Full Day Backcountry Fishing Charter in Key West
Our full-day backcountry charter gives you the time and range to dive deeper into the fishing opportunities surrounding Key West. With 8 hours on the water, we can go beyond the usual grounds—working the flats, channels, and mangrove edges at your pace, with the flexibility to follow the bite wherever it’s best. Depending on conditions, we may even venture west toward the remote Marquesas Keys, known for their rich marine life and pristine beauty.
Our captain is a lifelong angler and Army veteran who brings both local knowledge and a steady, thoughtful approach. There’s no set route or rigid schedule—just a focus on giving you the best possible day on the water. With a max of four guests, you’ll fish comfortably and get personalized insight into the backcountry’s changing tides and seasonal patterns. It’s a full day built for anglers who want to go further and get more from their time on the water.
Duration: 8 hours
- Free cancellation
- Private tour
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Key West 6Hour Private Fishing Charter on 47' Hatteras
Spend six hours fishing the waters of Key West aboard Sanctuary, our spacious 47-foot Hatteras with an air-conditioned cabin. Depart from Oceans Edge Resort & Marina with Cowboy Cowgirl Sportfishing Charters, a family-owned Key West fishing business since 1965.
This private charter gives your group more time than a half-day trip to explore fishing grounds and enjoy the action. Your captain selects fishing locations and techniques based on the weather, seasonal conditions, and what’s biting. Depending on conditions, you may target mahi-mahi, wahoo, tuna, sailfish, or other local species.
Whether you’re bringing first-time anglers, family, friends, or experienced fishermen, our crew offers hands-on guidance and a relaxed, welcoming atmosphere. Between bites, cool off in the air-conditioned cabin and enjoy your time on the water. Fishing opportunities vary with conditions, and catches are never guaranteed.
Duration: 6 hours
- Free cancellation
- Private tour
Key West Airport (EYW) to Key West - Round-Trip Private Transfer
Book your Private Round-Trip Transfer from Key West Int Airport (EYW) to Key West hotels and return.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private ,door to door airport transfer.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
Meeting with a Nameplate
We track your Flight
Door-to-door Service
No Hidden Charges
Clean cars & Professional drivers
Duration: 30 min
- Free cancellation
- Private tour
Key West Clothing-Optional Private Sandbar & Snorkeling Charter
This private clothing-optional Key West charter combines sandbar relaxation, snorkeling, paddleboarding, and wildlife viewing with clear privacy protections. It is a respectful, non-explicit experience for guests seeking a naturist-friendly day on the water. Photography and recording restrictions protect guests and crew, while the itinerary remains flexible and subject to current conditions.
Duration: 6 hours
- Free cancellation
- Private tour
Key West: Nautic Star 21 Ft Speed Boat 21ft 115 Horse Power Speedboat-6 Pass
Have a blast on the half day boat rental a 21ft Nautic Star speed boat. The boat holds up to 6 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 60 horse power, a Bimini Top, Radio and Comfortable Seats.
Remember to bring your bathing suits, sun glasses, sunscreen, towel, hats and favorite beverages.
Duration: 4 hours
Sandbar Tour Key West
Leave the crowds behind and spend the day at one of Key West's beautiful sandbars with a maximum of just 6 guests onboard. Your local captain will choose the best location based on the day's conditions, giving you the best chance to enjoy clear, shallow water and a relaxing atmosphere. Snorkeling gear, floaties, and onboard Bluetooth music are included, so all you need to do is jump in, float, explore, and enjoy the Florida Keys at your own pace.
Duration: 3 hours
- Free cancellation
- Private tour
Experience Florida Keys Boat Charter Private Tour
Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while soaking in the sun and taking in stunning views of luxurious homes and coastal landscapes. Keep your eyes peeled for dolphins, sea turtles, and tropical seabirds as you glide over the crystal-clear waters. You can choose between a scenic harbor cruise or an island swim stop at a sandy beach for a refreshing dip in the turquoise sea. This is the perfect way to create unforgettable memories in paradise.
- Enjoy a leisurely 1.5-hour cruise on a tiki bar boat
- Spot local wildlife, including dolphins and sea turtles
- Customize your cruise with a scenic harbor tour or beach swim
- Knowledgeable Captain shares local history and fun facts
Duration: 1 hr 30 min
- Free cancellation
- Private tour
6hr Offshore Big Game Fishing Adventure
Set sail for a thrilling morning on the Atlantic with this shorter offshore fishing trip. Departing at 8 AM, you'll head into the deep blue, fishing in depths exceeding 1500 feet. This adventure targets popular species like Mahi Mahi, Tuna, Wahoo, and Sailfish, allowing you to cast your line in some of the best fishing grounds in the state. Plus, if you land a trophy catch, arrangements can be made to have it beautifully mounted for display.
Duration: 6 hours
- Free cancellation
- Private tour
Sunset Powerboat Cruise
This private sunset cruise is the perfect way to enjoy a romantic evening or spend quality time with loved ones in the stunning surroundings of Key West. With everything taken care of, you can sit back, enjoy the views, and make lasting memories.
