all activities

Set sail aboard the luxurious Argo Navis for a two-hour sunset cruise where the Atlantic meets the Gulf of Mexico. Enjoy Florida craft beers, premium wines, specialty cocktails, and appetizing hors d’oeuvres. With exceptional service and a smoke-free, dog-friendly atmosphere, it’s the perfect way to experience Key West’s unforgettable sunsets.

Set sail on this top-rated 2‑hour Wind and Wine Sunset Sail from Danger Chandlery Store. Enjoy a historic Key West schooner cruise with eight exquisite wines, premium beers, and gourmet hors d’oeuvres while exploring serene west coast waters. Book now for an unforgettable, upscale sunset adventure!

Private for up to six Rum Runner passengers. A Dream Downtown Location for a Key West Harbor Sightseeing Trip! Duration 2 Hr Block SUNSET TIMES VARY (Departure Times) Our 2

Key points about this tour: Sailing on a schooner for sunset Up to 8 different varieties of wine Craft and domestic beers available Hors d'oeuvres complementing the wines Top rated

Book your perfect day charter with us now! Rates 2 Hour Charter: $699 3 Hour Charter: $900 4 Hour Charter: $1,100 6 Hour Charter: $1,500 8 Hour Charter: $1,799 Class

Duration 1-3 Hours & Daily Rentals Arrival Time Please arrive 15 minutes prior to your booking to complete waivers during check-in Be sure to complete your boat safety course prior

About This Sea Hunt 200 Escape is great for shallow or deep-water fishing, snorkeling, or just hanging out at the sandbars. 20-foot dual console 115 horsepower Yamaha outboard Capacity for

About This "unsinkable" center console top-of-the-line boat is great for shallow water fishing, reef fishing, snorkeling, or just hanging out at the sandbars. 25-foot center console 300 horsepower Yamaha outboard

This action packed 28 mile jetski tour stops at 5-6 different locations sharing some historic & fun facts about the island. The entertaining and experienced jetski guides will show you how to use the equipment then take you completely around the island to see the Key West coast line.

Jump on Key West’s newest catamaran, The Sandie Cat sailboat for a 3 hour snorkel adventure. Join for a beautiful afternoon sail out to the reef with a refreshing afternoon dip in the crystal clear waters!

Jump on Key West’s newest catamaran, The Sandie Cat sailboat for a 3 hour snorkel adventure. Come explore the world’s 3rd largest living coral reef on Key West’s newest & fastest snorkel boat. This trip is perfect for professionals and beginners.

All aboard for Key West’s legendary sunset dinner cruise celebration. Enjoy unbeatable views of the sunset along with an amazing tropical food buffet. Grab a tropical beverage and groove into the sunset as a local steel drum performer fills the air with tropical vibes.

Explore the Florida Keys’ crystal-clear waters on a paddle adventure. Spot diverse wildlife, including dolphins, iguanas, fish, and more. See coral, starfish, seagrass, and more through your clear kayak and capture stunning photos in picturesque mangrove tunnels.

All aboard for Key West’s legendary sunset dinner cruise celebration! Enjoy unbeatable views of the sunset along with an amazing tropical food buffet, open well bar & live music. Grab a tropical beverage and groove into the sunset as our live performer fills the air with tropical vibes.

Explore the keys in a fun & adventurous way with Glow Paddle’s Key West kayak rentals. Paddle around the calm waters & experience the thrill of night kayaking with LED lights and glass bottom kayaks. Book your Key West kayak rental online today and get ready for an unforgettable adventure!

We offer a brand new line-up of Yamaha VX Deluxe WaveRunners. Come play, discover and delve into the wonders of the Florida Keys. NO shirt or shoes required!

This is the tour seasoned ghost hunters seek out. Packed with local history, the spirits of Civil War soldiers and the world’s most haunted doll await you on a 90-minute ghost hunting adventure through the infamous Fort East Martello.

Enjoy a relaxing day of fishing out by the reef or along the mangroves. A great trip for the beginner fisherman or someone who just wants to give it a try. The focus is on fun, but we certainly will give it our best effort to catch some keepers!

Our snorkeling sites are off-the-beaten-path and in shallow, calm water. Explore coral reefs, shallow shipwrecks, underwater sandbars, and Sting Ray alley! All equipment, flotation and patient instruction provided.

Fly high above the crystal blue waters of Marathon! Each trip runs for an hour and each flying passenger will spend 8 – 10 minutes in the air.

