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 →

Explore Montego bay Jamaica toMartha Brae Rafting &Blue Hole Tour

This’s a CASHLESS AND HASSLE FREE DAY TOUR which allows you to think less about joining queue to used cash or cards payments, we give …More

Runaway Bay, Jamaica

5.0 (56)

Explore Montego bay Jamaica toMartha Brae Rafting &Blue Hole Tour

This’s a CASHLESS AND HASSLE FREE DAY TOUR which allows you to think less about joining queue to used cash or cards payments, we give...

8 hours Hotel pickup offered Free Cancellation

5.0 (56)

from
$254

Private YS Falls and Black River Safari from Runaway Bay

Explore the South Coast of Jamaica on this private, full-day tour from Runaway Bay. This scenic sightseeing adventure travels to the famous YS Falls, an …More

Runaway Bay, Jamaica

4.0 (2)

Private YS Falls and Black River Safari from Runaway Bay

Explore the South Coast of Jamaica on this private, full-day tour from Runaway Bay. This scenic sightseeing adventure travels to the famous YS Falls, an...

11 hours Hotel pickup offered Free Cancellation

4.0 (2)

from
$254

Award yourself with a unique, quintessential retreat, offering a tropical once in a lifetime memory, taking al fresco dinning to a Caribbean Paradise! Started in …More

Grand Case, St Maarten

4.4 (9)

Luxury Private Picnic in Paradise Beach

Award yourself with a unique, quintessential retreat, offering a tropical once in a lifetime memory, taking al fresco dinning to a Caribbean Paradise! Started in...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.4 (9)

from
$253

Full-Day Blue Hole Private Tour from Montego Bay with Zipline

We start your shore excursion with pickup directly from the Montego Bay Cruise Port or hotel lobby. A scenic ride in a fully Air Conditioned …More

Montego Bay, Jamaica

5.0 (1)

Full-Day Blue Hole Private Tour from Montego Bay with Zipline

We start your shore excursion with pickup directly from the Montego Bay Cruise Port or hotel lobby. A scenic ride in a fully Air Conditioned...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$252

Explore Montego Bay to Bob Marley Mausoleum Nine Miles& Blue Hole

This is a CASHLESS HASSLE FREE TOUR that Pickup from Cruise Ship or Hotel in Private style, breaking away from coach and large bus group …More

Lucea, Jamaica

5.0 (2)

Explore Montego Bay to Bob Marley Mausoleum Nine Miles& Blue Hole

This is a CASHLESS HASSLE FREE TOUR that Pickup from Cruise Ship or Hotel in Private style, breaking away from coach and large bus group...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$250

Cayman's Classic Food Tasting & Cultural Experience

We only offer private group tours which we can customize to the taste and preferences of our clients. Tour stops listed are only to give …More

4.9 (161)

Cayman's Classic Food Tasting & Cultural Experience

We only offer private group tours which we can customize to the taste and preferences of our clients. Tour stops listed are only to give...

4 hours Hotel pickup offered Free Cancellation

4.9 (161)

from
$250

Enjoy a 3 hours private tour of the highlights of Aruba. This tour is meant for up to 15 people and is one of the …More

Palm - Eagle Beach, Aruba

4.8 (87)

Private Tour: Essential Tour of Aruba

Enjoy a 3 hours private tour of the highlights of Aruba. This tour is meant for up to 15 people and is one of the...

3 hours Hotel pickup offered Free Cancellation

4.8 (87)

from
$250

This tour make 3(three) stops and enlightens visitors of life on the island . Firstly we tour the very historical former French and now British …More

4.9 (34)

Best of St. Kitts Highlight Tour.

This tour make 3(three) stops and enlightens visitors of life on the island . Firstly we tour the very historical former French and now British...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (34)

from
$250

Authentic Curacao : Private Full island Tour

Your group will be accompanied by a friendly local guide, who will take you to the most amazing spots. Stops mentioned above are an indication …More

Willemstad, Curacao

4.9 (135)

Authentic Curacao : Private Full island Tour

Your group will be accompanied by a friendly local guide, who will take you to the most amazing spots. Stops mentioned above are an indication...

