Things to Do in
Key West

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch for wildlife throughout the trip such as dolphins, sea turtles, fish, birds, and much more! A cooler filled with ice and bottled water will be provided. Feel free to bring any food or alcoholic beverages.

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature the perfect blend of natural beauty, maritime history, and the thrill of the open sea. Don't forget your camera – this is a photo opportunity you won't want to miss! Book your spot now and get ready to create memories that will last a lifetime.

Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into the beautiful water of the Florida Keys. Our 2-Hour Sunset Tiki Cruise transforms the spectacular Keys sunset into a private, moving masterpiece just for you. The Magic of the Sunset Cruise: Front-Row Seat to Nature’s Show: Glide across the tranquil, crystal-blue waters as the sky ignites in a breathtaking palette of reds, oranges, and pinks. You'll have the best, unobstructed view of the legendary Keys sunset from the comfort of your floating tiki bar. A Toast to Paradise: Whether you're celebrating a special occasion or simply savoring a perfect day, the sunset hour is magical. Bring your favorite beverages to toast the end of a perfect day as the stars begin to appear over the horizon. Secure your spot now and create a memory that will glow long after the sun goes down!

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing experience of a lifetime. It doesn’t matter if you are looking for a sunset cruise or to land the fish of a lifetime, Wet Tails Charters is here to make it happen. We offer 4,6,8 and 10hr fishing trips. Please remember if you had a great time to take care of your deck hand who works solely for tips.

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether you’re into sandbar hopping, snorkeling, or soaking up one of those legendary Key West sunsets, I’m all about creating the perfect day for you and your crew. Let me know what you’d love to do while you’re here, and together we’ll design a sandbar cruise that’s completely personalized, relaxed, and unforgettable. From hidden sandbars to vibrant reefs, it’s all about seeing my backyard playground—The Fabulous Florida Keys—like a local. Climb aboard the Casual Monday and let’s make some memories in paradise. See you on the water! Captain Zak

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.

Your Day, Your Way! Step aboard our 24’ center console and discover the best of Key West’s stunning waters! Perfect for groups of up to six people, this private, captain-guided adventure takes you through crystal-clear waters to beautiful sandbars and unspoiled beaches that can only be reached by boat. With comfortable seating and a T-top for shade, you’ll have everything you need for a fun and relaxing day exploring the breathtaking beauty of the Florida Keys!

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish. Marathon the hub for fishing in the Florida Keys, great beaches, shopping, and fantastic food. View the beautiful scenery, while experiencing the thrill of a chance to catch species such as Wahoo, Mahi Mahi, Tuna, Snapper, Grouper, King Mackerel and Shark that all swim around the reefs. Your tour is guided by a licensed Captain in a modern 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. Booking with confidence on TripAdvisor, it makes this charter an easy, reliable and enjoyable decision. Reserve Today to get hooked up! 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.

Short on time and want to do your own thing? Our supervised Freestyle Adventure is perfect for you. Our guide will take you to a secluded area where you can let loose and get your jet ski on. This jet ski rental is a great way to let loose and get your adrenaline fixed, or you just relax and chill if you prefer. It’s completely up to you. Some people don’t care for structured, guided tours. That’s why we came up with this freestyle alternative. Book yours today!

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the Lower Keys really well. So there are a few different areas to choose from on where to go and we can decide based on weather, wind, etc. There is the option to bring up to 2 kayaks ($25 rental fee per kayak). Snorkel equipment available (just let us know in advance sizes). The guide would be glad to hop in and point things out just let him know ahead of time. Possibility of seeing dolphins. We love the ocean and have a passion for being on or under the water! Also we are kid friendly!

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.

On your 4-hour backcountry charter, we’ll fish the local waters within 13 miles of Key West, exploring grassy flats, mangrove islands, and shallow wrecks that hold an impressive variety of species. Depending on the season, expect to target tarpon, jacks, permit, barracuda, sharks, snappers, and cobia. This trip is the perfect amount of time to get a feel for the rich fishing grounds of Key West’s backcountry. What makes it different? You’ll be fishing with Captain Ryan—a lifelong angler and veteran who runs every trip himself. With a max of four anglers, you’ll have plenty of room to cast, relax, and get personalized insight into the area’s changing tides and seasonal patterns. It’s an easygoing trip with serious fishing potential—and a local’s perspective you won’t find on a bigger boat.

Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar boat, where you can savor your favorite drinks while soaking up the sun. Keep your eyes peeled for dolphins, sea turtles, and vibrant seabirds as your knowledgeable captain shares insider secrets and local history of the Keys. Choose between a picturesque scenic harbor cruise or a refreshing swim stop at a beautiful sandy beach. This tour promises to be a memorable highlight of your Florida adventure. - 1.5-hour cruise on a unique tiki bar boat - Spot dolphins, turtles, and seabirds in their natural habitat - Learn local history and fun facts from your captain - Choose between a scenic cruise or a swim stop at the beach

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!

