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Top Caribbean Day Cruises

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Caribbean Tours

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San Juan Sunset Harbor Boat Ride

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical …More

Likely to Sell Out
Likely to Sell Out
Isla Verde, Puerto Rico
4.7 (1,424)

San Juan Sunset Harbor Boat Ride

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical...

1 hour 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (1,424)
from
$99
Sandy Toes The Original Rose Island and Swimming Pigs Tour

Experience a true taste of The Bahamas, with a day at Sandy Toes. Sandy Toes is home to a sanctuary of protected wildlife including our …More

Likely to Sell Out
Likely to Sell Out
Nassau, Bahamas
4.8 (1,242)

Sandy Toes The Original Rose Island and Swimming Pigs Tour

Experience a true taste of The Bahamas, with a day at Sandy Toes. Sandy Toes is home to a sanctuary of protected wildlife including our...

6 hours • Free Cancellation
4.8 (1,242)
from
$258
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

Take a fun and relaxing catamaran cruise along the west coast of Barbados! On board a spacious schooner, sail to two different snorkeling spots, where …More

Likely to Sell Out
Likely to Sell Out
4.9 (2,393)

Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

Take a fun and relaxing catamaran cruise along the west coast of Barbados! On board a spacious schooner, sail to two different snorkeling spots, where...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (2,393)
from
$85
Culebra Full Day Beach and Fun Experience by Catamaran

Upon departing Marina Puerto Del Rey, our guests enjoy the beautiful views of the Cordillera Islands, and the mountains of El Yunque fade into the …More

Likely to Sell Out
Likely to Sell Out
Fajardo, Puerto Rico
4.8 (654)

Culebra Full Day Beach and Fun Experience by Catamaran

Upon departing Marina Puerto Del Rey, our guests enjoy the beautiful views of the Cordillera Islands, and the mountains of El Yunque fade into the...

6 hours • Free Cancellation
4.8 (654)
from
$195
San Juan Catamaran Sunset Sail with Drinks Included

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran …More

Likely to Sell Out
Likely to Sell Out
5.0 (666)

San Juan Catamaran Sunset Sail with Drinks Included

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran...

2 hours • Free Cancellation
5.0 (666)
from
$119
Icacos Island Catamaran Day Sail from Fajardo

Live out your fantasy of island escape and hop aboard a catamaran to Cayo Icacos, a deserted island surrounded by the bright blue Caribbean. On …More

Likely to Sell Out
Likely to Sell Out
Fajardo, Puerto Rico
4.9 (1,581)

Icacos Island Catamaran Day Sail from Fajardo

Live out your fantasy of island escape and hop aboard a catamaran to Cayo Icacos, a deserted island surrounded by the bright blue Caribbean. On...

6 hours • Free Cancellation
4.9 (1,581)
from
$155
Premium Catamaran Morning Sail: Snorkeling, Mimosas and Brunch

Begin your day with freshly prepared appetizers, refreshing juice, and a sparkling mimosa as you set sail on the crystal-clear waters of the Caribbean. Welcome …More

4.8 (694)

Premium Catamaran Morning Sail: Snorkeling, Mimosas and Brunch

Begin your day with freshly prepared appetizers, refreshing juice, and a sparkling mimosa as you set sail on the crystal-clear waters of the Caribbean. Welcome...

3 hours • Free Cancellation
4.8 (694)
from
$80
4hr Group Half Day Snorkel Excursion in Grace Bay, Providenciales

Welcome to Providenciales, where we have been snorkeling daily for 20 years and know every fish, coral and turtle by name!! We look forward to …More

Likely to Sell Out
Likely to Sell Out
4.9 (2,873)

4hr Group Half Day Snorkel Excursion in Grace Bay, Providenciales

Welcome to Providenciales, where we have been snorkeling daily for 20 years and know every fish, coral and turtle by name!! We look forward to...

