At Sunset Key Cottages our guests are just a short boat ride away from the color and variety of all the things to do in Key West. Our Key West travel guide will provide you with vacation ideas, no matter what you are most interested in discovering in Key West.  Explore Key West attractions and discover the island's beauty when you stay at Sunset Key Cottages.

It’s the best place I’ve ever been anytime, anywhere.
— Ernest Hemingway upon discovering Key West


Key West is often described as quirky, eclectic, lush, colorful and sometimes downright odd. To capture the character of this southernmost place, pay a visit to several iconic spots. Be warned though – legend has it that many of the locals were once visitors who, once they felt the island’s languid tropical breezes and enjoyed its laidback vibe, decided to stay – permanently.


No trip here would be complete without paying a visit to the Ernest Hemingway Home & Museum, once the home of the island’s most legendary literary resident. Peek into his second-story writing studio and marvel at the manual Royal typewriter where he composed classics including “To Have and Have Not” and “For Whom the Bell Tolls.” The Spanish colonial villa with its lush surroundings and sprawling swimming pool is a registered National Historic Landmark. More than 40 six-toed cats (perhaps descendants of Hemingway’s cats) roam freely about the property, making this house and its gardens their home.

It’s no secret that Hemingway liked to drink, and during his Key West years (1931 to 1939), he was a regular at a watering hole – considered the original Sloppy Joe’s – that opened in 1851 on Greene Street. The bar was owned by his friend and fishing buddy Joe Russell; in 1937, Russell moved it across the street.

Today, it’s known as Captain Tony’s Saloon because it was bought in 1958 by the now-deceased boat captain and former Key West Mayor Tony Tarracino. Tarracino was a character known around the island as an avid storyteller; his memory and stories live on within the walls of his saloon. Soak up the history while enjoying a frosty one.


Don’t miss the current-day Sloppy Joe’s, on the corner of Greene and Duval streets. It’s a landmark open-air bar immediately recognizable thanks to its huge corner location, infectious live music pouring out and the annual Hemingway Look-Alike Contest held every July at the lively joint.


This photo op is a must: Just down the street from the Hemingway House is the Southernmost Point, a massive red, black and yellow concrete buoy erected in 1983 by the City of Key West to mark the southernmost point in the continental U.S. Today, it’s among the most-photographed landmarks on the island. Pose for a photo next to the iconic buoy that proudly stands just 90 miles from Cuba.


“See you at Sunset" has a special significance in Key West. It's an invitation to join in the celebration of watching another perfect sunset while jugglers, island musicians, artists, food vendors and friends entertain you each night as if you were a one person audience.

Many noted figures have enjoyed the sunset view from Mallory Square over the years. The congregation of street performers has grown significantly over the years, now extending to the pier. Audubon wrote glowingly of the glorious Key West sunsets while visiting the island in the early 1800's. Legend has it that famous American Playwright Tennessee Williams initiated the ritual of applauding the sunset at Mallory Square.

So do not miss the sunset on the pier located directly behind the Margaritaville Key West Resort & Marina along the waterfront. Enjoy one of our famous mojitos, have dinner on the waterfront during sunset at Bistro 245 or stroll along the vibrant harbor walk where you will discover some of the island’s best shopping right outside your room door. However you decide to celebrate, we will “See you at Sunset!”


For many travelers, shopping has moved beyond buying the requisite T-shirt or other traditional souvenir to become a vacation activity in its own right. Whether it means strolling art galleries for a unique piece to take home or browsing boutiques for an island dress or linen shirt, shopping has become an integral part of vacation relaxation and enjoyment.

Several notable shops are conveniently located near the dock at the Margaritaville Key West Resort & Marina. Little Switzerland features an enviable collection of designer jewelry and watches by Tiffany, Pandora, Lagos, Swarovski, Tag Heuer, Movado and Michael Kors. At the Fury Surf Shack, water enthusiasts will find famous names including Billabong, Skullcandy, Ray-Ban and Quiksilver. Anglers and boaters love Saltwater Angler for booking fishing charters and buying high-end rods and reels by Orvis and Shimano, sunglasses by Maui Jim, Oakley and Costa Del Mar and apparel by Columbia and Patagonia.

However, because Key West is a mecca for unique galleries and funky shops, it’s well worth embarking on an island shopping jaunt. Wander down Duval Street and stroll through Old Town – you’re bound to find something you just have to have, a piece of Key West that will remind you of your time in this island paradise.

