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 →

Private & Romantic Sunset Cruise Under Sails

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the …More

4.9 (17)

Private & Romantic Sunset Cruise Under Sails

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the...

2 hours 30 minutes Free Cancellation

4.9 (17)

from
$608

Experience the magic of an Aruban sunset aboard your own private catamaran. As the sky transforms into breathtaking hues of orange and pink, sip on …More

5.0 (7)

Private Sunset Tour in Aruba

Experience the magic of an Aruban sunset aboard your own private catamaran. As the sky transforms into breathtaking hues of orange and pink, sip on...

2 hours Free Cancellation

5.0 (7)

from
$2,150

Damajagua 7 Waterfalls Adventure – In Puerto Plata

Get ready for an unforgettable Damajagua adventure! Trek through lush rainforest with an experienced guide, then swim, slide and jump your way through 7 spectacular …More

Puerto Plata, Dominican Republic

4.8 (43)

Damajagua 7 Waterfalls Adventure – In Puerto Plata

Get ready for an unforgettable Damajagua adventure! Trek through lush rainforest with an experienced guide, then swim, slide and jump your way through 7 spectacular...

3 to 4 hours Hotel pickup offered Free Cancellation

4.8 (43)

from
$55

Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early …More

5.0 (2)

Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early...

2 hours Free Cancellation

5.0 (2)

from
$1,495

An Astronomical Moment: Aruba Celestial Sunset Cruise

A celestial sunset is the astronomical moment the sun disappears below the horizon, followed by three stages of twilight—civil, nautical, and astronomical—driven by the sun's …More

4.7 (6)

An Astronomical Moment: Aruba Celestial Sunset Cruise

A celestial sunset is the astronomical moment the sun disappears below the horizon, followed by three stages of twilight—civil, nautical, and astronomical—driven by the sun's...

2 hours 30 minutes Free Cancellation

4.7 (6)

from
$89

Curaçao Private Morning Snorkeling Boat Tour

Create unforgettable memories with this exclusive private sailing experience in Curaçao. Our elegant 48-ft sailing yacht Galaxie is reserved entirely for your group, allowing you …More

5.0 (4)

Curaçao Private Morning Snorkeling Boat Tour

Create unforgettable memories with this exclusive private sailing experience in Curaçao. Our elegant 48-ft sailing yacht Galaxie is reserved entirely for your group, allowing you...

3 hours Free Cancellation

5.0 (4)

from
$225

THE BEST Sunshine PARTY BOAT CATAMARAN IN DOMINICAN REPUBLIC

A catamaran or boat equipped for parties, with music, an open bar, and dancing. Water Activities: Snorkeling in coral reefs, visiting natural pools, and enjoying …More

Punta Cana, Dominican Republic

5.0 (50)

THE BEST Sunshine PARTY BOAT CATAMARAN IN DOMINICAN REPUBLIC

A catamaran or boat equipped for parties, with music, an open bar, and dancing. Water Activities: Snorkeling in coral reefs, visiting natural pools, and enjoying...

3 hours 30 minutes Hotel pickup offered

5.0 (50)

from
$69

We invite you to climb aboard one of our custom built, open air catamarans and allow our team to indulge you as you sit back …More

5.0 (1)

Discover Nassau by Land and Sea Tour

We invite you to climb aboard one of our custom built, open air catamarans and allow our team to indulge you as you sit back...

3 hours Free Cancellation

5.0 (1)

from
$109

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small …More

5.0 (6)

Bermuda By Sunset “Private Catamaran”

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small...

1 hour 30 minutes Hotel pickup offered Free Cancellation

5.0 (6)

from
$580

Negril: MORNING Catamaran Cruise Caves Swimming Reef Snorkeling

EARLY BIRD CRUISE....MORNING ONLY EXCURSION . Start your day in Jamaica with a beautiful, picturesque Catamaran cruise, we set sail from the 7 mile beach …More

Lucea, Jamaica

5.0 (6)

Negril: MORNING Catamaran Cruise Caves Swimming Reef Snorkeling

EARLY BIRD CRUISE....MORNING ONLY EXCURSION . Start your day in Jamaica with a beautiful, picturesque Catamaran cruise, we set sail from the 7 mile beach...

4 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$95

Private Sunset Charter on Wyuna Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury …More

5.0 (1)

Private Sunset Charter on Wyuna Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury...

