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: Lethe Bamboo Rafting with Foot Massage & Private Pickup Negril Seven Mile Beach and Ricks Cafe Tour from Montego Bay Grace Bay Sunset Cruise Buggie & atv adventure Jungle Adventure Bamboo Rafting Missile Atv Adventure and Ricks Cafe

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 →

St Thomas Full Day Private Tour (1-10 PPL)

This tour caters to your group only. You get a vehicle just for your group for the whole day. It offers the flexibility of choosing …More

Cruz Bay, US Virgin Islands

4.7 (32)

St Thomas Full Day Private Tour (1-10 PPL)

This tour caters to your group only. You get a vehicle just for your group for the whole day. It offers the flexibility of choosing...

6 hours Hotel pickup offered Free Cancellation

4.7 (32)

from
$1,050

Full-Day Gozalandia Private Tour in Puerto Rico

Experience an array of the enchantments Puerto Rico has to offer. From iconic beaches to a magical waterfall that is almost surreal. Our private excursion …More

5.0 (23)

Full-Day Gozalandia Private Tour in Puerto Rico

Experience an array of the enchantments Puerto Rico has to offer. From iconic beaches to a magical waterfall that is almost surreal. Our private excursion...

8 hours Hotel pickup offered Free Cancellation

5.0 (23)

from
$1,050

Guided boat tour to your choice of the following stops: • Stingray Sand Bar • Starfish Beach • Coral Gardens • Barrier Reef • Kaibo …More

Grand Cayman, Cayman Islands

5.0 (21)

Party Boat Cruise

Guided boat tour to your choice of the following stops: • Stingray Sand Bar • Starfish Beach • Coral Gardens • Barrier Reef • Kaibo...

4 hours Free Cancellation

5.0 (21)

from
$1,050

Montego Bay Tour to Blue Hole & Dunns River Falls

Embark on a thrilling 8-hour journey from Montego Bay to explore the captivating Blue Hole and the iconic Dunn’s River Falls. This private tour invites …More

Montego Bay, Jamaica

Montego Bay Tour to Blue Hole & Dunns River Falls

Embark on a thrilling 8-hour journey from Montego Bay to explore the captivating Blue Hole and the iconic Dunn’s River Falls. This private tour invites...

8 hours Hotel pickup offered

from
$1,094

Private Luxury Catamaran Champagne Sunset Cruise

Avoid the crowds. Step on to your fully customizable private sunset cruise with your friends and family. Our attentive office staff will help make your …More

5.0 (4)

Private Luxury Catamaran Champagne Sunset Cruise

Avoid the crowds. Step on to your fully customizable private sunset cruise with your friends and family. Our attentive office staff will help make your...

2 hours Free Cancellation

5.0 (4)

from
$1,095

Bermuda Private Catamaran:Snorkeling, Shipwrecks & Cliff Jumping

Private Catamaran Experience up to 12 people, which will begin with a cruise along Bermuda's shoreline, taking guests to a prime snorkel location. Next guests …More

5.0 (116)

Bermuda Private Catamaran:Snorkeling, Shipwrecks & Cliff Jumping

Private Catamaran Experience up to 12 people, which will begin with a cruise along Bermuda's shoreline, taking guests to a prime snorkel location. Next guests...

3 hours Free Cancellation

5.0 (116)

from
$1,098

Private Stingray City and Snorkeling Half Day Charter for 6 Guest

Make lasting memories and avoid the crowds with a completely private, full day boat charter in the crystal blue waters of Grand Cayman. Your 2-person …More

Grand Cayman, Cayman Islands

5.0 (177)

Private Stingray City and Snorkeling Half Day Charter for 6 Guest

Make lasting memories and avoid the crowds with a completely private, full day boat charter in the crystal blue waters of Grand Cayman. Your 2-person...

4 hours

5.0 (177)

from
$1,100

BBQ and Slide on a Private Catamaran with Unlimited Drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip you …More

Punta Cana, Dominican Republic

4.7 (3)

BBQ and Slide on a Private Catamaran with Unlimited Drinks

Enjoy an exciting excursion on a private catamaran that will take you to explore the crystal-clear waters of a tropical paradise. During the trip you...

4 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$1,100

Platinum Prívate Santo Domingo City Tour. (mínimum 4 people)

Explore Dominican Republic’s capital city on this full-day private tour of Santo Domingo. Navigate the historical colonial streets with your friendly, local guide, and see …More

Santo Domingo, Dominican Republic

4.2 (5)

Platinum Prívate Santo Domingo City Tour. (mínimum 4 people)

Explore Dominican Republic’s capital city on this full-day private tour of Santo Domingo. Navigate the historical colonial streets with your friendly, local guide, and see...

