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Top Caribbean Romantic Tours

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All Inclusive Sunset Dinner Cruise in Nassau Bahamas

We pride ourselves with the fact that we enjoy sailing capturing the beautiful sunset, all while enjoying island music with an all inclusive bar and …More

Nassau, Bahamas
4.4 (88)

All Inclusive Sunset Dinner Cruise in Nassau Bahamas

We pride ourselves with the fact that we enjoy sailing capturing the beautiful sunset, all while enjoying island music with an all inclusive bar and...

3 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.4 (88)
from
$138
Champagne Sunset Sail in St. Lucia

Cruise along the West Coast of St. Lucia on this 2-hour Sunset Cruise! Onboard one of our Spacious Catamarans, enjoy St Lucia's famous and beautiful …More

Choc, St Lucia
4.7 (197)

Champagne Sunset Sail in St. Lucia

Cruise along the West Coast of St. Lucia on this 2-hour Sunset Cruise! Onboard one of our Spacious Catamarans, enjoy St Lucia's famous and beautiful...

2 hours • Hotel pickup offered • Free Cancellation
4.7 (197)
from
$75
Punta Cana Hip Hop Party Boat Adults Only Live DJ & Open Bar

Get ready to experience an unforgettable Caribbean party! Step aboard our adults-only catamaran and enjoy an incredible experience off the coast of Punta Cana, featuring …More

Punta Cana, Dominican Republic
4.9 (1,308)

Punta Cana Hip Hop Party Boat Adults Only Live DJ & Open Bar

Get ready to experience an unforgettable Caribbean party! Step aboard our adults-only catamaran and enjoy an incredible experience off the coast of Punta Cana, featuring...

3 hours 20 minutes • Hotel pickup offered • Free Cancellation
4.9 (1,308)
from
$55
Private Sunset Horseback Riding in punta cana beach

Finish the perfect day in the Dominican Republic by watching the Sunset or Sunrise across the horizon. This 2 hours Macao beach horseback tour will …More

Punta Cana, Dominican Republic
4.6 (597)

Private Sunset Horseback Riding in punta cana beach

Finish the perfect day in the Dominican Republic by watching the Sunset or Sunrise across the horizon. This 2 hours Macao beach horseback tour will...

2 hours • Hotel pickup offered • Free Cancellation
4.6 (597)
from
$77
Lady Grace Signature Luxury Catamaran Sunset Sail

A day in the islands is not complete without a relaxing sunset sail. Join us aboard the luxury sailing catamaran Lady Grace to celebrate this …More

4.8 (390)

Lady Grace Signature Luxury Catamaran Sunset Sail

A day in the islands is not complete without a relaxing sunset sail. Join us aboard the luxury sailing catamaran Lady Grace to celebrate this...

1 hour 30 minutes • Free Cancellation
4.8 (390)
from
$119
Sunset & Champagne Cruise on a Classic Schooner with boat dogs

...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a glass of champagne, fresh Appetizers from the onboard …More

4.9 (208)

Sunset & Champagne Cruise on a Classic Schooner with boat dogs

...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a glass of champagne, fresh Appetizers from the onboard...

2 hours 30 minutes • Free Cancellation
4.9 (208)
from
$85
Private Sunset Sailor's Delight from Sapphire Marina

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones …More

Likely to Sell Out
Likely to Sell Out
5.0 (15)

Private Sunset Sailor's Delight from Sapphire Marina

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones...

2 hours • Free Cancellation
5.0 (15)
from
$795
Perfect Day at Saona Island by Speedboat - Completely Private

Our comprehensive package offers everything you need for a memorable excursion - Private land and water transfers⛵ - A customizable selection of the KIND OF …More

Punta Cana, Dominican Republic
4.8 (84)

Perfect Day at Saona Island by Speedboat - Completely Private

Our comprehensive package offers everything you need for a memorable excursion - Private land and water transfers⛵ - A customizable selection of the KIND OF...

8 hours • Hotel pickup offered • Free Cancellation
4.8 (84)
from
$155
Luxury Private Full-Day Catamaran Charter in St Maarten & Saint-Martin

Join our St Maarten/Saint-Martin luxury private catamaran charter for a fabulous day on our luxury 48-foot catamaran. Breakfast (Pastries, Fresh Fruits, Tea & Coffee), Appetizers, …More

Likely to Sell Out
Likely to Sell Out
5.0 (83)

Luxury Private Full-Day Catamaran Charter in St Maarten & Saint-Martin

Join our St Maarten/Saint-Martin luxury private catamaran charter for a fabulous day on our luxury 48-foot catamaran. Breakfast (Pastries, Fresh Fruits, Tea & Coffee), Appetizers,...

