Key West
Water destinations are dotted across the entire Floridian landscape, each with their individual style, local luxury and long list of reasons to visit. But there are times when we all need some Jimmy Buffet-style, “Changes in Latitude.” So, when looking for the perfect tropical island getaway, I make my way to the southernmost city in the Continental United States, Key West.
Closer to Cuba than to Miami, Key West is Florida’s independent and irreverent subtropical paradise. A unique confluence of history, climate, natural beauty, cultural diversity, architecture and unabashed romantic appeal make the island a destination far removed from the everyday world. A special destination, where the anything-goes ambiance have long provided a refuge for artists and free spirits seeking a place to soothe and satisfy the mind, body and soul.
Today the island’s colorful past is reflected in the carefree, eccentric attitude of its residents, making it a perfect place to find your changes in attitude. So here is our insider’s guide to the best of Key West.
Historic Key West
Key West was inhabited by the Calusa people for 1,000 years before it was first visited by Juan Ponce de León in 1521. When Florida became a Spanish territory, Cayo Hueso which literally means “bone key,” was a fishing and salvage village. While it became a British territory with the rest of Florida in 1763, no one really controlled the island as it passed through several international hands until 1821, when Florida was finally ceded to the United States. The city was incorporated in 1828 and was the only southern city to remain in the Union during the Civil War. The island has a long and colorful past of pirates and shipwrecks with large influences by the Cuban culture. Many buildings in the community are near or over a century old, and the city’s historical area, “Old Town,” features architecture combining the building styles of New England and the Bahamas. Homes once occupied by Ernest Hemingway, Tennessee Williams, President Harry Truman and John James Audubon are now museums that you should definitely visit.
Getting There
While making the drive to South Florida is fairly easy and could make for a fabulous road trip with stops along the way, getting to Key West for the weekend is as easy as a one hour flight direct from Orlando International Airport—just enough time to take a nap, which will come in handy upon arrival.
For a truly luxurious experience, you can charter a flight from Daytona Beach through National Air Charters. For a couple thousand dollars, you and your significant other can fly privately. There is also the option of fueling up the yacht and navigating the coast, but even with continuous travel the trip will take about 20 hours with fuel stops; but what an adventure that would be.
Regardless of how you get there, the beauty of the Conch Republic is that getting around here is very easy. You’ll actually want to park the car at the hotel and take advantage of the taxis, shuttles, island scooters and bikes, or simply wear some comfy shoes and let your legs take you—almost everything is within walking distance.
What to Do
One of Key West’s most popular attractions is the crystal blue waters that surround the island. For a complete collection of options and experiences, Fury Water Adventures at 2 Duval Street has been offering snorkeling, parasailing, jet skiing, kayaking, glass bottom boats and sunset cruises to water enthusiasts for over 30 years. Fury boasts one of the most luxurious catamaran fleets in the Keys and offers a variety of snorkeling excursions including the afternoon Reef n Ritas snorkeling trip and the Rum & Reggae sunset combo. They include complimentary margaritas, rum punch, beer and wine—need I say more?
Of course, if you have never been, you should do some of the touristy stuff like visiting the Southernmost Point, taking a tour that includes the cemetery and making the rounds at the famous bars on Duval Street. Our favorite tour? Lloyd’s Tropical Bike Tour, an irreverent and local lore-filled way to see the ecology of the island without wrecking it. Steeped in history and clothed in beauty, Key West is also home to numerous museums and botanical gardens that should be on everyone’s to-do list. Stop by the Key West Tropical Forest & Botanical Garden to see the country’s only frost-free tropical forest, tour the home where Hemingway penned some of his most notable works and explore Fort Zachary Taylor State Park.
Golfers will enjoy a Caribbean-style golf experience at the Key West Golf Club, where the 18-hole par 70 championship course is suitable to players of all levels. Known for its tropical landscaping and easy proximity to the island’s famous attractions, Key West Golf Club provides a setting that cannot be reproduced anywhere in the country.
What To Eat
A culinary melting pot, Key West is diverse in its collection of great restaurants with something for every palette. Eateries serve cuisine that reflect Bahamian and Caribbean influences. Tropical fruits figure prominently and as for local seafood: spiny lobster will be fresh from August to March and stone crabs from mid-October to mid-May. Don't you dare leave the islands without sampling conch fritters or ceviche and keep an eye out for authentic Key lime yellow custard in a graham-cracker crust. Here are a few of our favorite Key West eateries.
For authentic Key West personality, we love Blue Heaven Restaurant at 729 Thomas Street. Built in a former bordello frequented by some of the city’s most famous residents, Blue Heaven is one of those special places where the locals go. Head here for brunch and check out the blueberry pancakes, lobster benedict and homemade granola. Don’t mind the chickens, they are part of the experience.
For lunch you have to head to B.O.’s Fish Wagon at 801 Caroline Street. We wouldn’t call this a building, it’s more a local collection of stuff that has been made into walls. All that matters is that the experience is authentic, the bread is always Cuban and the conch fritters have been referred to as the best in the world.
Dinner is best off the beaten path and away from tourist traps. Our pick is a chicly, non-descript restaurant named Seven Fish at 632 Olivia Street. This is a local treasure that features an inventive and delicious menu of New-American cuisine. Eclectic dishes like tropical shrimp salsa, wild-mushroom quesadilla, banana chicken and meat loaf are must haves. If in doubt, the fresh fish of the day is the way to go, it’s always perfect.
For fine dining, Café Marquesa at 600 Fleming Street is truly a Key West tradition and at the top of our list. Chef Susan Ferry presents eight or more entrées per night in a collection where each dish is better than the last. Specialties include grilled meats and fresh, local seafood, complemented by inventive appetizers and salads, fresh baked breads and desserts made daily. In this 50-seat institution, everyone has a front row view of the kitchen as guests watch the culinary theater that performs every night. If you splurge on one dinner, this would be the place.
