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Walk toward Mallory Square and the Historic Seaport and you’ll come across the original headquarters of Pan Am airlines (which is now the aviation-themed First Flight Island Restaurant & Brewery), the Aquarium, Mel Fisher Maritime Museum, and the Audubon House, which feels preserved in time from 1840 and has a large rare-for-the-neighborhood courtyard and garden. The backyard is frequently used as an event space. With much of the decor and furniture still in place, it’s now known as the Truman Little White House and includes a gift shop for presidential history buffs. The main attraction of the Truman Annex is the former winter residence of President Harry Truman, which today is the only presidential museum in Florida.

Best Neighborhood in Key West for History Buffs: Truman Annex.

So head out on foot and enjoy the stroll. (It’s not uncommon to see joggers and bicyclists traveling through.) The Heart of Old Town is a great home base since it’s walkable to other neighborhoods in just minutes. The above-ground cemetery is curiously cheerful and although it’s still in operation, tourists are welcome. The former home of Ernest Hemingway was converted into a museum that makes for an easy tour, whether you want to explore it yourself or follow a guide. Wander around and admire the vintage homes and what feels like a bed-and-breakfast on every corner. The Heart of Old Town is where the preservation guidelines are strictest with thousands of colorful wood structures dating back well into the 1800s.

Best Neighborhood in Key West for Walking: Heart of Old Town.

The private beach at the Casa Marina 5-star resort. You may also notice an unusual amount of cats and chickens roaming the sidewalks. Just be ready for a fierce debate on whether Key Lime Pie should be topped with meringue or whipped cream.

Locals take an independent pride in being part of the “Conch Republic”, yet follow a “One Family” mentality that has long welcomed all demographics in a way that feels organic and effortless. The horizon sunsets alone are worth a visit, especially when viewed from the daily Mallory Square street celebrations. There are other more beach-oriented vacation spots in Florida, but you still have a few options for enjoying the sand and dipping your toes in the water. Key West is a unique mix of art, history, and an easy, waterside atmosphere.

Ride-sharing services are another inexpensive option for getting around and with parking tight, it’s best to leave any car back at the hotel.

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No matter where you stay, Old Town is easy to navigate on foot, the free Duval Loop bus shuttle, or the Old Town Trolley Tours with unlimited reboarding all day long. With that in mind, Old Town (also known as the Historic District) is the best area to stay, whether it’s a charming bed-and-breakfast in the Heart of Old Town or a more luxurious hotel in and around Downtown, Casa Marina, or the Historic Seaport.

The latter is where most visitors will spend the majority of their time with several neighborhoods that blend together and borders that aren’t easy to identify. At less than eight square miles, the island is easy to explore, divided between contemporary, residential New Town and character-rich, historic Old Town. The Best Area to Stay in Key WestĪs the southernmost city in the continental United States, Key West combines sun, culture, and positive energy with an off-the-grid feel. Idyllic Duval Street in the heart of downtown Key West.

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