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Top Caribbean Overnight Tours

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Kayak or Paddleboard Rentals Sosua, Cosita Rica, Neptuno Beach

You will experience a relaxing excursion where you can rent a kayak or a paddleboard where you can see the natural environment of the La …More

4.9 (20)

Kayak or Paddleboard Rentals Sosua, Cosita Rica, Neptuno Beach

You will experience a relaxing excursion where you can rent a kayak or a paddleboard where you can see the natural environment of the La...

1 day • Free Cancellation
4.9 (20)
from
$55
Private Tour From Ocho Rios or Runaway Bay To Negril 7 Miles Beach & Ricks Cafe

WELCOME TO TOUR JAMAICA TODAY. Rick's Cafe was the first public bar and restaurant of its type on the West End Cliffs, offering an alternative …More

Ocho Rios, Jamaica
5.0 (22)

Private Tour From Ocho Rios or Runaway Bay To Negril 7 Miles Beach & Ricks Cafe

WELCOME TO TOUR JAMAICA TODAY. Rick's Cafe was the first public bar and restaurant of its type on the West End Cliffs, offering an alternative...

1 day • Hotel pickup offered • Free Cancellation
5.0 (22)
from
$100
ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar

Discover the best of Punta Cana by land and sea with our unforgettable 2-day adventure package! This experience combines adrenaline, nature, culture, and celebration for …More

Punta Cana, Dominican Republic
5.0 (31)

ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar

Discover the best of Punta Cana by land and sea with our unforgettable 2-day adventure package! This experience combines adrenaline, nature, culture, and celebration for...

2 days • Hotel pickup offered • Free Cancellation
5.0 (31)
from
$69
The Grand Circle 24-Hour All-Inclusive Island Experience

Are you the kind of traveller who craves unique, personalized and bespoke experiences? Whether it's a layover, or you're here on vacation seeking something different. …More

Speyside, Trinidad and Tobago
5.0 (12)

The Grand Circle 24-Hour All-Inclusive Island Experience

Are you the kind of traveller who craves unique, personalized and bespoke experiences? Whether it's a layover, or you're here on vacation seeking something different....

1 day • Hotel pickup offered • Free Cancellation
5.0 (12)
from
$380
St. Thomas and St. John Two Day Tour

Explore the best of the Virgin Islands in 2 days! This comprehensive tour takes you to the top sights and attractions on both St. Thomas …More

Cruz Bay, US Virgin Islands
4.8 (5)

St. Thomas and St. John Two Day Tour

Explore the best of the Virgin Islands in 2 days! This comprehensive tour takes you to the top sights and attractions on both St. Thomas...

2 days • Hotel pickup offered • Free Cancellation
4.8 (5)
from
$175
Departure Shuttle to Airport, Club Mobay Fast Track & VIP Lounge Combo

Make travel out of Montego Bay’s Sangster International Airport comfy and hassle-free. This package gives you access to the VIP Club Mobay airport departure lounge; …More

Ocho Rios, Jamaica
4.6 (28)

Departure Shuttle to Airport, Club Mobay Fast Track & VIP Lounge Combo

Make travel out of Montego Bay’s Sangster International Airport comfy and hassle-free. This package gives you access to the VIP Club Mobay airport departure lounge;...

1 day • Hotel pickup offered
4.6 (28)
from
$60
St Lucia Private Custom Tour

While all St Lucia's adventures are worth the plane ride, there's a virtually undiscovered secret world on this island of mystical beauty. On this private …More

Anse La Raye, St Lucia
5.0 (14)

St Lucia Private Custom Tour

While all St Lucia's adventures are worth the plane ride, there's a virtually undiscovered secret world on this island of mystical beauty. On this private...

1 day • Hotel pickup offered • Free Cancellation
5.0 (14)
from
$70
2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night …More

5.0 (2)

2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night...

