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 and Luxury 2 Stop Snorkel in Bonaire National Marine Park

Cruise ship friendly! Welcome aboard your private Calypso Charters Bonaire two stop snorkel tour. While you're with us, you'll enjoy personalized service, tasty food and …More

5.0 (6)

Private and Luxury 2 Stop Snorkel in Bonaire National Marine Park

Cruise ship friendly! Welcome aboard your private Calypso Charters Bonaire two stop snorkel tour. While you're with us, you'll enjoy personalized service, tasty food and...

4 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$800

Private Catamaran Day Cruise Out of Soufriere for Up to 15 Guests

Depart from Soufriere and join us for a full day Snorkel and Sailing trip onboard one of our spacious catamarans. You will spend the day Sailing along the …More

5.0 (12)

Private Catamaran Day Cruise Out of Soufriere for Up to 15 Guests

Depart from Soufriere and join us for a full day Snorkel and Sailing trip onboard one of our spacious catamarans. You will spend the day Sailing along the...

7 hours Free Cancellation

5.0 (12)

from
$2,280

2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night …More

5.0 (2)

2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night...

2 days

5.0 (2)

from
$4,798

3 Hour Private Charter on Stingray City with Snorkeling

Avoid the crowds and join us on your own private boat with an experienced crew for an adventure of a lifetime! Enjoy an exciting one-on-one …More

Grand Cayman, Cayman Islands

5.0 (6)

3 Hour Private Charter on Stingray City with Snorkeling

Avoid the crowds and join us on your own private boat with an experienced crew for an adventure of a lifetime! Enjoy an exciting one-on-one...

3 hours 5 minutes Hotel pickup offered Free Cancellation

5.0 (6)

from
$750

Full Charter All Inclusive for Icacos and Palomino

The day includes visiting Icacos and Palomino, where we will go on a guided snorkeling tour at Tortuga Reef, and then we will visit two …More

Fajardo, Puerto Rico

5.0 (8)

Full Charter All Inclusive for Icacos and Palomino

The day includes visiting Icacos and Palomino, where we will go on a guided snorkeling tour at Tortuga Reef, and then we will visit two...

7 hours 30 minutes Free Cancellation

5.0 (8)

from
$1,350

Private Beach Day and 50ft Sun Seeker or 33ft Boat 1-10 Guests

The 50ft Sun Seeker Motor Yacht is the ideal vessel for beach days. Whether you're a young family that needs the extra shade, a small …More

5.0 (5)

Private Beach Day and 50ft Sun Seeker or 33ft Boat 1-10 Guests

The 50ft Sun Seeker Motor Yacht is the ideal vessel for beach days. Whether you're a young family that needs the extra shade, a small...

6 hours Free Cancellation

5.0 (5)

from
$1,760

Experience the BVI Like Never Before with TRC Powerboat Charters, we go beyond just boat charters—we create unforgettable, tailor-made experiences on the crystal-clear waters of …More

Tortola, British Virgin Islands

5.0 (31)

BVI Private Day Charters

Experience the BVI Like Never Before with TRC Powerboat Charters, we go beyond just boat charters—we create unforgettable, tailor-made experiences on the crystal-clear waters of...

4 to 8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$1,236

Private Catamaran Excursion to Sint Maarten with Snorkeling

1. An exceptional natural setting: crystal clear waters and preserved beaches offer an idyllic setting. 2. Marine richness : snorkeling allows you to explore a …More

5.0 (17)

Private Catamaran Excursion to Sint Maarten with Snorkeling

1. An exceptional natural setting: crystal clear waters and preserved beaches offer an idyllic setting. 2. Marine richness : snorkeling allows you to explore a...

8 hours

5.0 (17)

from
$132

Sail with captain Carl, safely along the calm, beautiful, majestic blue green beaches of Aruba. Let us show you historical shipwrecks, colorful sea animals and …More

5.0 (25)

Private Boat Tour in Aruba

Sail with captain Carl, safely along the calm, beautiful, majestic blue green beaches of Aruba. Let us show you historical shipwrecks, colorful sea animals and...

5 to 6 hours Free Cancellation

5.0 (25)

from
$1,400

Enjoy smooth sunset sailing on one of our catamarans along the coast of Bonaire. Let us get you spoiled with luxury snacks, drinks and chill …More

5.0 (16)

Sunset Bliss Catamaran Tour

Enjoy smooth sunset sailing on one of our catamarans along the coast of Bonaire. Let us get you spoiled with luxury snacks, drinks and chill...

2 hours 30 minutes

5.0 (16)

from
$80

Curacao Private Luxury Boat & Lunch Experience

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, offering everything from relaxed family cruises to romantic escapes in …More

5.0 (4)

Curacao Private Luxury Boat & Lunch Experience

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, offering everything from relaxed family cruises to romantic escapes in...

