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 →

Escape the ordinary and experience the best of Jamaica in one unforgettable day. Travel in comfort through the island’s scenic countryside to Kingston, then journey …More

Kingston, Jamaica

5.0 (9)

Exotic Blue Mountain Coffee Tour

Escape the ordinary and experience the best of Jamaica in one unforgettable day. Travel in comfort through the island’s scenic countryside to Kingston, then journey...

7 to 9 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$97

Rosehall Great House and Montego Bay Half Day Private Tour

We start from the Tourism Mecha of Montego Bay and witness the jaw dropping beauty and learn about the rich history of the city from …More

Montego Bay, Jamaica

5.0 (4)

Rosehall Great House and Montego Bay Half Day Private Tour

We start from the Tourism Mecha of Montego Bay and witness the jaw dropping beauty and learn about the rich history of the city from...

5 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$97

Leave your worries on dry land and escape to the laid-back seclusion of Jamaica’s Pelican Bar, a rustic chill spot on stilts surrounded by the …More

Montego Bay, Jamaica

5.0 (1)

Pelican Bar Private Tour

Leave your worries on dry land and escape to the laid-back seclusion of Jamaica’s Pelican Bar, a rustic chill spot on stilts surrounded by the...

5 to 8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$97

Visit Rose Hall Great House on this private evening tour from your hotel/villa. Learn about the legend of the White Witch of Rose Hall and …More

Montego Bay, Jamaica

5.0 (1)

Rose Hall Great House Night Tour

Visit Rose Hall Great House on this private evening tour from your hotel/villa. Learn about the legend of the White Witch of Rose Hall and...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$97

Waterfall and Beach Safari in Santa Lucia

Board one of our 4x4 open back jeeps for an exciting day of fun! After a 30-minute drive on the scenic seaside main road, you …More

Marigot Bay, St Lucia

5.0 (63)

Waterfall and Beach Safari in Santa Lucia

Board one of our 4x4 open back jeeps for an exciting day of fun! After a 30-minute drive on the scenic seaside main road, you...

6 hours Hotel pickup offered Free Cancellation

5.0 (63)

from
$97

Make the most of your time in port in Falmouth with a shore excursion to the island’s top spots the Blue hole or Secrets Falls. …More

Trelawny, Jamaica

5.0 (22)

Blue Hole Adventure from Falmouth

Make the most of your time in port in Falmouth with a shore excursion to the island’s top spots the Blue hole or Secrets Falls....

6 hours Hotel pickup offered Free Cancellation

5.0 (22)

from
$96

Dunns River Falls Half Day Private Tour Including Entry Fee.

Book your Dunn's River Falls Tour with Ultimate Excursions Tours and Taxi Service for an unforgettable adventure in Jamaica! Come experience the heart-pumping thrill that …More

Runaway Bay, Jamaica

4.9 (7)

Dunns River Falls Half Day Private Tour Including Entry Fee.

Book your Dunn's River Falls Tour with Ultimate Excursions Tours and Taxi Service for an unforgettable adventure in Jamaica! Come experience the heart-pumping thrill that...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$96

Blue Hole Secret Falls and Dunns River Falls Adventure

Discover the natural beauty of Jamaica with a visit to Blue Hole Secret Falls and Dunn’s River Falls. Experience exhilarating cliff diving, rope swings, and …More

Lucea, Jamaica

5.0 (3)

Blue Hole Secret Falls and Dunns River Falls Adventure

Discover the natural beauty of Jamaica with a visit to Blue Hole Secret Falls and Dunn’s River Falls. Experience exhilarating cliff diving, rope swings, and...

6 to 10 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$96

We start your shore excursion with pickup directly from the Montego Bay Cruise Port or hotel lobby. A relaxing ride in an air conditioned vehicle …More

Montego Bay, Jamaica

5.0 (8)

Montego Bay tour: Dunn's River Falls

We start your shore excursion with pickup directly from the Montego Bay Cruise Port or hotel lobby. A relaxing ride in an air conditioned vehicle...

6 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$96

Nine Miles located in the rural hills of St Ann is the birthplace and final resting place of Bob Marley. Bob Marley grew up in …More

Trelawny, Jamaica

5.0 (2)

Bob Marley Nine Mile Private Tour

Nine Miles located in the rural hills of St Ann is the birthplace and final resting place of Bob Marley. Bob Marley grew up in...

