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 →

Great River Rafting Tour With Limestone Body Massage From Negril

Located in the hills of Hanover great river is an amazing river tour where guest are piloted on a 30 ft hand crafted bamboo raft, …More

Negril, Jamaica

5.0 (3)

Great River Rafting Tour With Limestone Body Massage From Negril

Located in the hills of Hanover great river is an amazing river tour where guest are piloted on a 30 ft hand crafted bamboo raft,...

1 to 2 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$140

Montego Bay City Cultural Tour, Highlights & Shopping

About this experience: Ready to go beyond the beach? Join us for an unforgettable journey through Montego Bay’s rich culture, colorful streets, and unique shopping …More

Montego Bay, Jamaica

5.0 (3)

Montego Bay City Cultural Tour, Highlights & Shopping

About this experience: Ready to go beyond the beach? Join us for an unforgettable journey through Montego Bay’s rich culture, colorful streets, and unique shopping...

3 to 5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$140

Experience the best of Ocho Rios with two unforgettable adventures: Beach Horseback Riding and Dunn's River Falls exploration. Feel the thrill as you saddle up …More

Ocho Rios, Jamaica

4.2 (5)

Beach Horseback Riding and Dunn’s River Falls

Experience the best of Ocho Rios with two unforgettable adventures: Beach Horseback Riding and Dunn's River Falls exploration. Feel the thrill as you saddle up...

4 hours Hotel pickup offered Free Cancellation

4.2 (5)

from
$140

Private Tour of Blue Hole in Ocho Rios from Montego Bay

Take the scenic drive along Jamaica's coast, through local communities and into the mountains of Ocho Rios to experience this must do adventure! The Blue …More

Montego Bay, Jamaica

5.0 (1)

Private Tour of Blue Hole in Ocho Rios from Montego Bay

Take the scenic drive along Jamaica's coast, through local communities and into the mountains of Ocho Rios to experience this must do adventure! The Blue...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$140

This is the ultimate authentic Jamaican experience. You will be greeted by your professional raft captain who aims to provide you with the best river …More

Montego Bay, Jamaica

5.0 (1)

Private Lethe Bamboo River Rafting Adventure Montego Bay Jamaica

This is the ultimate authentic Jamaican experience. You will be greeted by your professional raft captain who aims to provide you with the best river...

90 to 120 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$140

We provide the best experience for visitors to Jamaica. With our passion, we can help you get the most out of your vacation. You’ll get …More

Ocho Rios, Jamaica

5.0 (1)

Worthy Park Estate Rum Private Tour

We provide the best experience for visitors to Jamaica. With our passion, we can help you get the most out of your vacation. You’ll get...

1 to 2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$140

Yerette Nature Reserve and Caroni Wildlife Tour

Hummingbird enthusiasts will be enchanted by Yerette in the scenic Maracas Valley, a private sanctuary named after the Amerindian word for hummingbird. Set among silk …More

4.0 (2)

Yerette Nature Reserve and Caroni Wildlife Tour

Hummingbird enthusiasts will be enchanted by Yerette in the scenic Maracas Valley, a private sanctuary named after the Amerindian word for hummingbird. Set among silk...

8 hours Hotel pickup offered Free Cancellation

4.0 (2)

from
$140

Blue Hole and River Tubing from Ocho Rios

Relax and immerse yourself in the stunning natural beauty of hidden Jamaica as we set off on this nature excursion. Your adventure kicks off right …More

Kingston, Jamaica

4.0 (4)

Blue Hole and River Tubing from Ocho Rios

Relax and immerse yourself in the stunning natural beauty of hidden Jamaica as we set off on this nature excursion. Your adventure kicks off right...

5 hours Hotel pickup offered Free Cancellation

4.0 (4)

from
$140

Family Heritage Walking Tour in Old San Juan

Explore the historic Old San Juan on this exclusive private family walking tour, designed to delight both kids and adults. Wander through ancient streets, colorful …More

5.0 (18)

Family Heritage Walking Tour in Old San Juan

Explore the historic Old San Juan on this exclusive private family walking tour, designed to delight both kids and adults. Wander through ancient streets, colorful...

3 hours Free Cancellation

5.0 (18)

from
$139

Kingston Day Trip -Devon House, Bob Marley & Murals in Kingston.

YOU CANNOT MISS OUT ON THIS 4 IN 1 PACKAGE DEAL + A BONUS! Let us take you on a journey where you’ll get to …More

Kingston, Jamaica

5.0 (48)

Kingston Day Trip -Devon House, Bob Marley & Murals in Kingston.

YOU CANNOT MISS OUT ON THIS 4 IN 1 PACKAGE DEAL + A BONUS! Let us take you on a journey where you’ll get to...