5 hours Free Cancellation

5.0 (4)

from
$285

Turtle Center, Starfish, Stingray, & Snorkeling(4-Stop Adventure)

A great way to explore the Islands most popular attractions in a day or less! ---PLEASE READ CAREFULLY--- Choosing Turtle Center Options; Turtle Safari - …More

Seven Mile Beach, Cayman Islands

4.4 (33)

Turtle Center, Starfish, Stingray, & Snorkeling(4-Stop Adventure)

A great way to explore the Islands most popular attractions in a day or less! ---PLEASE READ CAREFULLY--- Choosing Turtle Center Options; Turtle Safari -...

4 to 5 hours Free Cancellation

4.4 (33)

from
$99

Saona Island Relaxing Cruise by Sailing Catamaran

This sailing catamaran tour is ideal for travelers seeking a peaceful small-group experience to Saona Island, with a maximum of 20 guests on board for …More

4.8 (13)

Saona Island Relaxing Cruise by Sailing Catamaran

This sailing catamaran tour is ideal for travelers seeking a peaceful small-group experience to Saona Island, with a maximum of 20 guests on board for...

8 hours Hotel pickup offered Free Cancellation

4.8 (13)

from
$163

Aquaspace Morning Sail and Snorkel Tour on Bonaire with Lunch

Explore the stunning underwater world of Bonaire on this 4-hour morning sail and snorkel tour. Set sail from 09:00 to 13:00, enjoying all-inclusive snacks and …More

5.0 (5)

Aquaspace Morning Sail and Snorkel Tour on Bonaire with Lunch

Explore the stunning underwater world of Bonaire on this 4-hour morning sail and snorkel tour. Set sail from 09:00 to 13:00, enjoying all-inclusive snacks and...

4 hours Free Cancellation

5.0 (5)

from
$130

Group Catamaran 4 hr tour coral reef fun Iguana island adventure!

Explore the stunning waters of Turks and Caicos with a group Catamaran boat charter offering thrilling activities like snorkeling, swimming, diving off our on board …More

5.0 (10)

Group Catamaran 4 hr tour coral reef fun Iguana island adventure!

Explore the stunning waters of Turks and Caicos with a group Catamaran boat charter offering thrilling activities like snorkeling, swimming, diving off our on board...

4 hours Free Cancellation

5.0 (10)

from
$160

Dunn's River Falls & Luminous Lagoon Guided Tour from Montego Bay

Embark on an extraordinary, guided tour from Montego Bay to bask in the wonders of the legendary Dunn’s River Falls and experience the enchantment of …More

Falmouth, Jamaica

4.4 (35)

Dunn's River Falls & Luminous Lagoon Guided Tour from Montego Bay

Embark on an extraordinary, guided tour from Montego Bay to bask in the wonders of the legendary Dunn’s River Falls and experience the enchantment of...

9 hours Hotel pickup offered Free Cancellation

4.4 (35)

from
$190

Experience one of the top things to do on Bimini's top snorkeling adventure. Four sites, four experiences with four levels of adventure. Navigate through the …More

4.8 (12)

4-Stop Snorkeling Adventures in Bimini

Experience one of the top things to do on Bimini's top snorkeling adventure. Four sites, four experiences with four levels of adventure. Navigate through the...

3 hours Free Cancellation

4.8 (12)

from
$200

Crystal Caves, Aquarium, City of Hamilton and Ferry

Discover one of Bermuda’s oldest living treasures during this 5-hour tour of Crystal Caves, with stops in at the Bermuda Aquarium and nearby shopping. Explore …More

4.1 (41)

Crystal Caves, Aquarium, City of Hamilton and Ferry

Discover one of Bermuda’s oldest living treasures during this 5-hour tour of Crystal Caves, with stops in at the Bermuda Aquarium and nearby shopping. Explore...

5 hours Free Cancellation

4.1 (41)

from
$135

Half-Day at Green Cay Bahamas Snorkeling with Turtles

Enjoy an excursion to Pearl Island for snorkeling with lovely fish. Green Cay where you can swim right up to the turtles in their natural …More

Nassau, Bahamas

5.0 (11)

Half-Day at Green Cay Bahamas Snorkeling with Turtles

Enjoy an excursion to Pearl Island for snorkeling with lovely fish. Green Cay where you can swim right up to the turtles in their natural...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$1,500

Full-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, a fresh water shower, private facilities, and ample …More

4.8 (10)

Full-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, a fresh water shower, private facilities, and ample...

6 hours Free Cancellation

4.8 (10)

from
$1,950

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?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Cruises, Sailing & Water Tours are:

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?