At Besame Mucho, located at 315 Petronia Street in a local neighborhood known as Bahama Village, you will discover a romantic shop where one can escape and lose themselves in an atmosphere of charm that excites, inspires, and calms, all at the same time. Savor some of the old-world simplicity that has been lost to the past.

At the Alan S. Maltz Gallery, at 1210 Duval Street in the heart of the shopping district, photos of wildlife and nature scenes showcase the iconic photographer’s ability to capture the ephemeral tropical light.

If you are interested in Key West art, then be sure to visit the delightful SoDu Gallery located at 1100 Duval Street, just a short walk from the Alan S. Maltz Gallery. This gallery was created by six talented local artists, including: Judi Bradford, Janis Childs, Maritza Cresce, Lainie Davia, Fran Decker, and Leslie Kanter. Inside you will find an inspired collection of original works in a variety of mediums: paintings, pottery, fine-gold jewelry, gem-stone jewelry, sculpture, stained glass, photography, and furniture.

Away from the bustle of Duval Street, at 276 Margaret Street, sits Local Color, a local favorite (hence the name). Located in the heart of the Historic Seaport, its waterfront location makes for convenient shopping after a day of snorkeling or fishing. The shop’s original jewelry designs are popular – in particular the KW bracelet, KW ring and Caribbean hook bracelet.

A few doors down, at 616 Greene Street, is one of the funkiest spots in Key West, and that’s saying something. Shoppers who venture past the shack-like exterior of 90 Miles to Cuba will find an antiques shop and art gallery that is home to owner Linda Reike’s artwork from “Key West of Old.” In addition, nautical antiques, handmade modern and antique jewelry, original and reproduction graphic art and antique postcards of Key West and Cuba are sold here. Sign collectors will love the many original storefront signs available, such as the one from Garcia Cigar Shop, formerly on Fleming Street.

Over at Lucky Street Gallery, 540 Greene Street, about 30 featured artists showcase their fine, exuberant, contemporary artwork, including an array of paintings and boldly colored metal sculptures. In the gallery, which has been in business since 1983, the art is hung in such a way that customers can visualize the pieces in their own homes. There’s also an outdoor sculpture garden. New exhibitions are rotated every two weeks during season between Thanksgiving and May.

Just a short walk down the street is the famous Key West Aloe Shop. With two locations at 416 Greene Street and 419 Duval Street, The Key West Aloe Shop has a variety of products and gifts for family, friends and even pets! Originally founded in Key West in 1971, The Key West Aloe Shop was the first company to use Aloe Vera as the foundation of their products. All of their products are made in Florida, in small batches and are thoroughly researched with scientifically proven ingredients to provide high performing personal care products.


The nightlife scene in Key West is certainly in keeping with the island’s laidback atmosphere, though it’s much more than Jimmy Buffett tunes and Caribbean steel drums. In fact, the vast array of talented local musicians is what makes a night out on the town in Key West so memorable.

There’s no better example of live music done right than the Green Parrot, a longtime locals’ hangout where its history is found in the eccentric décor that adorns the walls. The centerpiece of this open-air spot with a Bahamian vibe is the bar, the perfect spot to catch the live musical acts on the adjacent stage. When the bands aren’t playing, the bar’s legendary jukebox is sure to please music fans with its classic rock, blues and funk selections. This corner saloon has been around since 1890. Before becoming the Green Parrot in the 1970s, it was a grocery store and the Brown Derby Bar, which was popular with submarine sailors stationed in Key West.

Another great spot for live local music is the Hog’s Breath Saloon, established in 1976. Hog’s Breath owner Art Levine boasts that they host three musical acts daily, which adds up to 1,100 musical acts a year. It’s impossible to stroll by this drinking establishment and not recognize the iconic hog logo that graces the entrance and their T-shirts. This is certainly the place to go for a rowdy good time.

The Smokin’ Tuna Saloon compound sits in the 200 block of Duval at 4 Charles Street. With so many singer/songwriters performing at the Smokin’ Tuna, it has been named the host site for the annual Key West Songwriter’s Festival, which is held every May.

For something a bit more high energy, Key West’s nightspot Aqua Bar and Nightclub is reminiscent of clubs found on Miami’s famed South Beach. A highlight at Aqua, which welcomes the gay and straight crowds, is the nightly “Reality is a Drag” show. It has attracted more than a few celebrities, including tennis great Martina Navratilova, actor Christian Slater and singers/songwriters the Indigo Girls. On Monday nights, the nightclub features dueling bartenders a la “Cocktail” and dancing following the 11 p.m. drag show.

