Top Caribbean Outdoor Activities

Q: Which Caribbean Outdoor Activities have Instant Confirmation?

Caribbean Outdoor Activities with Instant Confirmation include: Private Airport Transfers Roundtrip Punta Cana Hotels Punta Cana & Bávaro Private Transportation Secret Spots in North Puerto Rico: Self Guided Tour Puerto Rico West Coast Self Guided Tour JET SKI, Skim Board,& Wave Board Rentals Cabarete, Sosua View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Outdoor Activities have Hotel Pickup?

No problem. These Caribbean Outdoor Activities include Hotel Pickup: Private Airport Transfers Roundtrip Punta Cana Hotels Punta Cana & Bávaro Private Transportation Great River Raft and Full Limestone body Massage In Montego Bay Margaritaville/Jeski Tour or Snorkeling in Montego Bay Nature and Sightseeing at Phantasea Tropical Botanical Garden 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 →

Half or 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 29' or 32' Power Catamaran and explore the very best of …More

5.0 (156)

Half or 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 29' or 32' Power Catamaran and explore the very best of...

3 hours 30 minutes Free Cancellation

5.0 (156)

from
$895

Discover Puerto Rico Private 3 Day Package with hotel pickup

Have you discovered Puerto Rico? The Island inspires visitors to enjoy its hidden treasures, rainforests, hiking trails, pristine beaches, and many only-in-Puerto Rico wonders. With …More

Luquillo, Puerto Rico

5.0 (6)

Discover Puerto Rico Private 3 Day Package with hotel pickup

Have you discovered Puerto Rico? The Island inspires visitors to enjoy its hidden treasures, rainforests, hiking trails, pristine beaches, and many only-in-Puerto Rico wonders. With...

3 days Free Cancellation

5.0 (6)

from
$900

All inclusive Private Tour to Icacos and Palomino Island

UP TO 6 GUESTS ON YOUR PRIVATE CHARTER We are USCG certified vessel with years of experience in the east coast islands of PR including …More

Fajardo, Puerto Rico

5.0 (64)

All inclusive Private Tour to Icacos and Palomino Island

UP TO 6 GUESTS ON YOUR PRIVATE CHARTER We are USCG certified vessel with years of experience in the east coast islands of PR including...

4 hours Free Cancellation

5.0 (64)

from
$900

Private Bermuda Boat Charter Cliff Jumping, Islands & Sightseeing

Our boat "Island Vibez" is small enough to go where a lot of the larger charter boats cannot, yet she is extremely spacious and comfortable. …More

5.0 (74)

Private Bermuda Boat Charter Cliff Jumping, Islands & Sightseeing

Our boat "Island Vibez" is small enough to go where a lot of the larger charter boats cannot, yet she is extremely spacious and comfortable....

3 hours Free Cancellation

5.0 (74)

from
$900

Step aboard our 35’ Donzi center console for a private Cayman Islands adventure built entirely around you. A spacious layout, premium sound system, comfortable seating, …More

Grand Cayman, Cayman Islands

4.9 (26)

Private Boat Charter in Cayman Islands

Step aboard our 35’ Donzi center console for a private Cayman Islands adventure built entirely around you. A spacious layout, premium sound system, comfortable seating,...

3 hours Free Cancellation

4.9 (26)

from
$900

Customizable PRIVATE TOUR for a maximum of 7 passengers. Departure Cruise ship terminal Main City Fort de Fance /North Island Private tour, Visit the rain …More

5.0 (11)

Martinique North Island Private Tour

Customizable PRIVATE TOUR for a maximum of 7 passengers. Departure Cruise ship terminal Main City Fort de Fance /North Island Private tour, Visit the rain...

6 hours

5.0 (11)

from
$910

This is a private tour only your guests will participate, with a maximum of 7 passengers. Departure Cruise ship Terminal Main city fort de France. …More

5.0 (4)

Martinique South Island Private Tour

This is a private tour only your guests will participate, with a maximum of 7 passengers. Departure Cruise ship Terminal Main city fort de France....

6 hours

5.0 (4)

from
$910

Nassau Half Day Deep Sea and Light Tackle Fishing Charter

This is a great opportunity to get out on the open seas with our certified professional crew that puts your safety and concerns first and …More

4.0 (3)

Nassau Half Day Deep Sea and Light Tackle Fishing Charter

This is a great opportunity to get out on the open seas with our certified professional crew that puts your safety and concerns first and...

4 hours Free Cancellation

4.0 (3)

from
$920

Private Bahamas Half-Day Fishing Tour from New Providence

Depart Paradise Island on a comfortable 32ft Luhrs. Enjoy a short 20 minute ride where you can begin to set out your lines. You can …More

4.4 (12)

Private Bahamas Half-Day Fishing Tour from New Providence

Depart Paradise Island on a comfortable 32ft Luhrs. Enjoy a short 20 minute ride where you can begin to set out your lines. You can...