Our afternoon reef dives are in 25-35 feet in the Atlantic on the World’s 3rd largest Barrier Reef. The Captain will do his best to take you to the clearest and calmest water’s possible.

Book your Florida Keys Fishing Vacation with one of the best charter fishing guides in the area. Captain Magnus Nilsson is The Key West Fishing Viking and his First Mate Ross Baker – who has caught over 3600 Billfish – is Key West Famous!

Hemingway’s Whiskey is a well-maintained 55-foot Ocean Sport Fisher. She is fully equipped to fish, with a complete Furuno electronics package and all the tackle you need for your Key West deep sea fishing adventure. Your adventure on the water is waiting!

Rent a scooter from Barefoot Billy’s and discover Key West’s hidden gems the locals way.

Come play, discover and delve into the wonders of the Florida Keys. Rent a jet ski in South Florida with Tropic Water Sports. Book online now, limited amount available!

Get out on the water and try your luck sight-fishing for redfish, snook, trout, tarpon, bonefish, permit, and many other species that inhabit the shallow waters of Key Largo and Everglades National Park.

Hop aboard the M. V. Key Largo Princess for our daily 2-hour tours to view the exciting, beautiful, underwater world of the John Pennekamp Coral Reef State Park and the Key Largo National Marine Sanctuary.

Rent a jet ski in South Florida with Tropic Water Sports to experience the fast and exciting side of life on the ocean. Whether you’re local to Key Largo or vacationing, a jet ski rental in Florida is a must-try! Book online now, limited amount available!

Observe the underwater world beneath you! Our 100% see-through kayaks are the ideal way to explore our pristine Caribbean waters and mangrove trails.

“The Gilligan” is a three-hour adventure, a spectacular 45-minute boat ride Out There, over an hour of paddling and exploring, and the return boat ride.

Explore the sky in style! Our Florida Keys’ location is warm and sunny all year long, so book today to make memories that will last a lifetime.

A guide will show you all the sights around the island! 2 riders per jet ski max – Yamaha VX Deluxe – Includes all safety equipment.

Rent your Jetski a Yamaha VX Deluxe. Up to 2 Riders per Jetski!

Enjoy our Pontoon Boat/Jet Ski Package in Marathon, FL by choosing one of these options: 18′ Sun Tracker Party Barge or 22′ Trifecta Tritoon.

Enjoy our Pontoon Boat in Marathon, FL by choosing one of these options: 18′ Sun Tracker Party Barge or 22′ Trifecta Tritoon.

These trips go up to 1-7 miles offshore, depending the time of year. We stop to catch live bait via cast net or sabiki rigs first and then go to the reef to catch dinner.

Full day charters run for 8 hours. These trips go up to 10-30 miles offshore, mostly during the summer.

Want to go deep sea fishing without breaking the bank? Then a split charter is for you. Split charters require a minimum of 2 anglers per charter and a maximum of 4.

Islamorada Tarpon Fishing is bar none to anywhere else in the world. Our Florida Keys Tarpon Fishing charters are designed to cater to all types of anglers.

The 4 hour trip is typically limited to reef and wreck fishing up to 10 miles offshore.

Experience what makes kayaking one of Key West’s most popular activities. Barefoot Billy’s kayak rentals include kayak, paddle and personal flotation devices.

Paddleboarding is fun and suitable for people of all ages and abilities. Rentals ok for beginners too! We’ll give you a lesson before you leave the dock.

Our kayak rentals are a great way to explore the calm, clear waters and mangrove creeks between Key West and Stock Island. We’ll give you a map of the area highlighting spots that we recommend.

The narrow streets and very limited parking in Key West make traveling by scooter one of the best ways to get around the island.

Rent a scooter from Barefoot Billy’s and discover Key West’s hidden gems the locals way.

Follow a local guide, and go as fast or as slow as you want. There are 5 stops, just long enough to catch your breath and learn a little local Key West history.

Circle Key West in 90 minutes and experience a unique perspective as you glide from the Atlantic Ocean to the Gulf of Mexico and back to the Atlantic.

A Key West favorite, this 1 ½ – 2 hr high-speed tour takes you 26 miles around the entire island. Follow a local guide, and go as fast or as slow as you want.

Cruise into a Key West sunset aboard Barefoot Billy’s 45-foot power catamaran, Seabreeze. Our magnificent sunsets are best appreciated from the turquoise waters and will be a highlight of your Key West vacation.

Our 90-minute daytime cruise is steps away from the Historic Seaport and Cruise Ships Ports of call. A Little Piece of Key West History! Wrapped up in a Dream Downtown Location!

