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 →

We have a passion for showing people a great time fishing. Our trips are custom made to suit each of our clients' wishes. …More

Fishing Charter 10 Hours

We have a passion for showing people a great time fishing. Our trips are custom made to suit each of our clients' wishes....

10 hours Hotel pickup offered Free Cancellation

from
$2,000

Private Catamaran Day Cruise Out of Soufriere for Up to 15 Guests

Depart from Soufriere and join us for a full day Snorkel and Sailing trip onboard one of our spacious catamarans. You will spend the day Sailing along the …More

5.0 (12)

Private Catamaran Day Cruise Out of Soufriere for Up to 15 Guests

Depart from Soufriere and join us for a full day Snorkel and Sailing trip onboard one of our spacious catamarans. You will spend the day Sailing along the...

7 hours Free Cancellation

5.0 (12)

from
$2,280

Private Full-Day Tour to Saona Island from Bayahibe with Lunch

Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) it’s a …More

Punta Cana, Dominican Republic

5.0 (1)

Private Full-Day Tour to Saona Island from Bayahibe with Lunch

Saona Island is the most popular excursion offered in the Dominican Republic. The island is a natural park (protected as a natural reserve) it’s a...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,300

This vessel is fully equiprt for a luxury day on the water. See some of the best beaches and coves around the island. Our experienced …More

St John's, Antigua and Barbuda

4.8 (6)

Luxury Private Yacht Rafnar Cruise

This vessel is fully equiprt for a luxury day on the water. See some of the best beaches and coves around the island. Our experienced...

7 hours Free Cancellation

4.8 (6)

from
$2,300

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail. …More

5.0 (190)

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail....

4 hours Hotel pickup offered Free Cancellation

5.0 (190)

from
$2,380

Full Day Boat Charter - 50' Luxury Sea Ray Sundancer

Let our professional captain and first mate show you around the Virgin Islands while catering to your needs. Soak up the sun on the aft …More

4.7 (64)

Full Day Boat Charter - 50' Luxury Sea Ray Sundancer

Let our professional captain and first mate show you around the Virgin Islands while catering to your needs. Soak up the sun on the aft...

7 hours Free Cancellation

4.7 (64)

from
$2,400

Saona Island VIP Experience – Private Boat for Up to 20 People

Discover Saona Island Your Way: All-Inclusive Private Tour Live an exclusive experience with this private tour to Saona Island, designed for groups of up to …More

Punta Cana, Dominican Republic

4.1 (10)

Saona Island VIP Experience – Private Boat for Up to 20 People

Discover Saona Island Your Way: All-Inclusive Private Tour Live an exclusive experience with this private tour to Saona Island, designed for groups of up to...

6 hours Hotel pickup offered Free Cancellation

4.1 (10)

from
$2,400

Bottom fishing in the Turks and Caicos Islands can yield a variety of species, depending on the location and target species. Some common catches include …More

Half Day Bottom Fishing Private Charter

Bottom fishing in the Turks and Caicos Islands can yield a variety of species, depending on the location and target species. Some common catches include...

4 hours Free Cancellation

from
$2,400

Rose Island 3 Island Luxury Private Tour(8hrs)

This tour is one of a kind . Our boats are well maintained and captains and crew are highly trained. You get to experience 3 …More

5.0 (38)

Rose Island 3 Island Luxury Private Tour(8hrs)

This tour is one of a kind . Our boats are well maintained and captains and crew are highly trained. You get to experience 3...

8 hours Free Cancellation

5.0 (38)

from
$2,500

Private Half-Day Guided Snorkeling Charter in St. Thomas

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy …More

5.0 (50)

Private Half-Day Guided Snorkeling Charter in St. Thomas

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy...

4 hours

5.0 (50)

from
$2,540

Private Morning Half-Day Snorkeling Trip

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy …More

5.0 (27)

Private Morning Half-Day Snorkeling Trip

Avoid the crowds and get ready for fun, sun, and snorkeling on this unforgettable private trip! Perfect for friends and families who want to enjoy...