2 days
5.0 (2)
from
$4,882
SANTO DOMINGO/ City tour - the best Adventures & traditional

The typical city tour to Santo Domingo from Punta Cana offers you the opportunity to explore the oldest colonial city in the Americas, with its …More

Punta Cana, Dominican Republic
5.0 (6)

SANTO DOMINGO/ City tour - the best Adventures & traditional

The typical city tour to Santo Domingo from Punta Cana offers you the opportunity to explore the oldest colonial city in the Americas, with its...

2 days • Hotel pickup offered • Free Cancellation
5.0 (6)
from
$129
Horseback Riding along the Beach

You will take a fascinating 1 hour tour that takes you to 3 stops for you to experience the area of Macao beach. This tour …More

Punta Cana, Dominican Republic
5.0 (5)

Horseback Riding along the Beach

You will take a fascinating 1 hour tour that takes you to 3 stops for you to experience the area of Macao beach. This tour...

2 days • Hotel pickup offered • Free Cancellation
5.0 (5)
from
$69
Buggies Off Road Extreme From Punta Cana

Are you NOT afraid of getting dirty? If so, then DO keep reading this description! Ladies and gentlemen, start your engines! It's time to rip …More

Punta Cana, Dominican Republic
5.0 (2)

Buggies Off Road Extreme From Punta Cana

Are you NOT afraid of getting dirty? If so, then DO keep reading this description! Ladies and gentlemen, start your engines! It's time to rip...

2 days • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$50
Multi Day tour with Catamaran and Rick's Cafe from Montego Bay

Basically, this offers you the option of booking with the same company for two separate days so day 1 we pick you up take you …More

Montego Bay, Jamaica
5.0 (1)

Multi Day tour with Catamaran and Rick's Cafe from Montego Bay

Basically, this offers you the option of booking with the same company for two separate days so day 1 we pick you up take you...

2 days • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$285
Cano Hondo Rooms + Kayaking + Hiking + Natural Waterfall Swimming Pools

This is an adventure good for those looking to enjoy nature and an unique rainforest experience. Focused on providing a true local view of Dominican …More

5.0 (2)

Cano Hondo Rooms + Kayaking + Hiking + Natural Waterfall Swimming Pools

This is an adventure good for those looking to enjoy nature and an unique rainforest experience. Focused on providing a true local view of Dominican...

1 day 6 hours
5.0 (2)
from
$199
Horseback Ride/Swim, Blue Hole Falls, Bamboo Rafting, Rick's Cafe

PLEASE NOTE: THIS TOUR LASTED FOR 2 DAÝS, ( Day 1: Horseback Riding/Swim & Blue Hole Falls , Day 2: Lethe River Bamboo Rafting & …More

Lucea, Jamaica
5.0 (2)

Horseback Ride/Swim, Blue Hole Falls, Bamboo Rafting, Rick's Cafe

PLEASE NOTE: THIS TOUR LASTED FOR 2 DAÝS, ( Day 1: Horseback Riding/Swim & Blue Hole Falls , Day 2: Lethe River Bamboo Rafting &...

2 days • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$460
All day Tour of Ocho Rios

“Such a great experience!”

— John_M

“Such a great experience!”

— John_M

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a …More

Ocho Rios, Jamaica
5.0 (1)

All day Tour of Ocho Rios

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a...

2 days • Hotel pickup offered
5.0 (1)
from
$250
"1-Day Hike & Camp with Turtle Watching at Paria Bay"

Looking for an unforgettable overnight adventure? Join us as we journey to Paria Bay, one of the most breathtaking spots on the island. You'll have …More

5.0 (1)

"1-Day Hike & Camp with Turtle Watching at Paria Bay"

Looking for an unforgettable overnight adventure? Join us as we journey to Paria Bay, one of the most breathtaking spots on the island. You'll have...

2 days • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$160
Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation …More

Ocho Rios, Jamaica

Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation...

