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 →

This tour allows visitors to see a major part of Montego Bay Jamaica's second largest city and community's inside out, learn about our culture, history …More

Montego Bay, Jamaica

5.0 (40)

Montego Bay hi lite and culture tour

This tour allows visitors to see a major part of Montego Bay Jamaica's second largest city and community's inside out, learn about our culture, history...

3 hours Hotel pickup offered Free Cancellation

5.0 (40)

from
$90

With several years of experience in the tourism industry, I know all the fun, scenic and adventurous places in Jamaica. I provide exclusive transportation for …More

Montego Bay, Jamaica

4.9 (40)

Dunn's River Falls

With several years of experience in the tourism industry, I know all the fun, scenic and adventurous places in Jamaica. I provide exclusive transportation for...

5 to 6 hours Hotel pickup offered Free Cancellation

4.9 (40)

from
$60

JTAT Private Transfers & Tours, Saint John's, Antigua and Barbuda

As the ultimate vacation VIP, we're here to whisk you away in style and luxury with our superb, reliable, top-notch island-wide transportation services, offering not …More

Five Islands Village, Antigua and Barbuda

4.9 (40)

JTAT Private Transfers & Tours, Saint John's, Antigua and Barbuda

As the ultimate vacation VIP, we're here to whisk you away in style and luxury with our superb, reliable, top-notch island-wide transportation services, offering not...

300 to 500 minutes Hotel pickup offered Free Cancellation

4.9 (40)

from
$160

Half-Day Tour: A Taste of Paradise and History of Antigua

This historical sightseeing tour will introduce you to Antigua's history, heritage and beauty. A visit to Betty's Hope is a must. A former sugar plantation …More

Five Islands Village, Antigua and Barbuda

4.9 (40)

Half-Day Tour: A Taste of Paradise and History of Antigua

This historical sightseeing tour will introduce you to Antigua's history, heritage and beauty. A visit to Betty's Hope is a must. A former sugar plantation...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (40)

from
$115

Explore the captivating charm of Old San Juan in just one hour as you stroll through its historic streets lined with colorful colonial buildings and …More

5.0 (39)

Old San Juan Tour (1 Hour) by DUHO

Explore the captivating charm of Old San Juan in just one hour as you stroll through its historic streets lined with colorful colonial buildings and...

1 hour Free Cancellation

5.0 (39)

from
$25

Private and Customized Montego Bay City Tour

Montego Bay, often called “MoBay,” is rich in history and culture. Tours often include visits to historic landmarks like the Sam Sharpe Square, which commemorates …More

Falmouth, Jamaica

5.0 (39)

Private and Customized Montego Bay City Tour

Montego Bay, often called “MoBay,” is rich in history and culture. Tours often include visits to historic landmarks like the Sam Sharpe Square, which commemorates...

2 hours Hotel pickup offered Free Cancellation

5.0 (39)

from
$50

4 Hour British Virgin Islands Full Private Experience

Lets take you on a journey that unveils the mysteries of nature's little secret. Traverse the unbeaten paths, experience our local dishes, swim in our …More

Tortola, British Virgin Islands

4.9 (39)

4 Hour British Virgin Islands Full Private Experience

Lets take you on a journey that unveils the mysteries of nature's little secret. Traverse the unbeaten paths, experience our local dishes, swim in our...

4 hours Free Cancellation

4.9 (39)

from
$220

VIP Private Booze Cruise with Live Dj and BBQ in Punta Cana

Explore the beauty of the shores of Punta Cana, and get the best experience of your vacation, follow our animation team to enjoy dancing to …More

Punta Cana, Dominican Republic

5.0 (39)

VIP Private Booze Cruise with Live Dj and BBQ in Punta Cana

Explore the beauty of the shores of Punta Cana, and get the best experience of your vacation, follow our animation team to enjoy dancing to...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (39)

from
$148

Montego Bay - Exclusive Airport/Cruise Port Transfer

Start your trip to Jamaica, with our exclusive, private transportation services. With years of tourism experience, we provide direct airport and cruise port transfers, plus …More

Montego Bay, Jamaica

5.0 (39)

Montego Bay - Exclusive Airport/Cruise Port Transfer

Start your trip to Jamaica, with our exclusive, private transportation services. With years of tourism experience, we provide direct airport and cruise port transfers, plus...

10 to 30 minutes Free Cancellation

5.0 (39)

from
$31

Nine Mile Bob Marley Mausoleum Transportation [ Birthplace ]

Bob Marley's resting place is where the singer spent his early years, and his simple marble tomb is genuinely moving. the home where Bob Marley …More

Montego Bay, Jamaica

4.8 (39)

Nine Mile Bob Marley Mausoleum Transportation [ Birthplace ]

Bob Marley's resting place is where the singer spent his early years, and his simple marble tomb is genuinely moving. the home where Bob Marley...