Hip-shaking action with a Latin beat takes place at El Meson de Pepe, the Cuban restaurant next to Mallory Square. Every night at sunset, the salsa band Caribe of Key West performs on El Meson’s outdoor patio, bringing their saucy, percussion-heavy sounds to the crowds that gather there. Mojitos in hand, couples take to the cobblestone area, which becomes their dance floor, and begin the hip-swiveling celebration that is salsa dancing.

Some of the most sophisticated nightlife in Key West is found at Virgilio’s Martini Bar, which owner Bill Lay describes as “the last of the speakeasies – very sexy, very swanky.” The bar features live music seven nights a week, mixing it up with Latin, jazz, blues, rock, funk and even country acts. They’ve devised their own signature drink – the “Special” Martini, made with top-shelf Vanilla Stoli vodka, real espresso and three olives. Lay says it’s their homage to Key West’s Cuban roots. On Sunday nights, the club features interactive entertainment with audience participation.


Meander around Key West, from its outskirts right into the center of Old Town, and you’ll quickly see that history and culture permeate the island. Just for starters, search out a towering red brick building with unique exhibitions, a sculpture garden featuring the busts of historic figures who shaped the Conch Republic and a cigar factory that’s keeping the island’s Cuban history alive. And don’t miss a trip into a colorful neighborhood filled with the architecture and food native to its first settlers, a visit to a historic cemetery to see early residents’ final resting places, a climb to the top of a lighthouse and a tour of a fort that served as a military training site.


In the late 1800s and early 1900s, large numbers of Bahamians began immigrating to Key West, with many of them settling in what has become known as Bahama Village, a 16-block neighborhood in Old Town. Their colorful, lilting Bahamian English is still heard frequently on its streets today.

Aside from the churches of Bahama Village, some of the neighborhood’s most historic spots are the Lincoln Theatre, which today houses an art studio and gallery, and, next to it, the joint VFW Walter Mickens and William Weech American Legion Post. 

The latter is considered the gem of Bahama Village, having in its heyday hosted entertainers including B.B. King and James Brown, brought in by promoter Curtis Brown.

Native Bahamian foods are best tried at the most unconventional of places – Johnson’s Grocery Store. This little convenience store, run by a fifth-generation Bahama Village family, is a great gathering spot and place to sample authentic conch fritters and other delicacies. Wander the streets to find other Bahamian foods growing on trees: Spanish limes, sea grapes, sapodilla, soursop, hog plums, scarlet plums and Jamaican apples were all brought over by settlers.


For a history lesson featuring those settlers who founded Bahama Village, head to the Key West Cemetery. Here, gravestones bear the native Bahamian names of founding families, including Butler, Johnson, Allen, Smith and Berrington.

In various sections of the 19-acre cemetery lie the graves of other historic figures. Two dozen soldiers are buried flanking the USS Maine Monument, dedicated to those who perished when their battleship exploded in Havana Harbor. 

The gate leading to the section where Cuban freedom fighters are buried reads “A los martires de Cuba.” Also buried here: “Sloppy” Joe Russell, a well-known bar owner (he founded Sloppy Joe’s) and fishing guide and a good friend of Ernest Hemingway in the 1930s. Naturally, it wouldn’t be the Key West Cemetery without some humor, most notably Gloria Russell’s gravestone, which reads “I’m just resting my eyes,” and the one of local hypochondriac B.P. “Pearl” Roberts, which states “I told you I was sick.”


The Key West Art & Historical Society manages several major cultural and historic sites including the Custom House, Fort East Martello and the Key West Lighthouse and Keeper’s Quarters.

Completed in 1891, the Custom House is an architectural wonder built of 917,000 bricks shipped from New York State and iron brought in from Pennsylvania. Located off Mallory Square, the bright red roof tiles and dark red bricks remain the iconic image of a structure that, over the course of its history has handled customs operations and housed a post office, a government center and Naval offices. 

Today it’s known as the Key West Museum of Art & History at the Custom House. The various rooms and walls feature the colorful wood paintings of folk artist Mario Sanchez, artifacts and historic photographs of Ernest Hemingway’s life in Key West and a recounting of the war with Spain and sinking of the USS Maine.

The Civil War-era Fort East Martello’s eight-foot-thick granite walls were never completed and never saw hostile action. They are now home to a vast collection of Key West artifacts, historical records and military memorabilia. Great reasons to visit the fort: the panoramic view of Key West’s Atlantic Coast from atop the central tower, collections of painted wood carvings and drawings by Mario Sanchez and the island’s eerie Robert the Doll.

