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 →

Cruising through San Juan in Style, Sightseeing with a Breeze

See San Juan from a local perspective with Chris—your charismatic, knowledgeable pedicab guide who turns a simple ride into a full experience. Chris knows the …More

5.0 (10)

Cruising through San Juan in Style, Sightseeing with a Breeze

See San Juan from a local perspective with Chris—your charismatic, knowledgeable pedicab guide who turns a simple ride into a full experience. Chris knows the...

2 hours Hotel pickup offered

5.0 (10)

from
$85

Private Tour Horseback Riding from Ocho Rios or Runaway Bay

WELCOME TO TOUR JAMAICA TODAY. Your Tour begins as your driver meet you with a smile and a warm welcome. Leaving your hotel or cruise …More

Runaway Bay, Jamaica

5.0 (5)

Private Tour Horseback Riding from Ocho Rios or Runaway Bay

WELCOME TO TOUR JAMAICA TODAY. Your Tour begins as your driver meet you with a smile and a warm welcome. Leaving your hotel or cruise...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$85

If you are a hotel guest in Nevis then this is the tour for you. Nevis Island is the Queen of the Caribees. Take a …More

5.0 (3)

Discover Nevis, Island Tour (Private)

If you are a hotel guest in Nevis then this is the tour for you. Nevis Island is the Queen of the Caribees. Take a...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (3)

from
$85

Private Mayfield's Falls Experience with Transportation

At Mayfield Falls you feel like you are in a jungle there are lush plants everywhere. The grounds are immaculate and very well maintained. This …More

Montego Bay, Jamaica

5.0 (2)

Private Mayfield's Falls Experience with Transportation

At Mayfield Falls you feel like you are in a jungle there are lush plants everywhere. The grounds are immaculate and very well maintained. This...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$85

The central feature of this natural attraction is the large labyrinthine limestone cave with its numerous rock formations, its stalactites, stalagmites and abundance of overhead …More

Ocho Rios, Jamaica

5.0 (1)

Green Grotto Caves

The central feature of this natural attraction is the large labyrinthine limestone cave with its numerous rock formations, its stalactites, stalagmites and abundance of overhead...

1 hour 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$85

Private Dunn's River Falls and Park Adventure Ocho Rios Jamaica

Admission cost for adults and children are included in the total price. Dunn's River Falls in Ocho Rios, Jamaica, is a natural wonder steeped in …More

Kingston, Jamaica

5.0 (1)

Private Dunn's River Falls and Park Adventure Ocho Rios Jamaica

Admission cost for adults and children are included in the total price. Dunn's River Falls in Ocho Rios, Jamaica, is a natural wonder steeped in...

1 to 2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$85

Montego Bay City Tour with Sightseeing and Shopping

Purely Majestic Operators sets its Montego Bay City Tour apart by focusing on an authentic, immersive experience that highlights the local culture and history in …More

Montego Bay, Jamaica

5.0 (1)

Montego Bay City Tour with Sightseeing and Shopping

Purely Majestic Operators sets its Montego Bay City Tour apart by focusing on an authentic, immersive experience that highlights the local culture and history in...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$85

Bamboo Rafting and Catamaran Cruise Party Boat Tour Montego Bay

Experience the best of Jamaica with our Bamboo Rafting and Catamaran Party Boat adventure in Montego Bay! This unforgettable combination of relaxation and excitement offers …More

Montego Bay, Jamaica

4.0 (1)

Bamboo Rafting and Catamaran Cruise Party Boat Tour Montego Bay

Experience the best of Jamaica with our Bamboo Rafting and Catamaran Party Boat adventure in Montego Bay! This unforgettable combination of relaxation and excitement offers...

6 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$85

Full-Day Tour of Saona Island from Punta Cana

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) …More

Punta Cana, Dominican Republic

3.0 (1)

Full-Day Tour of Saona Island from Punta Cana

Saona island Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve)...

10 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$85

White River Tubing and Ocho Rios Private Tour with Hotel pickup

White River Calypso Tubing and Ocho Rios Sightseeing Tours. You will be driving and riding in style with the number 1 tour operator/driver. You will …More

Kingston, Jamaica

5.0 (3)

White River Tubing and Ocho Rios Private Tour with Hotel pickup

White River Calypso Tubing and Ocho Rios Sightseeing Tours. You will be driving and riding in style with the number 1 tour operator/driver. You will...

2 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (3)

from
$84

Green Grotto Caves Excursion from Falmouth

The Green Grotto Caves, known at various times as the Runaway Bay Caves, are among Jamaica's most prominent natural attractions. Having seen visitors since the …More

Falmouth, Jamaica

3.0 (1)

Green Grotto Caves Excursion from Falmouth

The Green Grotto Caves, known at various times as the Runaway Bay Caves, are among Jamaica's most prominent natural attractions. Having seen visitors since the...

