top of page

Key West


Key West is a pathway to paradise and one of my favorite places in the world. It is an island in the Straits of Florida, within the state of Florida. Also, it is the southernmost city in the contiguous United States and the westernmost island connected by highway in the Florida Keys. Cayo Hueso is the original Spanish name for the island of Key West. It means 'bone cay' and refers to a low island or reef. It is said that the island was littered with the remains (bones) of native inhabitants, who used the isle as a communal graveyard. In 1815, the Spanish governor of Cuba in Havana deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery posted in Saint Augustine, Florida. One year after Florida was transferred to the United States in 1821, Lieutenant Commander Matthew C Perry sailed the schooner USS Shark to Key West and planted the US flag, claiming the Keys as United States property. No protests were made over the American claim on Key West, so the Florida Keys became the property of the United States. Key West is the far frontier, edgier and more eccentric than the other Keys, and also far more fascinating. On one side of the road, there are literary festivals and upscale art galleries. On the other, an S&M fetishist parade and dive bars filled with bearded burnouts. With all that in mind, it's easy to find your groove in this setting, no matter where your interests lie. Key West is home to Hemingway, sunsets and Key lime pie.

Begin your odyssey at the Museum of Art & History at the Custom House, located at 281 Front Street. This excellent museum, set in a grand 1891 red brick building that once served as the Customs House, covers Key West's complicated history. Highlights include the archival footage from the building of the ambitious Overseas Highway (and the hurricane that killed 400 people), a model of the ill fated USS Maine (sunk during the Spanish American War) and the Navy's role in Key West (once the largest employer), who scavenged sunken treasure ships. There's also info on rum running to Havana during the Prohibition days and some excellent folk art - seek out Mario Sanchez' naive art paintings of Key West from the 1970s. Across the road at 200 Greene Street is the Mel Fisher Maritime Museum. For a fascinating glimpse into Key West's past, pay a visit to this popular museum near the waterfront. It's best known for its collection of gold coins, rare jewels and other treasures scavenged from Spanish galleons by Mel Fisher (famous treasure hunter) and crew. More thought provoking is the exhibition devoted to the slave trade, with artifacts from the wreck of the Henrietta Marie, a merchant slave ship that sank in 1700. Not far away at 111 Front Street is the Little White House. This is where President Harry S Truman used to vacation when he wasn’t directing post World War 2 global geopolitics in Washington. It's beautifully preserved and open only for guided tours, although you are welcome to visit one small gallery with photographs and historical displays (and a short video) on the ground floor.

The most famous home in town is the Hemingway House, found at 907 Whitehead Street. Key West's biggest darling, Ernest Hemingway, lived in this beautiful Spanish Colonial house from 1931 to 1939. The celebrated author moved here with his second wife, a (former) friend of his first wife (he left the house when he ran off with his third wife). His novel To Have and Have Not, and the non fiction work Green Hills of Africa were produced here, as well as many polydactyl (extra toes) cats, whose descendants continue to live on the grounds. Note: admission includes a guided tour with one of the knowledgeable guides, who share intriguing and amusing anecdotes about Papa Hemingway. You're also free to meander around the house and grounds on your own. Across the way at 938 Whitehead Street is the Key West Lighthouse. You can climb up 88 spiraling steps to the top of this snowy white lighthouse, built in 1846, for a lookout. You can also visit the lighthouse keeper's cottage, which has photographs and artifacts with historical tidbits on life for the keepers of the light. Key West Cemetery can be found at the corner of Margaret and Angela Streets. A darkly alluring Gothic labyrinth beckons at the center of this pastel town. Built in 1847, the cemetery crowns Solares Hill, the highest point on the island. Some of the oldest families in the Keys rest in peace (and close proximity) here. With body space at a premium, mausoleums stand practically shoulder to shoulder. Island quirkiness penetrates the gloom with seashells and macrame adorning the headstones.

