Top Key West Outdoor Activities - page 2

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

It's the only full 2-hour jet ski tour in Key West — a longer, more complete ride than the 60–90-minute harbor loops other operators run. ✅ A full 2 hours and a 28-mile loop all the way around the island ✅ Yamaha WaveRunner VX skis — fast, stable, and comfortable ✅ 5–6 scenic stops, from the Southernmost Point to sandbars and wildlife areas ✅ Small-group or fully private options ✅ Local guides who share island history and insider tips

Spend a stunning afternoon soaking up the sights of the Gulf of Mexico, chilling out at a sandbar, and watching dolphins at the Florida Marine Sanctuary. With the help of a fun and informative crew, you’ll explore the Floridian sea while your guides tell you all about the area’s history and wildlife. Enjoy lunch as well as unlimited beer, wine, and mimosas on your trip—just remember to drink responsibly.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach. With a range of departure times offered throughout the day, this tour is a popular, flexible choice for families. Your guide, who ensures that the small group has a personalized experience, takes photos and videos available for purchase after the trip.

Swim among coral and tropical fish in Key West's living reef on this snorkeling excursion. Sit back and relax on a custom-built boat, and sail to the reef where a professional crew is on hand to provide snorkeling instruction and guidance. After your swim, enjoy included beer, soft drinks, and water on the boat for your ride back. All snorkeling equipment is provided.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.

For the aquatic adventure of a lifetime, cruise to North America's only living coral barrier reef. No need to go diving or snorkeling for this great view—see tropical fish, sharks, turtles, colorful coral, and other sea life from the deck of the glass-bottom boat. Opt for an evening departure to enjoy a glass of Champagne as the sun sets into the Gulf of Mexico.

The best way to experience Key West is by getting out on the water, but with so many tours available, it can be hard to choose. This tour company has decades of experience of guiding visitors on jet skis through the waters they know so well and giving everyone plenty of time to let loose on the waves.

Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat for an easy day out. Whether you’re a beginner or an experienced angler, your captain and crew assist with your fishing skills. Fish for reef species like snapper, grouper, and mackerel. A fishing license and all bait are included, and the boat features restrooms, shaded seating, and a small galley with snacks and drinks for your convenience.

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

Save time and money in Key West on this all-inclusive, full-day excursion. Enjoy a day of sailing, snorkeling, and kayaking off the coast. Visit the Key West National Wildlife Refuge and explore an underwater world full of colorful fish and coral. Includes a buffet lunch with unlimited beer, wine, and soft drinks.

Take advantage of Key West’s paradisiacal scenery, and get up close and personal with its coral reefs and aquatic attractions, on this multi-stop snorkeling trip. Pick between daytime and sunset tour times (available seasonally), and hop aboard a speedy catamaran. Then, following professional instruction on board, grab your gear and snorkel around two different reef locations where you can see marine life before relaxing with beer and wine.

Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail toward the reef on a state-of-the-art catamaran. Receive snorkeling guidance from your crew—ideal for first-time snorkelers. Use of sanitized snorkel gear and reef-safe sunscreen means you don’t need to pack your own, plus cocktails and non-alcoholic drinks are provided after the snorkeling.

Kayaking is a great way to experience the Florida Keys but your views are typically limited to what's above the surface of the water. This small-group tour provides clear kayaks that let you discover the underwater world as well. As you paddle, you just need to look below to spot starfish, tropical fish, nurse sharks, turtles, jellyfish and more.

Cool off in Key West on a half-day water sports tour that features 10 different water activities for you to try, from jet skiing to parasailing to banana boat rides to snorkeling, and much more. Enjoy lunch and draft beer on the way back to the marina for those over the age of 21.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

Not only is Key West a playground paradise for adults, it is for dolphins, too. See how many of these playful creatures you can spot on this small-group sailing tour. You’ll board Our SQUID, we designed and built SQUID from scratch to ensure our guests, and the animals, have the best wildlife experience possible. This catamaran will take you and a crew trained by biologists into the waters around Key West. After watching dolphins swim, you’ll jump into the water and snorkel around the coral reefs to view other marine life.

Immerse yourself in nature in Key West on this small-group guided safari snorkeling adventure. Captain your own mini speedboat through 28 miles (45 kilometers) of Florida backcountry waters of the Florida Keys. Swim and snorkel in crystal clear waters of Mud Key, and keep your eyes for wildlife such as dolphins, turtles, and ospreys.

Get up close with some of Key West’s most fascinating creatures at the renowned Key West Aquarium. Located in bustling Mallory Square, the Key West Aquarium is home to alligators, jellyfish, sharks and many other local marine animals. With this 1-day admission ticket, check out the touch tank’s beautiful sea stars, sea urchins, giant hermit crabs and horseshoe crabs. Guests can enjoy guided aquarium tours as well as interactive shark feedings. It's one of Key West's most popular attractions for people of all ages.

Discover the vibrant underwater ecosystem of the Florida Keys on a Reef Snorkel Adventure to the renowned Sombrero Key Light Reef. Aboard the luxurious Marathon Mermaid, glide through the crystal-clear waters for an unforgettable snorkeling experience. This 3-hour excursion invites all ages to explore the colorful coral and diverse marine life, guided by a knowledgeable crew dedicated to your safety and enjoyment. After your underwater exploration, relax on the return trip while savoring fresh fruit and refreshing beverages, reminiscing about the aquatic wonders you’ve encountered.

Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.