The Key West Lighthouse, which dates back to 1847 and has seen many renovations since then, is the 15th oldest surviving lighthouse in the United States. Originally 46 feet tall, the tower was extended to 86 feet in 1894. Today, visitors climb 88 iron steps to take in the observation deck’s panoramic views. In 1886, the Keeper’s Quarters were torn down, and the current structure was built. The quarters, a clapboard bungalow, have been carefully restored; the museum within features historic furnishings and tells the stories of the hard-working keepers.


Many of the Cubans who helped shape Key West’s history are immortalized in the Key West Sculpture Garden by Mallory Square. Here, busts of Carlos M. DeCespedes and Eduardo Gato are displayed alongside other figures who influenced the island’s early history. DeCespedes, the son of the liberator who initiated the revolution at Bayamo, was elected mayor of Key West in 1876. His family’s role in Key West’s history is immortalized in the city’s San Carlos Institute, a Cuban heritage center.

Eduardo Gato emigrated from Cuba to New York and finally settled in Key West, bringing the cigar industry with him. Today, the Gato building on Simonton Street, which once served as a cigar factory, stands as a testament to his history.

For a glimpse into that cigar-rolling past, visit the Conch Republic Cigar Factory at 512 Greene Street, where an elderly Cuban woman rolls cigars near the window, allowing passersby to experience the lost art. At the Historic Cigar Alley at 1075 Duval Street, across the street from the historic Gato Factory, visitors can experience Key West’s largest humidor and learn about the history of cigars and cigar-making on the island.


Although Ernest Hemingway’s name is most often associated with Key West’s literary history, the island’s rich culture is wide and deep and includes Tennessee Williams, Robert Frost and numerous contemporary writers.


Hemingway lived in Key West during the 1930s and 1940s. His legacy lives on most visibly at the home he owned in Old Town, which since 1964 has been open to the public as the Ernest Hemingway Home & Museum. He spent his mornings writing some of his most notable works, including A Farewell to Arms, in his quaint second-story writing studio, where his manual Royal typewriter is on display. In the afternoons, he went fishing and enjoyed socializing at his favorite watering holes, including the original Sloppy Joe’s.

The home is still furnished as it was when Hemingway and his family lived there, including chandeliers they bought in Paris. The lush grounds, historic pool (the first swimming pool built in Key West) and resident six-toed cats round out the museum experience. Hemingway’s first residence in Key West, Casa Antigua (above a former car dealership and behind the Pelican Poop Shoppe) is a hidden gem that provides a glimpse into Hemingway’s early life on the island.

To commemorate the author’s birthday, the annual Hemingway Days are held in July. Events include readings, art exhibits, a marlin fishing tournament and a contest for stocky white-bearded men resembling “Papa” Hemingway.


Legendary poet laureate Robert Frost also spent time in Key West, wintering in a garden cottage at 410 Caroline Street from 1945 to 1960. Although the cottage is no longer open to the public, it’s a fine example of Key West conch architecture. Every spring, the Studios of Key West, a local arts community, hosts the Robert Frost Poetry Festival, which features poetry and haiku workshops and readings.

As further evidence of the island’s lively literary heritage, best-selling contemporary authors and other writers converge on Key West every January for the Key West Literary Seminar. The five-day event includes a variety of writing workshops and has featured such luminaries as Margaret Atwood, Joyce Carol Oates, Gore Vidal, Ian McEwen and Amy Tan. One year, seven U.S. poet laureates took part in events all over town.


For playwright Tennessee Williams, Key West provided the ideal hideaway to escape from his celebrity. He spent time on the island living virtually unnoticed in a small cottage at 1431 Duncan Street, mainly keeping to himself. He bought the residence in the 1940s and owned it until his death in 1983. It’s believed that he wrote the first drafts of A Streetcar Named Desire in Key West.

The playwright’s legacy is immortalized in Key West’s most recognized theater, the Tennessee Williams Theater on College Road. Located on the campus of Florida Keys Community College, the venue is the site of locally produced and traveling stage productions, as well as concerts by local music groups.


Whether you choose to peer into the water wearing a mask and snorkel or pull on scuba gear and take the plunge, exploring the spectacular blue waters surrounding the Lower Keys is a must. Diving or snorkeling among the coral reefs of the Florida Keys, protected within the Florida Keys National Marine Sanctuary, opens up a window to breathtaking underwater scenery and exhilarating encounters with nature.

