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 →

Bamboo Rafting, Margaritaville & Sightseeing Tour In Ocho Rios

One of the most calming and relaxing experience you can have in Jamaica is rafting on the White River. Located in the parish of St …More

Ocho Rios, Jamaica

5.0 (7)

Bamboo Rafting, Margaritaville & Sightseeing Tour In Ocho Rios

One of the most calming and relaxing experience you can have in Jamaica is rafting on the White River. Located in the parish of St...

3 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$65

Saona Catamaran Cruise with Lunch and Natural Swimming Pool

Our Saona Island tour offers a unique blend of relaxation, adventure, and authentic Dominican culture, designed to give you an unforgettable experience. Soak in the …More

Punta Cana, Dominican Republic

4.1 (29)

Saona Catamaran Cruise with Lunch and Natural Swimming Pool

Our Saona Island tour offers a unique blend of relaxation, adventure, and authentic Dominican culture, designed to give you an unforgettable experience. Soak in the...

8 hours Hotel pickup offered Free Cancellation

4.1 (29)

from
$80

Experience a Submarine Scooter with ScubaDoo Punta Cana

ScubaDoo Punta Cana is a diving and snorkeling adventure that takes you to some of the most beautiful and unspoiled areas in the Caribbean Sea …More

4.1 (13)

Experience a Submarine Scooter with ScubaDoo Punta Cana

ScubaDoo Punta Cana is a diving and snorkeling adventure that takes you to some of the most beautiful and unspoiled areas in the Caribbean Sea...

5 hours Hotel pickup offered Free Cancellation

4.1 (13)

from
$69

Immerse yourself in the unforgettable allure of Anguilla on your private boat, a day that will linger in your memory. Let Pierre be your expert …More

4.8 (16)

Full Day Anguilla Private Charter Tour

Immerse yourself in the unforgettable allure of Anguilla on your private boat, a day that will linger in your memory. Let Pierre be your expert...

8 hours Free Cancellation

4.8 (16)

from
$1,665

Soufriere Catamaran Excursion with Zip Lining from Castries

Join us for an action-packed day sailing to Soufriere, where you will see the world-famous pitons and visit Morne Coubaril Estate, Zip Lining and Marigot …More

Choc, St Lucia

5.0 (3)

Soufriere Catamaran Excursion with Zip Lining from Castries

Join us for an action-packed day sailing to Soufriere, where you will see the world-famous pitons and visit Morne Coubaril Estate, Zip Lining and Marigot...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$205

St.Martin-St.Maarten: Small Group, Nature Hike Secret Beach Tour

Explore St Martin’s wild side during this half day Nature Hike Secret Beach Tour (challenging hike). Discover something special, while enjoying gorgeous views and learning …More

4.0 (3)

St.Martin-St.Maarten: Small Group, Nature Hike Secret Beach Tour

Explore St Martin’s wild side during this half day Nature Hike Secret Beach Tour (challenging hike). Discover something special, while enjoying gorgeous views and learning...

4 hours Free Cancellation

4.0 (3)

from
$89

ATV, Bamboo Rafting & Horseback Ride Tour From Montego Bay

Experience a day of adventure on this combination tour, which includes ;an exciting off road ATV Ride , Horseback-riding n Swim and the Bamboo Rafting …More

Montego Bay, Jamaica

5.0 (6)

ATV, Bamboo Rafting & Horseback Ride Tour From Montego Bay

Experience a day of adventure on this combination tour, which includes ;an exciting off road ATV Ride , Horseback-riding n Swim and the Bamboo Rafting...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$120

Full Day ATV, Coffee, Chocolate Tasting & Party Boat

Join us on an exciting excursion that combines the adrenaline of an ATV with the relaxation of a catamaran! We will begin our ATV adventure …More

Punta Cana, Dominican Republic

5.0 (5)

Full Day ATV, Coffee, Chocolate Tasting & Party Boat

Join us on an exciting excursion that combines the adrenaline of an ATV with the relaxation of a catamaran! We will begin our ATV adventure...

6 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$110

3hr Private Luxury Yacht with Snorkeling, Bar, Food

3-Hour Cruise 1 Hors d'oeuvre (Assorted Sandwiches) Unlimited Rum Punch, Mimosas, Beer and Non-Alcoholic options Bluetooth Music Snorkeling with Gear Swimming with Toys Packaged Snack …More

5.0 (13)

3hr Private Luxury Yacht with Snorkeling, Bar, Food

3-Hour Cruise 1 Hors d'oeuvre (Assorted Sandwiches) Unlimited Rum Punch, Mimosas, Beer and Non-Alcoholic options Bluetooth Music Snorkeling with Gear Swimming with Toys Packaged Snack...