4 hours Free Cancellation

4.4 (12)

from
$925

Private 3-hour Stingray City Charter - Grand Cayman - BTC

Join us on your own private boat with our experienced Captain and crew of 16+ years. We will take you out to the crystal clear …More

Grand Cayman, Cayman Islands

5.0 (36)

Private 3-hour Stingray City Charter - Grand Cayman - BTC

Join us on your own private boat with our experienced Captain and crew of 16+ years. We will take you out to the crystal clear...

3 hours Free Cancellation

5.0 (36)

from
$930

1 Hour Private Parasailing Charter, Grace Bay, Providenciales

Parasailing has always been a group activity, however, due to the recent global pandemic, travelers are now seeking to do adventures that allow them to …More

5.0 (26)

1 Hour Private Parasailing Charter, Grace Bay, Providenciales

Parasailing has always been a group activity, however, due to the recent global pandemic, travelers are now seeking to do adventures that allow them to...

1 hour Hotel pickup offered Free Cancellation

5.0 (26)

from
$950

1. Educated tour guides to ensure you receive maximize experience and knowledge to any questions. 2. You will be in charge of your tour, having …More

5.0 (31)

Nassau Private Boat Tours

1. Educated tour guides to ensure you receive maximize experience and knowledge to any questions. 2. You will be in charge of your tour, having...

4 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$950

Make your Bonaire island vacation even more exciting with a deep-sea fishing trip. Book a 4, 5, 6, or 8-hour morning charter or a 4-hour …More

Kralendijk, Bonaire

5.0 (17)

Bonaire Calypso Fishing Charters

Make your Bonaire island vacation even more exciting with a deep-sea fishing trip. Book a 4, 5, 6, or 8-hour morning charter or a 4-hour...

4 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$950

We from Awa Salu Kiteboarding Curacao, offer you premium, high quality kite lessons. We are looking out for you with a high focus on technique …More

5.0 (34)

A Bunch of Kitecontrol

We from Awa Salu Kiteboarding Curacao, offer you premium, high quality kite lessons. We are looking out for you with a high focus on technique...

2 hours Free Cancellation

5.0 (34)

from
$950

4 hours 34ft Day Dream Private Charter in Nassau

Join on this private charter aboard 34ft Day Dream. You are in control so you can fully customize your charter to fit your needs. You're …More

4.9 (109)

4 hours 34ft Day Dream Private Charter in Nassau

Join on this private charter aboard 34ft Day Dream. You are in control so you can fully customize your charter to fit your needs. You're...

4 hours Free Cancellation

4.9 (109)

from
$968

Key to the Sea Parasailing- Private Charter

Turks and Caicos is a unique set of islands in the Caribbean with the most beautiful beaches and waters you've ever seen.Your best option to …More

5.0 (34)

Key to the Sea Parasailing- Private Charter

Turks and Caicos is a unique set of islands in the Caribbean with the most beautiful beaches and waters you've ever seen.Your best option to...

1 hour Free Cancellation

5.0 (34)

from
$974

FULL DAY BIG GAME FISHING Hours : 8.00 am - 04.00 pm Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions …More

Puerto Plata, Dominican Republic

5.0 (2)

Full Day Big Game Fishing

FULL DAY BIG GAME FISHING Hours : 8.00 am - 04.00 pm Location: Puerto Plata - Sosua - Cabarete - Amber Cove All excursions...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$980

Private Fishing & Snorkel Charters in St Kitts and Nevis

Over 25 years of marine safety and fishing experience in St Kitts and Nevis-your Captain will lead you to the FISH aboard 36' MY DREAM. …More

4.9 (15)

Private Fishing & Snorkel Charters in St Kitts and Nevis

Over 25 years of marine safety and fishing experience in St Kitts and Nevis-your Captain will lead you to the FISH aboard 36' MY DREAM....

6 hours Free Cancellation

4.9 (15)

from
$988

Private Tour of El Yunque Rainforest from San Juan

Visit a different area of the El Yunque Rainforest. With the guidance of your private guide you will embark on an estimate 30-minute hike that …More

Isla Verde, Puerto Rico

4.8 (4)

Private Tour of El Yunque Rainforest from San Juan

Visit a different area of the El Yunque Rainforest. With the guidance of your private guide you will embark on an estimate 30-minute hike that...

7 hours Hotel pickup offered Free Cancellation

4.8 (4)

from
$990

Punta Cana Private Catamaran: Open Bar, Snorkeling & Natural Pool

Ready to enjoy a private Punta Cana booze cruise with a small group of your family friends? Our Party Boat offers the best service for …More

4.0 (1)

Punta Cana Private Catamaran: Open Bar, Snorkeling & Natural Pool

Ready to enjoy a private Punta Cana booze cruise with a small group of your family friends? Our Party Boat offers the best service for...

4 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$990

Frequently Asked Questions

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

What are the best options for Caribbean Outdoor Activities?

What are the best kid-friendly options for Caribbean Outdoor Activities Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Outdoor Activities are:

View all kid-friendly Tours →

Which Caribbean Outdoor Activities have Instant Confirmation?

Which Caribbean Outdoor Activities have Free Cancellation?

Caribbean Outdoor Activities 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 Outdoor Activities have Hotel Pickup?

Got any more Caribbean trip ideas?

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