Top Caribbean Private Sightseeing Tours

Q: I need a ride! Which Caribbean Private Sightseeing Tours have Hotel Pickup?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup: Private Airport Transfers Roundtrip Punta Cana Hotels Souvenir Shopping Tour in Punta Cana. Transportation Included Great River Raft and Full Limestone body Massage In Montego Bay Ricks Cafe Negril and 7 Mile Beach Day Trip Punta Cana Shopping tour 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 →

ATV & Horseback Riding combo tour Montego Bay with Pickup

Experience a day of adventure on this combo tour, which includes an exciting off road ATV Ride along with Horsebackriding N swim tour. You will …More

Montego Bay, Jamaica

5.0 (2)

ATV & Horseback Riding combo tour Montego Bay with Pickup

Experience a day of adventure on this combo tour, which includes an exciting off road ATV Ride along with Horsebackriding N swim tour. You will...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$189

Our private tours are premium tours with connected and comfortable vehicles from a premium fleet. Our trips can be personalized to your liking, according to …More

5.0 (243)

Private Island Tour - Sint Maarten

Our private tours are premium tours with connected and comfortable vehicles from a premium fleet. Our trips can be personalized to your liking, according to...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (243)

from
$189

PRIVATE VIP tour Saona Island with Snorkeling, Starfish, Turtles

Be the first to discover Saona — just for you, no groups or crowds! A private journey where you arrive on the island before anyone …More

La Romana, Dominican Republic

5.0 (18)

PRIVATE VIP tour Saona Island with Snorkeling, Starfish, Turtles

Be the first to discover Saona — just for you, no groups or crowds! A private journey where you arrive on the island before anyone...

8 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$190

The new Jet Car is a fun and exciting experience you have the opportunity to drive a car on the ocean topping speed from 60 …More

Montego Bay, Jamaica

4.9 (9)

New Jet Car Activity In Montego Bay Jamaica

The new Jet Car is a fun and exciting experience you have the opportunity to drive a car on the ocean topping speed from 60...

1 hour Hotel pickup offered Free Cancellation

4.9 (9)

from
$190

Bob Marley Museum and Devon House Kingston Private Day Tour

Enjoy the comfort of your own private transportation to the Bob Marley Museum,which is the former home of the reggae legend. Bob’s home is filled …More

Montego Bay, Jamaica

4.9 (7)

Bob Marley Museum and Devon House Kingston Private Day Tour

Enjoy the comfort of your own private transportation to the Bob Marley Museum,which is the former home of the reggae legend. Bob’s home is filled...

7 to 9 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$190

Mojito - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private …More

5.0 (1)

Mojito - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private...

4 hours Free Cancellation

5.0 (1)

from
$190

You should book this ATV and shopping adventure for a thrilling and unique experience that combines the excitement of off-road exploration with the opportunity to …More

Negril, Jamaica

5.0 (2)

Half Day Private ATV & Shopping Adventure in Negril Jamaica

You should book this ATV and shopping adventure for a thrilling and unique experience that combines the excitement of off-road exploration with the opportunity to...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$190

Santo Domingo Colonial City walking tour

Step back in time and follow in the footsteps of Columbus and the conquerors as you explore the rich history of Santo Domingo. This captivating …More

5.0 (4)

Santo Domingo Colonial City walking tour

Step back in time and follow in the footsteps of Columbus and the conquerors as you explore the rich history of Santo Domingo. This captivating...

4 hours Free Cancellation

5.0 (4)

from
$190

Black River Safari and YS Falls Tour from Montego Bay

Embark on a Black River crocodile safari and spend time immersed in the YS Falls on this tour from Montego Bay. …More

Montego Bay, Jamaica

4.0 (1)

Black River Safari and YS Falls Tour from Montego Bay

Embark on a Black River crocodile safari and spend time immersed in the YS Falls on this tour from Montego Bay....

8 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$190

Experience our Tropical Island Private Tour of Martinique! Begin your visit at the Capital City's Saint-Louis Cathedral and Schoelcher Library. Enjoy the panoramic views and …More

Fort-de-France, Martinique

5.0 (2)

Tropical Island Private Tour of Martinique

Experience our Tropical Island Private Tour of Martinique! Begin your visit at the Capital City's Saint-Louis Cathedral and Schoelcher Library. Enjoy the panoramic views and...