7 to 9 hours • Free Cancellation
5.0 (83)
from
$240
Deluxe Sunset and Saxophone Sail on Luxury Catamaran

What could be a better end to a day full of Caribbean sun and surf than a relaxing sunset sail aboard a luxury sailing catamaran? …More

4.8 (55)

Deluxe Sunset and Saxophone Sail on Luxury Catamaran

What could be a better end to a day full of Caribbean sun and surf than a relaxing sunset sail aboard a luxury sailing catamaran?...

1 hour 30 minutes • Free Cancellation
4.8 (55)
from
$139
4 hours Tour in La Parguera Private Boat Charter

Private & Personalized Experience: Unlike crowded group tours, this is a private trip just for you and your guests (up to 6 people), offering a …More

5.0 (27)

4 hours Tour in La Parguera Private Boat Charter

Private & Personalized Experience: Unlike crowded group tours, this is a private trip just for you and your guests (up to 6 people), offering a...

4 hours • Free Cancellation
5.0 (27)
from
$85
ALL INCLUSIVE Full Day snorkeling & sunset cruise with boat dogs

Sail to the world-famous Underwater Sculpture Park and enjoy a fully guided snorkeling tour of each of the sculptures. Enjoy a freshly prepared and delicious …More

4.9 (76)

ALL INCLUSIVE Full Day snorkeling & sunset cruise with boat dogs

Sail to the world-famous Underwater Sculpture Park and enjoy a fully guided snorkeling tour of each of the sculptures. Enjoy a freshly prepared and delicious...

8 hours • Free Cancellation
4.9 (76)
from
$209
Nude Naturist Catamaran Boat Luxury Charter in St Maarten

Fabulous day sailing on our luxury 48 feet catamaran. SXM ISLAND TOUR We will sail around St Maarten/Saint-Martin. Stops at Long bay La Samana, Happy …More

Likely to Sell Out
Likely to Sell Out
4.9 (55)

Nude Naturist Catamaran Boat Luxury Charter in St Maarten

Fabulous day sailing on our luxury 48 feet catamaran. SXM ISLAND TOUR We will sail around St Maarten/Saint-Martin. Stops at Long bay La Samana, Happy...

9 hours • Free Cancellation
4.9 (55)
from
$255
Half Day Private Luxury Axopar Charter in Turks & Caicos

Hop aboard and relax on the sundeck of one of our stylish Axopar 37′ while your captain navigates you through the emerald waters of Grace …More

4.9 (24)

Half Day Private Luxury Axopar Charter in Turks & Caicos

Hop aboard and relax on the sundeck of one of our stylish Axopar 37′ while your captain navigates you through the emerald waters of Grace...

4 hours • Free Cancellation
4.9 (24)
from
$1,695
Bamboo River Rafting & horse back riding in Montego Bay

Embark on a serene and enchanting journey down the majestic Great River, surrounded by lush gardens that will leave you in awe. Your experienced raft …More

Montego Bay, Jamaica
5.0 (34)

Bamboo River Rafting & horse back riding in Montego Bay

Embark on a serene and enchanting journey down the majestic Great River, surrounded by lush gardens that will leave you in awe. Your experienced raft...

3 to 4 hours • Hotel pickup offered • Free Cancellation
5.0 (34)
from
$70
Private Luxury Catamaran Cruise in St. Lucia

Experience luxury on board our impressive 50ft Power Catamaran, complete with all the amenities. Our crew is dedicated to providing personalized trips that cater to …More

4.9 (119)

Private Luxury Catamaran Cruise in St. Lucia

Experience luxury on board our impressive 50ft Power Catamaran, complete with all the amenities. Our crew is dedicated to providing personalized trips that cater to...

4 to 8 hours • Free Cancellation
4.9 (119)
from
$2,000
Private Sunset Cruise in Punta Cana

Experience an unforgettable evening with our private sunset cruise in Punta Cana! Enjoy a serene and unique adventure as you sail along the stunning coastline, …More

Punta Cana, Dominican Republic
5.0 (14)

Private Sunset Cruise in Punta Cana

Experience an unforgettable evening with our private sunset cruise in Punta Cana! Enjoy a serene and unique adventure as you sail along the stunning coastline,...

2 to 3 hours • Hotel pickup offered • Free Cancellation
5.0 (14)
from
$690
St. Lucia Private Sunset Cruise - Marigot Bay and Rodney Bay

Romantic Private Sunset Cruise in St. Lucia. The Perfect End to Your Day! Imagine a serene evening on the tranquil Caribbean Sea, sailing along St. …More

Likely to Sell Out
Likely to Sell Out
Marigot Bay, St Lucia
5.0 (12)

St. Lucia Private Sunset Cruise - Marigot Bay and Rodney Bay

Romantic Private Sunset Cruise in St. Lucia. The Perfect End to Your Day! Imagine a serene evening on the tranquil Caribbean Sea, sailing along St....

