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 →

Curaçao: Affordable totally Customizable Private Tour :)

What makes us special is our focus on customization: every tour is fully tailored to your preferences based on an intake form, allowing you to …More

4.9 (83)

Curaçao: Affordable totally Customizable Private Tour :)

What makes us special is our focus on customization: every tour is fully tailored to your preferences based on an intake form, allowing you to...

4 hours Hotel pickup offered Free Cancellation

4.9 (83)

from
$285

Old and New San Juan History City and Street Art Tour

In San Juan, we are going to take you for an adventure full of beautiful sites and history. We will teach you about the history …More

4.9 (83)

Old and New San Juan History City and Street Art Tour

In San Juan, we are going to take you for an adventure full of beautiful sites and history. We will teach you about the history...

2 hours Hotel pickup offered Free Cancellation

4.9 (83)

from
$211

Your private cigar factory tour includes a cigar, coffee, tea, water or non-alcoholic beverage and a mamajuana shot. You will experience an educational cigar factory …More

Cabarete, Dominican Republic

4.9 (83)

Dominican Cigar Factory Tour

Your private cigar factory tour includes a cigar, coffee, tea, water or non-alcoholic beverage and a mamajuana shot. You will experience an educational cigar factory...

1 to 2 hours Hotel pickup offered Free Cancellation

4.9 (83)

from
$20

Luxury Private Full-Day Catamaran Charter in St Maarten & Saint-Martin

Join our St Maarten/Saint-Martin luxury private catamaran charter for a fabulous day on our luxury 48-foot catamaran. Breakfast (Pastries, Fresh Fruits, Tea & Coffee), Appetizers, …More

5.0 (83)

Luxury Private Full-Day Catamaran Charter in St Maarten & Saint-Martin

Join our St Maarten/Saint-Martin luxury private catamaran charter for a fabulous day on our luxury 48-foot catamaran. Breakfast (Pastries, Fresh Fruits, Tea & Coffee), Appetizers,...

7 to 9 hours Free Cancellation

5.0 (83)

from
$240

Half-day buggy adventure cenote and Macao beach in Punta Cana

Aventura en la Naturaleza y Todoterreno Los viajeros conducirán su propio buggy por senderos de tierra, atravesando caminos lodosos, colinas y paisajes impresionantes. Sentirán la …More

Punta Cana, Dominican Republic

5.0 (82)

Half-day buggy adventure cenote and Macao beach in Punta Cana

Aventura en la Naturaleza y Todoterreno Los viajeros conducirán su propio buggy por senderos de tierra, atravesando caminos lodosos, colinas y paisajes impresionantes. Sentirán la...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (82)

from
$25

[PRIVATE] Dunn's River Falls with Entrance Fees

Join us for an adventure of a lifetime. Our private transportation will pick you up from your resort or Airbnb. Your driver will introduce you …More

Lucea, Jamaica

5.0 (82)

[PRIVATE] Dunn's River Falls with Entrance Fees

Join us for an adventure of a lifetime. Our private transportation will pick you up from your resort or Airbnb. Your driver will introduce you...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (82)

from
$158

Private San Juan Bay Boat Sunset-Night Cruise

Enjoy an unforgettable experience in our unique private boat ride at the bay of San Juan. You will have the opportunity to know some history …More

5.0 (81)

Private San Juan Bay Boat Sunset-Night Cruise

Enjoy an unforgettable experience in our unique private boat ride at the bay of San Juan. You will have the opportunity to know some history...

1 hour 30 minutes Free Cancellation

5.0 (81)

from
$389

4 hours 38ft Reel Dreams Private Charter in Nassau

Join on this private, half-day charter onboard the 38ft Reel Dreams. You are in control so you can fully customize your charter to fit your needs. You're …More

4.9 (81)

4 hours 38ft Reel Dreams Private Charter in Nassau

Join on this private, half-day charter onboard the 38ft Reel Dreams. You are in control so you can fully customize your charter to fit your needs. You're...

4 hours Free Cancellation

4.9 (81)

from
$990

Montego Bay Airport transfers-Excellence,Royalton,Ocean Coral Spring(Round Trip)

We are the new fun and exciting way to explore Jamaica. Providing exceptional transportation service to travelers in a friendly and safe environment. Our hospitality, …More

Lucea, Jamaica

5.0 (81)

Montego Bay Airport transfers-Excellence,Royalton,Ocean Coral Spring(Round Trip)

We are the new fun and exciting way to explore Jamaica. Providing exceptional transportation service to travelers in a friendly and safe environment. Our hospitality,...

30 to 45 minutes Hotel pickup offered Free Cancellation

5.0 (81)

from
$100

Cayman Private Luxury Charters - Stingray City, Snorkel, & More

We provide a variety of tour options accommodating guests that'd like to make one stop or see it all. Our team are all born and …More

Grand Cayman, Cayman Islands

4.9 (80)

Cayman Private Luxury Charters - Stingray City, Snorkel, & More

We provide a variety of tour options accommodating guests that'd like to make one stop or see it all. Our team are all born and...

