Top Key West Outdoor Activities

Q: What are the best options for Key West Outdoor Activities?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Key West Outdoor Activities are: Go City: Miami All-Inclusive Pass with 35+ Attractions and Tours Private Marathon Backcountry Fishing Charter Key West Sandbar Adventure Cruise for All Ages Key West Clear Kayak Eco Tour Schooner Appledore Day Sail with Full Bar in Key West

Q: What are the best kid-friendly options for Key West Outdoor Activities Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Key West Outdoor Activities are: Schooner Appledore Day Sail with Full Bar in Key West Key West Clear Kayak Eco Tour Key West Parasailing Adventure with Island Time Parasail Key West Party Boat Fishing Charter Go City: Miami Explorer Pass - Choose 2, 3, 4 or 5 Attractions View all kid-friendly Tours →

Q: Which Key West Outdoor Activities have Instant Confirmation?

Key West Outdoor Activities with Instant Confirmation include: Florida Key West Self-Guided Driving Tour (7 Mile Bridge) Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours Schooner Appledore Day Sail with Full Bar in Key West Key West Clear Kayak Eco Tour Key West Parasailing Adventure with Island Time Parasail View all Tours with Instant Confirmation →

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

No problem. These Key West Outdoor Activities include Hotel Pickup: Guided Mangrove Eco Tours Kayak or Paddleboard Adventure Florida Keys Nature & History Tour from Key West View all Tours with Hotel Pickup →

Q: Got any more Key West trip ideas?

We sure do. Check out our curated lists of hand-picked Key West Tours. Top 10 Key West 2026 Senior-friendly tours Key West The best tours and activities for culture lovers in Key West Top Day Trips from Key West Things to do in Key West this summer View all Key West Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Key West?

Based on our sales data over the past year, the most popular styles of tours and activities in Key West are: Key West Kid Friendly Key West Kid Friendly Tours & Activities Key West Vehicle Rentals Key West Golf Cart Rentals Key West Water Sports View all tour styles in Key West →

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

5.0 (292)

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours Free Cancellation

5.0 (292)

from
$102

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

4.9 (119)

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours Free Cancellation

4.9 (119)

from
$119

Go City: Miami All-Inclusive Pass with 35+ Attractions and Tours

See more and spend less with a Go City All-Inclusive Pass - the best Miami pass for flexibility and savings. Enjoy unlimited access to 25+ …More

3.9 (30)

Go City: Miami All-Inclusive Pass with 35+ Attractions and Tours

See more and spend less with a Go City All-Inclusive Pass - the best Miami pass for flexibility and savings. Enjoy unlimited access to 25+...

1 to 5 days

3.9 (30)

from
$119

Key West Island Adventure: Sandbar, Kayak & Paddleboard Excursion with Sunset Option

Enjoy life like a Key West local with a picnic play day on the calm, clear waters and pure white sands of a Backcountry sandbar …More

4.9 (621)

Key West Island Adventure: Sandbar, Kayak & Paddleboard Excursion with Sunset Option

Enjoy life like a Key West local with a picnic play day on the calm, clear waters and pure white sands of a Backcountry sandbar...

3.5 Hours (approx.) Free Cancellation

4.9 (621)

from
$120

Key West Sandbar Adventure Cruise for All Ages

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through …More

4.9 (28)

Key West Sandbar Adventure Cruise for All Ages

Wake up and start your day in paradise the right way! We will give you an experience not easily forgotten, starting with a cruise through...

4 hours Free Cancellation

4.9 (28)

from
$126

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and …More

4.9 (576)

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...

4 hours Free Cancellation

4.9 (576)

from
$150

Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & …More

4.6 (42)

Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar &...

4 hours Free Cancellation

4.6 (42)

from
$150

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out …More

4.9 (425)

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out...

5 hours Free Cancellation

4.9 (425)

from
$161

Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike …More

4.6 (9)

Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike...

5 hours Free Cancellation

4.6 (9)

from
$161

Explore the productive reefs of the Florida Keys on a private Marathon reef fishing charter into the Atlantic. Marathon provides convenient access to an incredible …More

5.0 (33)

Private Marathon Reef Fishing Charters

Explore the productive reefs of the Florida Keys on a private Marathon reef fishing charter into the Atlantic. Marathon provides convenient access to an incredible...

4 hours Free Cancellation

5.0 (33)

from
$183

Key West Safari Eco Sandbar Tour Adventure with Snorkeling

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28 …More

4.7 (220)

Key West Safari Eco Sandbar Tour Adventure with Snorkeling

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28...

2 hours 30 minutes Free Cancellation

4.7 (220)

from
$197

Private Marathon Offshore Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and …More

5.0 (2)

Private Marathon Offshore Fishing Charter

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and...

4 hours Free Cancellation

5.0 (2)

from
$217

Experience the Florida Keys from the water on a private Marathon inshore fishing charter surrounded by turquoise seas, tropical scenery, and diverse fishing opportunities. Marathon's …More

5.0 (1)

Private Marathon Inshore Fishing Charter

Experience the Florida Keys from the water on a private Marathon inshore fishing charter surrounded by turquoise seas, tropical scenery, and diverse fishing opportunities. Marathon's...

4 to 8 hours Free Cancellation

5.0 (1)

from
$250

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you …More

4.8 (189)

Key West Mini Catamaran Eco Tour

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you...

1 hour 30 minutes Free Cancellation

4.8 (189)

from
$285

Private Marathon Backcountry Fishing Charter

Experience a side of the Florida Keys that can only truly be appreciated from the water. Marathon provides access to an incredible network of shallow …More

5.0 (1)

Private Marathon Backcountry Fishing Charter

Experience a side of the Florida Keys that can only truly be appreciated from the water. Marathon provides access to an incredible network of shallow...

4 hours Free Cancellation

5.0 (1)

from
$375

you'll be able to fish the Atlantic side of the Florida Keys and the Gulf side in the same outing if you so desire. …More

5.0 (45)

Private Fishing Charter from Ramrod Key

you'll be able to fish the Atlantic side of the Florida Keys and the Gulf side in the same outing if you so desire....

4 hours Free Cancellation

5.0 (45)

from
$500

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the …More

5.0 (13)

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the...

2 hours Free Cancellation

5.0 (13)

from
$599

Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the …More

5.0 (22)

Boat Excursion in Florida Keys with Snorkeling Equipment

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the...

4 hours Free Cancellation

5.0 (22)

from
$700

Great for families. Customizable. Not a crusty old fishing charter by any means! Lots of sea life in the Florida keys! We can pull stone …More

5.0 (9)

Private Fishing Charter Florida Keys

Great for families. Customizable. Not a crusty old fishing charter by any means! Lots of sea life in the Florida keys! We can pull stone...

4 hours Free Cancellation

5.0 (9)

from
$800

Marathon Florida Keys Fishing Experience

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing …More

5.0 (39)

Marathon Florida Keys Fishing Experience

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing...

4 hours Free Cancellation

5.0 (39)

from
$995