7 hours Hotel pickup offered Free Cancellation

4.2 (5)

from
$1,100

Spend a different time on board this boat animated by staff who will make you enjoy a pleasant time. A great way to spend a …More

Punta Cana, Dominican Republic

Private Party Boat from Punta Cana

Spend a different time on board this boat animated by staff who will make you enjoy a pleasant time. A great way to spend a...

3 hours Hotel pickup offered Free Cancellation

from
$1,100

Private party boat in Punta Cana (Half Day)

To privatize this great experience of a catamaran you only need 15 people minimum or payment equal to. This custom designed boat holds as many …More

Punta Cana, Dominican Republic

3.0 (1)

Private party boat in Punta Cana (Half Day)

To privatize this great experience of a catamaran you only need 15 people minimum or payment equal to. This custom designed boat holds as many...

4 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$1,125

Premium Full‑Day Private Adventure:Snorkel & Explore Hidden Spots

Step away from the crowds and spend the day like the locals do, surrounded by nature on Mangrove Island! This is your chance to fully …More

5.0 (50)

Premium Full‑Day Private Adventure:Snorkel & Explore Hidden Spots

Step away from the crowds and spend the day like the locals do, surrounded by nature on Mangrove Island! This is your chance to fully...

8 hours Free Cancellation

5.0 (50)

from
$1,140

Morgan's Pond Cave, Mile Gully Mountain and Christiana Blue Hole: these three attractions through their unique geo-beuty tell a story of how Manchester, Jamaica came …More

Morgan's Pond Cave and Christiana Extinct Volcanic Crater Hike

Morgan's Pond Cave, Mile Gully Mountain and Christiana Blue Hole: these three attractions through their unique geo-beuty tell a story of how Manchester, Jamaica came...

3 to 4 hours Hotel pickup offered Free Cancellation

from
$1,145

Private Yacht in Punta Cana, Unlimited Drinks and HipHop Music

Our 37 foot yacht is the ONLY one in Bavaro, Punta Cana. As you can expect, Picaflor comes equipped with air conditioner, plasma TV, bathroom, …More

Punta Cana, Dominican Republic

4.9 (21)

Private Yacht in Punta Cana, Unlimited Drinks and HipHop Music

Our 37 foot yacht is the ONLY one in Bavaro, Punta Cana. As you can expect, Picaflor comes equipped with air conditioner, plasma TV, bathroom,...

3 hours Free Cancellation

4.9 (21)

from
$1,150

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 Full Day Cruise Tour in Rose Island with Snorkeling

Take a trip out on the clear blue Bahamian seas and enjoy our most popular excursion. Cruise to one of our favorite spots for snorkeling …More

5.0 (9)

Private Full Day Cruise Tour in Rose Island with Snorkeling

Take a trip out on the clear blue Bahamian seas and enjoy our most popular excursion. Cruise to one of our favorite spots for snorkeling...

6 hours Free Cancellation

5.0 (9)

from
$1,150

Private Tour Island Hop Snorkel Turtles & Sip Bahama Mamas

Escape the crowds on this 4 hour private boat tour aboard our sleek 29 ft Seabird and experience the real Bahamas. Cruise across crystal clear …More

Nassau, Bahamas

5.0 (153)

Private Tour Island Hop Snorkel Turtles & Sip Bahama Mamas

Escape the crowds on this 4 hour private boat tour aboard our sleek 29 ft Seabird and experience the real Bahamas. Cruise across crystal clear...

4 hours Free Cancellation

5.0 (153)

from
$1,190

Private Sunset Catamaran Cruise Turks and Caicos Islands

A Caribbean vacation can't be complete without a private sunset Catamaran cruise. Romantic moment or festive moment with friends, you decide! Sip champagne in front …More

4.6 (9)

Private Sunset Catamaran Cruise Turks and Caicos Islands

A Caribbean vacation can't be complete without a private sunset Catamaran cruise. Romantic moment or festive moment with friends, you decide! Sip champagne in front...

1 hour 30 minutes Free Cancellation

4.6 (9)

from
$1,190

Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our Power Catamarans and explore the very best of St. John and …More

5.0 (70)

Full-Day Private Boat Charter from St. John or St. Thomas

Depart on your private island‑hopping adventure with Bonus Time Charters aboard one of our Power Catamarans and explore the very best of St. John and...

6 hours Free Cancellation

5.0 (70)

from
$1,195

Explore the Virgin Islands on a Private Boat Charter

Stormy Pirates Captains are long-time residents of the Virgins Islands. Not only will they safely drive you around the islands, they will give you a …More

5.0 (371)

Explore the Virgin Islands on a Private Boat Charter

Stormy Pirates Captains are long-time residents of the Virgins Islands. Not only will they safely drive you around the islands, they will give you a...

6 hours

5.0 (371)

from
$1,195

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?