5 to 7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$95

Welcome to the most unique and exhilarating tour in Aruba. Picture yourself driving your own trike around the stunning island feeling the warm Caribbean breeze. …More

4.8 (97)

Guided Trikes Tour Around Aruba Island

Welcome to the most unique and exhilarating tour in Aruba. Picture yourself driving your own trike around the stunning island feeling the warm Caribbean breeze....

180 to 185 minutes Free Cancellation

4.8 (97)

from
$95

St.Kitts See It All The Local Behind The Scenes Tour Of St. Kitts

Come and hang with the boys. When you are with us, you're no longer just a tourist. You are now a Kittitian. We want to …More

4.9 (804)

St.Kitts See It All The Local Behind The Scenes Tour Of St. Kitts

Come and hang with the boys. When you are with us, you're no longer just a tourist. You are now a Kittitian. We want to...

4 to 5 hours Hotel pickup offered Free Cancellation

4.9 (804)

from
$95

Private Tour to the East Side of Puerto Rico

At Paraiso PR, we strongly believe that the best way to experience a new place is to see through your own eyes. Our mission is …More

Fajardo, Puerto Rico

4.3 (13)

Private Tour to the East Side of Puerto Rico

At Paraiso PR, we strongly believe that the best way to experience a new place is to see through your own eyes. Our mission is...

5 to 8 hours Hotel pickup offered Free Cancellation

4.3 (13)

from
$95

Blue Hole / Secret Falls Private Tour including Entry Fee

Booking your Blue Hole/Secrets Falls Tour with Ultimate Excursions Tours and Taxi Service guarantees an unforgettable and personalized Jamaican experience. As a family-owned and locally …More

Falmouth, Jamaica

5.0 (20)

Blue Hole / Secret Falls Private Tour including Entry Fee

Booking your Blue Hole/Secrets Falls Tour with Ultimate Excursions Tours and Taxi Service guarantees an unforgettable and personalized Jamaican experience. As a family-owned and locally...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$95

Private Cultural Bamboo Rafting & Limestone Massage in Montego Bay

Experience our amazing local Bamboo Raft adventure on one of the most breathtaking rivers in Jamaica. Get on board a handcrafted 30ft bamboo raft at …More

Montego Bay, Jamaica

5.0 (31)

Private Cultural Bamboo Rafting & Limestone Massage in Montego Bay

Experience our amazing local Bamboo Raft adventure on one of the most breathtaking rivers in Jamaica. Get on board a handcrafted 30ft bamboo raft at...

4 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$95

We will see one of the many Forts on the Island, which provides great photo shots, great views of the turquoise blue waters and history …More

4.9 (91)

5 Hour Guided Private Tour of Bermuda

We will see one of the many Forts on the Island, which provides great photo shots, great views of the turquoise blue waters and history...

5 hours Hotel pickup offered Free Cancellation

4.9 (91)

from
$95

Private St. George's Tour with Old State House Access

Explore the UNESCO World Heritage Town of St. George's on a private 2.5-hour historical walking tour. Enjoy exclusive interior access to the Old State House, …More

5.0 (5)

Private St. George's Tour with Old State House Access

Explore the UNESCO World Heritage Town of St. George's on a private 2.5-hour historical walking tour. Enjoy exclusive interior access to the Old State House,...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$95

we package your experience with a professional video all included in the cost. So you get to take this unforgettable memory back home. …More

4.5 (19)

Snorkel, Swim & Snap-w/ Video

we package your experience with a professional video all included in the cost. So you get to take this unforgettable memory back home....

2 hours Free Cancellation

4.5 (19)

from
$95

Stunning Natural Beauty: St. Kitts is known for its breathtaking natural landscapes, including lush rainforests, volcanic peaks, and pristine beaches. The Scenic Escape tour takes …More

5.0 (4)

Tour St. Kitts A Scenic Experience

Stunning Natural Beauty: St. Kitts is known for its breathtaking natural landscapes, including lush rainforests, volcanic peaks, and pristine beaches. The Scenic Escape tour takes...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (4)

from
$95

Montego Bay Highlights Tour with Shopping and Bamboo Rafting

Discover the best of Montego Bay with an unforgettable blend of history, culture, shopping, and relaxation on the Montego Bay Highlights Tour with Shopping & …More

Montego Bay, Jamaica

5.0 (5)

Montego Bay Highlights Tour with Shopping and Bamboo Rafting

Discover the best of Montego Bay with an unforgettable blend of history, culture, shopping, and relaxation on the Montego Bay Highlights Tour with Shopping &...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$95

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?