Where To Shop
Shopping in Key West is a must. While you will find national chains and tacky t-shirt traps in the area, this destination is a shopper’s dream if you know where to go.
One of the town’s most fantastic shops is Fast Buck Freddie’s at 500 Duval Street. From bed linens to candlesticks and clothing to home decor, downtown’s oldest and most renowned department store is a hip and memorable experience. Check out the window displays, exquisitely eclectic. Insider’s tip: make sure you also check out Half Buck Freddie’s at 920 Caroline Street, the main store’s mini outlet for discontinued items.
Some other great finds are Key West Aloe at 419 Duval Street where they produce over 300 perfumes, sunscreens and skin care products. Off Duval you will find the charming and unique Besame Mucho at 315 Petronia Street, offering a romantic collection of international delights including French beauty products, exotic chocolate, housewares, and original jewelry. Don't skip The Key Lime Shop, located at the corner of Greene & Elizabeth, which, as the name implies, makes and sells items made from the legendary local citrus fruit. Caroline is another colorful Old Town street with eye-popping shops such as Local Color, Blue and Global Nomad.
For art lovers, galleries abound featuring oils and watercolors; sculpture of all sorts; Haitian primitives; collage; pottery; handcrafted jewelry; woodcarving; stained glass and blown glass; acrylics and a variety of fine crafts. Our picks are Lucky Street Gallery at 1130 Duval Street for contemporary local artists, and The Gingerbread Square Gallery at 1207 Duval Street—the oldest and most respected in the city.
Where to Stay & Play
With an immense selection of fine accommodations, there’s no shortage of places to rest and relax in Key West. With something in every price range, here are our picks for where to stay and play.
For private and slow paced luxury, the ultimate accommodations can be found at the Sunset Key Guest Cottages, a Westin Resort. This truly fantastic island resort is located 10 minutes off the Key West coast and reached by motor launch from the Westin Key West Resort & Marina. The comforts are first-class with one- to four-bedroom cottages at the water's edge. Baked goods, freshly squeezed juice and a newspaper are delivered each morning. With each of the accommodations having a kitchen, the resort offers a grocery shopping service. We absolutely love the secluded beach with its attendants, cabanas and great restaurant. Fair warning, once here you may not leave. And while it is worth every dollar, the $1,985 per night rate may limit the length of your stay.
For an experience in Old Town off Duval Street, our choice is The Gardens Hotel. Featured in the book 1,000 Places to See Before You Die, this 17 suite estate house is home to one of Florida’s oldest and most respected tropical gardens. The suites are spacious, and feature secluded garden seating and perfect plantation style furnishings. The only issue with this otherwise flawless property is the difficulty getting reservations. Stay for the Sunday night jazz and check out the wonderful wine bar. Rates start at $225 per night.
For the large resort experience, The Casa Marina, a Waldorf Astoria Resort is the way to go. Situated directly on the Atlantic Ocean, the 1920’s built property boasts breathtaking ocean views on the largest private beach in Key West. The 311 room oceanfront escape recently underwent a multi-million dollar renovation and is ideal for any Key West visitor.
An array of resort activities are offered at the Casa Marina. Here, I recommend you take advantage of Key West’s most amazing amenity—the water. The variety of activities available for the water lover in you include scuba diving, deep sea charter fishing, snorkeling, dolphin encounters and much more. If relaxing is more your speed, try lounging on the private beach or go over to the Spa al Mare for a rejuvenating experience. The Ocean Breeze Massage on the beach is one of the most popular choices, allowing you to soothe your mind and body amongst swaying palm trees.
One and two bedroom luxury suites are stylishly decorated with Italian tiled floors, sleeper sofas, and teak captain's chairs that add a lot of warmth. Fluffy bathrobes, espresso machines, iHome clock radios, and luxurious designer toiletries make it feel like a boutique hotel. Rates start at $340 per night.
Night Life
Some say that the real Key West comes to life when the sun goes down. Head to the center of Key West’s historic waterfront at Mallory Square to experience the sunset celebration on any evening. Two hours before the sun goes down, hundreds of tourists join local street performers and artists who help usher in the sunset.
With plenty of bars and clubs to choose from, you are sure to find a way to end the day in style. If you are looking for a real bar experience, there is always a debate, but our pick is Captain Tony’s Saloon. With tons of Key West lore and a reputation as the bar that truly inspired Hemmingway (and where he met his third wife), it is a must-do in Old Town.
Another great spot is Sunset Pier at the Ocean Key Resort and Spa located at 0 Duval Street. With its colorful décor, expansive views and nightly music it is a great place to grab a drink and have a good time with friends. On premise at Ocean Key is also the Liquid Lounge Pool Bar which provides an ultra-VIP experience with great music, dipping pool, luxurious cabanas and sleek contemporary feel. Our favorite place is The Afterdeck Bar at Louie’s Backyard at 700 Waddell Avenue. While it is home to one of the city’s most distinguished restaurants, the bar setting is everything you would expect from a Key West location: right on the Old Bahamian Channel and gorgeous. It is the most sophisticated yet low-key spot to grab a great glass of wine, a small plate and to leave the hustle and bustle of Duval Street behind.
It is incredible that in just over 4 square miles exists one of the world’s most vibrant destinations. With over four million annual visitors, it is unmatched in style and joie de vivre. Whether you’re looking for an active vacation or a laid-back beach getaway, Key West’s outstanding coral reefs, watersports, golf, dining, shopping, art and history offer the perfect tropical setting.
