Top Caribbean Private Sightseeing Tours

Q: Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include: Half-Day Buggy Tour to Cave, Macao Beach, and Local Farm Pirate Jeep Sightseeing Adventure! Nassau ATV Buggy Guided Tour Beach Stop Port Hotel Pickup Samples Buggy Tour in Punta Cana with Stops at the Beach and a Cave St.Kitts See It All The Local Behind The Scenes Tour Of St. Kitts View all Tours with Instant Confirmation →

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

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup: Half-Day Buggy Tour to Cave, Macao Beach, and Local Farm Pirate Jeep Sightseeing Adventure! Nassau ATV Buggy Guided Tour Beach Stop Port Hotel Pickup Samples Buggy Tour in Punta Cana with Stops at the Beach and a Cave Private Catamaran Cruise with Slide & unlimited drinks 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 →

3H or 4H | Private Boat Trip with Snorkeling and Swimming

With this private tour you decide the pace. We can take groups up to 8 people. The crew recommends a combination of snorkeling, sightseeing and …More

5.0 (17)

3H or 4H | Private Boat Trip with Snorkeling and Swimming

With this private tour you decide the pace. We can take groups up to 8 people. The crew recommends a combination of snorkeling, sightseeing and...

3 hours Free Cancellation

5.0 (17)

from
$600

Private Tour from Falmouth to Ocho Rios Blue Hole and Tubing

WELCOME TO TOUR JAMAICA TODAY. Your tour begins as you leave your hotel or cruise ship as your driver greet you with a smile and …More

Trelawny, Jamaica

4.8 (17)

Private Tour from Falmouth to Ocho Rios Blue Hole and Tubing

WELCOME TO TOUR JAMAICA TODAY. Your tour begins as you leave your hotel or cruise ship as your driver greet you with a smile and...

5 to 10 hours Hotel pickup offered Free Cancellation

4.8 (17)

from
$80

The Gros Piton Hike is a challenging yet rewarding hike done on the island. It is not for the faint of heart or for persons …More

Soufriere, St Lucia

4.8 (17)

Gros Piton Hike St Lucia

The Gros Piton Hike is a challenging yet rewarding hike done on the island. It is not for the faint of heart or for persons...

6 to 7 hours Hotel pickup offered Free Cancellation

4.8 (17)

from
$111

Bamboo Rafting & Limestone Foot Massage on the River

Embark on a captivating bamboo river rafting adventure at Lethe, Jamaica, where nature, culture, and relaxation blend effortlessly. This unforgettable experience takes you down the …More

Montego Bay, Jamaica

4.9 (17)

Bamboo Rafting & Limestone Foot Massage on the River

Embark on a captivating bamboo river rafting adventure at Lethe, Jamaica, where nature, culture, and relaxation blend effortlessly. This unforgettable experience takes you down the...

3 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$67

YS Falls, Black River Safari, and Floyd's Pelican Bar Day-Trip (Transportation)

This unique tour takes you through the interior of the rain forest. The first stop is Y.S. Falls where you can enjoy nature in its …More

Montego Bay, Jamaica

4.9 (17)

YS Falls, Black River Safari, and Floyd's Pelican Bar Day-Trip (Transportation)

This unique tour takes you through the interior of the rain forest. The first stop is Y.S. Falls where you can enjoy nature in its...

8 to 9 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$67

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

Full-Day Negril & Ricks Cafe Sunset Tour from Montego Bay

Negril Seven Miles Beach is one of the longest continuous stretches of white sand beach in Jamaica, known for its pristine sand and crystal-clear turquoise …More

Trelawny, Jamaica

5.0 (17)

Full-Day Negril & Ricks Cafe Sunset Tour from Montego Bay

Negril Seven Miles Beach is one of the longest continuous stretches of white sand beach in Jamaica, known for its pristine sand and crystal-clear turquoise...

6 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$90

Private Tour from Runaway Bay Ocho Rios to Blue Hole Sightseeing

WELCOME TO TOUR JAMAICA TODAY. Booking this experience is a great choice guarantee entry to this attractions that typically sell out, skip -the- line admission, …More

Runaway Bay, Jamaica

4.9 (17)

Private Tour from Runaway Bay Ocho Rios to Blue Hole Sightseeing

WELCOME TO TOUR JAMAICA TODAY. Booking this experience is a great choice guarantee entry to this attractions that typically sell out, skip -the- line admission,...

3 to 5 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$76

Full-Day Private Luxury Yacht Tour in Anguilla

Anguilla is a different island with a different culture. This is a must-do when you come to St Maarten. The good news is that it …More

5.0 (17)

Full-Day Private Luxury Yacht Tour in Anguilla

Anguilla is a different island with a different culture. This is a must-do when you come to St Maarten. The good news is that it...

