Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset!
Included in the tour price is bottomless house champagne Chandon Brut, 8 premium red and white still wines, ice-cold beers & White Claws, and a champagne-inspired Gourmet Cheese Buffet (naturally gluten free) that includes 4 incredible international cheeses, paired plump berry tray, local smoked fish dip, crunchy crisps and fresh-baked crusty bread. Two other Moët & Chandon champagnes are available for additional purchase - both at wholesale price - only for onboard guests.
Key West is famous for its tropical sunset, and there’s no better way to watch it than on this famous Sunset & Moët Cruise. This public trip is always limited to 14 adult passengers on a 28 person sailing catamaran, for guests comfort and quality control. And NO kids!
Duration: 2 hours
The Original Key West Island Jet Ski Tour from Barefoot Billy's
Billy started his Island Jet Ski Tour in 1992. There are many imitators, but only one Original Island Jet Ski tour! Our guides are licensed and local, so they know the waters surrounding our island like their backyard - because it is!
Full Island Loop: You completely circle Key West, a trek that is impossible for most larger boats due to shallow backcountry waters.
Sightseeing from the Water: You get unique vantage points of famous landmarks, including the Southernmost Point buoy, Mallory Square, and Sunset Key.
Marine Life: The route passes through the Key West backcountry (mangroves), where it's common to spot dolphins, sea turtles, rays, and tropical birds.
Freestyle "Play" Time: Unlike strictly regimented tours, this includes a dedicated "free play" segment where you can go full throttle, practice carves, or jump wakes in a safe, open-water zone.
Duration: 1 hr 30 min
- Free cancellation
Key West Clear Kayak Eco Tour
Discover the natural beauty of Key West on our 2-Hour Guided Clear Kayak Eco Tour. Paddle through crystal-clear waters in a completely transparent bottom kayak, giving you a unique view of tropical fish, seagrass beds, and vibrant marine life beneath you. Along the way, your guide will share fascinating insights into the local ecosystem and hidden gems of the Florida Keys. Perfect for couples, families, and adventurers looking to experience Key West like never before.
Duration: 2 hours
- Free cancellation
Key West Deep Sea Fishing: Big Fish
If you’re looking for some of the best fishing that money can buy out of Key West, Florida, you can’t go wrong with Corsair 2 Sportfishing. With over 3 decades of local fishing experience under his belt, Captain Russ McKinley is your man if you want to get the best out of these deep blue waters.
His boat is a 50’ Hatteras saltwater fishing boat that can take up to 6 anglers fishing at the same time. Powered by twin 550 HP Detroit Diesel engines, this fishing machine is unstoppable on the water.
The vessel comes rigged with state-of-the-art navigational electronics and safety equipment, outriggers, a fighting chair, a live bait tank, and ice-boxes. It’s also very comfortable and features 2 private restrooms, a kitchen, a flybridge, beds, and AC.
This beauty can take you for some amazing deep sea and reef fishing up to 18 miles offshore on full day trips. This trip will also provide higher chances of catching Marlin!
Duration: 4 hours
- Private tour
Private Luxury Sandbar Excursion in Key West
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
Duration: 4 hours
- Free cancellation
- Private tour
Dry Tortugas National Park Day Trip by Luxury Private Boat
Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury boat, ensuring a swift and comfortable journey through the stunning turquoise waters to Dry Tortugas National Park. Revel in top-class amenities perfect for sunbathing, sightseeing, and relaxing with your private group. Discover secluded islands and pristine tropical beaches on this guided full-day adventure. History buffs will be captivated by Fort Jefferson, while outdoor enthusiasts will relish the world-class snorkeling and breathtaking natural beauty. This unique voyage combines exhilarating open-sea travel with an intimate and personalized experience, creating memories that will last a lifetime.
Duration: 8 hours
- Free cancellation
- Private tour
Key West Shore Excursion: Hop-On Hop-Off Trolley Tour
When you arrive in port in Key West, take an independent, hop-on hop-off trolley tour shore excursion for the best way to explore the island. While you’re off your cruise ship, simply sit back and relax while your expert tour guide turns back the pages of history to the days of Indians, pirates, wreckers and the Civil War. You’ll get a full picture of Key West during your limited time ashore.
Duration: 1 hr 30 min
- Free cancellation
Sandbar Excursions with Snorkeling and Sunset Cruises in Key West
Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning sunsets. This intimate charter accommodates up to 6 guests, ensuring a personalized experience. Choose from hourly, half-day, or full-day trips to tailor your Florida Keys getaway. Unwind and create unforgettable memories in paradise with a guided tour that showcases the essence of the Keys.
- Snorkel in the clear waters of Key West with small group settings
- Relax on secluded beaches away from the crowds
- Enjoy breathtaking sunsets on the water
- Flexible trip duration options: hourly, half-day, or full-day
Duration: 4 hours
- Free cancellation
- Private tour
Marathon Snorkeling and Sandbar Adventure
Discover the best of the Florida Keys with a thrilling snorkeling and sandbar adventure from Marathon Mermaid. Begin at the stunning Sombrero Reef, where vibrant coral and tropical fish await beneath the clear blue waters. No matter your skill level, this snorkeling excursion promises unforgettable underwater sights. After your underwater exploration, glide over to a picturesque sandbar to continue the fun—swim, kayak, paddleboard, or simply soak up the sun in a serene island setting. With snorkel gear, kayaks, paddleboards, complimentary drinks, and light snacks provided, this trip is a perfect blend of adventure and relaxation.
Duration: 4 hours
- Free cancellation
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.
With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.
Duration: 2 hours
- Free cancellation
Half-Day Backcountry Fishing Charter from Key West
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.
