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 →

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail. …More

5.0 (190)

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail....

4 hours Hotel pickup offered Free Cancellation

5.0 (190)

from
$2,380

USVI Private Boat Charters - New, Fast Powerboats for Half and Full Day

Your group will spend the day enjoying the many isles and harbors of the U.S. Virgin Islands on your own private powerboat. MV Aquarius is …More

4.9 (331)

USVI Private Boat Charters - New, Fast Powerboats for Half and Full Day

Your group will spend the day enjoying the many isles and harbors of the U.S. Virgin Islands on your own private powerboat. MV Aquarius is...

4 to 7 hours Free Cancellation

4.9 (331)

from
$846

St Thomas Sea Turtle Snorkel Kayak Adventure Tour

Don't miss this unique small group kayak and snorkel tour! Avoid crowded tours on this half-day excursion. Snorkel in protected, calm waters with a guide …More

5.0 (62)

St Thomas Sea Turtle Snorkel Kayak Adventure Tour

Don't miss this unique small group kayak and snorkel tour! Avoid crowded tours on this half-day excursion. Snorkel in protected, calm waters with a guide...

4 hours Free Cancellation

5.0 (62)

from
$139

St Thomas~St John Snorkel, Swim & Beach Trip on MV Island Flyer

No overcrowding this is a semi-private excursion. A maximum of 12 guests will enjoy a 4 hr trip from St. Thomas to St John. At …More

4.8 (215)

St Thomas~St John Snorkel, Swim & Beach Trip on MV Island Flyer

No overcrowding this is a semi-private excursion. A maximum of 12 guests will enjoy a 4 hr trip from St. Thomas to St John. At...

4 hours Free Cancellation

4.8 (215)

from
$160

Nevis Panoramic Drive and Beach Experience

Two islands, one paradise. Experience the best of St Kitts-Nevis on this captivating 5-hour tour. Board your fast and comfortable custom-built powerboat direct from St …More

4.3 (95)

Nevis Panoramic Drive and Beach Experience

Two islands, one paradise. Experience the best of St Kitts-Nevis on this captivating 5-hour tour. Board your fast and comfortable custom-built powerboat direct from St...

5 hours Free Cancellation

4.3 (95)

from
$96

Taste some of Bermuda’s local rum on this 1.5-hour rum cruise! Sip on local rum while learning about the history and culture of the island. …More

4.8 (73)

Bermuda Rum Cruise

Taste some of Bermuda’s local rum on this 1.5-hour rum cruise! Sip on local rum while learning about the history and culture of the island....

1 hour 30 minutes Free Cancellation

4.8 (73)

from
$100

Full-Day Snorkeling Tour to Culebra Island with Lunch

Explore the best of Culebra Island - Flamenco Beach! Flamenco Beach is a worldwide attraction known for its white sandy beach and crystal clear, shallow …More

Fajardo, Puerto Rico

4.8 (373)

Full-Day Snorkeling Tour to Culebra Island with Lunch

Explore the best of Culebra Island - Flamenco Beach! Flamenco Beach is a worldwide attraction known for its white sandy beach and crystal clear, shallow...

7 hours Free Cancellation

4.8 (373)

from
$168

Private Half Day Charter: St Lucia Boat Tour to Soufriere

Cruise down the beautiful west coast of St Lucia in a private speedboat to Soufriere and the Pitons on this half day 4 hour tour. …More

Anse La Raye, St Lucia

4.9 (107)

Private Half Day Charter: St Lucia Boat Tour to Soufriere

Cruise down the beautiful west coast of St Lucia in a private speedboat to Soufriere and the Pitons on this half day 4 hour tour. ...

1 to 4 hours Hotel pickup offered Free Cancellation

4.9 (107)

from
$90

Punta Cana Private Catamaran Cruise with Drinks and Light Snacks

A Premium Powerboat Catamaran with Premium drinks and Professional Crew, Snorkel, Slide, Cruise, Paddle Board, Snorkel at the Natural Reserve near Cabo Engaño NOT where …More

Punta Cana, Dominican Republic

5.0 (295)

Punta Cana Private Catamaran Cruise with Drinks and Light Snacks

A Premium Powerboat Catamaran with Premium drinks and Professional Crew, Snorkel, Slide, Cruise, Paddle Board, Snorkel at the Natural Reserve near Cabo Engaño NOT where...

