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 →

Our tour to Samaná unique is the perfect combination of adventure, natural beauty, and moments of relaxation, all in a single day. From a delightful …More

Samaná, Dominican Republic

4.0 (1)

Samana Full Day From Punta Cana

Our tour to Samaná unique is the perfect combination of adventure, natural beauty, and moments of relaxation, all in a single day. From a delightful...

10 hours Free Cancellation

4.0 (1)

from
$170

Pure relaxation awaits on this trip to Saona Island. It’s an Insta picture-perfect paradise – covered in exotic flora, with softly swaying palm trees, powder …More

Puerto Plata, Dominican Republic

3.7 (3)

Saona Island Cruise & Private Beach

Pure relaxation awaits on this trip to Saona Island. It’s an Insta picture-perfect paradise – covered in exotic flora, with softly swaying palm trees, powder...

8 hours Hotel pickup offered Free Cancellation

3.7 (3)

from
$129

Clear Kayak Photoshoot in Montego Bay (Single)

Indulge in a mesmerizing Clear Kayak Photoshoot at one of Jamaica's hidden gems – a stunning, tranquil beach. Our seasoned team and skilled photographers ensure …More

Trelawny, Jamaica

4.3 (4)

Clear Kayak Photoshoot in Montego Bay (Single)

Indulge in a mesmerizing Clear Kayak Photoshoot at one of Jamaica's hidden gems – a stunning, tranquil beach. Our seasoned team and skilled photographers ensure...

1 to 2 hours Hotel pickup offered Free Cancellation

4.3 (4)

from
$198

A unique place you can drive a jet ski , no reef , no corals, the mangrove are fantastic. The natural pool are spectacular and …More

Punta Cana, Dominican Republic

4.0 (3)

Jet Ski Tour Punta Cana

A unique place you can drive a jet ski , no reef , no corals, the mangrove are fantastic. The natural pool are spectacular and...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.0 (3)

from
$260

Puerto Plata:Waterfalls + Safari buggy + Horseback (TOP3IN1)

WATERFALLS + BUGGIES + HORSEBACK RIDING Come with us on the most complete adventure of the north coast. We start the day heading to the …More

Puerto Plata, Dominican Republic

3.8 (4)

Puerto Plata:Waterfalls + Safari buggy + Horseback (TOP3IN1)

WATERFALLS + BUGGIES + HORSEBACK RIDING Come with us on the most complete adventure of the north coast. We start the day heading to the...

8 hours Hotel pickup offered Free Cancellation

3.8 (4)

from
$165

Saona Island Tropical Escape with Catamaran Party

What makes our Saona Island tour unique is the perfect combination of adventure, fun, and relaxation in one of the Caribbean’s most breathtaking destinations. Travelers …More

3.7 (7)

Saona Island Tropical Escape with Catamaran Party

What makes our Saona Island tour unique is the perfect combination of adventure, fun, and relaxation in one of the Caribbean’s most breathtaking destinations. Travelers...

8 to 10 hours Hotel pickup offered Free Cancellation

3.7 (7)

from
$70

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) …More

Punta Cana, Dominican Republic

4.0 (3)

Saona Island Day Trip

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve)...

8 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$85

Full-day Whale watching Tour in Samana Bay from Punta Cana

Embark on a 5-in-1 adventure that will take your breath away! Enjoy the impressive view of Samaná Bay and witness a unique whale show. Observe …More

Samaná, Dominican Republic

3.4 (9)

Full-day Whale watching Tour in Samana Bay from Punta Cana

Embark on a 5-in-1 adventure that will take your breath away! Enjoy the impressive view of Samaná Bay and witness a unique whale show. Observe...

8 hours Hotel pickup offered Free Cancellation

3.4 (9)

from
$130

Montego Bay Catamaran Cruise and Snorkeling Tour from Falmouth

Board a luxury catamaran and cruise along the Montego Bay coastline for a day of ultimate fun. Snorkel in the clear Caribbean Sea and enjoy …More

Falmouth, Jamaica

3.3 (3)

Montego Bay Catamaran Cruise and Snorkeling Tour from Falmouth

Board a luxury catamaran and cruise along the Montego Bay coastline for a day of ultimate fun. Snorkel in the clear Caribbean Sea and enjoy...

5 hours Hotel pickup offered Free Cancellation

3.3 (3)

from
$324

Full-Day Charter To The Baths Virgin Gorda British Virgin islands

Embark on the "Full-Day Charter to The Baths" and discover the splendor of the sea aboard our sumptuous 48 ft Cranchi Atlantique yacht. Your first …More

Tortola, British Virgin Islands

4.0 (2)

Full-Day Charter To The Baths Virgin Gorda British Virgin islands

Embark on the "Full-Day Charter to The Baths" and discover the splendor of the sea aboard our sumptuous 48 ft Cranchi Atlantique yacht. Your first...