One of the best artificial reefs for recreational divers in the world, the USS Vandenberg sits in 145 feet of water about seven miles offshore, with most of its interesting features shallower than 100 feet deep. The former transport and tracking ship is 525 feet long and 10 stories tall. Although the site can be enjoyed by snorkelers, it’s ideal for divers, especially advanced ones.

Over time, invertebrates including barnacles and corals have attached themselves to the wreck, creating an intricate structure that serves as a home for colonies of fish and other sea creatures. Since the ship’s sinking in 2009, nearly 200 species of fish have been spotted on the wreck, including giant parrotfish, barracuda, wahoo, sharks and mutton snapper.

Fort Jefferson/Dry Tortugas National Park is located 70 miles west of Key West. The 100-square-mile park set at the end of the reef provides a unique marine environment due to its remote location. The Dry Tortugas are considered one of the area’s most pristine dive and snorkel spots. Most snorkeling is done in the designated swim areas directly off the beaches of Fort Jefferson. Here, snorkelers see hard and soft corals and many species of reef fish including spotted eagle rays, goliath grouper, parrotfish, mangrove snapper, the occasional nurse and reef shark, as well as sea turtles and conch. The Yankee Freedom, docked at 240 Margaret Street, is the only public vessel making trips out to the Dry Tortugas.

The Sambos – a collection of reefs named Eastern, Middle and Western Sambo – range in depth from 10 to 50 feet. The reefs are located four miles south of Boca Chica Channel, which is less than 10 miles from Key West. At 40 feet, divers can marvel at coral heads with abundant sea life, while snorkelers can explore the shallower sections of the reef with their elkhorn and staghorn corals and colorful tropical fish.


  • Southpoint Divers is located on Front Street in Old Town. Their 46-foot dive boat, M/V Phoenix, makes morning and afternoon trips to the USS Vandenberg and the Cayman Salvage Master, a 163-foot-long former minelayer and research vessel.
  • Lost Reef Adventures, located at 261 Margaret Street, takes snorkelers and divers out on Dream, their custom-built dive boat. Their trips, which are for just snorkelers, just divers or a combination of the two, go to the Vandenberg, the Sambos, Joe’s Tug (in depths ranging from 45 to 65 feet), Cayman Salvage Master and Sand Key (seven miles west of Key West in depths of 35 to 75 feet and considered one of the area’s best snorkel and dive sites).
  • Captain’s Corner, located at 125 Ann Street, features the 60-foot, all-aluminum dive vessel Sea Eagle. Daily trips go to the Vandenberg, the Sambos, Western Dry Rocks, the Humps and the Eye of the Needle, which features a 20-mile stretch of reef.


Although the waters surrounding Key West and the Lower Keys are best-known for their deep-sea catches of sailfish, wahoo and tuna, exciting fishing takes place anywhere from the shallowest flats and backcountry waters to wrecks and reefs to the deepest blue water beyond.

Key West’s most famous resident fisherman, Ernest Hemingway, spent a lifetime in search of blue marlin, but avid anglers flock here knowing that Key West and the Lower Keys offer a great variety of world-class fishing year-round.

Captain Mark Schmidt, who operates Sundancer Charters out of the Margaritaville Key West Resort & Marina, has been a fishing guide in Key West and the Lower Keys since 1980, so he knows the local waters well. He says the reason the waters off Key West are such a fishing hotspot is because the Atlantic Ocean and Gulf of Mexico co-mingle there, bringing kingfish, sailfish and cobia migrating down from both the Gulf and Atlantic sides.

The variety of fishing grounds include offshore, reef, channel and wreck, on both the Gulf and Atlantic sides, and at depths ranging from less than 20 feet to 240 feet, which makes fishing these waters ideal for everyone, from beginners to pros. And the miles of flats, which feature plenty of interconnecting channels and basins, are ripe with a variety of fish.

On a typical day fishing offshore, past the reef’s edge, captains will slow-troll live bait for sailfish, kingfish, blackfin tuna, small barracuda and dolphin. In shallower water, they anchor off the reef and, using chum, attract those fish as well as yellowtail, mutton or mangrove snapper, cero mackerel and various species of jacks and grouper.


