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 →

Scuba Tour for Certified Divers in San Juan - Best Facilities

Scuba Dogs is a PADI 5-Star Dive Center; the only official operator with all gear, restrooms, showers, lockers and professional staff right there at the …More

4.9 (57)

Scuba Tour for Certified Divers in San Juan - Best Facilities

Scuba Dogs is a PADI 5-Star Dive Center; the only official operator with all gear, restrooms, showers, lockers and professional staff right there at the...

2 hours 30 minutes Free Cancellation

4.9 (57)

from
$91

Saona Island is a tropical paradise located in the heart of the Caribbean, part of the Cotubanamá National Park in the Dominican Republic. Famous for …More

Punta Cana, Dominican Republic

4.9 (68)

Full Day Tour in Isla Saona with Guide

Saona Island is a tropical paradise located in the heart of the Caribbean, part of the Cotubanamá National Park in the Dominican Republic. Famous for...

9 hours Hotel pickup offered Free Cancellation

4.9 (68)

from
$99

Build Your Private Charter: Snorkel, Stingrays, or Bio

**Accommodates up to 7 Passengers** Personalized Experience: Our small group sizes ensure a more intimate and personalized experience. You’ll have plenty of opportunities to ask …More

Grand Cayman, Cayman Islands

5.0 (41)

Build Your Private Charter: Snorkel, Stingrays, or Bio

**Accommodates up to 7 Passengers** Personalized Experience: Our small group sizes ensure a more intimate and personalized experience. You’ll have plenty of opportunities to ask...

2 to 4 hours Free Cancellation

5.0 (41)

from
$500

Mangrove Cay Motorized Clear Kayak Tour, Providenciales

Experience the natural beauty of Mangrove Cay from a unique motorized clear kayak - no paddling required. Unlike a traditional kayak tour, guests can relax …More

4.9 (14)

Mangrove Cay Motorized Clear Kayak Tour, Providenciales

Experience the natural beauty of Mangrove Cay from a unique motorized clear kayak - no paddling required. Unlike a traditional kayak tour, guests can relax...

1 hour 30 minutes Free Cancellation

4.9 (14)

from
$86

Private Boat in Punta Cana with Snorkel, Open Bar & Water Slide

This private catamaran tour in Punta Cana is unique because it combines exclusivity, fun, and a deep connection with nature in one package. Unlike group …More

5.0 (73)

Private Boat in Punta Cana with Snorkel, Open Bar & Water Slide

This private catamaran tour in Punta Cana is unique because it combines exclusivity, fun, and a deep connection with nature in one package. Unlike group...

3 hours Hotel pickup offered Free Cancellation

5.0 (73)

from
$720

Get ready for a breathtaking island escape filled with thrilling adventures, tropical beauty, and pure relaxation! Cruise from Nassau to a stunning private island paradise, …More

4.6 (23)

Rose Island Perfect Beach Day Escape

Get ready for a breathtaking island escape filled with thrilling adventures, tropical beauty, and pure relaxation! Cruise from Nassau to a stunning private island paradise,...

4 hours Free Cancellation

4.6 (23)

from
$59

Grand Cayman Stingray City Sandbar Catamaran Sunset Tour

Set sail on a 2-hour journey aboard the Buccaneer Catamaran, your gateway to the enchanting Stingray City Sandbar. This unforgettable experience allows you to interact …More

Grand Cayman, Cayman Islands

4.9 (78)

Grand Cayman Stingray City Sandbar Catamaran Sunset Tour

Set sail on a 2-hour journey aboard the Buccaneer Catamaran, your gateway to the enchanting Stingray City Sandbar. This unforgettable experience allows you to interact...

2 hours Free Cancellation

4.9 (78)

from
$59

Dindin’s Biobay Tours-CLEAR BOTTOM KAYAKS Tour in Mosquito Bay

Immerse yourself in the enchanting waters of Mosquito Bay on this captivating one-hour night kayak tour. Paddle through one of the world’s brightest bioluminescent bay, …More

Vieques, Puerto Rico

4.3 (108)

Dindin’s Biobay Tours-CLEAR BOTTOM KAYAKS Tour in Mosquito Bay

Immerse yourself in the enchanting waters of Mosquito Bay on this captivating one-hour night kayak tour. Paddle through one of the world’s brightest bioluminescent bay,...

1 hour 30 minutes Free Cancellation

4.3 (108)

from
$67

Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult

Set Sail in Punta Cana – Bavaro Luxury, Fun & VIP Vibes All in One! Perfect for birthdays, bachelorette parties, group getaways & more. WHAT’S INCLUDED? …More

La Romana, Dominican Republic

4.8 (77)

Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult

Set Sail in Punta Cana – Bavaro Luxury, Fun & VIP Vibes All in One! Perfect for birthdays, bachelorette parties, group getaways & more. WHAT’S INCLUDED?...