Key West locals have a love hate relationship with the most famous road in Key West (if not the Keys). Duval Street, Old Town's main strip, is a miracle mile of booze, tacky everything and bad behavior - but it’s a lot of fun. The Duval Crawl is one of the wildest pub crawls in the country. The mix of neon drink, drag shows, tee shirt kitsch, art studios and boutiques is more entertaining than disturbing. Note: I will discuss my favorite watering holes in the next section. The San Carlos Institute is located at 516 Duval Street. Founded in 1871 by Cuban exiles, the San Carlos is an impressive building constructed in classical Spanish mission style. The current structure dates from 1924. The interior is spackled with tile work from Cuba and Seville (Spain), Italian marble and statues of Cuban luminaries, including Jose Marti, who spoke here and dubbed the building La Casa Cuba. Today the building serves as library, art gallery, lecture hall and theater. Around the corner at 524 Southard Street is Key West Distilling. This tiny craft distiller, basically a one man operation, creates some excellent rums, two types of vodka (including one with horseradish), one gin and one whiskey. The focus is on quality (rather than quantity), and you won't find a better spiced rum in South Florida than its Rambunctious Rum. Note: stop in for a free tour and tasting. Nearby at 533 Eaton Street is The Studios of Key West (TSKW). This nonprofit gallery showcases about a dozen artists’ studios in a three story space and hosts some of the best art openings in town. Besides its public visual arts displays, TSKW hosts readings, literary and visual workshops, concerts, lectures and community discussion groups. Essentially, it has become the accessible heart of the city’s enormous arts movement and offers a good point of entry for visitors who want to engage in Key West’s creative scene.

From TSKW, make your way to Gallery on Greene at 606 Greene Street. Displaying work by more than three dozen artists, this is one of Key West's best art galleries. The collection focuses on artists from South Florida and Cuba. Frequent art openings feature works by some truly gifted contemporary painters. If all that art makes you thirsty, head to Key West First Legal Rum at 105 Simonton Street. Opened in 2013, this distillery makes some mighty fine rums, which are made with Florida sugarcane and infused with coconut, vanilla and Key lime - some of my favorite ingredients. Try up to eight rums in the shop for $10, which includes a shot glass. You can also take a self guided audio tour of the small one room operation or come for a livelier chef guided tour held throughout the week. After you fill up on the good stuff, trudge on over to Kermit's at 200 Elizabeth Street for more good stuff. Here, you can satisfy your innermost cravings for all things Key lime related at this long running institution near the waterfront. You'll find salsa, barbecue sauce, candies, ice cream, dog biscuits and even wine all bearing that distinctive Key lime flavor. Purists may prefer to settle for a pie (mini pies available) or perhaps a chocolate dipped Key lime popsicle.

Next, make a brief visit (depending on the size of the line) to the Southernmost Point landmark on your way out to the beach. The most photographed attraction on the island can be found at the corner of South and Whitehead Streets. This red and black buoy is said to be the southernmost point in the United States. From there, head east (by bike or car) out to Smathers Beach. One of Key West's largest public beaches, it's a pretty stretch of sand with a few palm trees providing shade. Smathers is the perfect spot to chill and go for a refreshing swim. Conclude your Key West adventure in Mallory Square. Take all those energies, subcultures and oddities of Keys life and focus them into one torchlit, playfully edgy, sunset enriched street party. The result of all these raucous forces is Mallory Square - one of the greatest shows on earth that starts in the hours leading up to dusk, the sinking sun a signal to bring on the madness that is Key West. Note: the Mallory Square Sunset Celebration is the ultimate place to view the sunset with a drink in hand.


Key West has several great places to eat and enjoy a drink or two. Start your day at Blue Heaven, located at 729 Thomas Street. This is one of the quirkiest venues on an island of oddities - patrons, together with free ranging roosters, flock to dine in this ramshackle, tropical plant filled backyard where Hemingway once officiated boxing matches. This rad place gets packed with customers who come for the delectable breakfasts like lobster Benedict, pancakes topped with bananas and pineapples, and the lobster and grits. Be sure to save room for the famous Key lime pie. Note: do not miss this place. Another groovy spot is Croissants de France, found at 816 Duval Street. France comes to the Caribbean at this lovely bistro, with predictably tasty results. Stop in for eggs Benedict, cinnamon brioche French toast or yummy pastries at breakfast, then pop back at lunch for baguette sandwiches, quiche and berry filled sweet crepes. Down the road at 115 Duval Street is Bagatelle. This popular brunch destination does a dynamite Bloody Mary, and the southern Benedict with poached eggs, citrus braised pork and Cajun hollandaise over toasted cornbread is out of this world. If you fancy donuts, make your way to Glazed Donuts at 420 Eaton Street. The varieties here are as eccentric as Key West itself and reflect the seasons: strawberry shortcake, blood orange marmalade, mango hibiscus and (of course) Key lime. Good coffee completes the perfect combination.