Although fishing in Key West is seasonal for such migratory species as tarpon, sailfish, kingfish and cobia, there are plenty of fish to catch year-round. Here’s a guide on what’s out there to catch when:

  • Year-round: Grouper around the reef and wrecks; Permit around the reef, wrecks and flats; Sharks around the reef, wrecks, blue water and flats; Snapper in the backcountry, flats and on the reef; Snook in the backcountry and around wrecks; Barracuda in blue water and around the flats, reef and wrecks.
  • January-May: Amberjack around the reef and wrecks
  • March-July: Tarpon in the flats and backcountry
  • March-November: Dolphin (Mahi Mahi/Dorado) in blue water
  • April-October: Bonefish around the flats
  • April-December: Blue Marlin in blue water
  • May-December: White Marlin in blue water
  • July-December: Redfish in the backcountry
  • September-May: King Mackerel around the reef and wrecks and in blue water
  • October-May: Sailfish around the reef and in blue water
  • October-August: Tuna in blue water
  • October-July: Wahoo in blue water and around the reef
  • November-April: Cobia around the reef, around wrecks and in the flats


To really immerse yourself in the natural tropical beauty of the Lower Keys, get out on the water. And why not? The options are numerous: Paddle a kayak through mangrove tunnels or around remote islands, stand up on a paddleboard for a workout and great views of marine life, try your hand at kiteboarding, which combines surfing and sailing, or sit astride a Jet Ski and take a tour around Key West.

Several companies around Key West accommodate adventure seekers who are eager to hit the water, get some exercise and try something new.


Capt. Andrea Paulson of Reelax Charters out of nearby Sugarloaf Key offers a kayaking experience that’s unlike others – they transport kayaks, customers, beach chairs and umbrellas by powerboat to remote islands, where they head out to explore by kayak.

“Our method is very different from others. Our 24-foot boat holds the kayaks, and once we’re anchored, we kayak around remote mangrove islands and beaches. It makes for a much more secluded and quiet trip since there’s no traffic noise,” Paulson said.

The clear, shallow water and sand flats around Sugarloaf Key give kayakers a window into all kinds of marine life including starfish, sharks, snappers, rays, barracudas and, on occasion, dolphins and sea turtles. Because their trips are small (maximum six people), it allows them to beach the kayaks, have a picnic lunch, take a leisurely walk and snorkel in the pristine water.


Located at Key West’s Hurricane Hole MarinaLazy Dog specializes in paddleboarding, also known as SUP, for stand-up paddleboarding.

Paddleboarding is the fastest-growing watersport and, according to the folks at Lazy Dog, it’s easier than it looks. With the largest fleet of paddleboards on the island, ranging from beginner boards to those for more experienced paddlers, they’re successful at getting everyone, even first-timers, standing up and paddling. The paddleboard features a non-skid middle section where paddlers stand.

Each of Lazy Dog’s tours and rentals begins with an instructional clinic. Then riders take off, paddling between Key West and Stock Island, where the waterway is protected and wind is minimal. Shallow, clear water means all kinds of sea life are visible. The Salt Ponds in Key West are an ideal spot for paddling through long, winding mangrove tidal creeks. More adventurous paddlers can try paddleboard yoga or boot camp exercise classes held on paddleboards.


A Jet Ski tour around Key West will fill your need for speed and exploration. Fury Water Adventures operates out of the Margaritaville Key West Resort & Marina, offering two Jet Ski tours.

Fury’s Ultimate Adventure is billed as the complete watersports experience. The fun begins as you leave the dock on a seven-mile trip aboard Fury’s 65-foot sailing catamaran. Snorkel on a living coral reef and explore the pristine waters by kayak, Jet Ski and parasail. The six-hour adventure includes breakfast, picnic lunch and afternoon snack.

Closer to land, Fury’s 90-minute Jet Ski tour is a 28-mile tour around the waters of Key West. The vehicles can accommodate up to three riders each. Guides take riders through by the Southernmost Point, along Mallory Square and around several remote islands. They stop at a sandbar, where riders can take a break and go for a swim.


Kiteboarding combines elements of wakeboarding, windsurfing and even sky diving, and Paul Menta at the Kitehouse has cornered this market in Key West. Although prior experience with sailing and board sports is helpful, it certainly isn’t necessary. At the Kitehouse, students are normally up on the board by the second day. Beginners start with one-on-one lessons in knee- to waist-high water, progressing to two and a half hours of kite flying time. Lessons for intermediate and advanced kiteboarders are also available.

Kiteboarding is wind-powered but, unlike windsurfing, very little wind is needed. The kite can be adjusted for different conditions like the sail on a boat, and the board acts as a rudder. Kiteboarders can tack upwind just like a sailboat, catching air as they hit waves.