5 to 6 hours Hotel pickup offered Free Cancellation

4.8 (39)

from
$47

Blue Hole Mineral Spring and Ricks Cafe Private Tour

This is a unique tour. A tour that move at easy pace and is not rushed. You are picked up in the comfort of your …More

Montego Bay, Jamaica

4.9 (39)

Blue Hole Mineral Spring and Ricks Cafe Private Tour

This is a unique tour. A tour that move at easy pace and is not rushed. You are picked up in the comfort of your...

5 to 8 hours Hotel pickup offered Free Cancellation

4.9 (39)

from
$105

Curaçao – Private City Tour with Insider Secrets

Private & Customizable Curacao City Highlights Tour with Dani Step into the heart of Curaçao with your private guide—Dani! This isn’t just a city tour; …More

Willemstad, Curacao

5.0 (39)

Curaçao – Private City Tour with Insider Secrets

Private & Customizable Curacao City Highlights Tour with Dani Step into the heart of Curaçao with your private guide—Dani! This isn’t just a city tour;...

4 hours Hotel pickup offered

5.0 (39)

from
$110

Rose Island 3 Island Luxury Private Tour(8hrs)

This tour is one of a kind . Our boats are well maintained and captains and crew are highly trained. You get to experience 3 …More

5.0 (38)

Rose Island 3 Island Luxury Private Tour(8hrs)

This tour is one of a kind . Our boats are well maintained and captains and crew are highly trained. You get to experience 3...

8 hours Free Cancellation

5.0 (38)

from
$2,500

1.5 Hour Private Mini Jeep Tour on St. Thomas

This 1.5 hour Mini Private Jeep Tour will take you to some of our famous landmarks, with native island guides sharing their culture, folklore and …More

4.9 (38)

1.5 Hour Private Mini Jeep Tour on St. Thomas

This 1.5 hour Mini Private Jeep Tour will take you to some of our famous landmarks, with native island guides sharing their culture, folklore and...

1 hour 30 minutes Hotel pickup offered Free Cancellation

4.9 (38)

from
$220

Baby Beach and San Nicolas Art Murals Private EZ Raider Adventure

This is a East Coast adventure with the exclusive Electric 4-wheeler EZ Raider with beach time at Baby Beach. Follow the tour guide to unique …More

5.0 (38)

Baby Beach and San Nicolas Art Murals Private EZ Raider Adventure

This is a East Coast adventure with the exclusive Electric 4-wheeler EZ Raider with beach time at Baby Beach. Follow the tour guide to unique...

3 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$165

We offer our guests personalized itinerary. Our boat is your boat. You can freestyle on the water or stick to a strict schedule. Either way …More

5.0 (38)

Honor Roll Private Bahamas Boat Charter

We offer our guests personalized itinerary. Our boat is your boat. You can freestyle on the water or stick to a strict schedule. Either way...

4 to 8 hours Free Cancellation

5.0 (38)

from
$1,750

3-Hour Private Tour in the Highlights of Montego Bay

Spice up your vacation when you book a highlight tour with us, where you'll be picked up from your respective locations (hotels etc.) in a …More

Montego Bay, Jamaica

5.0 (38)

3-Hour Private Tour in the Highlights of Montego Bay

Spice up your vacation when you book a highlight tour with us, where you'll be picked up from your respective locations (hotels etc.) in a...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$58

Bamboo River Rafting Experience with Limestone Foot Massage

Located in the hills of Hanover Lethe is the perfect combination of land and water with picturesque views from the hills to the tranquility of …More

Trelawny, Jamaica

5.0 (38)

Bamboo River Rafting Experience with Limestone Foot Massage

Located in the hills of Hanover Lethe is the perfect combination of land and water with picturesque views from the hills to the tranquility of...

2 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$100

Key to the Sea Half-Day Private Boat Charter: Sun & Snorkel Tour

Experience the ultimate crowd-free day on the water with our premium half-day private boat charter. Cruising aboard our immaculate 27-foot Sea Ray Sundeck (No-Ah'Genda), your …More

5.0 (38)

Key to the Sea Half-Day Private Boat Charter: Sun & Snorkel Tour

Experience the ultimate crowd-free day on the water with our premium half-day private boat charter. Cruising aboard our immaculate 27-foot Sea Ray Sundeck (No-Ah'Genda), your...

4 hours Free Cancellation

5.0 (38)

from
$1,599

Negril has an endless amount of place to see and things to do. Let us customize a tour for you so you can experience Negril. …More

Negril, Jamaica

5.0 (38)

Private Negril Highlights Tour

Negril has an endless amount of place to see and things to do. Let us customize a tour for you so you can experience Negril....

2 to 10 hours Free Cancellation

5.0 (38)

from
$25

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?