5 Brothers Grocery & Sandwich Shop can be found at 930 Southard Street. A Key West icon, this tiny grocery store and deli fires up some of the best Cuban style espresso this side of Miami. Join locals over cafe con leche (coffee with milk), guava pastries, and bacon and egg rolls, or stop by for delectable roast pork sandwiches. Note: there are a few plastic chairs on the sidewalk out front, perfect for taking in the neighborhood scene. For more taste of Havana, do visit El Siboney at 900 Catherine Street. This is a rough and ready Cuban joint where the portions are big and there’s no messing around with high end embellishment or bells and whistles. It's classic ingredients: rice, beans, grilled grouper, roasted pork, barbecue chicken and sweet plantains - all cooked with pride to belly filling satisfaction. Mo's Restaurant is at 1116 White Street. The dishes here are mainly Haitian and they’re delicious - the spicy pickles will inflame your mouth, which can get cooled down with a rich vegetable ‘mush’ over rice, or try the incredible signature snapper. BO's Fish Wagon is located at 801 Caroline Street. Looking like a battered old fishing boat that smashed onto the shore, it is awash with faded buoys, lifesavers and rusted license plates strung from its wooden rafters. The seafood is fantastic, with rich conch fritters, soft shell crab sandwiches and tender fish tacos. Note: BO's is a fun and lively spot for a meal, especially when there's live music - Thursday, Friday and Sunday.

Key West has a number of restaurants with killer water views. Salute! on the beach is at 1000 Atlantic Boulevard. This beachside sister eatery to Blue Heaven offers up casual fare like fish sandwiches and shrimp salad with waterfront views to boot. An added bonus is Blue Heaven’s celebrated Key lime pie also makes an appearance on the menu. The Southernmost Beach Cafe is located right on the beach at 1405 Duval Street. This open air spot on the Atlantic Ocean side of the island does classics like coconut shrimp and the blackened catch BLT wrap. Sunset Pier can be found at 0 Duval Street. This location on the water is just a short walk from Mallory Square and has some of the best seats in town for Key West’s legendary sunsets. With its colorful chairs and live music, Sunset Pier is a casual spot to watch boats float by as the sun sinks into the horizon. Lastly, there is the totally awesome Half Shell Raw Bar at 231 Margaret Street. What was once a shrimp packing building is now a watering hole for fishermen, locals and out of town visitors. It sits right on the Key West Bight Marina and serves up oysters, clams and peel ‘n’ eat shrimp. Note: don’t expect linen napkins at this iconic joint, but do enjoy the view and its seafaring characters.

For dinner, head to Thirsty Mermaid at 521 Fleming Street. This lovely restaurant serves fantastic seafood in an elegant, easygoing space. The menu is a collection of sea life culinary treasures such as an oyster bar, ceviche, middleneck clams and caviar. Among the main courses, seared diver scallops or togarashi spiced tuna with jasmine rice are outstanding. There are also luxurious sandwiches with lobster, fried oysters or local snapper fillings. Nearby at 915 Duval Street is Nine One Five. This beloved bistro and wine bar is housed inside a stylish Victorian home that dates back to the 1850s. The modern menu blends flavors and techniques from culinary cultures around the world. Highlights include the peach salad with goat cheese and candied pecans, tortelloni with pecorino cream sauce and shaved black truffle, and the seafood soup with Key West pink shrimp, clams, local snapper and mild green curry. Cafe Sole is at 1029 Southard Street. This locally and critically acclaimed venue is known for its cozy back porch ambience and innovative menus, cobbled together by a chef trained in southern French techniques who works with island ingredients. Do try the conch carpaccio with capers then move on to the hogfish with roasted red bell pepper hollandaise. Another excellent place is Cafe Marquesa, found at 600 Fleming Street. It is as elegant as it gets in Key West - all white tablecloths, candle light and great food to boot. The mains are French inspired with little Floridian and Asian twists, like yellowfin tuna with stir fry vegetables and wasabi or a rack of Australian lamb served with broccoli rabe over Israeli couscous. My favorite restaurant in Key West is Louie's Backyard, located at 700 Waddell Avenue. Housed in an oceanfront Victorian home, it offers fine dining with panoramic views of the Atlantic Ocean. I enjoyed the chilled sweet corn soup with pickled rock shrimp and the grilled pesto rubbed swordfish with yellow pepper coulis and orzo stuffed tomato. For dessert, I destroyed the Key lime pie with whipped cream and berries. Note: reservations are recommended.

