Top Key West On the Water - page 8

This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon: extended time at a shallow-water sandbar, snorkeling in clear backcountry waters, and a sunset on the water. Sailing aboard a historic schooner with a small group, guests enjoy a more personal experience in calm, less crowded areas of the Keys, all while soaking up one of the best afternoons Key West has to offer.

* US Coast Guard licensed Master Captain and Mate provided for your safety & comfort * Open bow and comfortable cushioned perimeter seating * Lots of shade available* Premium Bluetooth marine sound system with island vibe music * Enjoy cruising the Keys waters in comfort * Beautiful Florida Keys sunset from the water * Enjoy the relaxing Sandbar * Family friendly / fun for all ages * Make everlasting memories!

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.

We make your first dive unforgettable with small groups, expert PADI instructors, and the best gear on the market - SCUBAPRO. We start you off in the pool to help build confidence and to shake the rust off. Then you will head to our air conditioned facility in downtown Key West. After a quick check-in process you’ll board our custom built dive boat, The Phoenix, conveniently docked across the street behind the Hyatt Centric Hotel. Safe, fun, eco-friendly, and outfitted with premium equipment, we can’t wait to get you back in the water!

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!

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the sky transforms into a vibrant canvas of colors, providing an unforgettable backdrop for your evening. Bring your favorite beverages to toast the day's end in a romantic and relaxing atmosphere. Capture unique photo opportunities with breathtaking reflections in the water, making this experience perfect for couples or anyone looking to unwind after a day of exploration. - Enjoy a serene 2-hour cruise on the tranquil waters of the Florida Keys - Front-row seat to a spectacular sunset with unobstructed views - Bring your own beverages for a personal touch during the cruise - Perfect for couples or those seeking a relaxing escape after sightseeing

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.

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.

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.

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

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.

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.

Welcome to Key West Boat & Jet Ski Adventures! Enjoy a fully customizable 6-hour private boat charter exploring Key West’s stunning backcountry. Begin with a scenic cruise past iconic landmarks like Mallory Square and the Southernmost Point. Customize your stops to visit pristine sandbars such as Jewfish, Snipes, and Mud Key, where you can swim, sunbathe, and relax in crystal-clear waters. Snorkel vibrant reefs filled with colorful marine life and watch wild dolphins play freely at the Dolphin Playground. Glide through peaceful mangrove tunnels and soak up the natural beauty of this unique ecosystem. Throughout the day, unwind on the spacious swim deck, sip your favorite beverages, and enjoy the personalized attention of your licensed local captain. Perfect for families, couples, or groups looking for a private, flexible, and unforgettable Key West adventure tailored to your pace and interests.

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!

Fish for goliath grouper or sharks with an experienced captain who has three decades of experience fishing the waters of the Keys. Your captain knows the area waters and knows the techniques that will help you land your fish. Quality tackle, friendly service, and an attitude focused on putting you on the fish will make this a memorable trip!

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.

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!

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!

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.

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.

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.