Duration: 4 hours
- Free cancellation
- Private tour
Key West: Dolphin Watching cruise & Snorkeling unlimited beer & soda
Dolphins are widespread in the Florida waters especially Key West as they prefer the warm waters of the tropical ocean. As we visit the Dolphin pod in the Key West Waters don't be surprised to hear their vocals in the form of clicks and whistles. Dolphins are some of Earth's most intelligent animals and very social. At times we can see pods of dolphins in the 1000's. Dolphins love to play and often we can see them Jumping out of the water. When we finish the Dolphin watch we will cruise and enjoy one of the largest reefs in the world for a fun filled snorkeling adventure. On the way back enjoy an open bar serving unlimited cold draft beer and soft drinks.
We offer this trip daily in the Morning and in sunset.
Duration: 3 hours
- Free cancellation
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!
Duration: 2 hours
- Free cancellation
1 Hour Key West Jet Ski Freestyle Adventure
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!
Duration: 1 hour
- Free cancellation
Key West Cooking Show Chef Demonstration with Meal
Looking for an unforgettable culinary experience? The expert chefs are passionate about sharing the unique flavors of Key West while keeping you entertained. Watch as they bring fresh, local ingredients to life with traditional cooking techniques and island flair. From savory entrees to irresistible tropical desserts, you’ll enjoy an interactive and delicious experience—topped off with a taste of paradise!
Duration: 1 hour
- Free cancellation
Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters
Experience the Florida Keys like a true Conch! Our 4-hour Backcountry Sandbar Excursion takes you to a stunning location chosen by your captain based on the day's weather and tides. Immerse yourself in the intoxicating beauty of turquoise waters and deep blue skies. Keep an eye out for the incredible local wildlife – you might spot rays, turtles, fish, and even playful dolphins! Once we arrive at the sandbar, you'll have ample time to swim, soak up the sun, and simply unwind in this island paradise. Just bring your swimsuit, towel, sunscreen, and any snacks and drinks (including alcohol) you'd like to enjoy. This private trip is perfect for up to 6 passengers and runs daily from noon to 4 pm.
Duration: 4 hours
- Free cancellation
- Private tour
Champagne Dolphin Sail and Reef Snorkel
Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the wild dolphins that live, feed and breed right along the south side of Key West. Get that yacht feeling with Champagne Service from your professional crew.
Tickets are fully refundable if canceled outside of two weeks in advance!
Duration: 3 hours
Key West Historic Schooner When And If Sunset Cruise
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive.
Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champagne glass as the sun dips below the horizon, while your experienced crew handles the sails — or try your hand at steering this classic wooden schooner yourself. Glide along turquoise waters, spot playful dolphins and local wildlife, and enjoy an unforgettable evening that blends history, luxury, and adventure.
Highlights:
Historic schooner experience aboard the When And If, commissioned by General George Patton in 1939.
Champagne sunset toast included
Elegant and exclusive cruise - Avoid the crowds
Hands-on sailing opportunity: take the wheel under guidance from your experienced crew.
Spot dolphins, sea birds, and local marine wildlife.
Perfect for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted fare.
Duration: 2 hours
- Free cancellation
Key West: Robert the Doll After Dark Ghost Tour (1 Hour)
Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most legendary paranormal figures.
Your experience begins with a 30-minute guided ghost tour through the Civil War-era fort, exploring its dark history, unexplained activity and stories gathered over decades.
Then you'll spend 30 minutes seated directly with Robert the Doll. Hear the documented history behind the legend, separate fact from folklore, and discover the latest unexplained activity surrounding Robert.
USA TODAY has named Fort East Martello one of America's Top 10 Haunted Destinations. This isn't a ghost tour that simply tells you about Robert. You'll enter his fort and meet him after dark.
Duration: 1 hour
- Free cancellation
Key West Historic Old Town 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.
Duration: 2 hr 30 min
- Free cancellation
Key West SNUBA Experience
Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified!
Go Beyond Snorkeling into new depths for greater durations where you can easily and safely breathe underwater without heavy, cumbersome dive gear. Discover amazing coral formations, schools of tropical fish, and swim alongside colorful creatures as you glide effortlessly beneath the waves.
Duration: 3 hr 30 min
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.
Duration: 2 hours
- Free cancellation
Tiki Cocktail Class in Key West, Florida
Learn the History of Tiki and How to Make Authentic Tiki Cocktails!
Curious about the history of tiki?
Want to make authentic tiki cocktails?
Our tiki workshop is a two hour intimate learning experience where we guide you through the fundamentals of tiki mixology while teaching you the who, why and when of tiki culture. We'll show you how to do a proper rum tasting and how to light drinks on fire. We also give you the tools and ingredients to make one of the first recorded rum cocktails from the 1800s as well as one of the most famous tiki libations to this day, the Mai Tai.
Our price per person includes 1 rum tasting and 4 cocktails!
Classes are held every Wednesday and Saturday at Tiki House Key West, 203 Duval Street.
Must be 21 years of age to participate. We recommend eating before you arrive to the class.
Duration: 2 hours
- Free cancellation
- Private tour
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida
Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks such as Boot Key Harbor, the Atlantic Ocean, and the historic Seven Mile Bridge.
Relax on deck and enjoy the changing colors of the sky while sipping a complimentary champagne toast. The catamaran offers plenty of seating, shaded areas, an onboard restroom, and a cooler stocked with ice, water, and soda.
This tour provides a laid-back and memorable way to experience the Keys at golden hour—perfect for couples, families, and anyone who wants to unwind on the water.
Duration: 2 hours
- Free cancellation