4 hours • Free Cancellation
4.9 (2,873)
from
$125
Premium Catamaran Afternoon Sail: Snorkeling and Lunch

Your afternoon adventure begins with delicious lunch appetizers, refreshing beverages, and a sparkling toast as you set sail on the Caribbean’s warm, clear blue waters. …More

4.8 (598)

Premium Catamaran Afternoon Sail: Snorkeling and Lunch

Your afternoon adventure begins with delicious lunch appetizers, refreshing beverages, and a sparkling toast as you set sail on the Caribbean’s warm, clear blue waters....

3 hours • Free Cancellation
4.8 (598)
from
$75
Punta Cana Snorkeling Cruise and Dune buggy Combo Adventure

Discover the Dominican countryside while driving a powerful all offroad Dune Buggy, where you'll go on an exploration adventure you will always remember. As you …More

Punta Cana, Dominican Republic
4.8 (676)

Punta Cana Snorkeling Cruise and Dune buggy Combo Adventure

Discover the Dominican countryside while driving a powerful all offroad Dune Buggy, where you'll go on an exploration adventure you will always remember. As you...

8 hours • Hotel pickup offered • Free Cancellation
4.8 (676)
from
$129
Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a …More

Likely to Sell Out
Likely to Sell Out
4.9 (288)

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a...

5 hours • Free Cancellation
4.9 (288)
from
$149
Ultimate Anguilla Cays & Coves

Join the Ultimate Anguilla Cays & Coves tour for an unforgettable day sailing between some of the region's most beautiful beaches. Because conditions change day …More

4.7 (523)

Ultimate Anguilla Cays & Coves

Join the Ultimate Anguilla Cays & Coves tour for an unforgettable day sailing between some of the region's most beautiful beaches. Because conditions change day...

8 hours • Free Cancellation
4.7 (523)
from
$149
Bermuda Glass Bottom Boat Cruise

A glass bottom boat cruise is the best way to see Bermuda from above and below the water! Enjoy an informative and entertaining coastal sightseeing …More

Likely to Sell Out
Likely to Sell Out
4.7 (224)

Bermuda Glass Bottom Boat Cruise

A glass bottom boat cruise is the best way to see Bermuda from above and below the water! Enjoy an informative and entertaining coastal sightseeing...

1 hour 30 minutes • Free Cancellation
4.7 (224)
from
$78
Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no …More

4.7 (721)

Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no...

2 hours • Free Cancellation
4.7 (721)
from
$119
NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe ALL HOTELS

Lets set sail.. ! Your crew awaits. On Negril's Sweetheart Catamaran, SUNSHINE of the Seas, our staff are there to take care of you, as …More

Lucea, Jamaica
4.2 (356)

NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe ALL HOTELS

Lets set sail.. ! Your crew awaits. On Negril's Sweetheart Catamaran, SUNSHINE of the Seas, our staff are there to take care of you, as...

8 hours • Hotel pickup offered • Free Cancellation
4.2 (356)
from
$87
Visite guidée en français en bateau : Mangrove, ilets, snorkeling

Prêt pour une journée de rêve ? Découvrez le lagon & la mangrove en mode écolo avec des guides passionnés & passionnants ! Ton bateau …More

Likely to Sell Out
Likely to Sell Out
Basse-Terre Island, Guadeloupe
5.0 (954)

Visite guidée en français en bateau : Mangrove, ilets, snorkeling

Prêt pour une journée de rêve ? Découvrez le lagon & la mangrove en mode écolo avec des guides passionnés & passionnants ! Ton bateau...

4 hours 30 minutes • Free Cancellation
5.0 (954)
from
$57
San Juan Historical Bay Daytime Sailing Tour

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no …More

4.8 (191)

San Juan Historical Bay Daytime Sailing Tour

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no...

1 hour 30 minutes • Free Cancellation
4.8 (191)
from
$99
Icacos Beach Day Package with Water Taxi Transport from Fajardo

At East Coast Water Taxi we offer boat trips to Icacos Island, to what we like to call our Beach Day Package! In this package …More

Likely to Sell Out
Likely to Sell Out
Fajardo, Puerto Rico
5.0 (620)

Icacos Beach Day Package with Water Taxi Transport from Fajardo

At East Coast Water Taxi we offer boat trips to Icacos Island, to what we like to call our Beach Day Package! In this package...