8 hours Hotel pickup offered Free Cancellation

4.0 (2)

from
$4,750

The Most Exclusive Escape on Saona Island Discover a hidden paradise where luxury meets nature. At Playatao, the island’s only private beach club, you’ll enjoy …More

Punta Cana, Dominican Republic

4.0 (3)

Saona Island by Catamaran

The Most Exclusive Escape on Saona Island Discover a hidden paradise where luxury meets nature. At Playatao, the island’s only private beach club, you’ll enjoy...

9 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$110

Set sail on this 3 hour sunset cruise and take in the views of Jamaica's south coast from the best seat in the house! Stop by a …More

Negril, Jamaica

3.6 (5)

Reggae Sunset Cruise From South Coast

Set sail on this 3 hour sunset cruise and take in the views of Jamaica's south coast from the best seat in the house! Stop by a...

3 hours Hotel pickup offered Free Cancellation

3.6 (5)

from
$125

Marinarium Snorkeling Cruise from Bayahibe

Marinarium invites you to discover the wonders of the reef and the marine life. Join us for a fantastic half-day cruise during which you will …More

La Romana, Dominican Republic

4.0 (2)

Marinarium Snorkeling Cruise from Bayahibe

Marinarium invites you to discover the wonders of the reef and the marine life. Join us for a fantastic half-day cruise during which you will...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.0 (2)

from
$115

Full-Day Scuba Diving Catalina Island Tour from Bavaro

Enjoy a magical day underwater during this full-day scuba diving trip from Bavaro. Travel to picturesque Catalina Island and immerse yourself in its clear turquoise …More

La Romana, Dominican Republic

3.6 (5)

Full-Day Scuba Diving Catalina Island Tour from Bavaro

Enjoy a magical day underwater during this full-day scuba diving trip from Bavaro. Travel to picturesque Catalina Island and immerse yourself in its clear turquoise...

9 hours Hotel pickup offered Free Cancellation

3.6 (5)

from
$145

Experience the perfect mix of adventure, relaxation, and Dominican culture on a speedboat or catamaran journey to stunning Saona Island. Famous for its white sand …More

Punta Cana, Dominican Republic

4.0 (3)

Saona Island From Punta Cana

Experience the perfect mix of adventure, relaxation, and Dominican culture on a speedboat or catamaran journey to stunning Saona Island. Famous for its white sand...

10 hours 45 minutes Hotel pickup offered Free Cancellation

4.0 (3)

from
$73

Saona Island Adventure From Santo Domingo

This tour stands out by offering the perfect mix of adventure, relaxation, and authentic Dominican experiences. Starting with a scenic drive to Bayahibe, you'll board …More

Santo Domingo, Dominican Republic

4.3 (4)

Saona Island Adventure From Santo Domingo

This tour stands out by offering the perfect mix of adventure, relaxation, and authentic Dominican experiences. Starting with a scenic drive to Bayahibe, you'll board...

12 hours Free Cancellation

4.3 (4)

from
$89

Enjoy a 2 to 4-hour private wildlife tour on a 23ft boat. Observe diverse wildlife, including birds, manatees, caimans, and turtles, while cruising in 100% …More

4.3 (4)

Backwater Wildlife and Boat Tour

Enjoy a 2 to 4-hour private wildlife tour on a 23ft boat. Observe diverse wildlife, including birds, manatees, caimans, and turtles, while cruising in 100%...

2 to 4 hours Free Cancellation

4.3 (4)

from
$330

Highlights - Head to the hidden Saona Island from Bayahibe aboard a thrilling speedboat or a cruising catamaran - Take a dip near a sandbar …More

Punta Cana, Dominican Republic

3.7 (6)

Saona Island by Paradise Travel

Highlights - Head to the hidden Saona Island from Bayahibe aboard a thrilling speedboat or a cruising catamaran - Take a dip near a sandbar...

7 to 8 hours Hotel pickup offered Free Cancellation

3.7 (6)

from
$80

We present the only jet ski tour in Punta Cana, Dominican Republic. Enjoy the perfect mix between Adrenaline and Nature. For the duration of the …More

Punta Cana, Dominican Republic

3.5 (6)

Only Jet Ski Tour in Punta Cana

We present the only jet ski tour in Punta Cana, Dominican Republic. Enjoy the perfect mix between Adrenaline and Nature. For the duration of the...

5 hours Hotel pickup offered Free Cancellation

3.5 (6)

from
$100

Visit Jamaica's fascinating Mystic Lagoon on a night cruise! Cruise around the glowing lagoon in a small boat at night with your expert guide and …More

Montego Bay, Jamaica

3.5 (6)

Mystic Lagoon Guided Boat Ride and Swim

Visit Jamaica's fascinating Mystic Lagoon on a night cruise! Cruise around the glowing lagoon in a small boat at night with your expert guide and...

3 hours Hotel pickup offered Free Cancellation

3.5 (6)

from
$80

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?