Activities in Key West · Page 21
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Activities
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From US$95America's Most Haunted Firehouse
This is your chance to go beyond the ghost stories and become the investigator in a place where the past refuses to rest. Exclusive inside access after hours. More than a ghost tour - its an experience. Tickets benefit local non-profits. Locally owned and operated by the Sloan Family.
From US$695Private Key West Sunset Sail
2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for the perfect Key West sunset sail Peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks, bottled water and coolers stocked with ice provided for any adult beverages you choose to bring. Reserve ahead, there is after all, only one High Tide sunset sail per day! Price is for up to 6 guests, 12 guests max!.
From US$159.99Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours of free time before you come join us for an incredible Key West 2 hour Catamaran Sunset happy hour tropical dinner cruise with margaritas, rum runners, wine, beer and live music.
From US$475Key West Boat Rental with Seat, Sound and Fishing Upgrades
Discover the unparalleled joy of exploring Key West waters aboard this center console! Our fleet boasts the newest, most luxurious vessels, fully equipped with top-tier upgrades for your comfort and convenience. Nestled within our full-service marina, we've proudly served our community for 39 years, earning our reputation as the go-to destination for boat rentals in Key West. Join us and embark on an adventure of a lifetime – where every wave carries the promise of unforgettable memories!
From US$525Key West Golf Cart Sober Driver Tours
The main goal is to keep you safe with a SOBER driver. Let us take you on a guided golf cart tour around Key West with a seasoned and sober driver to stay out of trouble! Not only will you likely not know where you're going, but there are rules of the road in Key West for golf carts that folks do not know about and you can end up in trouble / aka: D.U.I. ! So, getting past that, Your pickup point can vary to your wish! We will gladly pick you up and drop you off at your hotel. Now the fun! We will cruise past Jimmy Buffett's studio, Mallory Square, Sloppy Joe's and Hog's Breath Saloon just to name a few of the great popular party places. Just let us know where you want to go and we will get you there (and back) safely! If you are wanting to party down we can help you get back home without the ticket!
From US$1,100Private Island & Fishing Charters in Key West 37ft Knotty Cowgirl
Experience the best of both worlds with our Island Fishing Tour, exclusively offered by Cowboy Cowgirl Sportfishing Charters. Unlike typical fishing charters, this unique excursion combines thrilling fishing action with serene island exploration. Cast your line in prime fishing spots, then hop between picturesque islands where you can take a break and enjoy your own picnic. Perfect for those who love both adventure and relaxation, this tour offers an unparalleled opportunity to catch the big one and discover the hidden gems of our beautiful coastline. Whether you're an avid angler or simply looking to enjoy a day on the water, our Island Fishing Tour promises an unforgettable experience.
From US$500Private Proposal and Engagement Shoot in Key West
We take the time to review YOUR vision for this special moment in life via a conference call - we offer suggestions and then send a full confirmation with map or diagram and all aspects to make this a perfect surprise to the love of your life and your lifetime partner.
From US$850Key West: 22ft Premier Pontoon Rental 115 HorsePower 10 passengers
Have a blast on the half day boat rental a Premier 22 foot Pontoon 115 HorsePower. The boat holds up to 10 passengers. You can cruise in the the ocean or the bay at key west, it is only 90 miles from Cuba. Tan in the sun, dock at a sand bar. The boat is equipped with 115 horse power, a Bimini Top, Radio and Comfortable Seats. Remember to bring your bathing suits, sun glasses, sunscreen, towel, hats and favorite beverages.
From US$1,150Key West Sportfishing Experience 4 Hours 47 Hatteras-Sanctuary
Private Offshore Fishing on Sanctuary – 47 ft Hatteras Experience the thrill of offshore fishing in Key West aboard Sanctuary, our 47 ft Hatteras. Led by an expert Captain and mate, we’ll take you to the best deep-sea fishing spots for an unforgettable adventure. Target Top Game Fish: Reel in mahi-mahi, king mackerel, sailfish, tuna, and more using trolling and bottom fishing techniques. Tailored to You: Whether you're a seasoned angler or a beginner, we customize each trip to match your skill level. Choose from half-day (4 hours), full-day, or multi-day charters. Comfort & Safety: Enjoy spacious decks, premium gear, a clean restroom, and all essential safety equipment for a smooth trip. Book your private offshore fishing adventure today!
From US$995Six Fins Key West Harbor Cruise – Private Scenic Boat Tour
Experience Key West’s waterfront the way locals do—by private boat. This harbor cruise offers a more comfortable experience, complete with narration and flexibility. With a USCG-licensed captain, you’ll glide past historic forts and the Historic Seaport, Navy installations, Mallory Square, and island landmarks while hearing stories of wreckers, pirates, and poets. Choose golden-hour glow or bright daytime views, customize pace and photo stops, and savor a quiet, upscale alternative to mass tours. ✅ Explore the Historic Seaport, Mallory Square, and island landmarks ✅ See Navy installations, historic forts, and working waterfronts ✅ Learn island history from a knowledgeable USCG-licensed captain ✅ Customize the pace with photo stops, narration, or quiet relaxation ✅ Choose daytime cruises for sunshine or golden-hour evening views This is a quiet, upscale alternative to mass tours — perfect for couples, families, and small groups seeking comfort, history, and stunning harbor scenery.
From US$139Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!
We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Our seasoned local guide will dive into the history of Old Fisherman’s Wharf & how it has transformed into Yacht Harbor! Learn about the historic wrecking and rum running days of old Key West! Sit at the bar Mel Fisher did while his treasure sat out front, on display, in the trunk of his car! Transition into the sunset where you’ll visit the area where locals have their annual celebration for the succession of our Conch Republic from the United States! Open your ears to live music and island vibes as you cocktail into World Famous Mallory Square’s Sunset Celebration!
From US$172Key West Jet Ski Tour: 1-hour Freestyle w/Sub Pits
Most Key West jet ski trips lock you into a fixed route and a big group. This one doesn't — it's a private, freestyle hour where the ride is yours to shape. ✅ A private, flexible alternative to large guided group tours ✅ No set route — open the throttle, cruise, or stop to swim, your call ✅ A short guided escort out, then the open-water zone is yours ✅ Ideal for repeat riders, thrill-seekers, or anyone short on time If you want speed, sightseeing, or just space to play on your own terms, the freestyle ride gives you the freedom a guided tour can't.