

4.3 (38)

Family Catamaran & Snorkeling Cruise Turks & Caicos

This 3 hour luxurious 65-ft. “Kitty Katt” family catamaran cruise will take you to one of Turks and Caicos' most stunning coral reefs, where you’ll...

3 hours Hotel pickup offered Free Cancellation

4.3 (38)

from
$150

St. Lucia Speedboat and Power Snorkel from Castries

Pilot your own 17 ft. speedboat along St. Lucia’s picturesque west coast to the islands main attraction area of Soufriere where you’ll power snorkel a …More

Choc, St Lucia

4.7 (30)

St. Lucia Speedboat and Power Snorkel from Castries

Pilot your own 17 ft. speedboat along St. Lucia’s picturesque west coast to the islands main attraction area of Soufriere where you’ll power snorkel a...

4 hours Hotel pickup offered

4.7 (30)

from
$296

Great River Rafting with Limestone Massage & Rasta Safari Experience Combo Tour

Basically this tour offers travelers two of Jamaica's most sort after attractions Great River Rafting, Limestone Massage and Rasta Safari. start off with the amazing …More

Montego Bay, Jamaica

5.0 (5)

Great River Rafting with Limestone Massage & Rasta Safari Experience Combo Tour

Basically this tour offers travelers two of Jamaica's most sort after attractions Great River Rafting, Limestone Massage and Rasta Safari. start off with the amazing...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$290

Punta Cana Private Party Boat with Snorkeling and Open Bar

Turn your day in Punta Cana into a private Caribbean party, combining snorkeling, tropical drinks, music and the famous natural pool along the Bávaro coastline. …More

Punta Cana, Dominican Republic

4.8 (9)

Punta Cana Private Party Boat with Snorkeling and Open Bar

Turn your day in Punta Cana into a private Caribbean party, combining snorkeling, tropical drinks, music and the famous natural pool along the Bávaro coastline....

4 hours Hotel pickup offered Free Cancellation

4.8 (9)

from
$89

Grand Cayman Bioluminescent Bay & Starfish Point Boat Tour

Grand Cayman is one of the world’s remarkable places to experience bioluminescence. Watch the island change from day to night on an evening that begins …More

Grand Cayman, Cayman Islands

4.5 (15)

Grand Cayman Bioluminescent Bay & Starfish Point Boat Tour

Grand Cayman is one of the world’s remarkable places to experience bioluminescence. Watch the island change from day to night on an evening that begins...

3 hours Hotel pickup offered Free Cancellation

4.5 (15)

from
$159

Cayman Adventure Stingrays Starfish plus Crystal Caves

Discover the magic of Grand Cayman with an adventure that brings together some of the island’s most iconic natural experiences. Step into the crystal-clear waters …More

Grand Cayman, Cayman Islands

5.0 (2)

Cayman Adventure Stingrays Starfish plus Crystal Caves

Discover the magic of Grand Cayman with an adventure that brings together some of the island’s most iconic natural experiences. Step into the crystal-clear waters...

3 to 5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$99

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on …More

5.0 (18)

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on...

5 hours

5.0 (18)

from
$3,210

Discovery and snorkeling with sea turtles

Embark on a modern traditional boat equipped with a paw and let yourself be guided by Captain Greg to discover the Caribbean coast. During this …More

5.0 (7)

Discovery and snorkeling with sea turtles

Embark on a modern traditional boat equipped with a paw and let yourself be guided by Captain Greg to discover the Caribbean coast. During this...

3 hours Free Cancellation

5.0 (7)

from
$74

Private Bahamas Boat Fishing and Turtle Snorkeling Tour

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even …More

4.8 (10)

Private Bahamas Boat Fishing and Turtle Snorkeling Tour

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even...

4 hours Free Cancellation

4.8 (10)

from
$2,200

Private Tour 45ft Powerboat to Nearby Islands

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even …More

5.0 (16)

Private Tour 45ft Powerboat to Nearby Islands

Enjoy an islanding hopping tour to nearby islands. You can choose to do snorkeling beautiful coral reefs, Gilligan's island, green cay and you can even...

