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 →

Enjoy one of Provo’s most glorious sunset charters along the world famous Grace Bay Coastline. Take in this beautiful setting while you dance into the …More

5.0 (20)

Sunset Cruise from Providenciales

Enjoy one of Provo’s most glorious sunset charters along the world famous Grace Bay Coastline. Take in this beautiful setting while you dance into the...

2 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$140

Bioluminescent Bay Kayak Adventure Tour from San Juan

This is one adventure not to be missed while in Puerto Rico! Join this fully-guided nighttime BioBay kayak adventure into one of the most amazing …More

4.1 (182)

Bioluminescent Bay Kayak Adventure Tour from San Juan

This is one adventure not to be missed while in Puerto Rico! Join this fully-guided nighttime BioBay kayak adventure into one of the most amazing...

6 hours Hotel pickup offered Free Cancellation

4.1 (182)

from
$108

Saona Island is paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees. We will pick you up in …More

Punta Cana, Dominican Republic

4.0 (298)

Full-Day Excursion in Saona Island

Saona Island is paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees. We will pick you up in...

10 hours Hotel pickup offered Free Cancellation

4.0 (298)

from
$64

Nassau Island Hopping Boat Tour Swimming Pigs Turtles Snorkeling

Ride on a Luxury 40ft Midnight Power Boat. On our first stop we visit the swimming pigs on Athol Island. You can feed them and …More

4.4 (104)

Nassau Island Hopping Boat Tour Swimming Pigs Turtles Snorkeling

Ride on a Luxury 40ft Midnight Power Boat. On our first stop we visit the swimming pigs on Athol Island. You can feed them and...

4 hours Free Cancellation

4.4 (104)

from
$150

4 hours 38ft Reel Dreams Private Charter in Nassau

Join on this private, half-day charter onboard the 38ft Reel Dreams. You are in control so you can fully customize your charter to fit your needs. You're …More

4.9 (81)

4 hours 38ft Reel Dreams Private Charter in Nassau

Join on this private, half-day charter onboard the 38ft Reel Dreams. You are in control so you can fully customize your charter to fit your needs. You're...

4 hours Free Cancellation

4.9 (81)

from
$990

VIP Morning Delight Champagne Sailing and Snorkeling with Lunch

Morning Delight Champagne Sailing and Snorkelling Cruise. A very small group of people on board, almost a private tour. Nice and calm waters. Sailing Black …More

4.9 (66)

VIP Morning Delight Champagne Sailing and Snorkeling with Lunch

Morning Delight Champagne Sailing and Snorkelling Cruise. A very small group of people on board, almost a private tour. Nice and calm waters. Sailing Black...

3 hours

4.9 (66)

from
$145

Private 6-Hour Island Hopping in US Virgin Islands - 500hp Hydro Sport

This is a "New Extremly Affordable, Private Option" offered by Stormy Pirates!! Be one of the first to experience this affordable option for a fast, …More

5.0 (80)

Private 6-Hour Island Hopping in US Virgin Islands - 500hp Hydro Sport

This is a "New Extremly Affordable, Private Option" offered by Stormy Pirates!! Be one of the first to experience this affordable option for a fast,...

6 hours

5.0 (80)

from
$1,150

Pizza Pi Shuttle (Official) - Jet Ski Trip St Thomas

This unique trip allows you to visit the world famous Pizza Pi floating pizza boat; only accessible by sea. Hop on one of our jet …More

4.7 (21)

Pizza Pi Shuttle (Official) - Jet Ski Trip St Thomas

This unique trip allows you to visit the world famous Pizza Pi floating pizza boat; only accessible by sea. Hop on one of our jet...

90 to 150 minutes Free Cancellation

4.7 (21)

from
$269

5 Hours Pigs and Turtles with Beach Stop in Bahamas

Swim with the infamous pigs along with turtles and reef snorkeling along with time at a stunning private beach, lunch and unlimited drinks on this …More

Nassau, Bahamas

4.5 (21)

5 Hours Pigs and Turtles with Beach Stop in Bahamas

Swim with the infamous pigs along with turtles and reef snorkeling along with time at a stunning private beach, lunch and unlimited drinks on this...

5 hours Hotel pickup offered Free Cancellation

4.5 (21)

from
$275

Private Half-Day Guided Snorkeling Charter in St. Thomas

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy …More

5.0 (50)

Private Half-Day Guided Snorkeling Charter in St. Thomas

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy...

4 hours

5.0 (50)

from
$2,540

Coral Sunset Sail with 3 Course Dinner in Aruba

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer …More

Palm - Eagle Beach, Aruba

4.8 (13)

Coral Sunset Sail with 3 Course Dinner in Aruba

Enjoy a private romantic sunset cruise and 3 course dinner for two or for a for a group of up to 6 friends. We offer...