Adventure through Mud Key, Snipe Key, Jewfish Basin and deserted sandbar islands! Bring lunch and drinks and see Key West like the locals do!

Join us in a fun, action-packed day on the best Key West booze cruise you’ll find! Just show up with your drinks and get ready to party! Fun…guaranteed!

Pedal, pedal…bottoms up! It’s time to book your party boat cruise! This is the party everyone’s talking about. Just show up with your drinks and get ready to party! Fun…guaranteed!

Enjoy a two-hour cruise to view the world-famous Key West sunset aboard a custom tiki bar catamaran.

Enjoy your romantic sunset sail aboard Key West’s most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0.

Take to the water on the Schooner America 2.0, namesake off the first sailboat to win the America’s Cup in 1851.

Catch the cool sea breeze as you head for a sun-soaked daysail out of Downtown Key West. Enjoy the view from the aqua water as you pick out the city’s most famous landmarks and sail around the harbor islands!

Did you know Key West has a vibrant and active dolphin population? We know where to find them! We head out of the marina in search for the most intelligent ocean dweller on Earth.

Get a little taste of everything on this trip showcasing the best things to do out on the Key West water. If there is only one trip you are thinking of going on, or if you only have one day to experience the Florida outdoors, this is the trip!

On this family-friendly cruise, we venture out to balmy Backcountry waters to snorkel in Key West’s wildlife sanctuary before searching the Gulf of Mexico’s backcountry’s balmy waters before searching for Key West’s dolphins.

What would a trip to our southernmost home be without getting out and seeing that Key West water? Our environment and location make Key West one of the best places on Earth for snorkeling and diving.

The Full Day Excursion is the perfect trip for you all that love being out on the water. We will spend plenty of time snorkeling as well as kayaking around one of the mangrove islands.

The best of both worlds! Enjoy a sail over to the spot where your captain will set the anchor for a swim call. There’s a lot to see!

During our morning wreck dive we explore the USNS General Hoyt S. Vandenberg, the world’s 2nd largest artificial reef.

Never been diving but want to give it a try? No time to get certified on this visit? Try our Discover SCUBA Course and do it in one day!

Our Key West Party Boat Fishing Charter is the longest-running deep sea fishing charter in Key West, Florida, catching payloads of fish since 1947. Your fishing adventure aboard Gulfstream IV includes fishing tackle, license, and bait.

Rent a kayak from Barefoot Billy’s and push off right from the beach to begin your journey through some of the most gorgeous scenery and waters in America.

Experience the feeling of walking on water and getting the best view of marine life at the same time with a Paddle Board rental from Barefoot Billy’s.

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West.

Venture into the world of spirits and hear tales of the ghosts that inhabit our Isle of Bones. Key West has a rich and interesting history, and you’ll learn more about our tiny little island and its fascinating past on your tour.

Looking for a unique way to spend an evening? Discover Key West’s haunted history with the people who know it best on a 90+ minute stroll through Old Town with visits to the island’s most haunted locations.

The Southernmost Walk is for people who are visiting Key West and want to learn the history and the culture of our tiny island in a short time.

Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA!

With your friendly & knowledgeable tour guide, this 5-hour VIP Tour of the South Keys & 7-Mile Bridge promises to amaze you.

En route, you’ll learn the history, culture, and ecology of the Florida Keys, listen to island music, & enjoy the breathtaking scenery! Feel free to ask questions, share your experiences, and point out wildlife.

With your friendly & knowledgeable tour guide, this half-day sightseeing tour of the Florida Keys promises to amaze you!

Off the tourist track & into local restaurants. Our signature tour includes iconic ‘must-eat’ foods like Key Lime Pie & Conch Fritters!

A ‘best-all-around’ food tour of fresh local ingredients straight from our waters. Taste maritime history as we walk the historic seaport!

Are you looking for the ultimate Key West tradition? Key West is famous for its bars. Enjoy a 2.5 hour guided tour, 5 delicious cocktails, contests, comedy & a beautiful souvenir T-Shirt to remember the fun!

Bone Island Haunted Crawl & Ghost Tour – Are you ready for some “spirited fun? Join us on a spine-tingling adventure through Bone Island. Rated one of the Top 5 most haunted places in America!

Join Us on a sip and stroll through Key West’s craftiest bars and hidden local gems enjoying 5 local cocktails & 2 generous tastings!

Our most popular helicopter tour, this trip was designed particularly for those marine life enthusiasts who want a bird’s eye view of the numerous sea-life swimming below.