4 hours

5.0 (16)

from
$3,800

Punta Cana Private Party Catamaran with Open Bar

The first stop is at the reef of Cabeza de Toro beach for an unforgettable snorkeling experience. All necessary and disinfected snorkeling equipment will be …More

Punta Cana, Dominican Republic

5.0 (17)

Punta Cana Private Party Catamaran with Open Bar

The first stop is at the reef of Cabeza de Toro beach for an unforgettable snorkeling experience. All necessary and disinfected snorkeling equipment will be...

4 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$890

Samaná Whale Watching and Bacardi Island from Punta Cana

Combine humpback whale watching in Samaná Bay with beach time on Cayo Levantado, also known as Bacardi Island, on a full-day excursion from Punta Cana. …More

Punta Cana, Dominican Republic

4.8 (12)

Samaná Whale Watching and Bacardi Island from Punta Cana

Combine humpback whale watching in Samaná Bay with beach time on Cayo Levantado, also known as Bacardi Island, on a full-day excursion from Punta Cana....

1 day Hotel pickup offered Free Cancellation

4.8 (12)

from
$169

our tour is the most complete activity in this area, first on the yacht you have 3 cabins with airconditioning , 45 minutes too get …More

Punta Cana, Dominican Republic

5.0 (2)

Catalina Yacht Private

our tour is the most complete activity in this area, first on the yacht you have 3 cabins with airconditioning , 45 minutes too get...

7 hours 45 minutes Hotel pickup offered Free Cancellation

5.0 (2)

from
$2,200

Private 3-Hour Catamaran Sunset Cruise from Soufriere for Up to 15 Guests

If it’s in the eyes of that special someone, celebrating a special occasion or with a group of friends, there's no better way to spend …More

4.8 (6)

Private 3-Hour Catamaran Sunset Cruise from Soufriere for Up to 15 Guests

If it’s in the eyes of that special someone, celebrating a special occasion or with a group of friends, there's no better way to spend...

3 hours Free Cancellation

4.8 (6)

from
$2,160

Private Beach Day and 50ft Sun Seeker or 33ft Boat 1-10 Guests

The 50ft Sun Seeker Motor Yacht is the ideal vessel for beach days. Whether you're a young family that needs the extra shade, a small …More

5.0 (5)

Private Beach Day and 50ft Sun Seeker or 33ft Boat 1-10 Guests

The 50ft Sun Seeker Motor Yacht is the ideal vessel for beach days. Whether you're a young family that needs the extra shade, a small...

6 hours Free Cancellation

5.0 (5)

from
$1,760

Frederiksted St Croix Sea Turtle Snorkeling Tour

Swim alongside the magnificent sea turtles of St. Croix on a two-hour guided snorkeling adventure at Frederiksted Pier! Discover an underwater world where green and …More

5.0 (7)

Frederiksted St Croix Sea Turtle Snorkeling Tour

Swim alongside the magnificent sea turtles of St. Croix on a two-hour guided snorkeling adventure at Frederiksted Pier! Discover an underwater world where green and...

2 hours Free Cancellation

5.0 (7)

from
$89

Private Catamaran Excursion in Anguilla with its Turquoise Waters

looking for new adventures, unforgettable experience and relaxing beach ? sail with us around Saint-Martin and its neighboring islands. we assure you a memorable experience. …More

5.0 (19)

Private Catamaran Excursion in Anguilla with its Turquoise Waters

looking for new adventures, unforgettable experience and relaxing beach ? sail with us around Saint-Martin and its neighboring islands. we assure you a memorable experience....

8 hours

5.0 (19)

from
$240

FOR THE BOLD. FOR THE CURIOUS. FOR THOSE WHO WANT MORE THAN A TYPICAL TOUR. Arrive to Boca de Yuma to meet your local guide, …More

5.0 (14)

Full-Day Boca de Yuma Adventure

FOR THE BOLD. FOR THE CURIOUS. FOR THOSE WHO WANT MORE THAN A TYPICAL TOUR. Arrive to Boca de Yuma to meet your local guide,...

6 to 7 hours Free Cancellation

5.0 (14)

from
$90

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?