3 hours Free Cancellation

5.0 (13)

from
$3,300

My family yacht only for you -3 hours Romantic tour Punta Cana

Private yacht experience in the Caribbean Sea, perfect for couples, birthdays, bachelorette and bachelor parties, proposals, and anniversaries. Is unique and unforgettable way to celebrate …More

5.0 (1)

My family yacht only for you -3 hours Romantic tour Punta Cana

Private yacht experience in the Caribbean Sea, perfect for couples, birthdays, bachelorette and bachelor parties, proposals, and anniversaries. Is unique and unforgettable way to celebrate...

3 hours Free Cancellation

5.0 (1)

from
$350

Curacao Private Romantic Sunset Sailing Tour for 2

Celebrate love with an unforgettable private romantic sailing experience in beautiful Curacao. Surprise your partner with a breathtaking sunset yacht escape designed for couples seeking …More

5.0 (4)

Curacao Private Romantic Sunset Sailing Tour for 2

Celebrate love with an unforgettable private romantic sailing experience in beautiful Curacao. Surprise your partner with a breathtaking sunset yacht escape designed for couples seeking...

3 hours Free Cancellation

5.0 (4)

from
$479

Montego Bay Bamboo River Rafting Limestone Foot Massage

Its a private transportation starts from Montego Bay Hotels and resorts to Lethe River will save your time of transportation, you get a Limestone Body …More

Montego Bay, Jamaica

4.9 (12)

Montego Bay Bamboo River Rafting Limestone Foot Massage

Its a private transportation starts from Montego Bay Hotels and resorts to Lethe River will save your time of transportation, you get a Limestone Body...

4 hours Hotel pickup offered Free Cancellation

4.9 (12)

from
$120

Great River Rafting With Limestone Massage From Montego Bay

Basically this completely customizable tour gives you a 3 pack combo Great River Rafting, Limestone Massage and sightseeing tour With a certified guide you can …More

Montego Bay, Jamaica

5.0 (6)

Great River Rafting With Limestone Massage From Montego Bay

Basically this completely customizable tour gives you a 3 pack combo Great River Rafting, Limestone Massage and sightseeing tour With a certified guide you can...

3 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$100

Classic 3hours Private Adventure:Snorkel & Explore Hidden Spots

Unleash the adventurer within a 3-hour full private exploration of Nos Isla's hidden treasures! Navigate clear waters with your captain on exhilarating snorkeling and paddle …More

5.0 (10)

Classic 3hours Private Adventure:Snorkel & Explore Hidden Spots

Unleash the adventurer within a 3-hour full private exploration of Nos Isla's hidden treasures! Navigate clear waters with your captain on exhilarating snorkeling and paddle...

3 hours Free Cancellation

5.0 (10)

from
$575

Seven Mile's Beach Snorkeling & Ricks Cafe Sunset Tour Day Trip

this activity is an all-day adventure exploring Jamaica's South Coast. Snorkeling and explore marine life by boarding a glass batton boat to the Pinic-Island, relax …More

Montego Bay, Jamaica

5.0 (11)

Seven Mile's Beach Snorkeling & Ricks Cafe Sunset Tour Day Trip

this activity is an all-day adventure exploring Jamaica's South Coast. Snorkeling and explore marine life by boarding a glass batton boat to the Pinic-Island, relax...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$101

Antigua Seafood Lunch Cruise From St. John's

Enjoy a day of carefree relaxation as you sail on a catamaran along the stunning Antiguan coastline. Journey along the west coast of the island …More

4.4 (15)

Antigua Seafood Lunch Cruise From St. John's

Enjoy a day of carefree relaxation as you sail on a catamaran along the stunning Antiguan coastline. Journey along the west coast of the island...

6 hours Hotel pickup offered

4.4 (15)

from
$184

3.5hr Private Catamaran Cruise with Snorkeling, DJ, Bar, Food

By booking our private charter, you and your guests will have exclusive access to our boat and our attentive and friendly staff. Because the cruise …More

4.9 (19)

3.5hr Private Catamaran Cruise with Snorkeling, DJ, Bar, Food

By booking our private charter, you and your guests will have exclusive access to our boat and our attentive and friendly staff. Because the cruise...

3 hours 30 minutes Free Cancellation

4.9 (19)

from
$3,900

Discover the Best of St. John - Snorkel, Beach & Shopping!

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Lady Lynsey. After snorkeling …More

Cruz Bay, US Virgin Islands

4.9 (7)

Discover the Best of St. John - Snorkel, Beach & Shopping!

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Lady Lynsey. After snorkeling...

5 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$129

Private Angelfish Snorkeling with Brunch in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical …More

Palm - Eagle Beach, Aruba

5.0 (3)

Private Angelfish Snorkeling with Brunch in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical...

3 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$707

Best of Both Worlds Land and Sea Adventure

Explore St. Lucia by both land and sea to experience the true beauty of this island. Start with an excursion to Morne Fortune, see banana …More

Choc, St Lucia

4.7 (32)

Best of Both Worlds Land and Sea Adventure

Explore St. Lucia by both land and sea to experience the true beauty of this island. Start with an excursion to Morne Fortune, see banana...

8 hours Hotel pickup offered Free Cancellation

4.7 (32)

from
$150

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?