7 hours 30 minutes Free Cancellation

5.0 (17)

from
$1,900

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

Tobago Tours are fun, relaxed and exciting tour. You will see an amazing tree, walk pristine beaches and enjoy the culture and cuisine of Tobago. …More

4.9 (17)

Half Day Tobago Tours with Transfers

Tobago Tours are fun, relaxed and exciting tour. You will see an amazing tree, walk pristine beaches and enjoy the culture and cuisine of Tobago....

5 to 7 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$200

Jamaica Sunset at Rick's Cafe Private Tour with Transfer

Rick's Café is known for having an unrivalled view of the sunset in Jamaica. Set in the West End atop a 35-foot high cliff, it …More

Montego Bay, Jamaica

4.9 (17)

Jamaica Sunset at Rick's Cafe Private Tour with Transfer

Rick's Café is known for having an unrivalled view of the sunset in Jamaica. Set in the West End atop a 35-foot high cliff, it...

4 to 5 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$55

Scenic Historical Tour to Fort Charlotte and Queens drive from IV Tours

This tour is exclusively provided by us on the island, 2 historic site Fort Charlotte stands about 635 feet (0.19 km) above sea level 360 …More

Kingstown, St Vincent and the Grenadines

4.9 (17)

Scenic Historical Tour to Fort Charlotte and Queens drive from IV Tours

This tour is exclusively provided by us on the island, 2 historic site Fort Charlotte stands about 635 feet (0.19 km) above sea level 360...

1 hour 45 minutes Free Cancellation

4.9 (17)

from
$53

Bob Marley Nine Mile Tour - From Montego Bay

Friendly courteous drivers who are very knowledgable on Bob Marley's life and legend. This tour provides a unique look into the life and legend of …More

Montego Bay, Jamaica

5.0 (17)

Bob Marley Nine Mile Tour - From Montego Bay

Friendly courteous drivers who are very knowledgable on Bob Marley's life and legend. This tour provides a unique look into the life and legend of...

6 hours Free Cancellation

5.0 (17)

from
$150

Gilmore tours offers top quality services, safe, reliable, friendly, and dependable, guaranteed to give you a memorable experience while you enjoy this beautiful island in …More

Kingston, Jamaica

5.0 (17)

Bamboo Rafting in Ocho Rios

Gilmore tours offers top quality services, safe, reliable, friendly, and dependable, guaranteed to give you a memorable experience while you enjoy this beautiful island in...

2 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$60

Private & Romantic Sunset Cruise Under Sails

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the …More

4.9 (17)

Private & Romantic Sunset Cruise Under Sails

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the...

2 hours 30 minutes Free Cancellation

4.9 (17)

from
$608

Half Day Big Game Fishing private charter

1/2 DAY BIG GAME FISHING All hours available, we pick you up any time! Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions …More

Puerto Plata, Dominican Republic

4.9 (17)

Half Day Big Game Fishing private charter

1/2 DAY BIG GAME FISHING All hours available, we pick you up any time! Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions...

4 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$490

Let's take a scenic drive through the local communities and charming fishing villages on our way to the best and Most Popular locations on the …More

Castries, St Lucia

5.0 (17)

Soufrière Adventure Private Tour

Let's take a scenic drive through the local communities and charming fishing villages on our way to the best and Most Popular locations on the...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$120

5 Hour Tour at Dark View Falls and Pirates of the Caribbean Set

Get a highlight tour of St. Vincent from the capital Kingstown on your way to our first location Dark View Falls. Pit stops can be …More

Kingstown, St Vincent and the Grenadines

4.9 (17)

5 Hour Tour at Dark View Falls and Pirates of the Caribbean Set

Get a highlight tour of St. Vincent from the capital Kingstown on your way to our first location Dark View Falls. Pit stops can be...

5 hours Hotel pickup offered Free Cancellation

4.9 (17)

from
$300

Seven Mile Beach and Rick’s Cafe Private Tour

Negril is known for its miles of sandy beaches on shallow bays with calm, turquoise waters. Seven Mile Beach. Negril is calm and tranquil and …More

Montego Bay, Jamaica

5.0 (17)

Seven Mile Beach and Rick’s Cafe Private Tour

Negril is known for its miles of sandy beaches on shallow bays with calm, turquoise waters. Seven Mile Beach. Negril is calm and tranquil and...

5 to 8 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$49

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?

Got any more Caribbean trip ideas?

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