Top Caribbean Private Sightseeing Tours

Q: 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: Rick's Cafe Negril & Sunset V.I.P North Caribbean deep forest Tour -The Green Martinique Bob Marley Mouseleum and museum from negril and Montego Bay Blue Hole & Secret Falls plus Bob Marley Birth Place Nine Mile Private Tour Blue Hole Secret Falls Private Tour

Q: 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: San Juan’s Historic Streets Audio Guided Walking Tour Montego Bay Private Hotel & Airport Transfer – MBJ Historical attractions of Alexander Hamillton Mother's Gravesite Ricks Cafe Negril and 7 Mile Beach Day Trip Montego Bay Shopping View all kid-friendly Tours →

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

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup: Private Airport Transfers Roundtrip Punta Cana Hotels Souvenir Shopping Tour in Punta Cana. Transportation Included Great River Raft and Full Limestone body Massage In Montego Bay Ricks Cafe Negril and 7 Mile Beach Day Trip Punta Cana Shopping tour 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 →

Punta Cana Private Catamaran Cruise with Drinks and Light Snacks

A Premium Powerboat Catamaran with Premium drinks and Professional Crew, Snorkel, Slide, Cruise, Paddle Board, Snorkel at the Natural Reserve near Cabo Engaño NOT where …More

Punta Cana, Dominican Republic

5.0 (295)

Punta Cana Private Catamaran Cruise with Drinks and Light Snacks

A Premium Powerboat Catamaran with Premium drinks and Professional Crew, Snorkel, Slide, Cruise, Paddle Board, Snorkel at the Natural Reserve near Cabo Engaño NOT where...

4 hours Hotel pickup offered Free Cancellation

5.0 (295)

from
$989

Let’s get out of the crowds and enjoy of the attractions of the Dominican Republic by doing it privately. Say goodbye to making big lines …More

Punta Cana, Dominican Republic

4.7 (50)

Private Saona Island Excursion

Let’s get out of the crowds and enjoy of the attractions of the Dominican Republic by doing it privately. Say goodbye to making big lines...

8 to 9 hours Hotel pickup offered Free Cancellation

4.7 (50)

from
$990

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

Private Tour of El Yunque Rainforest from San Juan

Visit a different area of the El Yunque Rainforest. With the guidance of your private guide you will embark on an estimate 30-minute hike that …More

Isla Verde, Puerto Rico

4.8 (4)

Private Tour of El Yunque Rainforest from San Juan

Visit a different area of the El Yunque Rainforest. With the guidance of your private guide you will embark on an estimate 30-minute hike that...

7 hours Hotel pickup offered Free Cancellation

4.8 (4)

from
$990

Have a blast on the water! Take a Hatteras 52 boat ride along the North Coast and have a party of your life, while dancing, …More

Cabarete, Dominican Republic

5.0 (4)

Private Cruise on a Hatteras 52

Have a blast on the water! Take a Hatteras 52 boat ride along the North Coast and have a party of your life, while dancing,...

4 to 5 hours Hotel pickup offered

5.0 (4)

from
$990

Blue Mountain Tour: A Half-Day Escape from Kingston

Embark on a breathtaking journey through Kingston’s Blue Mountains on this half-day tour. Feel the excitement as you drive through the vibrant streets of Kingston, …More

Kingston, Jamaica

Blue Mountain Tour: A Half-Day Escape from Kingston

Embark on a breathtaking journey through Kingston’s Blue Mountains on this half-day tour. Feel the excitement as you drive through the vibrant streets of Kingston,...

5 hours Hotel pickup offered

from
$992

Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

Explore the Virgin Islands in style aboard MV Poseidon, our beautiful 36 ft. TwinVee Ocean Cat. The TwinVee is known for its speed and stability …More

5.0 (210)

Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

Explore the Virgin Islands in style aboard MV Poseidon, our beautiful 36 ft. TwinVee Ocean Cat. The TwinVee is known for its speed and stability...

4 to 7 hours Free Cancellation

5.0 (210)

from
$995

2-Hour Luxury Axopar Private Charter! Explore the Turks in style!

Relax on the sundeck of our stylish Axopar while your private Captain navigates you through the emerald waters of Grace Bay. Snorkel at the 3rd …More

5.0 (8)

2-Hour Luxury Axopar Private Charter! Explore the Turks in style!

Relax on the sundeck of our stylish Axopar while your private Captain navigates you through the emerald waters of Grace Bay. Snorkel at the 3rd...

2 hours Free Cancellation

5.0 (8)

from
$995

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran …More

5.0 (302)

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran...

3 hours Free Cancellation

5.0 (302)

from
$999

Charter our tour services for your private event, weddings, birthday or company trip. We customize all trips per your specifications. Our basic package includes a …More

Cruz Bay, US Virgin Islands

4.6 (9)

Private Customized Tour in St Thomas

Charter our tour services for your private event, weddings, birthday or company trip. We customize all trips per your specifications. Our basic package includes a...

