Top Caribbean Private Sightseeing Tours

Q: Which Caribbean Private Sightseeing Tours have Instant Confirmation?

Caribbean Private Sightseeing Tours with Instant Confirmation include: Private Eleuthera Island: Swim With Pigs, Turtles & Stingrays Private Exuma Cays Day: Iguana, Shark, Pigs, Sandbar & Lunch 5-Day Private Tour in The Bahamas with Pickup Yacht YES DARLING - Private Boat St Martin, St Barth & Anguilla St Martin Gd-Case, Private Romantic Cruise 4 days View all Tours with Instant Confirmation →

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 →

Book your appointment today and let Krystal Kayaks take care of the rest for you. We will assist in all your poses in the clear …More

Lucea, Jamaica

5.0 (25)

Montego Bay Kayak Boys

Book your appointment today and let Krystal Kayaks take care of the rest for you. We will assist in all your poses in the clear...

1 hour 30 minutes Hotel pickup offered Free Cancellation

5.0 (25)

from
$99

VIP Dunn River Falls and Blue Hole Experience

Experience Jamaica’s most breathtaking adventure in VIP style with our Luxury Dunn’s River Falls & Blue Hole Experience. Travel in a private, air-conditioned vehicle with …More

Trelawny, Jamaica

5.0 (13)

VIP Dunn River Falls and Blue Hole Experience

Experience Jamaica’s most breathtaking adventure in VIP style with our Luxury Dunn’s River Falls & Blue Hole Experience. Travel in a private, air-conditioned vehicle with...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (13)

from
$99

Private E-bike Adventure Tours of Barbados

Just get on one of our amazing fat-tire electric bikes and you will feel like a kid again. But with one big difference, our Ebikes …More

4.2 (32)

Private E-bike Adventure Tours of Barbados

Just get on one of our amazing fat-tire electric bikes and you will feel like a kid again. But with one big difference, our Ebikes...

2 to 3 hours

4.2 (32)

from
$99

Irie Bamboo Rafting Tour on Great River Private!

You will travel into the hills to the small village of Lethe, where you’ll find the perfect setting of land and water. With picturesque views …More

Lucea, Jamaica

5.0 (1)

Irie Bamboo Rafting Tour on Great River Private!

You will travel into the hills to the small village of Lethe, where you’ll find the perfect setting of land and water. With picturesque views...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$99

Rose Hall Great House and Scotchies Private Tour from Montegobay

Experience the enchanting allure of Rose Hall Great House, where history meets mystery in the heart of Jamaica. Step back in time as you explore …More

Montego Bay, Jamaica

5.0 (1)

Rose Hall Great House and Scotchies Private Tour from Montegobay

Experience the enchanting allure of Rose Hall Great House, where history meets mystery in the heart of Jamaica. Step back in time as you explore...

2 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$99

Montego Bay’s Night Life Clubbing: Lounge 27/27 | Pier 1 | Taboo

Dance the night away on the Hip Strip in Montego Bay at the hottest clubs in town on our nightlife adventure. Some of the most …More

Trelawny, Jamaica

5.0 (1)

Montego Bay’s Night Life Clubbing: Lounge 27/27 | Pier 1 | Taboo

Dance the night away on the Hip Strip in Montego Bay at the hottest clubs in town on our nightlife adventure. Some of the most...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$99

Santo Domingo Private Tour from Punta Cana

Go with your group , family or friends (minimum 3 people up to 15) to Santo Dominingo City Colonial Day tour with the best. Spend …More

Punta Cana, Dominican Republic

4.1 (9)

Santo Domingo Private Tour from Punta Cana

Go with your group , family or friends (minimum 3 people up to 15) to Santo Dominingo City Colonial Day tour with the best. Spend...

8 to 10 hours Hotel pickup offered Free Cancellation

4.1 (9)

from
$99

Climb Aboard the Ultimate Party Bus Experience in the Bahamas! Get ready for an unforgettable night out as we roll through New Providence’s hottest weekend …More

Nassau, Bahamas

5.0 (1)

Bahamas Funtastic Party Bus Tours

Climb Aboard the Ultimate Party Bus Experience in the Bahamas! Get ready for an unforgettable night out as we roll through New Providence’s hottest weekend...

3 hours 30 minutes Free Cancellation

5.0 (1)

from
$99

The Tet Paul Nature Trail is one of St. Lucia’s most beloved walking trails. A tour Offering a unique combination of history, adventure, exquisite plant …More

Cap Estate, St Lucia

3.8 (5)

Tet Paul Nature Trail Tour

The Tet Paul Nature Trail is one of St. Lucia’s most beloved walking trails. A tour Offering a unique combination of history, adventure, exquisite plant...

45 to 60 minutes Hotel pickup offered Free Cancellation

3.8 (5)

from
$98

Private Half-Day Tour to El Yunque Rainforest

A private tour of the El Yunque Rain Forest We will drive through the only tropical rain forest within the US. See some of the …More

Luquillo, Puerto Rico

5.0 (25)

Private Half-Day Tour to El Yunque Rainforest

A private tour of the El Yunque Rain Forest We will drive through the only tropical rain forest within the US. See some of the...