Step aboard our 24’ center console for a private, unforgettable Sunset Cruise in Key West! Perfect for up to six guests, this two-hour adventure offers a relaxing and scenic way to experience the beauty of Key West’s waters as the sun sets over the horizon. Cruise through the tranquil waters of the Key West harbor, enjoying sweeping views of the open sea as the sky transforms with the colors of the sunset.
Relax and unwind with your friends or family while a professional captain guides your journey. Bring your own drinks (BYOB) or enjoy the bottled water and soda we provide. Set the perfect mood with your favorite tunes via Bluetooth speakers, and make this a truly special evening on the water.
Duration: 2 hours
- Free cancellation
- Private tour
Key West Private Bachelorette Yacht Party Cruise
This private Key West bachelorette boat charter is reserved for your group rather than shared with strangers. Celebrate aboard a Jeanneau NC 895 Weekender and tailor the outing around sandbar time, snorkeling, wildlife viewing, waterfront cruising, or sunset views when conditions permit. It combines a private yacht-party atmosphere with a flexible itinerary and a captain responsible for safe navigation.
Duration: 6 hours
- Free cancellation
- Private tour
Private Dry Tortugas National Park Boat Charter from Key West
Experience the Dry Tortugas on a private full-day charter from Key West, designed for travelers who want more freedom than a crowded ferry schedule allows. Your group can explore Fort Jefferson, snorkel in crystal-clear water, relax on remote beaches, and, when conditions allow, visit Loggerhead Key and its historic lighthouse. We depart early to maximize your time in the park and, when possible, arrive before the larger ferry crowds. Because this is a private charter, the itinerary can be tailored to your group, weather, and sea conditions for a more personalized Dry Tortugas experience.
Duration: 8 hours
- Private tour
Private Southernmost Key West History and Culture Walking Tour
Join us for the best walking tour in Key West!
You will be amazed by how much history and culture our small island has! 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!
Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States.
The private tour is the best way to explore Key West and have fun with your own group of friends or family!
Book Now and call us to schedule the time that is convenient for you!
This tour includes a slice of Kermit's Key Lime Pie for each traveler & a bottle of water.
What to bring and to wear:
Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
Duration: 2 hours
- Free cancellation
- Private tour
Key West Maternity Photography Experience
Whether you are expecting your first baby or adding to your growing family, your session is personalized to you. Your photographer will gently guide you throughout the shoot so you feel comfortable confident and beautiful in front of the camera. This is a beach shoot or garden shoot, One location, multiple outfits are permitted.
Whether just Mom or adding Dad in the photos as well, these images will create artwork that you will treasure long after your baby arrives. Request an upgrade for studio shoot.
Duration: 1 hour
- Free cancellation
- Private tour
Key West Private Tiki Bar Crawl by Boat
This private Key West tiki bar crawl travels by boat rather than on foot. Your group enjoys scenic waterfront cruising and direct dock access to participating venues when available. The itinerary is flexible, but the captain selects the safe route and adjusts stops according to venue access, timing, weather, marine traffic, and operating conditions.
Duration: 4 hours
- Free cancellation
- Private tour
Private Morning Tiki Boat Eco Cruise in Key West
See Key West and the Florida Keys from the nearshore waters on a private morning tiki boat cruise, with a US Coast Guard Certified Captain pointing out the sights as you go. The route passes Historic Charter Boat Row in Garrison Bight, Fleming Key, and Man of War Harbor, with time in Pearl Basin, also called the “Dolphin Playground.” Keep watch for rays, sharks, dolphins, turtles, and other marine life while cruising past charter boats, houseboats, mansions, and live-aboard boats. Bottled water is provided, and the cruise gives you a chance to photograph the coastline and wildlife from the boat.
Duration: 2 hours
- Free cancellation
- Private tour
Private Boat Tour of Flagler's Famous Bridges from Big Pine Key
This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise up the bay side and back down the ocean side (or vice versa). Learn the history of the bridges and the Flagler Railway, and see mangroves and beaches. A great way to see the keys!
Duration: 1 hour
- Free cancellation
- Private tour
Scooter Rental Explore at Your Own Pace
Key West is a small island with a big personality, and the only way to truly experience it is on your own terms. Island Safari Rentals Rentals gives you a reliable, comfortable two-passenger scooter, a full tank of gas, and the freedom to write your own itinerary.
A well-maintained fleet and seamless pickup process. Two convenient locations mean you're never far from getting started.
Unlike a guided tour, there's no bus to wait for and no group to keep up with. Want to circle the island twice? Linger over lunch at a waterfront spot? Ride to the Southernmost Point at sunrise? It's entirely your call.
Rentals flex from a quick 3-hour spin to a full month, and same-day bookings are welcome.
Ride like a local. Explore like it's yours.