6 hours Hotel pickup offered Free Cancellation

5.0 (48)

from
$139

Caving Exploration Adventure at Harrison's Cave

- Elbow pads, knee pads and helmets are provided - Participate in a 10-minute demonstration with the Spelunking Guide on the types of crawls you …More

5.0 (18)

Caving Exploration Adventure at Harrison's Cave

- Elbow pads, knee pads and helmets are provided - Participate in a 10-minute demonstration with the Spelunking Guide on the types of crawls you...

3 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (18)

from
$139

Negril PRIVATE CHARTER Catamaran (rate for 21 persons)

The minimum persons required to pay is 21 The private charter can accommodate up to 120 persons You may choose any 2 stops from the …More

Negril, Jamaica

4.9 (14)

Negril PRIVATE CHARTER Catamaran (rate for 21 persons)

The minimum persons required to pay is 21 The private charter can accommodate up to 120 persons You may choose any 2 stops from the...

4 hours Hotel pickup offered

4.9 (14)

from
$139

Blue Hole Waterfalls and Bamboo Rafting with Transportation

On this tour, you will get to experience the Blue Hole Secret Waterfalls and Bamboo River rafting on the Great White River. travel comfortably in …More

Ocho Rios, Jamaica

5.0 (5)

Blue Hole Waterfalls and Bamboo Rafting with Transportation

On this tour, you will get to experience the Blue Hole Secret Waterfalls and Bamboo River rafting on the Great White River. travel comfortably in...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$139

Private Nine Mile, Bob Marley Tour from Ocho Rios

Discover Nine Mile, the birthplace of reggae legend Bob Marley, on this private 5-hour tour. Visit Marley's home and take a tour led by Rastafarian …More

Kingston, Jamaica

5.0 (4)

Private Nine Mile, Bob Marley Tour from Ocho Rios

Discover Nine Mile, the birthplace of reggae legend Bob Marley, on this private 5-hour tour. Visit Marley's home and take a tour led by Rastafarian...

5 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$139

VIP Private Dunn's River Falls Ocho Rios Private Experience

What Makes This Tour Unique? This VIP Private Dunn’s River Falls Ocho Rios Experience is fully private and tailored to your pace — no large …More

Montego Bay, Jamaica

4.9 (18)

VIP Private Dunn's River Falls Ocho Rios Private Experience

What Makes This Tour Unique? This VIP Private Dunn’s River Falls Ocho Rios Experience is fully private and tailored to your pace — no large...

2 to 6 hours Hotel pickup offered Free Cancellation

4.9 (18)

from
$138

Private MEGA El Yunque Full Day Tour: Rainforest, Rivers, Beaches

Let's explore Puerto Rico's most amazing northeastern region and its 5 unique municipalities on our full-day private or semi-private (up to 6 pax. max.)cultural tour …More

5.0 (21)

Private MEGA El Yunque Full Day Tour: Rainforest, Rivers, Beaches

Let's explore Puerto Rico's most amazing northeastern region and its 5 unique municipalities on our full-day private or semi-private (up to 6 pax. max.)cultural tour...

8 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (21)

from
$138

Sailing Adventure Cruise from Montego Bay

Let's go sailing! Imagine diving into the crystal clear waters over a coral reef filled with exotic fish, turtles and starfish. You can even participate in …More

Montego Bay, Jamaica

5.0 (6)

Sailing Adventure Cruise from Montego Bay

Let's go sailing! Imagine diving into the crystal clear waters over a coral reef filled with exotic fish, turtles and starfish. You can even participate in...

4 hours

5.0 (6)

from
$138

Martha Brae River Rafting Private Tour with Transportation

The Martha Brae River is one of Jamaica, most popular rafting mainly because of the Legend of the Martha Brae River. (Martha) the river Located …More

Lucea, Jamaica

5.0 (6)

Martha Brae River Rafting Private Tour with Transportation

The Martha Brae River is one of Jamaica, most popular rafting mainly because of the Legend of the Martha Brae River. (Martha) the river Located...

1 to 2 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$138

Private Blue Hole Mineral Spring Tour From Montego Bay

Experience the thrill of jumping off the cliff (or climb down a ladder) 22 ft. to swim in Blue Hole's cool mineral water reputed to …More

Montego Bay, Jamaica

5.0 (2)

Private Blue Hole Mineral Spring Tour From Montego Bay

Experience the thrill of jumping off the cliff (or climb down a ladder) 22 ft. to swim in Blue Hole's cool mineral water reputed to...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$138

9 mile Bob Marley Musoleum Private Day Trip From Montego Bay

If your a true Bob Marley fan, then why not check out his Birth place in nine mile St Ann’s . It’s a long adventurous …More

Montego Bay, Jamaica

3.0 (1)

9 mile Bob Marley Musoleum Private Day Trip From Montego Bay

If your a true Bob Marley fan, then why not check out his Birth place in nine mile St Ann’s . It’s a long adventurous...

2 to 3 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$138

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?