End your evening in Key West with a drink or two, or three. The place where most people first visit is Sloppy Joe's, located at 201 Duval Street. Founded in 1933 and in its current location since 1937, this popular and highly entertaining bar was a hangout for Ernest Hemingway. It is always busy and the large stage attracts the best bands playing in Old Town. Be sure to wet your whistle with Sloppy Joe's famous Sloppy Rita. Around the corner at 428 Greene Street is Captain Tony's Saloon. Propagandists would have you believe Sloppy Joe’s was Hemingway’s original bar, but the physical place where the old man drank was right here, the original Sloppy Joe’s location - before it was moved onto Duval Street. It's a dark dive, with bras hanging from the rafters, a grizzled but laid back crowd and the occasional guitarist taking to the small stage. Note: Hemingway’s third wife (a journalist sent to profile Papa) seduced him in this very bar. The Hog's Breath Saloon is at 400 Front Street. This rockin’ outdoor spot retains the feel of a biker bar despite its obvious appeal to the tourist trade. In typical Key West tradition, live bands and bikini contests dominate the entertainment calendar. From there, head to Conch Republic at 631 Greene Street. Overlooking the waterfront, this sprawling open sided eatery and drinking space is a fun place to get you in the Key West spirit. The allure - a festive happy hour, the easygoing crowd, island breezes and live music. Note: the seafood is also quite good.

Continue the infamous Duval Pub Crawl at Irish Kevin’s, found at 211 Duval Street. One of the most popular bars on Duval, this Irish pub includes weekly live performances by Irish Kevin himself, an immigrant who settled in Key West in 1992. Perched atop The Bull and Whistle Bar at 224 Duval Street is The Garden of Eden. This aptly named paradise is Key West's only clothing optional bar. Note: before you get too excited, cameras aren’t allowed and most people come clothed. On the less rowdy end of Duval Street (number 810), Vinos pours a good selection of wines from around the globe - Spanish Tempranillos, Argentine Malbecs, Californian Cabs - in a cozy setting with a touch of Key West eccentricity. Grab a seat at the bar and have a chat with the knowledgeable staff or retreat to one of the tables on the porch. For the best cocktail in the Keys, head to General Horseplay at 423 Caroline Street. This relaxed speakeasy in an old brick house has friendly bartenders, tomfoolery and top notch drinks. Do try the Murricane - treaty oak bourbon, watermelon, lemon, elderflower and basil. Finish up at my favorite saloon in town, The Green Parrot. Located at 601 Whitehead Street, it is the oldest bar (established 1890) in Key West. Known as 'a sunny place for shady people', its ramshackle interior, with local artwork on the walls and a parachute stretched across the ceiling, only adds to the atmosphere - as does the fun loving, colorful crowd. Note: the bar always has great live music and there is never a cover charge.


Key West offers a number of places to call home during your stay and there are 2 that I especially enjoyed. Both are in prime locations and provide exceptional service, modern amenities and comfort. The first is Hotel Marquesa, located at 600 Fleming Street. This tranquil Victorian era boutique property is close to Mallory Square and is a brief stroll from the Hemingway House. The refined rooms offer free WiFi, flat screen TVs and marble bathrooms. Upgraded quarters add sitting areas and covered porches. Amenities at this quiet retreat include lush interior gardens, three sparkling pools and dinner at the superb and previously mentioned Cafe Marquesa.

A second option is Sunset Key Cottages, located at 245 Front Street. Situated on a private twenty seven acre island, this elegant oceanfront resort is a short boat ride from all the action in Old Town. Bright, one to four bedroom cottages feature complimentary WiFi, flat screen TVs, coffee makers and pillow top mattresses - as well as living and dining areas. Upgrades add ocean view balconies or patios and some have whirlpool tubs. Other perks include the fantastic Latitudes restaurant, a poolside bar, a spa and a beach. Plus, ferry transfers to and from Key West are on the house.

Key West has colorful characters, tropical breezes and laid back vibes. It treated me well and I look forward to returning.

bottom of page