Top Caribbean Multi-day & Extended Tours

Q: I need a ride! Which Caribbean Multi-day & Extended Tours have Hotel Pickup?

No problem. These Caribbean Multi-day & Extended Tours include Hotel Pickup: ATV o Buggy Adventure and Hip Hop Party Boat Combo with Open Bar Private Tour from Ocho Rios to Negril Beach and Ricks Cafe Dunn's River Falls and Ocho Rios Sightseeing with Shopping St Lucia Private Custom Tour The Grand Circle 24-Hour All-Inclusive Island Experience 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 →

Multi Day tour with Catamaran and Rick's Cafe from Montego Bay

Basically, this offers you the option of booking with the same company for two separate days so day 1 we pick you up take you …More

Montego Bay, Jamaica

5.0 (1)

Multi Day tour with Catamaran and Rick's Cafe from Montego Bay

Basically, this offers you the option of booking with the same company for two separate days so day 1 we pick you up take you...

2 days Hotel pickup offered Free Cancellation

5.0 (1)

from
$285

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a …More

Ocho Rios, Jamaica

5.0 (1)

All day Tour of Ocho Rios

This is the most wonderful tour in Jamaica right now on the north coast of thd island just come and experience it Consisting of a...

2 days Hotel pickup offered

5.0 (1)

from
$250

"1-Day Hike & Camp with Turtle Watching at Paria Bay"

Looking for an unforgettable overnight adventure? Join us as we journey to Paria Bay, one of the most breathtaking spots on the island. You'll have …More

5.0 (1)

"1-Day Hike & Camp with Turtle Watching at Paria Bay"

Looking for an unforgettable overnight adventure? Join us as we journey to Paria Bay, one of the most breathtaking spots on the island. You'll have...

2 days Hotel pickup offered Free Cancellation

5.0 (1)

from
$160

Dominican Republic: See Almost it ALL in 6 Days, 1st Class Custom Tours

You absolutely will not find another tour out there as packed with activities and attractions as this one, provided by CharlieTheTraveler. You will also not …More

Punta Cana, Dominican Republic

5.0 (1)

Dominican Republic: See Almost it ALL in 6 Days, 1st Class Custom Tours

You absolutely will not find another tour out there as packed with activities and attractions as this one, provided by CharlieTheTraveler. You will also not...

6 days

5.0 (1)

from
$2,963

Multi-day Barbados 4WD Tour from Accra Beach Hotel

Experience, culture, and history of the Bajan on Barbados all-inclusive family vacation. Take in scenic views and splendid architecture, feast on the delicious local cuisine, …More

5.0 (1)

Multi-day Barbados 4WD Tour from Accra Beach Hotel

Experience, culture, and history of the Bajan on Barbados all-inclusive family vacation. Take in scenic views and splendid architecture, feast on the delicious local cuisine,...

7 days Hotel pickup offered

5.0 (1)

from
$3,900

Departure Shuttle to Airport, Club Mobay Fast Track & VIP Lounge Combo

Make travel out of Montego Bay’s Sangster International Airport comfy and hassle-free. This package gives you access to the VIP Club Mobay airport departure lounge; …More

Ocho Rios, Jamaica

4.6 (28)

Departure Shuttle to Airport, Club Mobay Fast Track & VIP Lounge Combo

Make travel out of Montego Bay’s Sangster International Airport comfy and hassle-free. This package gives you access to the VIP Club Mobay airport departure lounge;...

1 day Hotel pickup offered

4.6 (28)

from
$60

The Ultimate Self-Guided Hidden Gems Tour in Puerto Rico

Discover the 20 most spectacular spots locals love — and tourists almost never find. Hidden and famous beaches, crystal-clear rivers, magical caves, and must visit …More

4.7 (18)

The Ultimate Self-Guided Hidden Gems Tour in Puerto Rico

Discover the 20 most spectacular spots locals love — and tourists almost never find. Hidden and famous beaches, crystal-clear rivers, magical caves, and must visit...

4 days

4.7 (18)

from
$5

Grenada Grenadines: 7-Day Skippered Catamaran Charter Cruise

With this 7 days itinerary, you will experience the best of Grenada's Grenadines. Our luxury catamaran is fully equipped to make sure you can fully …More

4.7 (6)

Grenada Grenadines: 7-Day Skippered Catamaran Charter Cruise

With this 7 days itinerary, you will experience the best of Grenada's Grenadines. Our luxury catamaran is fully equipped to make sure you can fully...

7 days

4.7 (6)

from
$13,000

Jamaica Bob Sled, Blue Hole & Bob Marley Nine Miles, 3 Tours from Ocho Rios

Add a hassle free, 3 days adventure tour package to your vacation in the beautiful town of Ocho Rios. Experience Bob Sled at Mystic Mountain, Blue …More

Ocho Rios, Jamaica

4.0 (1)

Jamaica Bob Sled, Blue Hole & Bob Marley Nine Miles, 3 Tours from Ocho Rios

Add a hassle free, 3 days adventure tour package to your vacation in the beautiful town of Ocho Rios. Experience Bob Sled at Mystic Mountain, Blue...