3 hours Hotel pickup offered Free Cancellation

4.8 (13)

from
$859

Nude Naturist Catamaran Boat Luxury Charter in St Maarten

Fabulous day sailing on our luxury 48 feet catamaran. SXM ISLAND TOUR We will sail around St Maarten/Saint-Martin. Stops at Long bay La Samana, Happy …More

4.9 (55)

Nude Naturist Catamaran Boat Luxury Charter in St Maarten

Fabulous day sailing on our luxury 48 feet catamaran. SXM ISLAND TOUR We will sail around St Maarten/Saint-Martin. Stops at Long bay La Samana, Happy...

9 hours Free Cancellation

4.9 (55)

from
$255

Enjoy an afternoon on a catamaran to the coast of Bávaro and visit a natural pool. Enjoy this half-day boat tour that includes snorkeling, coolers, …More

Punta Cana, Dominican Republic

5.0 (16)

Party Boat Catamaran Punta Cana

Enjoy an afternoon on a catamaran to the coast of Bávaro and visit a natural pool. Enjoy this half-day boat tour that includes snorkeling, coolers,...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (16)

from
$59

Float & Feast Private Party Cruise with Premium Buffet & Open Bar

Our tour is not just a boat ride — it’s your own private party at sea! What sets us apart is the perfect mix of …More

Punta Cana, Dominican Republic

5.0 (18)

Float & Feast Private Party Cruise with Premium Buffet & Open Bar

Our tour is not just a boat ride — it’s your own private party at sea! What sets us apart is the perfect mix of...

4 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$1,700

Saona Island Tour and Catamaran Party from Punta Cana

Saona Island is like a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment invites you …More

Punta Cana, Dominican Republic

4.6 (28)

Saona Island Tour and Catamaran Party from Punta Cana

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

9 hours Hotel pickup offered Free Cancellation

4.6 (28)

from
$74

Curaçao tours Semi submarine Underwater Seaworld Explorer

Explore the underwater wonders of Curacao in our Semi-submarine SeaWorld Explorer The SeaWorld Explorer is a state-of-the- art air-conditioned semi-submarine. The vessel always remains above …More

4.7 (35)

Curaçao tours Semi submarine Underwater Seaworld Explorer

Explore the underwater wonders of Curacao in our Semi-submarine SeaWorld Explorer The SeaWorld Explorer is a state-of-the- art air-conditioned semi-submarine. The vessel always remains above...

1 hour Free Cancellation

4.7 (35)

from
$39

Montego Bay Catamaran Party & Snorkeling Cruise with Open Bar/ DJ

Embark on an unforgettable catamaran cruise where relaxation meets adventure on the open sea. Enjoy sunbathing on the spacious deck, sip on refreshing beverages, and …More

Montego Bay, Jamaica

4.6 (32)

Montego Bay Catamaran Party & Snorkeling Cruise with Open Bar/ DJ

Embark on an unforgettable catamaran cruise where relaxation meets adventure on the open sea. Enjoy sunbathing on the spacious deck, sip on refreshing beverages, and...

3 hours Hotel pickup offered Free Cancellation

4.6 (32)

from
$46

Are you ready to experience the best of Grand Cayman from the water? Come join us at Cayman Ocean Adventures, a proud Kelly family-owned business. …More

Seven Mile Beach, Cayman Islands

5.0 (18)

Stingray City Private Charter

Are you ready to experience the best of Grand Cayman from the water? Come join us at Cayman Ocean Adventures, a proud Kelly family-owned business....

4 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$1,850

Saona Island Excursion by Catamaran and Speedboat

Discover paradise on Saona Island, where white sandy beaches, clear turquoise waters, and countless palm trees provide an unspoiled environment that vacation dreams are made …More

3.9 (122)

Saona Island Excursion by Catamaran and Speedboat

Discover paradise on Saona Island, where white sandy beaches, clear turquoise waters, and countless palm trees provide an unspoiled environment that vacation dreams are made...

10 hours Hotel pickup offered Free Cancellation

3.9 (122)

from
$89

Catamaran Cruise Full Day Tour- Reef, Rick's Cafe & Negril Beach

Join us for an unforgettable day trip to Negril, Jamaica! Start your day with a guided scenic bus ride on Jamaica's North Coast to Negril, …More

Ocho Rios, Jamaica

4.2 (362)

Catamaran Cruise Full Day Tour- Reef, Rick's Cafe & Negril Beach

Join us for an unforgettable day trip to Negril, Jamaica! Start your day with a guided scenic bus ride on Jamaica's North Coast to Negril,...

4 to 12 hours Hotel pickup offered Free Cancellation

4.2 (362)

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?

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?