4 to 8 hours Hotel pickup offered Free Cancellation

4.9 (135)

from
$250

Horseback Ride, Blue Hole, Secret Falls, River Rafting & Tubing

Enjoy 4 activities in 1 day. This is for the ultimate thrill seeker. Horseback riding, river tubing,blue hole and secrets falls mixed with river rafting. …More

Montego Bay, Jamaica

4.8 (20)

Horseback Ride, Blue Hole, Secret Falls, River Rafting & Tubing

Enjoy 4 activities in 1 day. This is for the ultimate thrill seeker. Horseback riding, river tubing,blue hole and secrets falls mixed with river rafting....

5 to 8 hours Hotel pickup offered Free Cancellation

4.8 (20)

from
$250

Flexible Stops: We understand that every traveler has different interests and preferences. That's why our tour allows you to make stops at iconic landmarks and …More

Isla Verde, Puerto Rico

4.5 (25)

Old San Juan Driving Tour

Flexible Stops: We understand that every traveler has different interests and preferences. That's why our tour allows you to make stops at iconic landmarks and...

3 hours Hotel pickup offered Free Cancellation

4.5 (25)

from
$250

You can enjoy the Dominican habit, share with local people, learn about their customs, go from store to buy gifts for your friends and family, …More

Punta Cana, Dominican Republic

4.5 (11)

Private City Tours Higüey

You can enjoy the Dominican habit, share with local people, learn about their customs, go from store to buy gifts for your friends and family,...

3 to 4 hours Hotel pickup offered Free Cancellation

4.5 (11)

from
$250

Explore the west coast of St. Lucia in as a group or privately with your driver-guide who shows you the sights from Castries to around …More

5.0 (2)

St. Lucia 360 Island Tour

Explore the west coast of St. Lucia in as a group or privately with your driver-guide who shows you the sights from Castries to around...

2 to 6 hours Free Cancellation

5.0 (2)

from
$250

Old San Juan Private Tour with Barrilito Rum Experience

Join us and visit Hacienda Santa Ana, the home of the world’s best sipping rum! Submerge into the history of the heritage of the Fernandez …More

5.0 (4)

Old San Juan Private Tour with Barrilito Rum Experience

Join us and visit Hacienda Santa Ana, the home of the world’s best sipping rum! Submerge into the history of the heritage of the Fernandez...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$250

Future Tours always ensure that all our guests needs and expectations are met and goes over and beyond. Our team of knowledgeable, experienced and fun-loving …More

Grand Anse, Grenada

4.8 (14)

Fun Tours in Grenada

Future Tours always ensure that all our guests needs and expectations are met and goes over and beyond. Our team of knowledgeable, experienced and fun-loving...

4 to 8 hours Hotel pickup offered Free Cancellation

4.8 (14)

from
$250

Private Boat Tour:St.Lucia private charter

Experience the rejuvenating mud bath, stroll through the enchanting Tunnel of Love, and marvel at the majestic Waterfall. Explore the ancient tunnel of love and …More

Gros Islet, St Lucia

5.0 (11)

Private Boat Tour:St.Lucia private charter

Experience the rejuvenating mud bath, stroll through the enchanting Tunnel of Love, and marvel at the majestic Waterfall. Explore the ancient tunnel of love and...

5 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$250

Cigar rolling is an art that isn't just reserved for the masters. During these 2-hours cigar aficionados will learn how to roll their very own …More

Nassau, Bahamas

4.8 (6)

Cigar Rolling Lesson in Nassau

Cigar rolling is an art that isn't just reserved for the masters. During these 2-hours cigar aficionados will learn how to roll their very own...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.8 (6)

from
$250

Our tours are designed to Suite your need so you can do these tours in any order, spend as much time as needed stop anywhere …More

Negril, Jamaica

4.9 (7)

Black River Safari and YS Falls

Our tours are designed to Suite your need so you can do these tours in any order, spend as much time as needed stop anywhere...

5 to 6 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$250

ATV Experience, cultural and social tour

This is a private tour. The tour commences when you are picked up by our well trained driver/guide Explore the Jamaican country side you will …More

Negril, Jamaica

4.8 (5)

ATV Experience, cultural and social tour

This is a private tour. The tour commences when you are picked up by our well trained driver/guide Explore the Jamaican country side you will...

5 to 8 hours Hotel pickup offered

4.8 (5)

from
$250

Our airport transfers are by far one of St Lucia's most popular transfers with a scenic drives from the Hewanorra internation airport (UVF) or George …More

5.0 (8)

Private Luxury Transfers

Our airport transfers are by far one of St Lucia's most popular transfers with a scenic drives from the Hewanorra internation airport (UVF) or George...

1 hour 15 minutes Free Cancellation

5.0 (8)

from
$250

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?