2 days • Hotel pickup offered • Free Cancellation
from
$1,077
Blue Mountains, Port Royal and Kingston 2-Day Tour from Runaway Bay

Leave Runaway Bay behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation …More

Runaway Bay, Jamaica

Blue Mountains, Port Royal and Kingston 2-Day Tour from Runaway Bay

Leave Runaway Bay behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation...

2 days • Hotel pickup offered • Free Cancellation
from
$1,128

Frequently Asked Questions

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

Recent tour reviews
Villa delivery!!!
New York City
Kayak or Paddleboard Rentals Sosua, Cosita Rica, Neptuno Beach
jefferyg958, Aug 2026
Villa delivery!!!
I needed an inflatable paddleboard at the last minute, and Supremo Water Sports came through! They were able to arrange free delivery directly to my villa, which made everything incredibly convenient. The paddleboard was clean, easy to use, and official they also gave me a extra lifejacket to use. Great communication responded back pretty fast the day of delivery, friendly service, and they went above and beyond to accommodate a last-minute request. Highly recommend Supremo Water Sports!
Read more
Shuttle and Mobay
New York City
Departure Shuttle to Airport, Club Mobay Fast Track & VIP Lounge Combo
AspiringVagab0nd, Jul 2026
Shuttle and Mobay
Mobay lounge is always a good choice. Worth the cost. Driver friendly and on time.
Read more
Alles perfekt 👌
New York City
Departure Shuttle to Airport, Club Mobay Fast Track & VIP Lounge Combo
Thomaslesgourmet, Jul 2026
Alles perfekt 👌
It was a very Great and friendly experience with our driver Bernard ! Thanks you Bernard 👍🏻
Read more
I love Dominicans
New York City
Kayak or Paddleboard Rentals Sosua, Cosita Rica, Neptuno Beach
theodorel670, Jun 2026
I love Dominicans
We rented an inflatable paddleboard during our vacation on the resort and had a great experience. The board was delivered on time, it was very stable on the wateThe rental process was simple, and the owner was friendly, responsive, and helpful with setup and instructions. Having the paddleboard delivered directly to us made everything even more convenient.
Read more
Fantastic Service and Experience
New York City
The Grand Circle 24-Hour All-Inclusive Island Experience
renesF7413KI, Jun 2026
Fantastic Service and Experience
We went with David and Anna on an island tour as well as the Castara bon fire experience. It was absolutely enjoyable!My sister and I visting from Canada are both in our 80's and David made this such an enjoyable experience with such care and consideration. His knowledge and professionalism was impressive. I highly recommend using island girl.
Read more
The Real Tobago
New York City
The Grand Circle 24-Hour All-Inclusive Island Experience
33JohnK, Mar 2026
The Real Tobago
My wife and I actually did several of the Island Girl tours during our 3 month stay in Tobago and they were all absolutely fantastic. Island Girl Tours is definitely a "go to" resource for Trinidad & Tobago. David & Anna love Tobago deeply and it shows. They showed us, not just the tourist sites, like Fort King George and Argyle Falls (which were wonderful), but they introduced us to local people so we could get to know Tobago through the eyes of the people who live there - Allister, the coconut man, Miss Shurland, who runs the hummingbird sanctuary (incredible experience). They took us off the beaten track to hidden palm fringed beaches, with golden sand we had all to ourselves. We ate incredible, delicious street food and they recommended great local restaurants. Their main focus is Tobago, but they also arranged a 3 day tour of Trinidad for us.One of the great thing about Island Girl tours is that they customized destinations and activities to suit us. I'm active and adventurous. My wife has mobility issues. David & Anna made it work for both of us.Highlights: Shurland James Hummingbird Nature Park, walking on unspoiled undeveloped beaches, the trails of the Main Ridge Forest Preserve, Feathered Friends parrot & macaw rehabilitation center (Trinidad). And most of all the warm, friendly people of Tobago.
Read more
Wonderful day in St. Lucia!
New York City
St Lucia Private Custom Tour