4 hours Hotel pickup offered Free Cancellation

4.8 (77)

from
$50

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs …More

5.0 (17)

Private Catamaran Charter on Wyuna

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs...

3 hours Free Cancellation

5.0 (17)

from
$2,120

3 Hours Private Boat Includes Snorkeling & Swim with turtles

Experience Aruba’s stunning coastline aboard a private speed boat charter. This exclusive 3 hour adventure is perfect for families, friends, and small groups looking for …More

5.0 (43)

3 Hours Private Boat Includes Snorkeling & Swim with turtles

Experience Aruba’s stunning coastline aboard a private speed boat charter. This exclusive 3 hour adventure is perfect for families, friends, and small groups looking for...

3 hours Free Cancellation

5.0 (43)

from
$900

Private Premium Whale and Dolphin Safari St Lucia

Spend the day out on the water off the coast of St Lucia on this whale and dolphin watching cruise! With 85% chance of sightings, …More

4.7 (70)

Private Premium Whale and Dolphin Safari St Lucia

Spend the day out on the water off the coast of St Lucia on this whale and dolphin watching cruise! With 85% chance of sightings,...

4 hours Free Cancellation

4.7 (70)

from
$2,000

Beach Trip Along The West Coast Of Curacao

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as …More

4.9 (44)

Beach Trip Along The West Coast Of Curacao

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as...

8 hours Free Cancellation

4.9 (44)

from
$140

Catamaran Snorkel & BBQ Sail (cruise friendly)

The only catamaran tour that includes guided snorkeling and on board lunch prepared on the grill! Our schedule is perfectly attuned to arrival and departure …More

4.9 (206)

Catamaran Snorkel & BBQ Sail (cruise friendly)

The only catamaran tour that includes guided snorkeling and on board lunch prepared on the grill! Our schedule is perfectly attuned to arrival and departure...

4 hours

4.9 (206)

from
$120

Water Taxi to the Swimming Pigs of Rose Island Nassau Bahamas

Meet, pet, and interact with Rose Island's famous swimming pigs in a beautiful tropical setting. Enjoy playful encounters with these friendly animals, capture unforgettable photos, …More

4.8 (32)

Water Taxi to the Swimming Pigs of Rose Island Nassau Bahamas

Meet, pet, and interact with Rose Island's famous swimming pigs in a beautiful tropical setting. Enjoy playful encounters with these friendly animals, capture unforgettable photos,...

4 hours Free Cancellation

4.8 (32)

from
$69

Local Legend Charters: Explore St. John! (Full or Half Day)

3rd generation Family/locally owned/operated business providing Private, customizable Boat Charters, Day trips and tours of the Virgin Islands, including sightseeing, boating, swimming, snorkeling, beach and …More

Cruz Bay, US Virgin Islands

5.0 (43)

Local Legend Charters: Explore St. John! (Full or Half Day)

1 to 11 hours Hotel pickup offered Free Cancellation

5.0 (43)

from
$950

Swim with the Pigs Safari in Bahamas (2hrs)

Cruise the shores of the Bahamas with us on an exciting, fun filled boat ride to visit three islands and cays. Enjoy crystal clear waters …More

5.0 (49)

Swim with the Pigs Safari in Bahamas (2hrs)

Cruise the shores of the Bahamas with us on an exciting, fun filled boat ride to visit three islands and cays. Enjoy crystal clear waters...

2 hours Free Cancellation

5.0 (49)

from
$175

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran …More

5.0 (302)

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran...

3 hours Free Cancellation

5.0 (302)

from
$999

Bermuda Private Boat Charter: Snorkel, Cliff Jumping & Sightseeing

Our boat "Island Vibez" is small enough to go where a lot of the larger charter boats cannot, yet she is extremely spacious and comfortable. …More

5.0 (229)

Bermuda Private Boat Charter: Snorkel, Cliff Jumping & Sightseeing

Our boat "Island Vibez" is small enough to go where a lot of the larger charter boats cannot, yet she is extremely spacious and comfortable....

4 hours Free Cancellation

5.0 (229)

from
$1,200

Weekly update: Beautiful conditions, October 12- 16. Book now!! *If you loved the experience & wish to leave a tip we accept Venmo, PayPal or …More

Rincón, Puerto Rico

5.0 (153)

Snorkeling Adventure in Aguadilla

Weekly update: Beautiful conditions, October 12- 16. Book now!! *If you loved the experience & wish to leave a tip we accept Venmo, PayPal or...

2 hours Free Cancellation

5.0 (153)

from
$98

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?