4 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$83

Puerto Plata Challenge: City Tour & 7 Waterfalls of Damajagua

This private tour is much more than just an excursion; it is an experience that takes us to know nature in its purest form, we …More

Puerto Plata, Dominican Republic

4.6 (13)

Puerto Plata Challenge: City Tour & 7 Waterfalls of Damajagua

This private tour is much more than just an excursion; it is an experience that takes us to know nature in its purest form, we...

4 to 5 hours Hotel pickup offered Free Cancellation

4.6 (13)

from
$83

We aim to provide an authentic local experience to all our visitors. All our drivers also serve as tour guides with a wealth of historical …More

Vieux Fort, St Lucia

4.9 (33)

Soufriere Tour

We aim to provide an authentic local experience to all our visitors. All our drivers also serve as tour guides with a wealth of historical...

4 to 6 hours Hotel pickup offered Free Cancellation

4.9 (33)

from
$82

Private transportation from Montego Bay to Rose Hall Great House Day Tour

The entry price and travel costs are included in this hassle-free and cashless half Day tour. On this private tour from Montego Bay, Learn about …More

Montego Bay, Jamaica

5.0 (2)

Private transportation from Montego Bay to Rose Hall Great House Day Tour

The entry price and travel costs are included in this hassle-free and cashless half Day tour. On this private tour from Montego Bay, Learn about...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$82

St Thomas Private Group Tour (11 or more ppl)

This tour caters to your group of more than 11 only. You get a vehicle just for your group for the whole day. It offers …More

Cruz Bay, US Virgin Islands

4.2 (5)

St Thomas Private Group Tour (11 or more ppl)

This tour caters to your group of more than 11 only. You get a vehicle just for your group for the whole day. It offers...

4 to 6 hours Hotel pickup offered Free Cancellation

4.2 (5)

from
$82

Lethe River Rafting Limestone Massage & Roundtrip transportation

Enjoy an escape from the hustle and bustle on a bamboo raft with our trained rafting captains on the Great River. Round-Trip transportation is available …More

Negril, Jamaica

4.8 (103)

Lethe River Rafting Limestone Massage & Roundtrip transportation

Enjoy an escape from the hustle and bustle on a bamboo raft with our trained rafting captains on the Great River. Round-Trip transportation is available...

4 hours Hotel pickup offered Free Cancellation

4.8 (103)

from
$81

Blue Hole Waterfalls Tour from Ocho Rios

Come check out this hidden treasure in the hills of Ocho Rios. With gorgeous views of lush greenery and cascading waterfalls, refreshing water to jump …More

Kingston, Jamaica

5.0 (4)

Blue Hole Waterfalls Tour from Ocho Rios

Come check out this hidden treasure in the hills of Ocho Rios. With gorgeous views of lush greenery and cascading waterfalls, refreshing water to jump...

4 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$81

Private St. George's Bermuda History Walking Tour

Explore historic St. George's on a private 2.5-hour walking tour designed exclusively for your group. Discover the streets, churches, museums and landmarks of this UNESCO …More

5.0 (97)

Private St. George's Bermuda History Walking Tour

Explore historic St. George's on a private 2.5-hour walking tour designed exclusively for your group. Discover the streets, churches, museums and landmarks of this UNESCO...

2 hours 30 minutes Free Cancellation

5.0 (97)

from
$81

Blue Hole Mineral Spring, Seven Mile Beach, Ricks Cafe/ Shopping Private Tour

Explore the highlights and landmarks of Negril with your own dedicated driver/guide during this private tour. Pick 3 of the locations listed: Seven Mile Beach, …More

Montego Bay, Jamaica

5.0 (7)

Blue Hole Mineral Spring, Seven Mile Beach, Ricks Cafe/ Shopping Private Tour

Explore the highlights and landmarks of Negril with your own dedicated driver/guide during this private tour. Pick 3 of the locations listed: Seven Mile Beach,...

6 to 9 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$80

Rick's Café and Seven Mile Beach Private Tour

Discover Negril's legendary Seven Mile Beach on this 7-hour tour from your hotel/ resort. After a scenic journey along the northern coastline, arrive at the …More

Montego Bay, Jamaica

4.9 (9)

Rick's Café and Seven Mile Beach Private Tour

Discover Negril's legendary Seven Mile Beach on this 7-hour tour from your hotel/ resort. After a scenic journey along the northern coastline, arrive at the...

7 hours Hotel pickup offered Free Cancellation

4.9 (9)

from
$80

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?