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) San Juan Sunset Harbor Boat Ride Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise Full-Day Aruba History and Must-See Landmarks Tour Small-Group El Yunque Waterfall & Waterslides with Pickup 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 →

Sail aboard your private and exclusive catamaran to discover the best places to snorkel. You can also go paddleboarding if you wish. Ben the captain …More

Snorkeling Paddle Private Catamaran 1/2 Day Turks and Caicos

Sail aboard your private and exclusive catamaran to discover the best places to snorkel. You can also go paddleboarding if you wish. Ben the captain...

4 hours Free Cancellation

from
$1,990

Catamaran Excursions to Noah’s Ark Beach Club! Discover the ultimate day trip with our exclusive catamaran excursions to Noah’s Ark Beach Club, a tropical oasis …More

Noah's Ark Beach Club Tour on a Private Catamaran

Catamaran Excursions to Noah’s Ark Beach Club! Discover the ultimate day trip with our exclusive catamaran excursions to Noah’s Ark Beach Club, a tropical oasis...

4 hours

from
$2,000

Private Samana Full-Day Excursion - Pickup from Bayahibe

This excursion is full day. And we leave from the hotels in Bayahibe We visit the waterfall, Lemon Leap, We will arrive at Miches and …More

Samaná, Dominican Republic

Private Samana Full-Day Excursion - Pickup from Bayahibe

This excursion is full day. And we leave from the hotels in Bayahibe We visit the waterfall, Lemon Leap, We will arrive at Miches and...

10 hours Hotel pickup offered Free Cancellation

from
$7,950

Enjoy our catamaran with unrivalled comfort and privatized, with your family or friends. Enjoy our delicious cocktails and homemade appetizers facing the beauty of the …More

St Martin Grand Case: Private cruise after sunset

Enjoy our catamaran with unrivalled comfort and privatized, with your family or friends. Enjoy our delicious cocktails and homemade appetizers facing the beauty of the...

2 hours 30 minutes Free Cancellation

from
$1,569

Unique in Saint Martin, embark on our private cruise catamaran for you and let yourself be carried away in this romantic and idyllic setting, with …More

St Martin Gd-Case, Private Romantic Cruise 4 days

Unique in Saint Martin, embark on our private cruise catamaran for you and let yourself be carried away in this romantic and idyllic setting, with...

4 days

from
$6,146

Private Catamaran Cruise and Snorkeling in Montego Bay Area

Basically you get this completely private for your group. Mimosas, cold towels, and an onboard DJ set this Montego Bay Private All-inclusive Catamaran Cruise apart …More

Montego Bay, Jamaica

Private Catamaran Cruise and Snorkeling in Montego Bay Area

Basically you get this completely private for your group. Mimosas, cold towels, and an onboard DJ set this Montego Bay Private All-inclusive Catamaran Cruise apart...

3 to 4 hours Hotel pickup offered

from
$3,700

Private Luxury Dinner Sunset Cruise in St. Lucia

Join us for a Private Dinner Sunset Cruise with a Chef onboard to provide a culinary experience that is second to none. We will cruise …More

Choc, St Lucia

Private Luxury Dinner Sunset Cruise in St. Lucia

Join us for a Private Dinner Sunset Cruise with a Chef onboard to provide a culinary experience that is second to none. We will cruise...

3 hours Hotel pickup offered Free Cancellation

from
$1,600

Private Catamaran and Sunset Cruise to Ricks Cafe from Negril

Basically this completely private cruise is family friendly and perfect for small groups and special celebrations such as birthdays, anniversaries ect. We cater for any …More

Negril, Jamaica

Private Catamaran and Sunset Cruise to Ricks Cafe from Negril

Basically this completely private cruise is family friendly and perfect for small groups and special celebrations such as birthdays, anniversaries ect. We cater for any...

4 to 5 hours Hotel pickup offered

from
$4,100

Discover the best of Turks & Caicos Islands aboard this catamaran combining luxury and comfort. Ideal to enjoy a day with friends, family or in …More

Private Sunset Tour Catamaran 44 Big Ben

Discover the best of Turks & Caicos Islands aboard this catamaran combining luxury and comfort. Ideal to enjoy a day with friends, family or in...