2 hours • Hotel pickup offered • Free Cancellation
5.0 (12)
from
$97
Private Sunset Dinner Cruise in Bonaire w/ Sailing & Snorkeling

This private tour has it all! Sailing, snorkeling, sunset dinner cruise, and star-gazing. Our 4.5 hour tour starts at 3:00 p.m. and ends at 7:30 …More

5.0 (21)

Private Sunset Dinner Cruise in Bonaire w/ Sailing & Snorkeling

This private tour has it all! Sailing, snorkeling, sunset dinner cruise, and star-gazing. Our 4.5 hour tour starts at 3:00 p.m. and ends at 7:30...

4 hours 30 minutes • Free Cancellation
5.0 (21)
from
$1,499
Luxury Catamaran Sunset Sail with Saxophone on Princess Grace

What could be a better end to a day full of Caribbean sun and surf than a relaxing sunset sail aboard a luxury sailing catamaran? …More

4.9 (13)

Luxury Catamaran Sunset Sail with Saxophone on Princess Grace

What could be a better end to a day full of Caribbean sun and surf than a relaxing sunset sail aboard a luxury sailing catamaran?...

1 hour 30 minutes • Free Cancellation
4.9 (13)
from
$139

Frequently Asked Questions

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

Recent tour reviews
Highly recommend! Special experience.
New York City
Perfect Day at Saona Island by Speedboat – Completely Private
FrequentFlier776984, Sep 2026
Highly recommend! Special experience.
Smooth experience from start to finish. Our guide picked us up on time and even allotted us enough time to make a pit stop to buy things before arriving on the boat - little tip, you get dropped off right outside the marina (~10 minute walk), and there's plenty of shops around for you to buy last minute necessities (i.e., hats, sunblock, beverages (alcoholic and non-alcoholic)). Our entire tour crew was beyond attentive and helpful throughout the entire day. I booked this trip for 4 adults - we started the day out at the natural pool, where you can get in the water, touch starfish, have a drink and just relax. From there they take you to an island, private area but you will be sharing the space with other clientele from this tour operator, as well as other operators but still relatively calm and relaxing atmosphere. Lunch was fried chicken, rice, salad and pasta. Everything was good - not a 5 star meal but it certainly exceeded my expectations for this type of excursion. The beach here was a little rocky and the shore was shady so my group and I decided we wanted to go back to the natural pool area - what's so great about this private trip is you are fully in control of the itinerary - if you're not feeling a spot, tell the captain and he will quickly remedy the situation. On our way back to the natural pool they took us to an area to see sea turtles - we were so lucky that we saw a bunch this day. The crew even mentioned they'd never seen so many out at once. Crew made sure our cups were full all day and that we were happy and enjoying our time. 10/10 recommend.
Read more
Absolutely Wonderful
New York City
Perfect Day at Saona Island by Speedboat – Completely Private
debow2022, Sep 2026
Absolutely Wonderful
We booked a private tour and ended up with Stanley and Tole, and these guys were absolutely fantastic!From the very beginning, everything was on point. They picked us up at the exact time they said they would, and Stanley’s English was impeccable, which made communication easy throughout the entire excursion.The day was packed with incredible experiences without ever feeling rushed. We fed the fish, relaxed in the Natural Pool, visited Saona Island for lunch, explored the Dominican mangroves, and saw the channel where the Caribbean Sea meets the Atlantic Ocean. We also fed clownfish, saw starfish and underwater turtles, and even got to see the area where Survivor was filmed.One of the highlights was when Stanley went and got a starfish and brought it back so my wife could take pictures with it. That was such a cool and memorable touch.And I have to give Tole his credit — he handled that speedboat like a PRO! We felt completely comfortable with him behind the wheel, and he definitely added to the fun of the experience.Overall, we were extremely happy with our tour. Stanley and Tole were professional, friendly, knowledgeable, and made the entire day enjoyable from beginning to end.If you don't want the hassle of a large group excursion and would rather enjoy the experience at your own pace with a private tour, this is definitely the way to go. I would absolutely recommend this company, and if you can get Stanley and Tole, you're in great hands!
Read more
The cruise was phenomenal, we thoroughly enjoyed the music, food and drinks. The steelpan player was excellent.
New York City
Champagne Sunset Sail in St. Lucia
SHERON_N, Sep 2026