3 days Free Cancellation

4.0 (1)

from
$303

Unlock the most spectacular spots locals love — and tourists miss completely. From crystal-clear beaches and scenic rivers to legendary landmarks and off-the-map natural escapes. …More

3.3 (4)

Puerto Rico West Coast Self Guided Tour

Unlock the most spectacular spots locals love — and tourists miss completely. From crystal-clear beaches and scenic rivers to legendary landmarks and off-the-map natural escapes....

3 days

3.3 (4)

from
$5

Unique in Saint Martin, embark on our private cruise catamaran for you and let yourself be carried away in this romantic and idyllic setting, with …More

St Martin Gd-Case, Private Romantic Cruise 4 days

Unique in Saint Martin, embark on our private cruise catamaran for you and let yourself be carried away in this romantic and idyllic setting, with...

4 days

from
$6,146

Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation …More

Ocho Rios, Jamaica

Blue Mountains, Port Royal and Kingston 2-Day Tour from Ocho Rios

Leave Ocho Rios behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation...

2 days Hotel pickup offered Free Cancellation

from
$1,077

5 Day Package to Santiago and Puerto Plata with Accommodation

Immerse yourself in the Dominican essence with our exclusive 4 nights and 5 days package! Start your adventure in the heart of Santiago de los …More

Puerto Plata, Dominican Republic

5 Day Package to Santiago and Puerto Plata with Accommodation

Immerse yourself in the Dominican essence with our exclusive 4 nights and 5 days package! Start your adventure in the heart of Santiago de los...

5 days Free Cancellation

from
$3,440

7-Day Bus Tour Across Jamaica from Montego Bay

Experience Jamaica, its people, places, culture, heritage and delicious local cuisines! Travel along coastal roads with the blue Caribbean Sea as your backdrop. Pass through …More

Montego Bay, Jamaica

7-Day Bus Tour Across Jamaica from Montego Bay

Experience Jamaica, its people, places, culture, heritage and delicious local cuisines! Travel along coastal roads with the blue Caribbean Sea as your backdrop. Pass through...

7 days Free Cancellation

from
$2,769

Blue Mountains, Port Royal and Kingston 2-Day Tour from Runaway Bay

Leave Runaway Bay behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation …More

Runaway Bay, Jamaica

Blue Mountains, Port Royal and Kingston 2-Day Tour from Runaway Bay

Leave Runaway Bay behind and see the UNESCO World Heritage panoramic Blue Mountains, visit historic city of Kingston member of the Creative Cities Network Organisation...

2 days Hotel pickup offered Free Cancellation

from
$1,128

A 9 Day Private Tour Experience in Jamaica

Exploring Jamaica on this 9-day sightseeing vacation tour package which will take you across Jamaica to experience some of the most amazing locations the island …More

Ocho Rios, Jamaica

A 9 Day Private Tour Experience in Jamaica

Exploring Jamaica on this 9-day sightseeing vacation tour package which will take you across Jamaica to experience some of the most amazing locations the island...

9 days Hotel pickup offered Free Cancellation

from
$3,750

Experience nature and the beauty of Jamaica with the Family Eco Adventure Tour, a true learning experience for both you and the family. Best of …More

Ocho Rios, Jamaica

Island Explorer 7 Days North Coast Tour

Experience nature and the beauty of Jamaica with the Family Eco Adventure Tour, a true learning experience for both you and the family. Best of...

7 days Hotel pickup offered Free Cancellation

from
$2,750

When was the last time you went out for a casual drive and ended up inside a volcano? A surreal scenario comes to life at …More

Discover St.Lucia Multi day Tour

When was the last time you went out for a casual drive and ended up inside a volcano? A surreal scenario comes to life at...

5 days Hotel pickup offered Free Cancellation

from
$1,200

This Multi-day Group Tour Will Take You To 6 Of The Best Beaches Of The Dominican Republic in 7 Days. It Includes All The Basics …More

7 Days, 6 Beaches: All-Inclusive Dominican Escape

This Multi-day Group Tour Will Take You To 6 Of The Best Beaches Of The Dominican Republic in 7 Days. It Includes All The Basics...

7 days

from
$2,199

5-Day Luxury ADULT ONLY Vacation in Negril

Embark on an unforgettable Jamaican journey starting with a luxurious 5-day stay at Hedonism II, where indulgence reigns supreme. Then, venture to the iconic Rick's …More

Montego Bay, Jamaica

5-Day Luxury ADULT ONLY Vacation in Negril

Embark on an unforgettable Jamaican journey starting with a luxurious 5-day stay at Hedonism II, where indulgence reigns supreme. Then, venture to the iconic Rick's...

5 days Hotel pickup offered Free Cancellation

from
$2,150

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Caribbean Multi-day & Extended Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Multi-day & Extended Tours are:

What are the best kid-friendly options for Caribbean Multi-day & Extended Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Multi-day & Extended Tours are:

View all kid-friendly Tours →

Which Caribbean Multi-day & Extended Tours have Instant Confirmation?

Caribbean Multi-day & Extended Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Caribbean Multi-day & Extended Tours have Free Cancellation?

Caribbean Multi-day & Extended 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 Multi-day & Extended Tours have Hotel Pickup?

Got any more Caribbean trip ideas?

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