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 crab traps (Oct 15-May 1st). Or get in and go for a swim or stop in at a sandbar! Captain has almost 20 years fishing experience. Take your catch to a restaurant to be cooked! Snorkel gear is available. Lobster diving charters are available in season (Aug 6-March 31). Pets are welcome
Duration: 4 hours
- Free cancellation
- Private tour
Island Sandbar Tour Catamaran Cruise in Marathon FL
Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares information about the local area and points out interesting sights along the way.
Once you arrive at the sandbar, step into shallow turquoise water perfect for swimming, floating, and relaxing. Use the provided water floats and noodles, or simply unwind on deck and enjoy the sunshine and music.
This relaxed and family-friendly tour offers plenty of space to move around the boat, shaded seating, onboard restrooms, and a cooler with ice, soda, and water. Ideal for couples, families, and groups, this experience lets you enjoy Marathon’s sandbars the way locals do—easygoing, fun, and surrounded by the natural beauty of the Keys.
Duration: 4 hours
- Free cancellation
Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY
Experience an Unforgettable Fishing Adventure in Key West!
Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both seasoned anglers and first-timers, ensuring an unforgettable experience.
Reel in magnificent mahi, wahoo, sailfish, and more. Our knowledgeable crew will guide you to prime fishing spots, employing techniques like trolling, reef, or wreck fishing and many more to maximize your chances of landing a trophy catch. Choose from flexible charter options: 1/2-day, 3/4-day, full-day, or extended 10-12 hour trips tailored to your preferences.
Our 36-foot Hatteras "Cowboy" offers comfort and safety with clean facilities, restrooms, , a flybridge, and state-of-the-art equipment. Book now and discover why our private charters are the ultimate choice for a thrilling day on the water in Key West.
Duration: 4–12 hours
- Free cancellation
- Private tour
Key West Center Console Boat Rental With Sound and Seat Upgrade
We are Key West's largest boat rental service and have been helping travelers explore our local waterways for over 39 years. Our boats are located at a full service marina with ice, gas, snacks, drinks, beer, fishing equipment, bait and so much more. We are your one stop shop for everything you need to enjoy your time on the water. Our expert staff will guide you through the boat and give directions to local hotspots. Book with Sunset Watersports and see the difference.
Duration: 4 hours
- Free cancellation
Key West Island Jetski Tour: Double Passenger Jetski
27 Miles and 90 Minutes of pure exhilarating watersports bliss. Your Key West Island Jet-ski Tour starts in the shallow cove, The Ibis Bay Resort dock area.
From the Gulf of Mexico to the Atlantic Ocean.....and back to the Gulf of Mexico. From sea to Ocean and back again. After your exhilarating 90-minute adventure, many guests celebrate their experience with a drink and the freshest seafood at the Stoned Crab Restaurant.
Duration: 1 hr 30 min
- Free cancellation
Half Day Luxury Boat Tour in Key West with Snorkeling
Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutter Ingham Maritime Museum, Smathers Beach, Southernmost Point of your list.
Duration: 4 hours
- Free cancellation
- Private tour
Key West Historic Private Food Tour with 5 Authentic Tastings
Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influences. Start with a refreshing iced coffee before biting into golden, crispy conch fritters—a true island classic. Savor authentic Cuban cuisine that reflects Key West’s cultural heritage, then indulge in rich chocolate-covered Key lime pie, the city’s most famous dessert. Along the way, your guide will share stories of pirates, poets, and island life, bringing the history and charm of Key West to life. To end, you’ll taste our exclusive Secret Dish, a surprise that makes the experience truly unforgettable. This is Key West beyond the postcard—an authentic taste of its food, culture, and soul.
As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience.
Duration: 2 hr 30 min
- Free cancellation
- Private tour
Ultimate Key West Day: Dolphin & Snorkel Combo with Sunset Sail
What a fun day in the sun with a 10am checkin and 11am departure to a 3 hours snorkeling and Dolphin watching adventure. At 4:45pm get ready for the Keywest sunset, dinner, live music and open bar.
Duration: 6 hours
- Free cancellation
Private Sandbar Charter & Island Escape in Key West
Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with a drink in hand, explore the local marine sanctuary, or simply enjoy a laid-back day on the water.
Your captain will tailor the experience to your preferences, taking you to the best sandbar spots and providing everything you need for a carefree day in paradise. Enjoy sunshine, calm waters, and unforgettable views of Key West’s natural beauty.
This is the ultimate way to experience the islands—your day, your way, in the heart of the Florida Keys.
Duration: 4 hours
- Free cancellation
- Private tour
Florida Keys Backcountry Eco Tour from Big Pine Key
This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands that make up the Backcountry and Great White Heron National Wildlife Refuge. We will slow down and look for marine life and birdlife. Maybe see a turtle or dolphin. We will take you through "Skinny Water" and look for starfish, rays and sharks. It's a fun adventure not to be missed when visiting the Keys.
Duration: 2 hours
- Free cancellation
- Private tour
Jet Ski 90 Min Ride in Key West
Climb on Key West’s newest jetskis for the best tour around the island. This trip includes a free second rider. Join us for the best deal in Key West
Duration: 1 hr 30 min
- Free cancellation
2-Hour Live Music Guided Tour in Key West
Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for upcoming events, digital download of local artists music, and historical overviews of the venues and artists who have left their mark on the island.
Learn from a local about the diverse music scene and creative island life that continues to inspire so many.
