by Christie Grotheim  |  Published October 16, 2014

It’s been said that Key West is a place where you can “be yourself, find yourself, or re-invent yourself.” That is true, and it’s also a place you can lose yourself—for a luxurious weekend or a longer retreat.

Key West (Ed Schipul via Flickr)

Key West (Ed Schipul via Flickr)

Literary greats such as Ernest Hemingway and Tennessee Williams found inspiration in Key West’s laid back lifestyle and southern charm, while singer-songwriter Jimmy Buffett discovered the perfect spot to fine-tune his beach bum persona and enjoy the island escapism portrayed in his music. Closer to Cuba than Miami, technically it’s the southernmost point in the United States, but it’s the Caribbean flavor that comes through. From the boozy nightlife on Duval Street and the ramshackle eateries in town to the lush flora, hand-painted signage and modest bungalows on side streets—where chickens and roosters roam free—the vibe is altogether relaxed, tropical and exotic.

Even though Key West has its own small airport, for a dramatic entrance travel by car, bus or shuttle down from Miami on Highway 1; the skinny strip of highway surrounded by the azure and aqua waters intensifies the journey. Also called the Overseas Highway, the 113 miles of roadway over 42 oversea bridges is an incredible engineering feat offering breathtaking views that add to the experience.

Once on the island, settle into your hotel. Two great choices that offer something more unique than the chains are the Eden House and the The Gardens Hotel. Key West’s oldest hotel originally built in 1924, the Eden House has been run by the amicable Mike Eden since 1975. Complimentary drinks are served by a helpful staff upon checking in and happy hour starts at 4:00 every day where guests make their own cocktails, contributing to the friendly atmosphere. Popular with couples, the hotel’s amenities include a heated pool and Jacuzzi surrounded by lush palms and waterfalls, an elevated sundeck, shaded hammocks, porch swings and a garden café—at surprisingly affordable rates.

For an upscale treat, stay at The Gardens Hotel, an historic hotel with rooms overlooking a full acre of botanical gardens on the grounds. The garden has a fascinating history of its own, cultivated from 1930 until 1968 by Peggy Mills, who collected plants from all over the world. Just as much attention to detail is paid to the interior, from the pearly white grand piano in the lobby to the décor of the guestrooms, including imported yew or mahogany furniture and original artwork by local artists.

Beyond the gorgeous setting, the boutique hotel offers complimentary island breakfast, a wine tasting room with an excellent selection, a pool bar and concierge services. Enjoy live piano music from 5:00 to 7:00 p.m. Wednesday through Saturday, and jazz outdoors on Sunday evenings from 5:30 to 8:00. The Gardens Hotel has been showered with awards and accolades, recently called “The Prettiest Hotel in Key West” by the New York Times, named as Fodor’s top choice and listed by Travel and Leisure Magazine as one of their top 21 favorite beachside hotels.

By land or by sea

You’ll want to delve into the inviting waters of the Gulf Sea right away. Go snorkeling or scuba diving in the Florida Keys National Marine Sanctuary, home to the only coral reef in North America and the third largest barrier reef in the world! Dive Key West is the largest and most experienced dive center in the Lower Keys offering plenty of classes and packages to choose from. Outdoor activities and water sports abound in Key West; other options include parasailing, deep-sea fishing, and sunset sails.

To get the full underwater experience, visit the Shipwreck Treasure Museum. Especially fun for kids and history buffs, you’ll discover Key West’s unique maritime heritage. Enter the world of 1856, the era of the wreckers when over 100 ships per day passed by Key West, the treacherous waters havocking approximately one wreck a week. Tours are led by a jubilant cast of characters that will appeal to your inner pirate. Get an up close look at treasures and booty, including actual artifacts from the wreckage, and then climb the lookout tower for a spectacular bird’s eye view of the island.

Key West Shipwreck Treasures Museum. (Photo: Olf:P via Flickr)

Key West Shipwreck Treasures Museum. (Photo: Olf:P via Flickr)

After exploring an underwater world full of all things that swim and float, don’t miss the creatures that flutter and fly. The Key West Butterfly & Nature Conservatory is a delightful treat for children and adults alike. Housing 50 to 60 varieties of butterflies from around the world as well as an impressive collection of colorful birds and plants, this inviting habitat is spacious and its windy walking path is well manicured. It’s the perfect environment in which to watch the butterflies frolic as you enter their magical world and feel your own stress float away.