4 hours Hotel pickup offered Free Cancellation

5.0 (295)

from
$989

Yunque Rainforest River Rope Swing with Waterslide and Beach Tour

This action pack day will start by visiting two natural rock waterslides, one for beginners and another for the adrenaline seekers, swimming in natural water …More

5.0 (133)

Yunque Rainforest River Rope Swing with Waterslide and Beach Tour

This action pack day will start by visiting two natural rock waterslides, one for beginners and another for the adrenaline seekers, swimming in natural water...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (133)

from
$109

Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our Power Catamarans and explore the very best of St. John and …More

5.0 (70)

Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our Power Catamarans and explore the very best of St. John and...

6 hours Free Cancellation

5.0 (70)

from
$1,195

Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

Explore the Virgin Islands in style aboard MV Poseidon, our beautiful 36 ft. TwinVee Ocean Cat. The TwinVee is known for its speed and stability …More

5.0 (210)

Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

Explore the Virgin Islands in style aboard MV Poseidon, our beautiful 36 ft. TwinVee Ocean Cat. The TwinVee is known for its speed and stability...

4 to 7 hours Free Cancellation

5.0 (210)

from
$995

Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba

Discover Aruba's Beauty Embark on the Tropical Sailing Experience from Varadero Marina Aruba, with morning and afternoon sails available. Cruise past the picturesque Spanish Lagoon, …More

Palm - Eagle Beach, Aruba

4.9 (252)

Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba

Discover Aruba's Beauty Embark on the Tropical Sailing Experience from Varadero Marina Aruba, with morning and afternoon sails available. Cruise past the picturesque Spanish Lagoon,...

4 hours Hotel pickup offered Free Cancellation

4.9 (252)

from
$135

Half Day Private Sailing Catamaran and Snorkel Trip to St John

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and …More

5.0 (127)

Half Day Private Sailing Catamaran and Snorkel Trip to St John

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and...

3 hours 30 minutes Free Cancellation

5.0 (127)

from
$165

St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran …More

5.0 (114)

St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran...

6 hours 30 minutes Free Cancellation

5.0 (114)

from
$1,650

Barbados Catamaran Turtle Snorkel with Lunch and Open Bar

Come sail on the catamaran Stiletto on the calm, crystal clear waters of Barbados coastline, laying anchor just offshore where you can experience the unforgettable …More

Diamond Valley, Barbados

4.9 (1,595)

Barbados Catamaran Turtle Snorkel with Lunch and Open Bar

Come sail on the catamaran Stiletto on the calm, crystal clear waters of Barbados coastline, laying anchor just offshore where you can experience the unforgettable...

5 hours Hotel pickup offered Free Cancellation

4.9 (1,595)

from
$110

Join us as we take you on a trip to Klein Curaçao. As our guest, you have access to our exclusive beach house. With a …More

4.7 (222)

Klein Curaçao Full Day Boat Trip

Join us as we take you on a trip to Klein Curaçao. As our guest, you have access to our exclusive beach house. With a...

9 hours 30 minutes Free Cancellation

4.7 (222)

from
$155

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boat. Designed for intimate gatherings of up to 15 guests, this …More

4.9 (242)

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boat. Designed for intimate gatherings of up to 15 guests, this...

4 hours Free Cancellation

4.9 (242)

from
$130

Dominica Shore Excursion: River Tubing Safari

Step off your cruise ship in Dominica and head out on a river tubing shore excursion. Dominica is filled with rivers and other natural features …More

4.8 (141)

Dominica Shore Excursion: River Tubing Safari

Step off your cruise ship in Dominica and head out on a river tubing shore excursion. Dominica is filled with rivers and other natural features...

3 hours Free Cancellation

4.8 (141)

from
$50

Punta Cana: Catamaran Tour, Reef Snorkeling and Unlimited Drinks!

Embark on a thrilling catamaran ride, where you can relax and enjoy the stunning Caribbean views. Sip on refreshing drinks as you cruise along the …More

Punta Cana, Dominican Republic

4.9 (174)

Punta Cana: Catamaran Tour, Reef Snorkeling and Unlimited Drinks!

Embark on a thrilling catamaran ride, where you can relax and enjoy the stunning Caribbean views. Sip on refreshing drinks as you cruise along the...

3 hours Hotel pickup offered Free Cancellation

4.9 (174)

from
$74

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?