Top Caribbean Private Sightseeing Tours

Q: Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include: Private Eleuthera Island: Swim With Pigs, Turtles & Stingrays Private Exuma Cays Day: Iguana, Shark, Pigs, Sandbar & Lunch 5-Day Private Tour in The Bahamas with Pickup Yacht YES DARLING - Private Boat St Martin, St Barth & Anguilla St Martin Gd-Case, Private Romantic Cruise 4 days View all Tours with Instant Confirmation →

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 →

Exceptional service, complimentary drinks, reliable and trusted drivers where safety is our priority for all tours. …More

Soufriere, St Lucia

4.9 (94)

Soufriere Private Tour

Exceptional service, complimentary drinks, reliable and trusted drivers where safety is our priority for all tours....

5 to 6 hours Free Cancellation

4.9 (94)

from
$100

Explore and learn about the serene mangrove habitats, nursery grounds, the iguana sanctuary, marine life, birds and coastal ecology. We provide a fun, unique experience …More

4.7 (105)

Mangroves Kayak Tour

Explore and learn about the serene mangrove habitats, nursery grounds, the iguana sanctuary, marine life, birds and coastal ecology. We provide a fun, unique experience...

2 hours Free Cancellation

4.7 (105)

from
$100

As a local expert with over 15 years of experience in guided tours and private chauffeuring, my company and I will share with you all …More

4.9 (66)

Private Puerto Plata City Tour

As a local expert with over 15 years of experience in guided tours and private chauffeuring, my company and I will share with you all...

4 to 5 hours Hotel pickup offered Free Cancellation

4.9 (66)

from
$100

Explore the best of St. Lucia on a private half-day excursion. Spend a day soaking up the sun, discovering various beaches, swimming, and snorkeling. Head …More

Rodney Bay, St Lucia

5.0 (56)

Private Charter Tour in St Lucia

Explore the best of St. Lucia on a private half-day excursion. Spend a day soaking up the sun, discovering various beaches, swimming, and snorkeling. Head...

5 hours Free Cancellation

5.0 (56)

from
$100

Are you ready to explore St. Maarten/St. Martin in the most amazing way? Get excited we’re here to help you create a truly unforgettable tour …More

4.9 (143)

St.Maarten / St.Martin Private Tour

Are you ready to explore St. Maarten/St. Martin in the most amazing way? Get excited we’re here to help you create a truly unforgettable tour...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (143)

from
$100

Bamboo River Rafting Experience with Limestone Foot Massage

Located in the hills of Hanover Lethe is the perfect combination of land and water with picturesque views from the hills to the tranquility of …More

Trelawny, Jamaica

5.0 (38)

Bamboo River Rafting Experience with Limestone Foot Massage

Located in the hills of Hanover Lethe is the perfect combination of land and water with picturesque views from the hills to the tranquility of...

2 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$100

Private Hiking Tour in British Virgin Island with the Best 360 View

Highly rewarding hike uses a bush trail that winds up Mount Alma, the 736ft hill looming over Trellis Bay and Bluff Bay on Beef Island. …More

Tortola, British Virgin Islands

5.0 (24)

Private Hiking Tour in British Virgin Island with the Best 360 View

Highly rewarding hike uses a bush trail that winds up Mount Alma, the 736ft hill looming over Trellis Bay and Bluff Bay on Beef Island....

2 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (24)

from
$100

Private Tour from Ocho Rios to Negril Beach and 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 to Negril Beach and 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

The Montego Bay Scenic Tour offers a few hours of learning about the history of Jamaica's second city - Montego Bay. You will learn about …More

Lucea, Jamaica

5.0 (26)

Montego Bay Scenic Tour

The Montego Bay Scenic Tour offers a few hours of learning about the history of Jamaica's second city - Montego Bay. You will learn about...

1 to 4 hours Hotel pickup offered Free Cancellation

5.0 (26)

from
$100

Blue Hole Private Custom Day Trip from Montego Bay

This excursion is already customized to suit you’re needs but, you can add a few other stop or you’re choice in between the pick up …More

Runaway Bay, Jamaica

5.0 (17)

Blue Hole Private Custom Day Trip from Montego Bay

This excursion is already customized to suit you’re needs but, you can add a few other stop or you’re choice in between the pick up...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$100

Montego Bay Airport transfers-Excellence,Royalton,Ocean Coral Spring(Round Trip)

We are the new fun and exciting way to explore Jamaica. Providing exceptional transportation service to travelers in a friendly and safe environment. Our hospitality, …More

Lucea, Jamaica

5.0 (81)

Montego Bay Airport transfers-Excellence,Royalton,Ocean Coral Spring(Round Trip)

We are the new fun and exciting way to explore Jamaica. Providing exceptional transportation service to travelers in a friendly and safe environment. Our hospitality,...