Located several blocks away in the heart of Old Town Key West, The Ernest Hemingway Home & Museum is another significant stop on your tour. Visit the property that was home to one of America’s most honored and respected authors and witnessed the most prolific period of his Nobel Prize-winning writing career. Yet you don’t need to be a lover of literature to appreciate the Spanish colonial style architecture, the extensive, bountiful gardens, or the vast furniture collection dating from 17th and 18th centuries.

Built in 1851, the massive restoration and remodeling that Hemingway undertook in the early 1930’s turned the home into the National Historic Landmark, practically unchanged to this day. The $13 entrance fee includes a 30-minute guided tour where you can look for the penny Papa Hemingway pressed into the patio as well as the collection of six-toed polydactyl cats, also called gypsy cats and thought to bring good luck; most are direct descendants of Hemingway’s cat, Snowball, a gift from a sailor. The bookstore stocks a full array of Hemingway’s novels, poems, short stories and biographies so you can purchase reading material for the rest of your trip.

After a full day, head to the nightly Sunset Celebration at Mallory Square beginning two hours before sunset for the best views of the sun sinking over the water amidst a golden pastel sky. The site of many live events and festivals, the Square is always filled with magicians, jugglers, tightrope walkers, artists and psychics as well as visitors from all over the world. The nearby trolley stations offer tours, so you can buy a ticket for the following day if you so choose. After dark you will be perfectly located near a plethora of shops and restaurants to choose from.

Drinks and Debauchery on Duval Street

Start your bar hopping at the South end of Duval street, but not before making the short walk to the Southernmost Point Landmarker, a giant brightly-colored buoy. Made of concrete, it was actually an old sewer junction that was dug up in the area and found too heavy to move, so it was painted to look like a buoy and is now one of the most photographed attractions in Key West, making for a perfect Facebook post. From there have a beer at the Southernmost Beach Café, a quite nice restaurant with a large, sand-friendly bar that extends to lounge chairs on the beach. Take a dip between drinks at the picturesque if small beach.

Walking north on Duval, hit Jimmy Buffet’s Margaritaville, a good place for “Wastin’ Away”—and grab some grub before the debauchery truly begins. Try the “Cheeseburger in Paradise” which gets good reviews, and enjoy the tiki-like ambiance complete with plastic parrots.

The Bull & Whistle is actually three bars in one. The Bull on the grounds floor offers live entertainment and in a cozy setting surrounded by hand-painted murals depicting local scenes, while the Whistle on the second floor is great for people-watching from its wraparound balcony. For a different kind of people-watching, lose your inhibitions at The Garden of Eden on the rooftop, a clothing-optional bar.

Sloppy joe's bar on Duval Street. (Photo:  clarkmaxwell via Flickr)

Sloppy joe’s bar on Duval Street. (Photo: clarkmaxwell via Flickr)

Further up Duval, hit Hog’s Breath Saloon, one of the last old-school open air bars with true island atmosphere; hens and roosters are often seen strutting around underfoot in between the trees, mingling with the masses. The interior is of the ramshackle hangout is decorated like a dive bar should be, the walls lined in license plates, bras hanging from the old wooden bar, stickers plastering every surface, and dollar bills from around the world stuffed up in the rafters.

Sloppy Joe’s Bar is one of the many, many bars where Hemingway used to drink when it was a rowdy, come-as-you-are saloon full of gambling and 15-cent whiskey. Sloppy Joe’s starts serving beer at 9:00 a.m. and live music begins at noon, so it’s a great place to stop in any time of day—and the food is not to be overlooked. If you need another meal to soak up all the alcohol, have a Sloppy Joe at this Historic Landmarked tavern, where the sandwich was originated.

November is packed full of festivals and events, and in fact the high season in Key West runs from New Years to Easter due to the mild weather even in winter months, with highs averaging from 76 and 74 degrees in December and January.