6 hours Hotel pickup offered Free Cancellation

4.6 (9)

from
$999

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private …More

Cruz Bay, US Virgin Islands

5.0 (13)

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private...

2 to 3 hours Free Cancellation

5.0 (13)

from
$1,000

Private Charter 34f Express Cruiser Stingray City Reef Snorkeling

A one of a kind Private Charter on our beautiful 34ft Luhrs Sport Cruiser. The boat can accomodate up to 12 guests. You will be …More

Grand Cayman, Cayman Islands

5.0 (211)

Private Charter 34f Express Cruiser Stingray City Reef Snorkeling

A one of a kind Private Charter on our beautiful 34ft Luhrs Sport Cruiser. The boat can accomodate up to 12 guests. You will be...

4 to 8 hours Free Cancellation

5.0 (211)

from
$1,000

4 hour Private Boat charter to Stingray City, Snorkeling and More

Avoid the crowds and join us on your own private boat with an experienced crew for an adventure of a lifetime! Enjoy an exciting one-on-one …More

Grand Cayman, Cayman Islands

5.0 (52)

4 hour Private Boat charter to Stingray City, Snorkeling and More

Avoid the crowds and join us on your own private boat with an experienced crew for an adventure of a lifetime! Enjoy an exciting one-on-one...

4 hours 5 minutes Hotel pickup offered Free Cancellation

5.0 (52)

from
$1,000

Private Full Day or Half Day Charter - 37' Midnight Express

Experience dual-country boat trips, explore numerous popular destinations with our 37' Midnight Express – a distinctive blue and white vessel powered by 3x 300HP outboards. …More

Cruz Bay, US Virgin Islands

5.0 (3)

Private Full Day or Half Day Charter - 37' Midnight Express

Experience dual-country boat trips, explore numerous popular destinations with our 37' Midnight Express – a distinctive blue and white vessel powered by 3x 300HP outboards....

4 to 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,000

Punta Cana Private Boat Tour with Transportation Included

This tour differs from the others ,for everything it will provide.Spend a different time aboard this boat animated by a staff that will give you …More

Punta Cana, Dominican Republic

4.8 (9)

Punta Cana Private Boat Tour with Transportation Included

This tour differs from the others ,for everything it will provide.Spend a different time aboard this boat animated by a staff that will give you...

3 hours Hotel pickup offered Free Cancellation

4.8 (9)

from
$1,000

Private Express Cruise Tour in Punta Cana

Escape the ordinary with our Private Catamaran Tour along Punta Cana's stunning coastline. Perfect for groups of up to 8 people, this exclusive 4-hour journey …More

Punta Cana, Dominican Republic

Private Express Cruise Tour in Punta Cana

Escape the ordinary with our Private Catamaran Tour along Punta Cana's stunning coastline. Perfect for groups of up to 8 people, this exclusive 4-hour journey...

4 hours Hotel pickup offered Free Cancellation

from
$1,000

6-Day Bird Watching Tour in the Sierra de Bahoruco

Embark on an unforgettable bird watching trip in the beautiful Sierra de Bahoruco in Barahona. This 6-day tour will immerse you in a unique experience …More

Santo Domingo, Dominican Republic

6-Day Bird Watching Tour in the Sierra de Bahoruco

Embark on an unforgettable bird watching trip in the beautiful Sierra de Bahoruco in Barahona. This 6-day tour will immerse you in a unique experience...

6 days Hotel pickup offered Free Cancellation

from
$1,007

Private Bioluminescence Tour in Grand Cayman

The Bioluminescence Bay here in Grand Cayman is one of few places in the world that you can experience amazing phenomenon. We will drive you …More

Grand Cayman, Cayman Islands

5.0 (14)

Private Bioluminescence Tour in Grand Cayman

The Bioluminescence Bay here in Grand Cayman is one of few places in the world that you can experience amazing phenomenon. We will drive you...

2 hours 30 minutes Free Cancellation

5.0 (14)

from
$1,025

Punta Cana Private Catamaran – Exclusive Snorkel & Sail Adventure

This is an excellent way to spend amazing time with your family and friends if you want to get an unforgettable experience on an exiting …More

Punta Cana, Dominican Republic

Punta Cana Private Catamaran – Exclusive Snorkel & Sail Adventure

This is an excellent way to spend amazing time with your family and friends if you want to get an unforgettable experience on an exiting...

3 hours Hotel pickup offered

from
$1,025

Local, expert guides who share their knowledge of the island. Complimentary drinks and light snacks for your enjoyment Let the gentle Caribbean breeze and stunning …More

5.0 (1)

Grace Bay Sunset Cruise

Local, expert guides who share their knowledge of the island. Complimentary drinks and light snacks for your enjoyment Let the gentle Caribbean breeze and stunning...

2 hours Hotel pickup offered

5.0 (1)

from
$1,049

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?

Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include:

View all Tours with 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?