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 →

Day Yacht Excursions throughout the US or British Virgin Islands

Discover the heights of luxury at sea level with Magic Moments. This company is available on St Thomas and St John, has been voted BEST …More

4.9 (180)

Day Yacht Excursions throughout the US or British Virgin Islands

Discover the heights of luxury at sea level with Magic Moments. This company is available on St Thomas and St John, has been voted BEST...

6 to 8 hours Free Cancellation

4.9 (180)

from
$2,950

A day in the British Virgin Islands aboard our black Midnight Express 37' Open named Obsidian. Stand out from the crowd on this ultra luxurious …More

5.0 (133)

Midnight Sun Charters - 37ft OBSIDIAN

A day in the British Virgin Islands aboard our black Midnight Express 37' Open named Obsidian. Stand out from the crowd on this ultra luxurious...

5 to 8 hours Free Cancellation

5.0 (133)

from
$2,333

Nassau, Rose Island Swimming Pigs, Turtles, Beach, Snorkeling

Create memories that last a lifetime. Experience high quality charter service. Go beyond the shores of Nassau on our guided boat excursion to Rose Island. …More

5.0 (28)

Nassau, Rose Island Swimming Pigs, Turtles, Beach, Snorkeling

Create memories that last a lifetime. Experience high quality charter service. Go beyond the shores of Nassau on our guided boat excursion to Rose Island....

4 hours Free Cancellation

5.0 (28)

from
$259

We offer our guests personalized itinerary. Our boat is your boat. You can freestyle on the water or stick to a strict schedule. Either way …More

5.0 (38)

Honor Roll Private Bahamas Boat Charter

We offer our guests personalized itinerary. Our boat is your boat. You can freestyle on the water or stick to a strict schedule. Either way...

4 to 8 hours Free Cancellation

5.0 (38)

from
$1,750

Private Sailing Tour of Pirate Waters and Shipwrecks

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquistadors, Buccaneers, and Pirates, and appears almost …More

4.9 (24)

Private Sailing Tour of Pirate Waters and Shipwrecks

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquistadors, Buccaneers, and Pirates, and appears almost...

2 hours Free Cancellation

4.9 (24)

from
$75

Trio Tour: El Yunque, Luquillo Beach, and Bio Bay Night Kayaking

Blend a little excitement to your vacation with our Rainforest River – Luquillo Beach & Bio Bay Night Kayaking Trio! This adventure is a full-day …More

Luquillo, Puerto Rico

4.5 (37)

Trio Tour: El Yunque, Luquillo Beach, and Bio Bay Night Kayaking

Blend a little excitement to your vacation with our Rainforest River – Luquillo Beach & Bio Bay Night Kayaking Trio! This adventure is a full-day...

12 hours Hotel pickup offered Free Cancellation

4.5 (37)

from
$189

Christmas Cove and Pizza Pi Happy Hour Sail Tour

Departing from Red Hook, join us sailing to Christmas Cove, where we will visit the one and only floating pizza boat! Order a pizza, enjoy …More

5.0 (27)

Christmas Cove and Pizza Pi Happy Hour Sail Tour

Departing from Red Hook, join us sailing to Christmas Cove, where we will visit the one and only floating pizza boat! Order a pizza, enjoy...

3 hours Free Cancellation

5.0 (27)

from
$185

St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the …More

4.6 (43)

St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the...

4 hours Free Cancellation

4.6 (43)

from
$129

Punta Cana ATV and Catamaran Combo Tour with Open Bar

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

Punta Cana, Dominican Republic

4.7 (26)

Punta Cana ATV and Catamaran Combo Tour with Open Bar

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

8 hours Hotel pickup offered Free Cancellation

4.7 (26)

from
$110

Catamaran Party in Punta Cana with Unlimited Drinks

Board a beautiful catamaran bound for the Bavaro coast and enjoy this half-day boat tour that includes snorkeling, snacks, dancing, and unlimited drinks. Soak up …More

Punta Cana, Dominican Republic

5.0 (22)

Catamaran Party in Punta Cana with Unlimited Drinks

Board a beautiful catamaran bound for the Bavaro coast and enjoy this half-day boat tour that includes snorkeling, snacks, dancing, and unlimited drinks. Soak up...

3 hours 15 minutes Hotel pickup offered Free Cancellation

5.0 (22)

from
$60

Punta Cana Catamaran Party Cruise with Unlimited Drinks

Spend a different time aboard this boat animated by a staff that will make you enjoy a pleasant time. A great way to spend a …More

Punta Cana, Dominican Republic

4.3 (206)

Punta Cana Catamaran Party Cruise with Unlimited Drinks

Spend a different time aboard this boat animated by a staff that will make you enjoy a pleasant time. A great way to spend a...

