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 →

The Best of Port Antonio Day-Trip from Ocho Rios

Explore the parish of Portland on this day trip from Ocho Rios. Journey with a local guide and visit the town of Port Antonio and …More

Boscobel, Jamaica

5.0 (8)

The Best of Port Antonio Day-Trip from Ocho Rios

Explore the parish of Portland on this day trip from Ocho Rios. Journey with a local guide and visit the town of Port Antonio and...

7 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$250

Bob Marley Nine Mile and Blue Hole Tour from Montego bay

Enjoy the drive through the hills and countryside of Jamaica, traveling to the Bob Marley Nine Mile, the birthplace of the legendary Bob Marley. This day …More

Montego Bay, Jamaica

5.0 (4)

Bob Marley Nine Mile and Blue Hole Tour from Montego bay

Enjoy the drive through the hills and countryside of Jamaica, traveling to the Bob Marley Nine Mile, the birthplace of the legendary Bob Marley. This day...

5 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$250

Negril Day Experience -From Montego Bay, Negril, Ocho Rios

Stop At: Seven Mile Beach, Negril Jamaica The first stop is by Margarita Ville, where you get to enjoy the 7 mile stretch of White …More

Lucea, Jamaica

5.0 (2)

Negril Day Experience -From Montego Bay, Negril, Ocho Rios

Stop At: Seven Mile Beach, Negril Jamaica The first stop is by Margarita Ville, where you get to enjoy the 7 mile stretch of White...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$250

Rastasafari Experience ATV Adventure and Local Day Out

Are you a history-loving adventure seeker? Well, come and play your way on adventures through history. If you've always wanted to learn about Rastafarian culture …More

Montego Bay, Jamaica

5.0 (4)

Rastasafari Experience ATV Adventure and Local Day Out

Are you a history-loving adventure seeker? Well, come and play your way on adventures through history. If you've always wanted to learn about Rastafarian culture...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$250

Bamboo Rafting, Limestone Foot Massage, Parasailing Private Tour

Take a journey in the rural parts of Montego Bay{Country) and rap yourself with with nature.Lethe Bamboo Rafting is the best way to have REAL …More

Montego Bay, Jamaica

5.0 (3)

Bamboo Rafting, Limestone Foot Massage, Parasailing Private Tour

Take a journey in the rural parts of Montego Bay{Country) and rap yourself with with nature.Lethe Bamboo Rafting is the best way to have REAL...

3 to 6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$250

This is a cashless hassle free day tour that goes through the mountainous terrain of Jamaica south coast, and passes under over lapping tunnel of …More

Montego Bay, Jamaica

5.0 (4)

Explore Montego Bay Jamaica to Country Side Appleton & Y S Falls

This is a cashless hassle free day tour that goes through the mountainous terrain of Jamaica south coast, and passes under over lapping tunnel of...

8 to 10 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$250

Paradise Unveiled Full Day Island Escape

Embark on a full-day adventure exploring Grenada’s lush beauty and vibrant culture. Begin with a visit to one of Grenada’s majestic waterfalls, perfect for a …More

5.0 (4)

Paradise Unveiled Full Day Island Escape

Embark on a full-day adventure exploring Grenada’s lush beauty and vibrant culture. Begin with a visit to one of Grenada’s majestic waterfalls, perfect for a...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$250

Whenever you're touring with FutureTours, let's just say you'll instantly become Grenadian............minutes and hours no longer exist because you're free to just let go and …More

Grand Anse, Grenada

5.0 (3)

Historical Tours of Grenada

Whenever you're touring with FutureTours, let's just say you'll instantly become Grenadian............minutes and hours no longer exist because you're free to just let go and...

4 to 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$250

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a …More

Ocho Rios, Jamaica

5.0 (1)

All day Tour of Ocho Rios

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a...

2 days Hotel pickup offered

5.0 (1)

from
$250

Martha Brae Bamboo River Rafting & Horse Back Riding Private Tour

Come and experience two of Jamaica’s most popular activities Bamboo Rafting and horseback riding and swimming. Your Horseback Ride and Swim Adventure starts with pickup …More

Montego Bay, Jamaica

5.0 (1)

Martha Brae Bamboo River Rafting & Horse Back Riding Private Tour

Come and experience two of Jamaica’s most popular activities Bamboo Rafting and horseback riding and swimming. Your Horseback Ride and Swim Adventure starts with pickup...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$250

Montaña Redonda & Horseback Riding 2-in-1 Tour from Punta Cana

Discover two unforgettable adventures in one private tour – Montaña Redonda & Horseback Riding! This experience combines breathtaking mountain views with the tranquility of a …More

Punta Cana, Dominican Republic

4.7 (3)

Montaña Redonda & Horseback Riding 2-in-1 Tour from Punta Cana

Discover two unforgettable adventures in one private tour – Montaña Redonda & Horseback Riding! This experience combines breathtaking mountain views with the tranquility of a...

