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Key West is famed for its glorious sunsets but the most popular spots to take them in are usually crowded and noisy. Swap the bustling streets of Key West for the calm of the sea. This sunset cruise lets you see the sun dipping below the horizon while you relax on the deck while enjoying great food and drinks.

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.

Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.

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.

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.

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.

Follow in the footsteps of Ernest Hemingway during a walking tour that focuses on food, culture, and history. Exploring Key West on foot means that you'll get a more intimate glimpse into the historic area, which is characterized by its charming bars and plethora of museums. Plus, you'll receive personalized attention as you explore in a small group limited to only 15 other travelers.

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!

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.

Key West is known for its beautiful coastal scenery and its lively bar scene, but there are few opportunities to combine the two. This tour takes you out onto the crystal-clear water, traveling by a small motor boat that glides through mangrove tunnels on its way to two or three waterfront bar and restaurants.

Head out into the open waters on this small-group kayaking and snorkeling ecotour adventure. Follow your captain through scenic mangrove tunnels and over calm waters as you make your way to one of the area's most-stunning snorkeling destinations. Learn about local wildlife before taking a dip and get an underwater look. Gear is provided on this tour that's perfect for all levels.

Spotting dolphins frolicking in the sea is a highlight of a trip to Key West but you need to know where to find them. This guided tour is led by locals who known the Key West waters like their own backyard. They'll take you to the best places to see dolphins then to the backcountry waters where you can enjoy some snorkeling fun.

Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land!

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.

Escape the Florida Keys crowds by heading into the backcountry on this private fishing tour. In the company of just your party and the crew, you'll enjoy your guide's undivided attention as you fish for a variety of species such as tarpon, bonefish, permit, barracuda, snapper and sea trout in the shallows and flats. Most likely, you'll be fishing depths of two to eight feet.

See Key West from the water on an adrenaline-filled jet ski adventure. Beginning at uncrowded south end of Key West, set off for an exhilarating ride all the way around the island—meaning you'll see much more than on a boat tour. See landmarks such as Mallory Square from the water and watch for marine life including sea turtles and dolphins then relax or play in the water at a deserted sandbar.

A haunted adventure that is unusual and off the beaten path! The historic Key West Firehouse has a reputation as one of the more active haunted locations in the Florida Keys. Our historically accurate audio tours are researched and narrated by Ghosts of Key West author David L. Sloan and deliver a great mix of hauntings, strange crimes, history, and mystery. Our ghost tour explores hauntings on the grounds and inside the 4000-square-foot firehouse, still furnished with original artifacts. Both floors of the firehouse are air-conditioned, too, though often it's the ghosts providing the chills. This is one of the few family-operated ghost tours in Key West. Take a walk off the beaten path and see why this is the least-known and best-loved ghost tour in Old Town. The ghosts are dying to meet you.

Explore the Gulf of Mexico from Stock Island and witness an unobstructed view of the sunset on this guided kayaking tour. This tour is designed for all skill levels and includes all of the necessary kayaking gear including lifejackets, lights, and whistles. Plus, score beautiful photos of your experience with an assist from your guide.

Explore the literary highlights of Key West during this walking tour, inspired by David A. Kaufelt’s original literary walking tour. An in-the-know guide whisks you around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost. Since this is a small-group tour, you’ll have plenty of time to ask questions, too.

Cruise around the waters of Key West on this guided jet ski tour. A local, licensed guide will lead you and up to a dozen others on an adventure around the island. You’ll completely circle the island, going up to 45mph and seeing all of Key West’s backcountry. As you ride, you’ll learn about Key West’s history, stop to see the popular landmarks, and play in the waters at a deserted sandbar.

Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.

Any sail onboard the historic Schooner When And If is a memory of a lifetime! Step aboard the beautiful teak decks of the 1939 wooden Schooner Yacht built for General George Patton before the war. The Ship was named by Patton "When the war is over and if I live through it, Bea and I are to sail the world" Loved and enjoyed as a private yacht for much of her life, When And If is open to the Public to Enjoy the Sailing Comfort, Style and Grace of a superb classic yacht. Sit Back, Relax or Romance the sail away as our experienced Key West Captain and Crew set sail, pour wine and share their passion of sailing, Key West, the sea and best of all.... Sunsets! Sail and Unwind Like No Other Key West Sunset Cruise