Carmen_L, Mar 2026
Wonderful day in St. Lucia!
Our driver Jamal was amazing. We really wanted to see and do a couple things and then we wanted to see the island through a locals eyes. He did just that! We couldn't ask for anyone better!
Read more
Wonderful trip
New York City
SANTO DOMINGO/ City tour – the best Adventures & traditional
G7198AVstellam, Mar 2026
Wonderful trip
I had the best experience of my life to have traveled to that beautiful place since I wanted to know that wonderful place know its culture its typical dishes its traditions I fell in love
Read more
Excellent
New York City
Private Tour From Ocho Rios or Runaway Bay To Negril 7 Miles Beach & Ricks Cafe
Coastal19869798633, Feb 2026
Excellent
Winston is just fantastic. He's professional, courteous and makes sure you're okay. His prices are good. I recommend it 500%
Read more
Overnight sail St. Marteen to St. Barts.
New York City
2 days 1 night by private catamaran from St Martin to St Barth
Mary_W, Jan 2026
Overnight sail St. Marteen to St. Barts.
The four of us enjoyed a first class experience on the Zephyr traveling from Grand Case to St. Barts with Captain Karin and Sophie. Sophie treated us to numerous gourmet meals. We stopped in numerous small bays where we snorkeled and paddle boarded. Sleeping out on the ocean was a dream. The winds were perfect to sail back to St. Martin! We highly recommend this wonderful experience with a crew who go over the top to take care of your needs!
Read more
Wonderful tour on a wonderful island.
New York City
St Lucia Private Custom Tour
howardmQ4142DU, Dec 2025
Wonderful tour on a wonderful island.
Our guide was Boogie. Communication before was great. We particularly wanted to see the Pitons. He did great! We also visited the drive in volcano. And at our request stopped at KFC on our return to our hotel. It was worth it. Wholeheartedly recommend this tour with hotel pick up.
Read more
The best tour
New York City
ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar
rosangelapE1353WC, Sep 2025
The best tour
The best tour of our life we liked so much that I will repeat again Antonio was super friendly the best tour 🥹🥹🥹🥹🥹
Read more
Love and fun
New York City
ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar
Freedom46246268531, Sep 2025
Love and fun
Antonio is the best admiration for eze beautiful human being very good I went with my wife was the best tour of our life 🙂‍↕️🙂‍↕️
Read more
AMAZING Private Tour from Ocho Rios to Negril and Rick’s Cafe!! Highly Recommended!!!
New York City
Private Tour From Ocho Rios or Runaway Bay To Negril 7 Miles Beach & Ricks Cafe
nkm9603, Aug 2025
AMAZING Private Tour from Ocho Rios to Negril and Rick’s Cafe!! Highly Recommended!!!
We had the absolute pleasure of having Winston as our driver in Jamaica, and he was outstanding from start to finish! Winston is not only a safe and reliable driver, but also one of the friendliest and most knowledgeable people you will meet.He always greeted us with a warm smile and made every ride comfortable and stress-free. What really stood out was his deep knowledge of Jamaica — he shared history, culture, and even pointed out hidden gems along the way that we would have completely missed on our own.Winston went above and beyond to make sure we were well taken care of, and by the end of our trip we felt like we were riding with a friend, not just a driver. If you’re visiting Jamaica and want someone trustworthy, professional, and genuinely kind, we highly recommend Winston. He made our trip unforgettable!
Read more
Excellent boat
New York City
Multi Day tour with Catamaran and Rick’s Cafe from Montego Bay
abi0sehc, Jun 2025
Excellent boat
I love this boat it was wonderful and lovely staff crew the boat was lively and speakers was very good I enjoyed my birthday love the boat
Read more
Great service surely recommend this activity.
New York City
Horseback Ride/Swim, Blue Hole Falls, Bamboo Rafting, Rick’s Cafe
fabionm2025, Jun 2025
Great service surely recommend this activity.
Our 2 day experience with Ellis Tours was great, this excursion lasted 2 day and we love every moment. .................
Read more
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