Top Key West On the Water

This 90-minute guided tour covers 26 miles around Key West, offering a longer and more complete riding experience than a one-hour freestyle ride while requiring less time than the two-hour flagship tour. Groups are limited to a maximum of six jet skis, and experienced local guides adjust the route to current conditions. It combines island sightseeing, backcountry riding, open-water stretches, and—when conditions allow—time in the shallow waters near Boca Chica.

The 21' Hurricane Sundeck is the perfect blend of comfort, versatility, and performance, making it a top choice for adventurers and families alike. Whether you’re fishing, snorkeling, or cruising, this boat delivers an exceptional experience on the water. Why It Stands Out: Smooth & Safe Ride: Handles well in all conditions for a worry-free outing. Versatile Design: Ideal for fishing trips, family adventures, or group excursions. Premium Features: Includes a Bimini top for shade, live well, rod holders, swim ladder, spacious deck, and comfortable seating. Perfect Size: 21 feet long with capacity for up to 10 passengers—room for everyone without sacrificing maneuverability. Adventure Ready: Great for sandbar hopping, snorkeling, or simply relaxing in style.

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwind in a refined and intimate setting away from crowded party boats. Enjoy complimentary beer, wine, champagne, and soft drinks throughout the cruise, with cocktails available for purchase. Savor a selection of hors d’oeuvres including cheese and crackers, fresh vegetables with dip, and shrimp cocktail — perfectly paired with a breathtaking Florida Keys sunset. Watch the sky transform into vibrant shades of orange, pink, and gold as the sun dips below the horizon, creating unforgettable photo opportunities. Perfect for couples, celebrations, or anyone seeking one of the top-rated experiences in Key West. Advance reservations are highly recommended, as this popular sunset sail often sells out.

Spend the afternoon exploring the crystal-clear waters of the Florida Keys before ending your day with an unforgettable Key West sunset. We'll cruise to one of Key West's famous remote sandbars where you'll have plenty of time to swim, relax, paddle, and enjoy the turquoise water. After soaking up the sun, we'll raise anchor and cruise home while watching the sky transform into brilliant shades of orange, pink, and purple over the Gulf of Mexico. Whether you're celebrating, relaxing, or simply making the most of your vacation, this is the perfect combination of adventure and sunset cruising.

Head out to sea or stay close to land around Key West and the various other island. Led by your experienced captain and owner this charter offers a chance to catch a variety of fish while soaking up the sun and enjoying the stunning ocean views. Whether you're an experienced angler or a beginner, the friendly crew ensures a memorable day on the water, complete with all necessary gear and guidance. Experience the thrill of reeling in your catch in one of Florida’s prime fishing destinations.

This experience combines the thrill of fishing with a relaxed, fun atmosphere. You’ll be guided by a seasoned captain who knows the best local fishing spots—hidden honey holes full of fish and stories. Unlike typical charters, we offer hands-on tips for beginners and seasoned anglers alike, ensuring everyone learns something new while having a great time. It’s more than just fishing—it’s an adventure filled with laughter, connection, and unforgettable moments on the water.

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.

The 24' Hurricane Sundeck stands out as the ultimate choice for families and groups looking for comfort and versatility on the water. Its spacious design and thoughtful features make every outing enjoyable and stress-free. Why You’ll Love It: Perfect Balance: Combines generous space with easy maneuverability for smooth cruising. Room for Everything: Plenty of space for coolers, gear, and unforgettable memories. Premium Features: Wraparound seating, built-in cooler space, Bimini shade top, stereo system, swim ladder, and a wide deck area for lounging. Ideal for Any Occasion: Great for family outings, sandbar trips, sightseeing, or celebrating with friends. Capacity: Comfortably accommodates up to 12 passengers.

Create your own adventure: fish, snorkel, paddleboard, or just cruise in style! The newest fleet in town! Our spacious pontoons provide plenty of space and shade while you make your way through our beautiful local waterways! What’s Included: 12 Passenger Pontoon Boat Rental (Children and babies count as passengers) Safe, reliable, and well-maintained equipment Includes a 70qt cooler (purchase ice at check-in) Life vests for all passengers Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+ Optional Add Ons: Paddleboards- A fun and suitable activity for people of all ages and abilities. Lily Pad- This floating foam island allows you to rest, kick-back, tan, run, and play on.

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!

Double Decker Pontoon Boat with slides for up to 14 passenger Rental in sunny Key West, Florida. 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!

Experience the ultimate adventure aboard our 25' Cobia Center Console with twin engines, designed for power, stability, and comfort. Perfect for fishing trips, sandbar cruising, or exploring offshore waters, this vessel offers unmatched versatility. Highlights A safe, comfortable ride that handles well in all conditions, making it a favorite for those who want flexibility on the water. • Length: 25 feet • Capacity: Up to 9 passengers • Features: T-top shade, live well, rod holders, swim ladder, spacious deck, and premium seating • Best For: Fishing enthusiasts, families wanting versatility, or groups looking for comfort and style

Your family is the only group aboard - this is never a shared or attended scattering, where ashes go out with a stranger's. A USCG-licensed local captain plans the ceremony with you by phone beforehand: the readings, the music, who will scatter, and anyone who needs extra care. Offshore he shuts the engine down and the time is yours, for as long as you need it, past the three-nautical-mile line federal rules require. Six Fins files the EPA burial-at-sea notice afterward so you are not left with paperwork. Best suited to families and small groups up to six who want an unhurried, dignified service on calm turquoise water, including elderly guests and children - there is shade, seating, and a private head aboard. Departs Stock Island with free parking steps from the dock. A note on our photos: at families' request, our images show the boat and local waters only - never memorial guests or ceremonies.

This private eco boat tour focuses on the Key West National Wildlife Refuge and its mangroves, islands, flats, and coastal habitats. Your group can prioritize wildlife viewing, photography, snorkeling, swimming, or relaxed exploration. The flexible itinerary responds to current conditions and refuge protections, giving guests a private and respectful way to experience Key West’s backcountry environment.

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!

The Experience: Don't miss your chance to experience a luxury charter in the Florida Keys, versatile enough for any on-water activity you can envision. Whether you're interested in snorkeling, light tackle fishing, sandbar hopping, sunset cruises, dolphin watching, sightseeing, trips to the intercostal from key west to miami, we do it all! Fun for the entire family! We also offer poker runs, with our 36 Contender powered by triples give us a whopping 1,050 hp YOUR day, YOUR way: Probably the best thing about our boat service is we don't do cookie-cutter trips. Every trip is personalized to who and what is important to you. As a bareboat/demise charter, this vessel offers ultimate freedom—the itinerary is entirely up to you. With endless possibilities in the Keys, our seasoned team, in conjunction with the captain you choose, will tailor the journey to your dream day's desires. We'll provide you with a curated list of recommended captains, ensuring a seamless, expert-guided adventure.

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.

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.

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.

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.

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.

The Marquesas Keys offer one of the most remote private boat experiences available from Key West. This full-day charter gives your group time to prioritize snorkeling, beaches, sandbars, paddleboarding, wildlife viewing, photography, or relaxation. Unlike a fixed group tour, the preferred itinerary is tailored to your interests while the captain determines the safest route for the day’s conditions.

This private Florida Keys yacht charter combines daytime exploration with an overnight stay aboard a Jeanneau NC 895 Weekender. The preferred itinerary can include cruising, snorkeling, sandbars, dining stops, or marina time, subject to conditions and availability. Up to four guests can enjoy a more personal alternative to a scheduled group cruise while the captain manages safe navigation.