2 hours Free Cancellation

from
$1,490

Discover the best of Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or in …More

Private Sunset Tour Fjord 38 Ben

Discover the best of Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or in...

2 hours Free Cancellation

from
$1,490

For parties 8 persons and smaller, the “Serendipity” provides a solid, comfortable, and well-equipped boat for bottom fishing or combination days. Serendipity is a 37’ …More

Pirate Cave Adventure Charter

For parties 8 persons and smaller, the “Serendipity” provides a solid, comfortable, and well-equipped boat for bottom fishing or combination days. Serendipity is a 37’...

8 hours Free Cancellation

from
$5,258

For parties 10 persons and smaller, the “Serendipity” provides a solid, comfortable, and well-equipped boat for bottom fishing or combination days. Serendipity is a 37’ …More

South Caicos History Tour and Cruise Full Day Private Charter

For parties 10 persons and smaller, the “Serendipity” provides a solid, comfortable, and well-equipped boat for bottom fishing or combination days. Serendipity is a 37’...

8 hours Free Cancellation

from
$6,970

Discover the pristine beauty of Culebra on a luxurious 6-hour boat tour aboard a 36 ft yacht. Experience a secure and comfortable navigation and discover …More

Culebra All Inclusive Luxury Private Yacht Tour

Discover the pristine beauty of Culebra on a luxurious 6-hour boat tour aboard a 36 ft yacht. Experience a secure and comfortable navigation and discover...

6 hours Free Cancellation

from
$2,700

Exuma, located just 40 miles from Nassau , is a stunning tropical paradise known for its crystal-clear turquoise waters, pristine white sandy beaches, and an …More

Private Exuma Cays Day: Iguana, Shark, Pigs, Sandbar & Lunch

Exuma, located just 40 miles from Nassau , is a stunning tropical paradise known for its crystal-clear turquoise waters, pristine white sandy beaches, and an...

8 hours Free Cancellation

from
$8,500

Private Sunset Serenade Begin your exclusive 2-hour journey with a warm welcome at our secluded pier, complete with refreshing cold towels and personalised attention. Voyage …More

Sunset Deluxe 2-Hour Private Charter in Montego Bay, Open Bar

Private Sunset Serenade Begin your exclusive 2-hour journey with a warm welcome at our secluded pier, complete with refreshing cold towels and personalised attention. Voyage...

2 hours Free Cancellation

from
$227

Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or …More

Montego Bay, Jamaica

Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or...

3 hours Hotel pickup offered Free Cancellation

from
$2,844

Discover the best of the Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or …More

Private Full Day Tour Fjord 38 Ben

Discover the best of the Turks & Caicos Islands aboard this motorboat combining luxury and comfort. Ideal to enjoy a day with friends, family or...

8 hours Free Cancellation

from
$3,490

Robinson Crusoe Island Beach Hideaway Cruise Come aboard in Turks and Caicos for your amazing adventure on the crystal clear waters of TCI. We welcome …More

Robinson Crusoe Island Beach Hideaway Cruise

Robinson Crusoe Island Beach Hideaway Cruise Come aboard in Turks and Caicos for your amazing adventure on the crystal clear waters of TCI. We welcome...

4 hours Hotel pickup offered Free Cancellation

from
$2,963

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We …More

Private Half Day Afternoon Snorkel and Cruise on Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We...

4 hours Hotel pickup offered Free Cancellation

from
$2,897

Indulge in the ultimate luxury with a private charter to St. Barts. Experience unparalleled comfort aboard high-end vessel, customized to your desires. Whether you're cruising …More

Saint Barth Prestige Private Charter

Indulge in the ultimate luxury with a private charter to St. Barts. Experience unparalleled comfort aboard high-end vessel, customized to your desires. Whether you're cruising...

6 to 8 hours Free Cancellation

from
$1,600

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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?