30 to 45 minutes Hotel pickup offered Free Cancellation

5.0 (81)

from
$100

Montego Bay Highlights Tour With Bamboo Rafting Experience

After collecting you, our first stop will be the picturesque Lethe Estate where you can enjoy rafting and a limestone foot massage while drifting through …More

Montego Bay, Jamaica

5.0 (17)

Montego Bay Highlights Tour With Bamboo Rafting Experience

After collecting you, our first stop will be the picturesque Lethe Estate where you can enjoy rafting and a limestone foot massage while drifting through...

3 to 5 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$100

Great River/Lethe rafting with Massage (All fees included)

Take a journey in the rural parts of montego bay Jamaica {Country) and rap yourself with with nature.Lethe Bamboo Rafting is the best way to …More

Trelawny, Jamaica

4.6 (26)

Great River/Lethe rafting with Massage (All fees included)

Take a journey in the rural parts of montego bay Jamaica {Country) and rap yourself with with nature.Lethe Bamboo Rafting is the best way to...

1 to 2 hours Hotel pickup offered Free Cancellation

4.6 (26)

from
$100

Negril's Private Day Trip with Margaritaville and Rick's Cafe

Come take a comfortable scenic ride on the northwest coast of Jamaica from Montego Bay to Negril. Here you will enjoy Negril's 7 miles beach, …More

Montego Bay, Jamaica

4.9 (15)

Negril's Private Day Trip with Margaritaville and Rick's Cafe

Come take a comfortable scenic ride on the northwest coast of Jamaica from Montego Bay to Negril. Here you will enjoy Negril's 7 miles beach,...

6 hours Hotel pickup offered Free Cancellation

4.9 (15)

from
$100

Bali Style Swing with Dress Rental, Drone Shoot and Pick Up

Soar above Jamaica’s lush tropical scenery on this Bali-style swing experience, offering breathtaking panoramic views of the island’s stunning landscapes. Perfect for adventurers, couples, and …More

Falmouth, Jamaica

4.8 (5)

Bali Style Swing with Dress Rental, Drone Shoot and Pick Up

Soar above Jamaica’s lush tropical scenery on this Bali-style swing experience, offering breathtaking panoramic views of the island’s stunning landscapes. Perfect for adventurers, couples, and...

1 hour Hotel pickup offered Free Cancellation

4.8 (5)

from
$100

Step beyond the tourist experience and into a real Jamaican community—sit in the yard, share stories, cook over open fire, play dominoes and cards, and …More

Ocho Rios, Jamaica

5.0 (1)

Yaad Vibes Experience

Step beyond the tourist experience and into a real Jamaican community—sit in the yard, share stories, cook over open fire, play dominoes and cards, and...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$100

Santo Domingo Unfiltered : Gualey//Colonial Area (PRIVATE TOUR)

From Gualey to the Colonial Zone – A Journey Through the Soul of Santo Domingo Don’t miss this unique experience in Santo Domingo! Embark on …More

Santo Domingo, Dominican Republic

5.0 (22)

Santo Domingo Unfiltered : Gualey//Colonial Area (PRIVATE TOUR)

From Gualey to the Colonial Zone – A Journey Through the Soul of Santo Domingo Don’t miss this unique experience in Santo Domingo! Embark on...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (22)

from
$100

Private Blue Hole and River Tubing from Ocho Rios

Come experience the heart-pumping adventure that is sure to turn up the thrill in every thrill seeker. No matter what your family fun vacation looks …More

Kingston, Jamaica

5.0 (12)

Private Blue Hole and River Tubing from Ocho Rios

Come experience the heart-pumping adventure that is sure to turn up the thrill in every thrill seeker. No matter what your family fun vacation looks...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$100

Sand-Covered Beaches This area has so many amazing beaches to explore, including but not limited to: Faro de las Cabezas de San Juan (which includes …More

5.0 (3)

Full Day Eastern Island Tour

Sand-Covered Beaches This area has so many amazing beaches to explore, including but not limited to: Faro de las Cabezas de San Juan (which includes...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$100

Dunn's River Falls / Ocho Rios Tour from Kingston

Our day tours to Dunns River Falls and Island Village have been enjoyed by many visitors. We offer an enriching travel experience - accompanying and …More

Kingston, Jamaica

5.0 (3)

Dunn's River Falls / Ocho Rios Tour from Kingston

Our day tours to Dunns River Falls and Island Village have been enjoyed by many visitors. We offer an enriching travel experience - accompanying and...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$100

Frequently Asked Questions

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

What are the best options for Caribbean Private Sightseeing Tours?

What are the best kid-friendly options for Caribbean Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Private Sightseeing Tours are:

View all kid-friendly Tours →

Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Which Caribbean Private Sightseeing Tours have Free Cancellation?

Caribbean Private Sightseeing 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 Private Sightseeing Tours have Hotel Pickup?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?