Duration: 2 hours
- Free cancellation
Eco Conscious Reef Diving with Southpoint Divers
Explore the only living barrier reef in America with Southpoint Divers on eco-friendly dive trips tailored for certified divers. Begin your day at your air-conditioned dive shop near the Hyatt Centric, where you’ll be equipped with top-of-the-line SCUBAPRO gear. Cruise past stunning views of Sunset Key and Fort Zachary Taylor Beach as you head to the reef. Dive into vibrant coral gardens teeming with tropical fish, turtles, and rays. With PADI-certified instructors ensuring safety and personalized attention in small groups, your underwater adventure also supports vital conservation efforts in the Florida Keys.
Duration: 4 hours
- Free cancellation
Key West Ghost Tours: Southernmost Shadows and Ghosts
Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate storytellers, you’ll wander through historic Old Town, where every corner hides a ghostly tale. As you walk under the moonlight, prepare to be captivated by chilling stories of spirits from Key West’s history.
This tour visits nine to thirteen of the most haunted spots in Key West, where you’ll stand on the very ground where ghostly encounters have happened. While the tour doesn’t enter private buildings, just being near these haunted places is thrilling. Picture yourself standing by the historic Curry Mansion or the mysterious Casa Antigua, hearing the true, spine-tingling tales that have been told for generations.
Covering a mile of haunted history, this tour is perfect for history lovers, thrill-seekers, and anyone curious about the supernatural. Southernmost Ghosts promises a night of unforgettable stories and lasting chills.
Duration: 1 hour
- Free cancellation
Key West’s Old Town Treasures: A Self-Guided Audio Tour
See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour.
• Find out how the town nearly went bankrupt before reinventing itself as ‘The Conch Republic’ in the 1900s
• Hear from producer Ed Owen, a seasoned Key West traveller and tour guide
• Do it all in 90 minutes or linger at stops along the way with complete control over when you start and finish
• Get unlimited use before your booking date and after it
• Use the virtual tour option at home
• This tour does not enter or include entry to any of the attractions mentioned en route
Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code.
The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.
Duration: 1 hr 30 min – 2 hours
- Free cancellation
- Private tour
Skip the Line: Mel Fisher Maritime Museum Admission Ticket and Audio Tour
Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story - it is also a nationally recognized research institution.
Duration: 1–4 hours
- Free cancellation
- Skip the line
Private 2-Hour Tiki Boat Party in Key West & Mini Sandbar
Set Sail for Tiki Revelry in Key West's Historic Seaplane Basin!
Cruise to Key West's unique Seaplane Basin. In the early 1900s, this spot buzzed with activity as seaplanes took off and landed. Today, it's a vibrant harbor where colorful houseboats bob gently, creating a charming island atmosphere.
Gear up for an afternoon of tropical fun on our 2-hour Tiki Boat Party & Mini Sandbar Escape! Let your captain navigate the turquoise waters as we head to a secluded swimming hole, the perfect setting for a tiki celebration.
Duration: 2 hours
- Free cancellation
- Private tour
Key West - Museum Culture Pass
The Key West Museum Culture Pass is an excellent way to explore the rich cultural history of this vibrant city. With the pass, you can access four unique and diverse museums.
Duration: 4–5 hours
- Free cancellation
Key West Airport (EYW) to Key West - Arrival Private Transfer
Book your private arrival transfer from Key West Int Airport (EYW) to Key West hotels.
Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer.
Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination.
• We track your flight.
• Our driver greets you with a name plate.
• We provide door-to-door service.
• There are no hidden charges.
• We use clean cars and professional drivers.
Duration: 25 min
- Free cancellation
- Private tour
Key West Private Sandbar Charter with Swimming & Snorkeling
This private Key West sandbar charter gives your group flexibility to swim, wade, float, snorkel, or relax at a pace that suits you. Rather than promising one fixed destination, the captain selects an appropriate sandbar or shallow-water area based on tides, weather, depth, traffic, safety, and operating conditions.
Duration: 4 hours
- Free cancellation
- Private tour
Mel Fisher Maritime Museum Admission Ticket
Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story - it is also a nationally recognized research institution!
Duration: 1–2 hours
- Free cancellation
PRIVATE Guided Mangrove Eco-Tour Adventure
Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty of the Florida Keys. Paddle through tranquil mangroves where your expert guide highlights local wildlife and ecological wonders, from tropical bird habitats to vibrant sea turtles. This eco-friendly adventure is suitable for all skill levels, ensuring a relaxing time as you navigate the peaceful waterways. Discover hidden gems and soak in the lush surroundings, all while enjoying small group sizes for a personalized experience.
Duration: 2 hours
- Free cancellation
- Private tour
Private Customizable Charter in Marathon Florida
This snorkeling adventure goes beyond the ordinary by offering crystal-clear waters, vibrant coral reefs, and an incredible variety of marine life—all in a serene, picturesque setting. Unlike standard tours, we prioritize your safety and comfort with a dedicated crew, allowing you to fully relax and enjoy the experience. It’s not just a snorkeling trip—it’s an immersive journey into the beauty of the ocean, designed for both beginners and seasoned explorers.
Duration: 1 day
- Free cancellation
- Private tour
Advanced Wreck Diving at USNS General Hoyt S. Vandenberg
The USNS General Hoyt S. Vandenberg, a retired Air Force missile tracking ship, lies 160 feet beneath the waves, offering advanced certified divers an unparalleled underwater adventure. Explore its expansive 520-foot structure, where vibrant coral and diverse marine life thrive. Navigate through radar dishes, intricate passageways, and expansive decks, all teeming with fish, turtles, and majestic Goliath groupers. This signature dive in Key West promises unforgettable photo opportunities and a chance to witness the beauty of an artificial reef, making it a must for any experienced diver's bucket list.
Duration: 4 hours
- Free cancellation