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: Clear Kayak Photoshoot in Montego Bay (Single) San Juan’s Historic Streets Audio Guided Walking Tour Blue Hole Falls & White River Tubing from Falmouth Jamaica Private Rio Bueno River Adventure from Runaway Bay Hotels Flying Dress Photoshoot in Jamaica

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 →

Explore St Maarten Shore and part of nature reserve of St Martin on a 3.5 - hour speedboat and snorkeling trip. With your expert captain …More

Private Snorkeling Charter to Creole Rock 3 hours

Explore St Maarten Shore and part of nature reserve of St Martin on a 3.5 - hour speedboat and snorkeling trip. With your expert captain...

3 hours 30 minutes Free Cancellation

from
$1,250

Deep Sea Fishing Private Boat Charter in San Juan

Experience some of the greatest sport fishing waters in the world when you take a full day or half day fishing charter from San Juan, …More

4.6 (10)

Deep Sea Fishing Private Boat Charter in San Juan

Experience some of the greatest sport fishing waters in the world when you take a full day or half day fishing charter from San Juan,...

4 hours Free Cancellation

4.6 (10)

from
$1,282

Private Catamaran Sunset Cruise from St Lucia for Up to 15 Guests

View the famous green flash! If it’s in the eyes of that special someone, celebrating a special occasion or with a group of friends, there's …More

Choc, St Lucia

5.0 (13)

Private Catamaran Sunset Cruise from St Lucia for Up to 15 Guests

View the famous green flash! If it’s in the eyes of that special someone, celebrating a special occasion or with a group of friends, there's...

2 hours Free Cancellation

5.0 (13)

from
$1,285

Discover Barbados with Inaja's Transport and Tours

Well-regarded operator with over 15 years of experience and proven track record of customer satisfaction, excellent customer service, knowledge of Barbados …More

4.2 (5)

Discover Barbados with Inaja's Transport and Tours

Well-regarded operator with over 15 years of experience and proven track record of customer satisfaction, excellent customer service, knowledge of Barbados...

3 to 4 hours Free Cancellation

4.2 (5)

from
$1,287

Full Day Saint Thomas Private Group Excursion

A customized sightseeing tour with us is the way to go as you can customize your tour to what you want for you and your …More

Cruz Bay, US Virgin Islands

4.0 (4)

Full Day Saint Thomas Private Group Excursion

A customized sightseeing tour with us is the way to go as you can customize your tour to what you want for you and your...

5 to 7 hours Hotel pickup offered Free Cancellation

4.0 (4)

from
$1,295

Private Clear Boat experience in Grace Bay

Come aboard our truly unique 100% Clear Boats. These are NOT your average glass bottom boat but a 100% clear boat. This tour is for …More

5.0 (5)

Private Clear Boat experience in Grace Bay

Come aboard our truly unique 100% Clear Boats. These are NOT your average glass bottom boat but a 100% clear boat. This tour is for...

1 hour 15 minutes Free Cancellation

5.0 (5)

from
$1,299

Create-Your-Own Luxury Adventure in Bimini with photographer

The Be Your Own Captain adventures offer guests the perfect opportunity to enjoy the turquoise waters at their own pace and in complete privacy. Whether …More

5.0 (4)

Create-Your-Own Luxury Adventure in Bimini with photographer

The Be Your Own Captain adventures offer guests the perfect opportunity to enjoy the turquoise waters at their own pace and in complete privacy. Whether...

3 hours Free Cancellation

5.0 (4)

from
$1,300

Grand Cayman Private Customized Bus Tour

Gather a group of friends or family and get ready to explore Grand Cayman at your own pace on this 3 hour private guided bus …More

Grand Cayman, Cayman Islands

5.0 (4)

Grand Cayman Private Customized Bus Tour

Gather a group of friends or family and get ready to explore Grand Cayman at your own pace on this 3 hour private guided bus...

3 hours Free Cancellation

5.0 (4)

from
$1,300

Visit the famous Dunn's River Falls on an exhilarating day tour from Negril. Cool off in the natural freshwater pools, climb around the series of …More

Negril, Jamaica

Negril to Dunn's River Small Group Tour

Visit the famous Dunn's River Falls on an exhilarating day tour from Negril. Cool off in the natural freshwater pools, climb around the series of...

7 hours Hotel pickup offered Free Cancellation

from
$1,300

Private Boat Charter Saint Martin & natural reserve

Private boat with captain to discover SAINT MARTIN Discover our new private charter boat, ready to take you for an unforgettable day at sea! You …More

5.0 (7)

Private Boat Charter Saint Martin & natural reserve

Private boat with captain to discover SAINT MARTIN Discover our new private charter boat, ready to take you for an unforgettable day at sea! You...