2 to 4 hours

5.0 (27)

from
$2,540

Enjoy a luxurious all inclusive day in our 47 feet Power Catamaran. Our Captain will choose one of the beautiful locations the east cost of …More

Fajardo, Puerto Rico

5.0 (16)

Catamaran Charter Puerto Rico Jenica

Enjoy a luxurious all inclusive day in our 47 feet Power Catamaran. Our Captain will choose one of the beautiful locations the east cost of...

6 hours Free Cancellation

5.0 (16)

from
$2,600

Punta Cana Private Catamaran for Up to 40 Guests – Large Group

Welcome to an unforgettable offshore experience! Our boat trip stands out for several reasons that make it a unique and attractive activity. Sail through breathtaking …More

Punta Cana, Dominican Republic

5.0 (1)

Punta Cana Private Catamaran for Up to 40 Guests – Large Group

Welcome to an unforgettable offshore experience! Our boat trip stands out for several reasons that make it a unique and attractive activity. Sail through breathtaking...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,600

Private Yacht Tour Montego Bay with DJ Open Bar and Water Sports

Elevate your event with an unforgettable cruise aboard the luxurious Sea Ray 540 Sundancer. Whether you're hosting a lively party or seeking a serene escape, …More

Montego Bay, Jamaica

Private Yacht Tour Montego Bay with DJ Open Bar and Water Sports

Elevate your event with an unforgettable cruise aboard the luxurious Sea Ray 540 Sundancer. Whether you're hosting a lively party or seeking a serene escape,...

3 hours Free Cancellation

from
$2,600

8HR Catch and Grill in Turks and Caicos Islands

Imagine spending the day cruising in the Beauty by nature Turks and Caicos waters, snorkeling, Island hoping, visit the La famille express ship wreck and …More

5.0 (106)

8HR Catch and Grill in Turks and Caicos Islands

Imagine spending the day cruising in the Beauty by nature Turks and Caicos waters, snorkeling, Island hoping, visit the La famille express ship wreck and...

8 hours Hotel pickup offered Free Cancellation

5.0 (106)

from
$2,688

4 hours 53ft Dream Works Private Charter in Nassau

At Reel Dreams Charters you will experience Bahamas Fishing at its absolute finest with a crew dedicated to customer service and a fleet that will …More

5.0 (4)

4 hours 53ft Dream Works Private Charter in Nassau

At Reel Dreams Charters you will experience Bahamas Fishing at its absolute finest with a crew dedicated to customer service and a fleet that will...

4 hours Free Cancellation

5.0 (4)

from
$2,700

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

Private Half-Day Morning Bottom Fishing on Serendipity

For parties 8 persons and smaller, the “Serendipity” provides a solid, comfortable and well-equipped boat for reef and bottom fishing or combination days. Serendipity is …More

5.0 (1)

Private Half-Day Morning Bottom Fishing on Serendipity

For parties 8 persons and smaller, the “Serendipity” provides a solid, comfortable and well-equipped boat for reef and bottom fishing or combination days. Serendipity is...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$2,885

Private 1/2 Day Afternoon Charter Deep Sea Fishing on Wahooter's

World-Famous Turks and Caicos Deep Sea Fishing In summer we catch blue marlin, yellowfin, blackfin, bigeye, skipjack, albacore tuna, and mahi mahi. In winter we …More

4.8 (6)

Private 1/2 Day Afternoon Charter Deep Sea Fishing on Wahooter's

World-Famous Turks and Caicos Deep Sea Fishing In summer we catch blue marlin, yellowfin, blackfin, bigeye, skipjack, albacore tuna, and mahi mahi. In winter we...

4 hours Hotel pickup offered Free Cancellation

4.8 (6)

from
$2,897

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We …More

Private Half Day Afternoon Snorkel and Cruise on Serendipity

Bottom Fishing Come on board in Turks and Caicos. Our friendly crew will have you smiling and catching fish in no time ! We...

4 hours Hotel pickup offered Free Cancellation

from
$2,897

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?