5 hours • Free Cancellation
5.0 (620)
from
$100
Boat trip visit Mangroves, islets and lagoon

The lagoon of the Grand Cul de sac marin closed by the largest coral reef in the Lesser Antilles contains multiple biodiversity, mangroves, islands of …More

Likely to Sell Out
Likely to Sell Out
Basse-Terre Island, Guadeloupe
5.0 (688)

Boat trip visit Mangroves, islets and lagoon

The lagoon of the Grand Cul de sac marin closed by the largest coral reef in the Lesser Antilles contains multiple biodiversity, mangroves, islands of...

4 hours • Free Cancellation
5.0 (688)
from
$58
San Juan Bay Day Sail with Drinks Included

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze …More

5.0 (560)

San Juan Bay Day Sail with Drinks Included

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze...

1 hour 30 minutes • Free Cancellation
5.0 (560)
from
$99

Frequently Asked Questions

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

Recent tour reviews
Hidden Gem
New York City
San Juan Sunset Harbor Boat Ride
Thomas_H, Sep 2026
Hidden Gem
The experience was amazing!! Not only is this a sunset cruise, it is also a historical/ sightseeing/ party/ celebration cruise. The team was very knowledgeable and accommodating. They tended to every need and ensured you got the most out of your experience.
Read more
Had a great time! The...
New York City
Premium Catamaran Morning Sail: Snorkeling, Mimosas and Brunch
Kanesha_G, Sep 2026
Had a great time! The...
Had a great time! The weather was nice music was great! My friends and I really enjoyed the experience
Read more
Enjoy the Aqua waters here!
New York City
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise
Brenda_W, Sep 2026
Enjoy the Aqua waters here!
My lovely experience today was super ...from booking, to pick-up from my hotel, to onboarding the most comfortable catamaran sail boat, and then the best ever snorkeling adventure! We swam with only 1 turtle, but thats okay because we swam with beautiful fish of all colors ... as close as I was to them could never touch a single one! Our captain & crew were great and we never went wanting for anything! The history lessons were entertaining, the careful guidance to the sunken sea vessels & the call of the fish made me feel safe & in good hands the entire day! The food was great, and we had your choice of drinks - bottomless! Five star rating!
Read more
Fun in the sun
New York City
Premium Catamaran Afternoon Sail: Snorkeling and Lunch
dawnsE6386KM, Sep 2026
Fun in the sun
We had a great experience from start to finish. Great crew, drinks and amazing sights … we even got to see a few sea turtles. We highly recommend Octopus Aruba!
Read more
HIGHLY RECOMMEND
New York City
Ultimate Anguilla Cays & Coves
cherielp2026, Sep 2026
HIGHLY RECOMMEND
One of the best experiences of my life! I went with my husband and 2 kids (5 & 1). My oldest son’s birthday is coming up and they made him feel so special. They were so good with my kids! I was a little nervous bringing them on the boat, but it was an incredible experience. The crew was awesome! They let my husband reel in a mahi mahi and that made him really happy. I will definitely be back next time we come visit. Truly an unforgettable experience!
Read more
You will not be dissapointed.
New York City
Sandy Toes The Original Rose Island and Swimming Pigs Tour
robertaV2791IO, Sep 2026
You will not be dissapointed.
Simply Amazing. One small note, we did get lucky bc it was the off season so it was a very small group. That said, every staff member there was wonderful. They were having fun and really helpful. I was very nervous about my seven year old daughter being afraid to snorkel, but the team at ST was so great and comforting, they helped her right along. I wish I remembered everyone's names so I could be specific, but genuinely, they were all great. We had a private beach, hilarious time with the adorable pigs, a mini snorkeling adventure and a delicious lunch with postcard views the entire time.
Read more
Great experience
New York City
Premium Catamaran Afternoon Sail: Snorkeling and Lunch
DaanE90, Sep 2026
Great experience