4 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$98

Private fun fill tour from Montego Bay to dunns river & blue hole

Booking with me means you'll get an authentic Jamaican experience tailored to showcase the best of what my country has to offer. As a local, …More

Trelawny, Jamaica

5.0 (25)

Private fun fill tour from Montego Bay to dunns river & blue hole

Booking with me means you'll get an authentic Jamaican experience tailored to showcase the best of what my country has to offer. As a local,...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$98

Discover Old San Juan: A Private Half-Day Tour

Step into the soul of Puerto Rico with this customizable private tour of Old San Juan. With comfortable transportation and a flexible itinerary, you’ll explore …More

Isla Verde, Puerto Rico

5.0 (5)

Discover Old San Juan: A Private Half-Day Tour

Step into the soul of Puerto Rico with this customizable private tour of Old San Juan. With comfortable transportation and a flexible itinerary, you’ll explore...

4 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$98

Private Transportation from Montego Bay to Mystic Mountain and Dunn's River Fall

This tour is a private compact tour filled with excursions allot of things to do. Both tour spot duns river fall and mystic mountain adventure …More

Montego Bay, Jamaica

4.9 (12)

Private Transportation from Montego Bay to Mystic Mountain and Dunn's River Fall

This tour is a private compact tour filled with excursions allot of things to do. Both tour spot duns river fall and mystic mountain adventure...

2 to 4 hours Hotel pickup offered Free Cancellation

4.9 (12)

from
$98

We’re not just another tour we’re your gateway to the real Bahamas! With thrilling rides, hidden gems, and a personal touch that no big company …More

Nassau, Bahamas

4.6 (25)

Ride Paradise Live Adventure and ATV Tours at Nassau Bahamas

We’re not just another tour we’re your gateway to the real Bahamas! With thrilling rides, hidden gems, and a personal touch that no big company...

3 to 4 hours Hotel pickup offered Free Cancellation

4.6 (25)

from
$98

Cocoa & Artisan Chocolate Route with an Historical Tour in Puerto Plata City

Experience the Cocoa production process from planting to harvesting. We invite you to enjoy through your senses one of the secrets that surround this great …More

Puerto Plata, Dominican Republic

4.4 (11)

Cocoa & Artisan Chocolate Route with an Historical Tour in Puerto Plata City

Experience the Cocoa production process from planting to harvesting. We invite you to enjoy through your senses one of the secrets that surround this great...

6 hours Hotel pickup offered Free Cancellation

4.4 (11)

from
$98

Private Transportation from Montego Bay to White River Tubing and Blue Hole

- Great Tour for Family - Travelers Seeking Adventure - Affordable Price for a Customized Adventure Tour - Tour Provides a Dedicated and down to …More

Montego Bay, Jamaica

5.0 (2)

Private Transportation from Montego Bay to White River Tubing and Blue Hole

- Great Tour for Family - Travelers Seeking Adventure - Affordable Price for a Customized Adventure Tour - Tour Provides a Dedicated and down to...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$98

Grand Turk Eco-Tourism Clear Kayak Tour!

Indulge on a breathtaking experience through the vibrant mangrove eco system in north creek which is considered the largest natural inlet in the Caribbean! , …More

3.2 (14)

Grand Turk Eco-Tourism Clear Kayak Tour!

Indulge on a breathtaking experience through the vibrant mangrove eco system in north creek which is considered the largest natural inlet in the Caribbean! ,...

1 hour 20 minutes Free Cancellation

3.2 (14)

from
$98

Luminous Lagoon and Rose Hall Haunted Night Tour from Runaway Bay

If you're looking for something to do in Jamaica, the Rose Hall Great House is a great choice. You’re sure to feel goosebumps as these …More

Runaway Bay, Jamaica

5.0 (1)

Luminous Lagoon and Rose Hall Haunted Night Tour from Runaway Bay

If you're looking for something to do in Jamaica, the Rose Hall Great House is a great choice. You’re sure to feel goosebumps as these...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$97

St. Lucia Private Sunset Cruise - Marigot Bay and Rodney Bay

Romantic Private Sunset Cruise in St. Lucia. The Perfect End to Your Day! Imagine a serene evening on the tranquil Caribbean Sea, sailing along St. …More

Marigot Bay, St Lucia

5.0 (12)

St. Lucia Private Sunset Cruise - Marigot Bay and Rodney Bay

Romantic Private Sunset Cruise in St. Lucia. The Perfect End to Your Day! Imagine a serene evening on the tranquil Caribbean Sea, sailing along St....

2 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$97

Rockland Bird Sanctuary plus Montego Bay Highlights & Shopping Private Tour

Bird lovers will find this tour very fascinating as many different birds will fly from trees to the ground for you to feed them.( This …More

Montego Bay, Jamaica

5.0 (5)

Rockland Bird Sanctuary plus Montego Bay Highlights & Shopping Private Tour

Bird lovers will find this tour very fascinating as many different birds will fly from trees to the ground for you to feed them.( This...

3 to 5 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$97

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?

No problem. These Caribbean Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?