The cruise was phenomenal, we thoroughly enjoyed the music, food and drinks. The steelpan player was excellent.
We did the cruise the night before we departed for home, it was an excellent send off and a great way to end our vacation. Highly recommended 👌 👍
Read more
Magical
New York City
Champagne Sunset Sail in St. Lucia
Neil_R, Sep 2026
Magical
A magical two hours on the party boat. Plenty of drinks and decent finger buffet and a leisurely cruise around the bay.
Read more
Must Do
New York City
ALL INCLUSIVE Full Day snorkeling & sunset cruise with boat dogs
piglady50, Sep 2026
Must Do
This was one of the best excursions we have done. Everything went smoothly from pick up to drop off. The boat was FANTASTIC, the food AWESOME, the Crew was OUTSTANDING! The best part was the dogs, Harry and Schnitzel! The sunset cruise was with sail and that alone was worth the trip. Shout out to the cook(cant remember her name), Dereck the captain(super informative) along with Terek (super nice and friendly) and then there is Alvin. Super informative and we hope to see him sail the boat on his own when we return in two years. The underwater sculptures were so cool. Captain made a short video of the trip for us to buy. I would HIGHLY recommend ths trip. Thanks guys for a Great experience.
Read more
Punta Cana trip
New York City
Punta Cana Hip Hop Party Boat Adults Only Live DJ & Open Bar
946schneiderm, Sep 2026
Punta Cana trip
If you are looking for fun go to this party boat
Read more
Hiphop party
New York City
Punta Cana Hip Hop Party Boat Adults Only Live DJ & Open Bar
sandramV1040BS, Sep 2026
Hiphop party
Good time…book it in the area.
Read more
The sailing took my breath away!
New York City
Lady Grace Signature Luxury Catamaran Sunset Sail
elizajanea2026, Sep 2026
The sailing took my breath away!
Captain Tim and Jess were the best crew, so friendly. When the sails went up and filled with the wind, it took by breath away! Even better was it was jazz night and Deangelo was making me swoon with his saxophone!
Read more
Great Time on Sunset Cruise
New York City
All Inclusive Sunset Dinner Cruise in Nassau Bahamas
Carl_F, Sep 2026
Great Time on Sunset Cruise
We were fortunate enough to be in a small group of travelers which made the experience awesome. The crew was so friendly and did a great job. Always checking on everyone and making sure we were enjoying our experience. The sunset was beautiful. The views were so beautiful. It was so relaxing. The food was good. But really M&M and her crew made it a trip we will never forget.
Read more
Sunset cruise to end our trip
New York City
Lady Grace Signature Luxury Catamaran Sunset Sail
J3855FScindyf, Sep 2026
Sunset cruise to end our trip
Great experience! Crew was very nice and attentive. Pick up and drop off were very easy.
Read more
The best!!
New York City
Private Sunset Horseback Riding in punta cana beach
Wanderer36705181182, Sep 2026
The best!!
The owner is very nice, we had a lot of fun, I really recommend!!! Especially for couples it was the best experience!!
Read more
Luxury boat trip
New York City
Half Day Private Luxury Axopar Charter in Turks & Caicos
68amelieh, Sep 2026
Luxury boat trip
The whole experience was so enjoyable, from being out on the water to snorkeling and also getting to explore Iguana Island. The crew was friendly, helpful, and made the day feel easy and relaxed. The lunch was also delicious. It was definitely one of our favorite experiences of the trip and something we would happily do again! This is the type of luxury experience that we were looking for. Highly recommend!
Read more
Relaxing Birthday Trip
New York City
Half Day Private Luxury Axopar Charter in Turks & Caicos
taxk2018, Aug 2026
Relaxing Birthday Trip
Crew was great!!! We had a great time. The island tour was amazing!
Read more
Ocean Coral Spring resort
New York City
Bamboo River Rafting & horse back riding in Montego Bay
746aaliyaha, Aug 2026
Ocean Coral Spring resort
Syd was a great host and driver!
Read more
Amazing Tour. Excellent Guide. 1000/10
New York City
Bamboo River Rafting & horse back riding in Montego Bay
yesicac151, Aug 2026
Amazing Tour. Excellent Guide. 1000/10
Amazing experience, driver was respectful, on time and trust worthy. Very attentive to our request and went out of his way to make sure we were happy and having an amazing time. Thank you again.
Read more
The sunset views you need
New York City
Deluxe Sunset and Saxophone Sail on Luxury Catamaran
Flyer761257, Aug 2026
The sunset views you need
A must do when you’re in Turks and Caicos!! Me and my husband enjoyed ourselves from start to finish. Everyone is super friendly. The drinks were also good.
Read more
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