Very nice snorkeling tour going to the ship wreck and afterwards in the second stop closer to shore. The lunch served was diverse and really good and the drinks if you wanted kept coming, many coconut rum pineapples were consumed.Crew was really nice and helpful!
Read more
Just book it!
New York City
Bermuda Glass Bottom Boat Cruise
jus, Sep 2026
Just book it!
Awesome glass bottom boat cruise. We were with Jesse and Melvin and they were super funny and awesome. Saw the wreck of the HMS Vixen and some cool coral reefs (even saw some sea turtles on the way back to the dock). Jesse and Melvin made us laugh the whole trip and played absolute bangers for music. They have a little bar on board (also includes soda & water) and a bathroom aswell. We went for our last day in Bermuda and had plenty of time afterwards to grab a bite to eat and get back on the ship to depart. Book this! And tip, these guys deserve it!
Read more
it was so much fun the...
New York City
San Juan Sunset Harbor Boat Ride
Michelle_R, Sep 2026
it was so much fun the...
it was so much fun the crew was the best they made our day and my daughter birthday special food and drinks were great to !! would def do it again when in san juan
Read more
Snorkeling Trip
New York City
4hr Group Half Day Snorkel Excursion in Grace Bay, Providenciales
erikabM2421VC, Sep 2026
Snorkeling Trip
So much fun! Their guide and captain were amazing hosts.
Read more
Sandy Toes - Couples Trip
New York City
Sandy Toes The Original Rose Island and Swimming Pigs Tour
930justinu, Sep 2026
Sandy Toes - Couples Trip
The sandy toes rose island tour was very well organized. The tour guides were very friendly and funny without being over the top. We did snorkeling, swimming with the pigs and enjoyed the beach. You could tell they really cared about the animals they took care of on the island.
Read more
Amazing sailing trip
New York City
Historical San Juan Bay Sunset Sailing Tour
Monique_C, Sep 2026
Amazing sailing trip
Wonderful experience on this sunset sailing trip. The captain was very personable and extremely knowledgeable about the history of Puerto Rico. Drinks were included and delicious. A relaxing and low key vibe. Just a really fun and amazing sailing experience. Would definitely do it again next time we are on the island.
Read more
HIGHLY RECOMMEND!!
New York City
Icacos Island Catamaran Day Sail from Fajardo
Z9318QRamandao, Sep 2026
HIGHLY RECOMMEND!!
Celebrated my best friend’s 40th birthday with a group of 12 people. Luis , Nathan , Paola & crew were helpful, fun and made the experience amazing. Would highly recommend & am looking forward to doing it again ! 💙🇵🇷🛥️
Read more
Outstanding snorkeling & service.
New York City
Premium Catamaran Morning Sail: Snorkeling, Mimosas and Brunch
bobcU8402QW, Sep 2026
Outstanding snorkeling & service.
Shaka & our captain (sorry forgot his name), and our bartender were all excellent!! Highly recommend this adventure!!
Read more
SUCH A GREAT TIME.
New York City
Culebra Full Day Beach and Fun Experience by Catamaran
Sightseer258864, Sep 2026
SUCH A GREAT TIME.
My boyfriend and I had an amazing time. The food the vibes the boat everything was fantastic. We will be coming back!
Read more
The best by far
New York City
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise
piggin66, Sep 2026
The best by far
We have been on many tours in various islands and I have to say this has been the best by far, all the crew were magnificent, joyful and willing to help in every way, from getting picked up at our hotel to being dropped off it ran so smoothly ( all over in a flash ). The equipment was cleaned after every use and plenty to go round, they gave us information whilst in the sea about the fish and the shipwrecks that we saw. Plenty of free drinks, lots of non alcoholic drinks. Now the food, it was amazing, fried fish ,chicken, salad, coleslaw, macaroni pie, seconds if you want it. Cake and coffee when you first board, and cake on the return journey. All in all a fantastic day, with the crew and new friends. Please book this trip it is definitely value for money . Thanks guys . 🤩
Read more
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