3 hours Free Cancellation

5.0 (1)

from
$2,150

Exclusive 41ft Yacht Charter Experience in Klein Curaçao

Set sail on a luxury adventure aboard our spacious 38ft private boat to Klein Curaçao, the ultimate island escape just off the coast of Curaçao. …More

5.0 (13)

Exclusive 41ft Yacht Charter Experience in Klein Curaçao

Set sail on a luxury adventure aboard our spacious 38ft private boat to Klein Curaçao, the ultimate island escape just off the coast of Curaçao....

6 hours Free Cancellation

5.0 (13)

from
$225

Private Luxury 28ft Boat Trip Coastline Trip Curacao

Experience the ultimate in luxurious island living aboard our 28-foot private boat, accompanied by a trusted captain and knowledgeable tour guide. Discover the breathtaking beauty …More

5.0 (36)

Private Luxury 28ft Boat Trip Coastline Trip Curacao

Experience the ultimate in luxurious island living aboard our 28-foot private boat, accompanied by a trusted captain and knowledgeable tour guide. Discover the breathtaking beauty...

3 hours Free Cancellation

5.0 (36)

from
$135

Grand Cayman Bioluminescent Bay Adventure

Grand Cayman is one of the few places in the world where you can experience the incredible natural phenomenon of bioluminescence Discover the enchanting magic …More

Grand Cayman, Cayman Islands

4.4 (52)

Grand Cayman Bioluminescent Bay Adventure

Grand Cayman is one of the few places in the world where you can experience the incredible natural phenomenon of bioluminescence Discover the enchanting magic...

3 hours Hotel pickup offered Free Cancellation

4.4 (52)

from
$149

Half-Day Luxury Private Rose Island Pigs and Turtles Excursion

Our luxury boat offers comfortable seating for a group of 8, perfect for getting that summer glow, fresh water shower, private facilities and ample storage …More

5.0 (32)

Half-Day Luxury Private Rose Island Pigs and Turtles Excursion

Our luxury boat offers comfortable seating for a group of 8, perfect for getting that summer glow, fresh water shower, private facilities and ample storage...

4 hours Free Cancellation

5.0 (32)

from
$750

8 hours 38ft Reel Dreams Private Charter Nassau

Join on this private, full-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 (36)

8 hours 38ft Reel Dreams Private Charter Nassau

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

8 hours Free Cancellation

4.9 (36)

from
$1,980

Private Bahamas Half-Day Fishing Tour from New Providence

Depart Paradise Island on a comfortable 32ft Luhrs. Enjoy a short 20 minute ride where you can begin to set out your lines. You can …More

4.4 (12)

Private Bahamas Half-Day Fishing Tour from New Providence

Depart Paradise Island on a comfortable 32ft Luhrs. Enjoy a short 20 minute ride where you can begin to set out your lines. You can...

4 hours Free Cancellation

4.4 (12)

from
$925

Great Exuma: Private Island-Hopping Boat Tour with Swimming Pigs

We are the premier choice for boat tours in The Bahamas with over 20 years of industry experience. The Bahamas islands is your playground, let …More

Great Exuma, Bahamas

4.9 (11)

Great Exuma: Private Island-Hopping Boat Tour with Swimming Pigs

We are the premier choice for boat tours in The Bahamas with over 20 years of industry experience. The Bahamas islands is your playground, let...

8 hours Free Cancellation

4.9 (11)

from
$6,000

Exotic half day private charters to Rose Island, Pigs and Turtles

Experience a one-of-a-kind adventure under the guidance of your own private captain. Where the open seas become a canvas for unforgettable memories and a deeper …More

5.0 (34)

Exotic half day private charters to Rose Island, Pigs and Turtles

Experience a one-of-a-kind adventure under the guidance of your own private captain. Where the open seas become a canvas for unforgettable memories and a deeper...

4 hours Free Cancellation

5.0 (34)

from
$860

Deep Sea Fishing Private Boat Charter in San Juan

Experience some of the greatest sport fishing waters in the world when you take a full day or half day fishing charter from San Juan, …More

4.6 (10)

Deep Sea Fishing Private Boat Charter in San Juan

Experience some of the greatest sport fishing waters in the world when you take a full day or half day fishing charter from San Juan,...

4 hours Free Cancellation

4.6 (10)

from
$1,282

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?