2 to 6 hours Free Cancellation

4.9 (80)

from
$850

Private 6-Hour Island Hopping in US Virgin Islands - 500hp Hydro Sport

This is a "New Extremly Affordable, Private Option" offered by Stormy Pirates!! Be one of the first to experience this affordable option for a fast, …More

5.0 (80)

Private 6-Hour Island Hopping in US Virgin Islands - 500hp Hydro Sport

This is a "New Extremly Affordable, Private Option" offered by Stormy Pirates!! Be one of the first to experience this affordable option for a fast,...

6 hours

5.0 (80)

from
$1,150

Private Walking Tour of Old San Juan, and the forts

Experience San Juan the best possible way...through a private tour. Focus on what you are most excited about. Learn about the history and the untold …More

4.9 (78)

Private Walking Tour of Old San Juan, and the forts

Experience San Juan the best possible way...through a private tour. Focus on what you are most excited about. Learn about the history and the untold...

2 hours Free Cancellation

4.9 (78)

from
$38

Paradise Taxi & Tours USVI -St. Thomas, Virgin Islands-Private Group-Island Tour

✨ Private St. Thomas Tour – Unforgettable Experiences! ✨ Make your visit to St. Thomas truly unforgettable with a private 6-hour tour designed just for …More

Cruz Bay, US Virgin Islands

4.8 (78)

Paradise Taxi & Tours USVI -St. Thomas, Virgin Islands-Private Group-Island Tour

✨ Private St. Thomas Tour – Unforgettable Experiences! ✨ Make your visit to St. Thomas truly unforgettable with a private 6-hour tour designed just for...

6 hours Hotel pickup offered Free Cancellation

4.8 (78)

from
$770

Costumizable East to West Curaçao Island Tour Experience

This private tour for 4 passengers gives you an overall view and understanding of the islands geology, people, culture, architecture, language, history, food and nature. …More

Willemstad, Curacao

5.0 (75)

Costumizable East to West Curaçao Island Tour Experience

This private tour for 4 passengers gives you an overall view and understanding of the islands geology, people, culture, architecture, language, history, food and nature....

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (75)

from
$725

Imagine spending the day luxuriating on your own private boat with your friends and family. Our private charter will take you on an experience like …More

5.0 (75)

8HR Fullday Private Boat in Gracebay

Imagine spending the day luxuriating on your own private boat with your friends and family. Our private charter will take you on an experience like...

8 hours Hotel pickup offered Free Cancellation

5.0 (75)

from
$2,688

Private Bermuda Boat Charter Cliff Jumping, Islands & Sightseeing

Our boat "Island Vibez" is small enough to go where a lot of the larger charter boats cannot, yet she is extremely spacious and comfortable. …More

5.0 (74)

Private Bermuda Boat Charter Cliff Jumping, Islands & Sightseeing

Our boat "Island Vibez" is small enough to go where a lot of the larger charter boats cannot, yet she is extremely spacious and comfortable....

3 hours Free Cancellation

5.0 (74)

from
$900

[PRIVATE] Blue Hole & Secret Falls Tour with Entrance Fees

Blue Hole & Secret Falls - Two natural wonders in one place You don't want to miss out on this once-in-a-lifetime opportunity. Take a dip, …More

Negril, Jamaica

5.0 (74)

[PRIVATE] Blue Hole & Secret Falls Tour with Entrance Fees

Blue Hole & Secret Falls - Two natural wonders in one place You don't want to miss out on this once-in-a-lifetime opportunity. Take a dip,...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (74)

from
$167

Rafting at the Martha Brae is rated number one activity in Jamaica. You will be rafted by an educated tour guide helping you to discover …More

Montego Bay, Jamaica

4.9 (73)

Martha Brae River Rafting Private Tour

Rafting at the Martha Brae is rated number one activity in Jamaica. You will be rafted by an educated tour guide helping you to discover...

2 to 5 hours Hotel pickup offered Free Cancellation

4.9 (73)

from
$140

Ride in comfort while exploring rural Barbados with a courteous, honest, friendly and well informed driver/guide. On this Barbados Half Day Private Tour, travelers will …More

4.9 (71)

Barbados Half Day Private Tour

Ride in comfort while exploring rural Barbados with a courteous, honest, friendly and well informed driver/guide. On this Barbados Half Day Private Tour, travelers will...

4 to 5 hours Hotel pickup offered Free Cancellation

4.9 (71)

from
$196

Private Full-day Tour in Grenada with Pickup

Discover the vibrant island of Grenada on our exhilarating full-day tour! From the moment you step in, you'll be immersed in the lively local culture. …More

St. George's, Grenada

4.9 (71)

Private Full-day Tour in Grenada with Pickup

Discover the vibrant island of Grenada on our exhilarating full-day tour! From the moment you step in, you'll be immersed in the lively local culture....

7 to 8 hours Hotel pickup offered Free Cancellation

4.9 (71)

from
$150

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?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Private Sightseeing Tours are:

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?