4 to 6 hours Hotel pickup offered

4.7 (3)

from
$250

Private Jet Ski and Parasailing Tour from Montego Bay

If you’re in Jamaica and you love to do water activity and want to have a day full of fun and adventure, this activity will …More

Montego Bay, Jamaica

5.0 (1)

Private Jet Ski and Parasailing Tour from Montego Bay

If you’re in Jamaica and you love to do water activity and want to have a day full of fun and adventure, this activity will...

2 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$250

Traveling to another country makes sense when we venture to walk through its streets, interact with its people and above all try its gastronomy. Higüey, …More

Punta Cana, Dominican Republic

5.0 (1)

Higuey Cultural Sightseeing

Traveling to another country makes sense when we venture to walk through its streets, interact with its people and above all try its gastronomy. Higüey,...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$250

Luminous Lagoon Small Group Tour from Montego Bay

Located in Falmouth, Trelawny the Luminous Lagoon (Glistening Waters) is a natural wonder, it is a phosphorescent lagoon where guests are taken on a beautiful …More

Montego Bay, Jamaica

3.8 (5)

Luminous Lagoon Small Group Tour from Montego Bay

Located in Falmouth, Trelawny the Luminous Lagoon (Glistening Waters) is a natural wonder, it is a phosphorescent lagoon where guests are taken on a beautiful...

45 minutes Hotel pickup offered Free Cancellation

3.8 (5)

from
$250

Ocho Rios to Kingston Sightseeing Day-Trip

Get personalized attention and enjoy a flexible itinerary during this private tour of Kingston's highlights from Ocho Rios. Spend a full day visiting important sites …More

Ocho Rios, Jamaica

5.0 (1)

Ocho Rios to Kingston Sightseeing Day-Trip

Get personalized attention and enjoy a flexible itinerary during this private tour of Kingston's highlights from Ocho Rios. Spend a full day visiting important sites...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$250

Time will be spent at Eight River Lounge for drinks and music entertainment which is night club vibes and Shades night club is more of …More

Negril, Jamaica

4.5 (2)

Ocho Rios Nightlife

Time will be spent at Eight River Lounge for drinks and music entertainment which is night club vibes and Shades night club is more of...

3 to 4 hours Hotel pickup offered Free Cancellation

4.5 (2)

from
$250

Private Appleton Estate Rum Tour & Tasting from Montego Bay

Go on a journey to the picturesque south coast of Jamaica during this 5-hour rum tasting tour from Montego Bay. Visit the exotic Appleton Estate, …More

Montego Bay, Jamaica

5.0 (1)

Private Appleton Estate Rum Tour & Tasting from Montego Bay

Go on a journey to the picturesque south coast of Jamaica during this 5-hour rum tasting tour from Montego Bay. Visit the exotic Appleton Estate,...

6 to 15 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$250

The fact that you can have a flying dress princess photoshoot at one of the most beautiful island in the Caribbean. A mix of Sumptuousness …More

Montego Bay, Jamaica

4.3 (4)

Flying Dress Photoshoot in Jamaica

The fact that you can have a flying dress princess photoshoot at one of the most beautiful island in the Caribbean. A mix of Sumptuousness...

1 hour Free Cancellation

4.3 (4)

from
$250

Island Tours Your Way, Your Time! 2, 4 or 6hrs - St. Thomas USVI

Choose your adventure – 2, 4, or 6 hours of island fun. Tour Options: Customizable 2-Hour: Island Sampler Scenic Drive Catch the highlights! A short …More

Cruz Bay, US Virgin Islands

5.0 (57)

Island Tours Your Way, Your Time! 2, 4 or 6hrs - St. Thomas USVI

Choose your adventure – 2, 4, or 6 hours of island fun. Tour Options: Customizable 2-Hour: Island Sampler Scenic Drive Catch the highlights! A short...

2 to 6 hours Hotel pickup offered Free Cancellation

5.0 (57)

from
$249

Best Of St Maarten Private Nightlife Tour

There's a reason why locals call St. Maarten "The Night Life Capital of The Caribbean'. Tour the gorgeous island paradise at night with our Local …More

Philipsburg, St Maarten

5.0 (8)

Best Of St Maarten Private Nightlife Tour

There's a reason why locals call St. Maarten "The Night Life Capital of The Caribbean'. Tour the gorgeous island paradise at night with our Local...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$249

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?