Duration: 3 hours
- Free cancellation
Miami Key West Day Tour With Private Driver & Guide
Explore the charming streets of historic Key West at your own pace. Enjoy a personalized experience as you visit iconic sites like the Hemingway House, famous for its feline residents, and the stunning views from the Key West Lighthouse. Relax at Smather's Beach and indulge in a unique alligator snack. Capture memories at the 90 Mile to Cuba buoy and discover the Truman White House. With private vehicle transport and flexible itinerary, this tour is perfect for those who value freedom and personal choice.
- Private vehicle for a comfortable, no-crowd journey
- Tailor your own itinerary to explore Key West's highlights
- Visit memorable spots like the Hemingway House and Smather's Beach
- Pickup and drop-off at your hotel for convenience
Duration: 12–16 hours
- Free cancellation
- Private tour
Luxury Sandbar and Snorkeling trip in Key West
Snorkeling in Key West is a must-do on any vacation. The Florida Keys are home to the only living coral reef in the continental United States—but it’s offshore, so the only way to get there is by boat.
Skip the crowded “cattle boats” packed with tourists and treat yourself to a private experience instead. With Casual Monday Charters, you’ll have the boat to yourself, a flexible itinerary, and the chance to explore the reef at your own pace. No elbow-to-elbow crowds, no noise—just you, your crew, and the stunning waters of Key West.
Whether it’s snorkeling vibrant coral gardens, spotting dolphins on the ride out, or relaxing at a sandbar with friends, Captain Zak will craft a trip that feels like your perfect day on the water.
Duration: 4 hours
- Free cancellation
- Private tour
Tiki Party Boat with Slide from Key West
Set sail for adventure with our Tiki Party Boat rental, cruising the breathtaking waters! Whether you're soaking up the sun, spotting local marine life, or enjoying refreshing drinks on deck, our 14-passenger tiki boat is the perfect way to experience paradise. Complete with bar top and chairs, take your party to the sea!
Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!
Duration: 4 hours
- Free cancellation
Summertime Morning Swim in the Florida Keys Catamaran
Start your day with a soothing adventure aboard Island Girls Excursions' 53-foot catamaran. The Summertime Morning Swim is a family-friendly experience designed to immerse you in the stunning waters of Marathon, Florida. Cruise through crystal-clear waters, enjoying scenic views and the chance to spot dolphins and sea turtles. Once you reach your destination, dive into shallow turquoise waters, search for sand dollars, and soak up the natural beauty of the Keys. Perfect for families and friends, this excursion includes complimentary coffee, breakfast items, and comfortable onboard amenities.
- Family-friendly catamaran excursion in the scenic Florida Keys
- Spot dolphins, sea turtles, and rays during your cruise
- Swim in shallow turquoise waters and search for sand dollars
- Enjoy complimentary prepackaged breakfast items and beverages onboard
Duration: 3 hours
- Free cancellation
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 fantastic food. View the beautiful scenery, while experiencing the thrill of a chance to catch species such as Sailfish, Wahoo, Mahi Mahi, Tuna, Snapper, Grouper, King Mackerel, and Shark.
Your tour is guided by a licensed Captain in a 30” open fishing style boat with t-top for shade. All the fishing rods and reels, right and left-handed and all the tackle you need, as well as all other necessities including safety equipment. Travelers that have enjoyed our fishing charters also have enjoyed The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.
Duration: 4 hours
- Free cancellation
- Private tour
Private Key West Boudoir Photo shoot in Studio
What makes this Experience unique - Ten years Duval Street Gallery owners, nationally recognized sensual photographic partnership. Two local Key West artists. One completely personal experience.
It's a personal, artistic experience "Lovers Art" created by John and Bernadette McCall, Key West's Premier husband & wife photograph team with the experience of creating sensual fine art photography, they have been featured in books and earned them a unique place in the world of sensual photography. Exclusive sensual artist for the "Better Than Sex" Restaurants Nationwide.
Arrive to our studio, We will review the vision for your session as well as any personal items you've bought and then get started.
A recent client said it best "It was absolutely amazing. I had boudoir photos done. They made me feel comfortable right from the start. Trust me I was nervous. The quality of the photos were amazing. Hire Senses at Play you will not be disappointed. "
Duration: 2 hours
- Free cancellation
- Private tour
Key West: Smathers Beach & activities with a Sunset Catamaran & Open Bar
Fun in the sun when you make it over to Smathers Beachand have the best day with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella and enjoy the sun. Make sure to be at the check in for you sunset cruise with live music and open bar no later than 4:15 check in for a 5pm departure. On the 2 hour Sunset cruise you will have an open well bar which includes rum-runners, margaritas, mixed drinks, draft beer, wine, champagne & soft drinks. We will service finger food appetizers like Jamaican jerk chicken sliders on Hawaiian rolls, BBQ meatballs, veggie trays, cheese & cracker trays, Pita & hummus.
Duration: 10 hours
- Free cancellation