Top Key West Outdoor Activities

Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.

Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.

Get up close with sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.

Escape to the secluded islands and tropical beaches off the coast of Key West on this guided, full-day adventure to historic Dry Tortugas National Park. History buffs and outdoor enthusiasts alike will love this unique voyage, where getting there is half the fun on board the Yankee Freedom III, a luxurious, state-of-the-art catamaran. Enjoy snorkeling (equipment provided) in the crystal blue waters and take in the military fort, national park, campground, sandy beaches and coral reefs that make this area special. Breakfast and lunch included.

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

Get a bird’s-eye view of Key West from high above the crystal blue waters of the Atlantic Ocean on this parasailing tour. Experience the thrill of flying while watching the bustling activity along the coastline and the abundance of marine life below. See dolphins, turtles, fish, and more from 300 feet in the air. Enjoy gentle, dry takeoffs and landings.

Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.

Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail aboard a state-of-the-art catamaran as you voyage toward the reef. Receive snorkeling guidance from your knowledgeable crew, making this experience perfect for first-time snorkelers. Use of sanitized snorkel gear and beer, water, and champagne on the morning trip or margaritas on the afternoon trip provided.

Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.

Explore the best that Key West has to offer on this narrated, Conch Train Tour. See Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original, and most iconic, sightseeing tour.

Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.

Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.

Discover some of Key West’s deepest, darkest secrets on a 60-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.

Experience Key West’s tropical blue waterways on this Jet Ski tour along the Atlantic Ocean and/or the Gulf of Mexico. Enjoy panoramic island views and watch for dolphins, stingrays, sea turtles, manatees and more while gliding over warm ocean water. Bring a waterproof camera to capture this southernmost point in the continental United States.

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, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.

Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.

Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour jet ski tour. With four daily tours, you can easily find a time that fits with your schedule. The tour is priced per jet ski, so you can ride tandem with a friend at no additional cost. Your guide is on hand at all times to lead the way on your aquatic adventure.

Get ready for fun in the sun on this dolphin watch and snorkeling adventure off the coast of Key West. Cruise away from the island city of Key West and see dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breeze and select from a variety of refreshing beverages on board the boat.

Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.

Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.

Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.

For the aquatic adventure of a lifetime, take this cruise to North America's only living coral barrier reef. No need to go scuba diving or snorkeling for this great view — from the deck of a glass-bottom catamaran boat, see more than 600 species of tropical fish, sharks, turtles, lobsters and crabs, plus colorful coral and a vast collection of other sea life. Upgrade to a sunset cruise to enjoy a glass of Champagne as the sun settles into the Gulf of Mexico.

Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

While you’re in Key West, head out on the deep blue waters on this sportfishing charter. The saltwater fishing boat holds up to six anglers, and is rigged with state-of-the-art navigational electronics and safety equipment, outriggers, a fighting chair, a live bait tank, and ice boxes. Plus, it features two private restrooms, a kitchen, flybridge, beds, and air conditioning.