4 hours Hotel pickup offered Free Cancellation

4.3 (206)

from
$59

FAMOUS SHIPWRECK, Tiki Bar & Iguana Island Private Jet Ski Tour

You will get to explore the waters of the Turks and Caicos Islands using our Sea-Doo GTI's watercraft on this guided tour. Visit The La …More

4.8 (22)

FAMOUS SHIPWRECK, Tiki Bar & Iguana Island Private Jet Ski Tour

You will get to explore the waters of the Turks and Caicos Islands using our Sea-Doo GTI's watercraft on this guided tour. Visit The La...

2 hours Free Cancellation

4.8 (22)

from
$479

Speedboat Tour to Saona Island Vip with Open Bar and Meals!

Have you ever imagined walking alone on a paradisiacal beach with many kilometers ahead of you? The success of this activity has been, without a …More

Punta Cana, Dominican Republic

4.9 (36)

Speedboat Tour to Saona Island Vip with Open Bar and Meals!

Have you ever imagined walking alone on a paradisiacal beach with many kilometers ahead of you? The success of this activity has been, without a...

7 to 8 hours Hotel pickup offered Free Cancellation

4.9 (36)

from
$110

Full-Day ATV + Party Boat Package w Snorkel & coffee tasting

Discover the Dominican countryside by ATV, then explore the coastline by double-decker catamaran. There are countless delights on this full-day tour: sample organic products; explore …More

5.0 (105)

Full-Day ATV + Party Boat Package w Snorkel & coffee tasting

Discover the Dominican countryside by ATV, then explore the coastline by double-decker catamaran. There are countless delights on this full-day tour: sample organic products; explore...

8 hours Hotel pickup offered Free Cancellation

5.0 (105)

from
$109

Private Small Group, Snorkeling Cruise, Natural Pool & Exclusive Virgin Beach

Suitable for small and large groups. A great option to unveil the true beauty of Punta Cana while you sail the coast from the luxury …More

5.0 (23)

Private Small Group, Snorkeling Cruise, Natural Pool & Exclusive Virgin Beach

Suitable for small and large groups. A great option to unveil the true beauty of Punta Cana while you sail the coast from the luxury...

3 hours 30 minutes Free Cancellation

5.0 (23)

from
$698

Eco Saona Island Excursion from Punta Cana

If you are looking for an eco excursion without crowded beaches, this is the right one for you. We bring you to the places of …More

4.8 (112)

Eco Saona Island Excursion from Punta Cana

If you are looking for an eco excursion without crowded beaches, this is the right one for you. We bring you to the places of...

7 to 8 hours Hotel pickup offered Free Cancellation

4.8 (112)

from
$155

Saona Island Full Day Excursion 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

3.9 (48)

Saona Island Full Day Excursion 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...

7 to 8 hours Hotel pickup offered Free Cancellation

3.9 (48)

from
$79

1 Hour Jet Ski Tour in the Virgin Islands from Westin St. John

Zoom out of Great Cruz Bay and follow our guide through the pristine waters of the Caribbean between St. Thomas and St. John in the …More

4.9 (39)

1 Hour Jet Ski Tour in the Virgin Islands from Westin St. John

Zoom out of Great Cruz Bay and follow our guide through the pristine waters of the Caribbean between St. Thomas and St. John in the...

1 hour Free Cancellation

4.9 (39)

from
$169

Full Day Tour to Isla Saona and Altos de Chavon

This selection also includes a visit to Alto Chavón. Altos de Chavón is a recreation of a Mediterranean-style European village located on the Chavón River …More

4.9 (20)

Full Day Tour to Isla Saona and Altos de Chavon

This selection also includes a visit to Alto Chavón. Altos de Chavón is a recreation of a Mediterranean-style European village located on the Chavón River...

12 hours Hotel pickup offered Free Cancellation

4.9 (20)

from
$85

3 ADVENTURES: Sailing Catamaran Cruise - Hooka Diving - Snorkeling

Discover the amazing underwater world at Punta Cana on this 4-hour party cruise. Enjoy the open bar, snorkeling, and hooka diving with a professional guide. …More

Punta Cana, Dominican Republic

4.9 (164)

3 ADVENTURES: Sailing Catamaran Cruise - Hooka Diving - Snorkeling

Discover the amazing underwater world at Punta Cana on this 4-hour party cruise. Enjoy the open bar, snorkeling, and hooka diving with a professional guide....

4 hours Hotel pickup offered Free Cancellation

4.9 (164)

from
$105

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?