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on a 75–90-minute tropical fruit hunting tour. This engaging experience takes you through the grove where you'll learn about its 70+ year journey of restoration and resilience. Depending on the season, guests may even have the chance to pick ripe fruits directly from the trees. The tour includes a scenic walking exploration, followed by a delightful tasting session in an outdoor tasting room featuring prepared exotic fruits. - 75–90-minute tour revealing the history of Grimal Grove - Guided walking tour with opportunities to pick fruit (seasonal) - Outdoor tasting experience with a variety of exotic fruits - Learn about the 70+ years of restoration and resilience at the grove

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and shocking history exposed where it happened. More thrilling than a ghost tour and more revealing than a history tour, Key West’s underworld comes alive, Key West-style. Be the next eyewitness. We're bringing crime to the streets!

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.

Explore the vibrant & diverse underwater world of the Florida Keys with Salty Paws' Reef Snorkel Trip! Our experienced & knowledgeable crew will take you on a journey to the best snorkeling sites in the area, where you will witness breathtaking views of colorful coral reefs, tropical fish, and other marine life all of which call the reef home. Our Reef Snorkel Trip is perfect for both beginners & experienced snorkelers. Our crew will provide you with snorkeling gear and give you a safety briefing before entering the water. You'll be amazed at the sights you'll see and the memories you'll make during this once in a lifetime experience. During the trip, our experienced captains will take you to some of the most stunning locations around the reef where you can snorkel among the vibrant coral formations and observe an incredible range of marine creatures, including colorful fish, sea turtles, and even dolphins. All of which call the reef home.

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you to create your own adventure. Connect with Key West's abundant wildlife as you cruise the waters in search of our resident coastal dolphins. From there, we'll head to a secluded sandbar, a pristine shallow-water oasis where you can unwind and enjoy the tranquility. This tour is ideal for those who prefer to relax and socialize. Spend your time floating, swimming, or simply lounging with a cold beverage in hand. While snorkeling is an option, it is not a guided activity on this trip, making it perfect for guests who are more interested in a leisurely day on the water than a structured snorkel excursion. We'll provide a snack of fresh, organic fruit from Date & Thyme, and the trip is BYOB so you can bring your favorite drinks.

Experience the Thrill of Offshore Fishing in Key West Join us for a 4-hour shared deep-sea fishing adventure aboard a top-tier 6-passenger sportfishing boat(max is 6 on a boat)! This trip is perfect for solo anglers or small groups looking to target some of the most exciting offshore species in the waters off Key West. What to Expect Target Species: Depending on the season, you’ll chase Mahi-Mahi, Tuna, Wahoo, Sailfish, Kingfish, and more! Expert Crew: Our experienced captain and mate will guide you every step of the way. Top-Notch Gear: High-quality rods, reels, and tackle are provided! Comfort & Convenience: With a max of 6 guests, you'll have plenty of space to fish and enjoy the experience. Trip Details: Duration: 4 hours Departure: Leaves from Key West Group Size: Max 6 anglers (shared trip) Languages: English Whether you're a seasoned fisherman or a first-timer, this is your chance to experience world-class offshore fishing in Key West! Book your spot now!

Get ready for an exhilarating adventure on the vibrant waters of Key West with our private deep sea fishing charters. Led by the skilled and experienced Captain, our team is dedicated to making your fishing trip unforgettable. Reel in the fight of a lifetime as you battle magnificent mahi, king mackerel, sailfish, and more. Our knowledgeable captain and mate will guide you to the sharky hotspots and employ various techniques, including trolling and bottom fishing, to maximize your chances of landing a trophy catch. We believe in providing personalized service. Whether you're a seasoned angler or a curious first-timer, we'll tailor the experience to your skill level and preferences. We offer well-equipped vessels, clean facilities, and essential safety gear for a smooth journey

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.

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.

Enjoy the waters of the Florida Keys, don't have experience on the waters around Cudjoe Key? We have separate colored tracks to spots on the water on the 9" GPS.

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

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

Explore the stunning waterways of the Florida Keys with our kayak and stand-up paddleboard rentals. Perfect for all ages and skill levels, this self-guided adventure allows you to navigate through beautiful mangrove tunnels and trails at your own pace. Enjoy a 2-hour rental with the option to extend and receive all necessary safety equipment, paddle instruction, and a satellite view map of the area. - Choose from single kayaks, tandem kayaks, or paddleboards - Discover the unique ecosystem of the Florida Keys - Perfect for both beginners and experienced paddlers - All rentals include safety equipment and instructional guidance

Unleash your adventurous spirit with a jet ski rental from Seahorse Water Adventures in Marathon, Florida. Explore stunning coastal views and encounter native wildlife at your own pace, whether you’re seeking excitement or relaxation. With both half-day and full-day rental options available, you can conveniently tailor your experience to fit your schedule. Enjoy the freedom of the open water while we ensure a smooth rental process, including safety gear. - Explore the beautiful waters of the Florida Keys at your leisure - Encounter native wildlife and stunning coastal views - Safety gear included for a worry-free adventure

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Key West, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results