5 hours 30 minutes Hotel pickup offered

5.0 (2)

from
$191

Jamaica Best Water Falls Tour,Mobay Bay to Dunn's River/Blue Hole

This is a Hassle Free Tour, which INCLUDES ENTRANCE FEES AND TRANSPORTATION COSTS. We picks you up at your hotel or cruise ship port. A …More

Kingston, Jamaica

5.0 (44)

Jamaica Best Water Falls Tour,Mobay Bay to Dunn's River/Blue Hole

This is a Hassle Free Tour, which INCLUDES ENTRANCE FEES AND TRANSPORTATION COSTS. We picks you up at your hotel or cruise ship port. A...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (44)

from
$192

Here are a few reasons why you should choose us for your Negril trip: 1. Expertise: We have years of experience in planning trips to …More

Montego Bay, Jamaica

5.0 (1)

Negril Adventure Tour: ATV & Zipline

Here are a few reasons why you should choose us for your Negril trip: 1. Expertise: We have years of experience in planning trips to...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$192

Bob Marley Mouseleum and museum from negril and Montego Bay

Welcome to Jamaica!!! Ready to experience the REAL Jamaica? Catch A Cab N Tours is here with an experienced, local guide to provide transit and …More

Negril, Jamaica

5.0 (1)

Bob Marley Mouseleum and museum from negril and Montego Bay

Welcome to Jamaica!!! Ready to experience the REAL Jamaica? Catch A Cab N Tours is here with an experienced, local guide to provide transit and...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$192

Blue Hole Falls with Horseback Ride Adventure from Montego Bay

Embark on a day full of adventure and natural beauty with our Horseback Riding and Blue Hole tour, departing from Montego Bay! Start your journey …More

Ocho Rios, Jamaica

5.0 (6)

Blue Hole Falls with Horseback Ride Adventure from Montego Bay

Embark on a day full of adventure and natural beauty with our Horseback Riding and Blue Hole tour, departing from Montego Bay! Start your journey...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$194

YS Falls, Black River Safari, Appleton Rum Tour OR Pelican Bar (Choose Up to 3)

PRIVATE TOUR. [Choose Up to 3 ATTRACTIONS] Take a tour down to the South Coast of Jamaica and explore its natural beauty on a private …More

Lucea, Jamaica

4.9 (92)

YS Falls, Black River Safari, Appleton Rum Tour OR Pelican Bar (Choose Up to 3)

PRIVATE TOUR. [Choose Up to 3 ATTRACTIONS] Take a tour down to the South Coast of Jamaica and explore its natural beauty on a private...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (92)

from
$195

Be Happy - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group, …More

5.0 (10)

Be Happy - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group,...

4 hours Free Cancellation

5.0 (10)

from
$195

Martha Brae River Rafting & Luminous Lagoon Private Tour Falmouth

Make the most out of your travel when in Jamaica. Book your private transfer with us and we will take you on an amazing journey. …More

5.0 (6)

Martha Brae River Rafting & Luminous Lagoon Private Tour Falmouth

Make the most out of your travel when in Jamaica. Book your private transfer with us and we will take you on an amazing journey....

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$195

Bamboo Rafting Limestone Foot Massage/Negril 7 Miles Beach/Ricks Cafe Combo

Bamboo rafting in Jamaica is a serene, culturally rich experience where you float gently on a traditional bamboo raft down calm rivers. It’s popular here …More

Montego Bay, Jamaica

5.0 (7)

Bamboo Rafting Limestone Foot Massage/Negril 7 Miles Beach/Ricks Cafe Combo

Bamboo rafting in Jamaica is a serene, culturally rich experience where you float gently on a traditional bamboo raft down calm rivers. It’s popular here...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$195

Blue Hole and Martha Brae Full-Day Tour from Montego Bay

Your tour begins directly from your hotel. Travel in air-conditioned comfort on this 2-hour journey into the hills of Ocho Rios. En route, your knowledgeable …More

Montego Bay, Jamaica

4.9 (9)

Blue Hole and Martha Brae Full-Day Tour from Montego Bay

Your tour begins directly from your hotel. Travel in air-conditioned comfort on this 2-hour journey into the hills of Ocho Rios. En route, your knowledgeable...

7 hours Hotel pickup offered Free Cancellation

4.9 (9)

from
$195

Window Cave and Indian Cave private tour with an archaeologist as guide

Explore the famous Window Cave and Indian Cave with an Archaeologist as your guide! Ride in the comfort of our Audi Q7 luxury SUV! In …More

4.6 (10)

Window Cave and Indian Cave private tour with an archaeologist as guide

Explore the famous Window Cave and Indian Cave with an Archaeologist as your guide! Ride in the comfort of our Audi Q7 luxury SUV! In...

5 to 6 hours Hotel pickup offered Free Cancellation

4.6 (10)

from
$195

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?

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

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

Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include:

View all Tours with 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?

Got any more Caribbean trip ideas?

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