7 to 8 hours Free Cancellation

5.0 (7)

from
$1,312

Private Yacht for Excursions in Punta Cana, Snorkeling and Booze

The yatch comes equipped with air conditioner, plasma TV, bathroom, full kitchen, amazing stereo system, wifi, king size bed, two couches, snorkeling equipment, two paddle …More

5.0 (26)

Private Yacht for Excursions in Punta Cana, Snorkeling and Booze

The yatch comes equipped with air conditioner, plasma TV, bathroom, full kitchen, amazing stereo system, wifi, king size bed, two couches, snorkeling equipment, two paddle...

3 hours Hotel pickup offered Free Cancellation

5.0 (26)

from
$1,350

Full Charter All Inclusive for Icacos and Palomino

The day includes visiting Icacos and Palomino, where we will go on a guided snorkeling tour at Tortuga Reef, and then we will visit two …More

Fajardo, Puerto Rico

5.0 (8)

Full Charter All Inclusive for Icacos and Palomino

The day includes visiting Icacos and Palomino, where we will go on a guided snorkeling tour at Tortuga Reef, and then we will visit two...

7 hours 30 minutes Free Cancellation

5.0 (8)

from
$1,350

Punta Cana Sunset Private Yacht Cruise with BBQ and Open Bar

Enjoy an unforgettable experience with our sunset yacht excursion in Punta Cana. Sail through the crystal-clear Caribbean waters as the sun sets on the horizon, …More

Punta Cana, Dominican Republic

Punta Cana Sunset Private Yacht Cruise with BBQ and Open Bar

Enjoy an unforgettable experience with our sunset yacht excursion in Punta Cana. Sail through the crystal-clear Caribbean waters as the sun sets on the horizon,...

4 hours Hotel pickup offered Free Cancellation

from
$1,360

Enjoy a wonderful and unforgettable boat trip in the clear blue waters of St Martin. On our eye-catching 30ft speedboat, you will get to appreciate …More

5.0 (4)

Full Day Private Sxm Boat Charter

Enjoy a wonderful and unforgettable boat trip in the clear blue waters of St Martin. On our eye-catching 30ft speedboat, you will get to appreciate...

6 to 7 hours Free Cancellation

5.0 (4)

from
$1,362

Love Story Photoshoot: A Romantic Couples’ Experience In Ponce’s Most Beautiful Locations With Profesional Photographer, Private Driver and Transportation In Luxury Black Sedan. Celebrate your …More

Private Love Story Photoshoot for Couples in Ponce

Love Story Photoshoot: A Romantic Couples’ Experience In Ponce’s Most Beautiful Locations With Profesional Photographer, Private Driver and Transportation In Luxury Black Sedan. Celebrate your...

6 hours Hotel pickup offered Free Cancellation

from
$1,399

Private Powerboat Tour - The Best Customizable Tour In The BVI!

Sleek, and spirited — the go-anywhere, do-anything powerboat for those who prefer spontaneity over schedule. It beaches where others can’t, slips into hidden lagoons, and …More

Tortola, British Virgin Islands

5.0 (7)

Private Powerboat Tour - The Best Customizable Tour In The BVI!

Sleek, and spirited — the go-anywhere, do-anything powerboat for those who prefer spontaneity over schedule. It beaches where others can’t, slips into hidden lagoons, and...

5 hours 30 minutes Free Cancellation

5.0 (7)

from
$1,400

Fajardo: Full-Day Private Fishing Charter with Snorkeling, Beach

This Inshore Fishing Trip is designed by Pure Adventure’s Marine Biologist and fishing experts to ensure a sure catch in a short period, so everybody …More

Fajardo, Puerto Rico

5.0 (3)

Fajardo: Full-Day Private Fishing Charter with Snorkeling, Beach

This Inshore Fishing Trip is designed by Pure Adventure’s Marine Biologist and fishing experts to ensure a sure catch in a short period, so everybody...

7 hours Free Cancellation

5.0 (3)

from
$1,400

Sail with captain Carl, safely along the calm, beautiful, majestic blue green beaches of Aruba. Let us show you historical shipwrecks, colorful sea animals and …More

5.0 (25)

Private Boat Tour in Aruba

Sail with captain Carl, safely along the calm, beautiful, majestic blue green beaches of Aruba. Let us show you historical shipwrecks, colorful sea animals and...

5 to 6 hours Free Cancellation

5.0 (25)

from
$1,400

Benefit from a power boat excursion around the island of Anguilla that allows you to access multiple gorgeous bays and beaches just in one day. …More

5.0 (2)

Anguilla Beach Hopping Private Charter

Benefit from a power boat excursion around the island of Anguilla that allows you to access multiple gorgeous bays and beaches just in one day. ...

6 hours Free Cancellation

5.0 (2)

from
$1,400

Catalina Island awaits with its stunning beaches and crystal-clear waters on this half or full-day private yacht cruise. Begin with convenient pickup from your hotel …More

Half Day Private Yacht Cruise to Catalina Island with Snorkeling

Catalina Island awaits with its stunning beaches and crystal-clear waters on this half or full-day private yacht cruise. Begin with convenient pickup from your hotel...

4 hours Free Cancellation

from
$1,400

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?