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Talk about the definition of living the tropical paradise dream! If you’ve ever considered an extended stay at the southernmost point in the continental United States but thought it would take too much planning, know that it’s easier than you think. Read our guide of helpful tips and tricks for spending a month long vacation in Key West, including how to get around the island and things to do.

Secure a Vacation Rental
The first step to beginning your extended stay in Key West is to secure that charming conch cottage in Old Town shaded by palm fronds with bright bougainvillea crawling across the white picket fence. The best way to get a sense of the inventory in town and to pick the spot that meets your needs and budget is to go through a local realtor like Preferred Properties. We know the island from the hidden gems to the popular sites and are here to help you find the perfect island getaway.


Travel Around by Bicycle
If you’re staying in Old Town, the best way to get around the island is by bicycle. You can rent one from a local bike shop, but sometimes buying a clunker off of the used rack is more cost effective for an extended stay. Either way, this mode of transportation is the best of everything. Not only does a bike mean no more worrying about parking, but it’s also a fun and easy way to get some exercise.

Join the Community
A month long stay in Key West is the ultimate way to fully relax and leave your worries behind on the main land. Even better, you’ll be feeling like a Key West local by the end of it. Join the Conch Republic community by finding a temporary job or volunteer opportunity on the island. You could be a deckhand on a snorkeling catamaran and spend your days on the water. Or if the Key West nightlife is more your style, you could pick up a few shifts tending bar to meet locals and tourists alike. Perhaps you’re interested in the arts and culture. You could volunteer to work the concession stand at Key West’s indie movie theater, Tropic Cinema.

Take on a Hobby
Key West offers the kind of diversions you won’t find in other cities. With the sparkling Atlantic Ocean and Gulf of Mexico converging on the island’s shores, it’s a great opportunity to try your hand at watersports. Whether it’s boating, wakeboarding, paddleboarding or fishing, Key West has so much to offer beginner and experienced watersports enthusiasts.

There’s also a strong creative community in Key West. Whether you want to explore painting, theater, writing or gardening, there are many organizations to join. For starters, check out the Studios of Key West to meet like-minded individuals, sign up for a class or workshop and attend gallery openings and performances.


Visit the Sights
Hemingway House – Nobel and Pulitzer Prize winning author Ernest Hemingway is easily Key West’s most famous former resident. He and his second wife Pauline occupied a home on Whitehead Street during most of the 1930s. Today, it’s a museum dedicated to the author, his writing and his adventurous life in Key West.

Fort Zachary Taylor State Park & Beach – Fort Zach is Key West’s most beautiful beach. Located at the southern edge of the island with views out to the Atlantic Ocean, it’s also home to a Civil War fort and nature trails.

Key West Lighthouse – Get a bird’s eye view of the beautiful island by scaling to the top of this coastal beauty.

Custom House – The Custom House is home to the Key West Art & Historical Society. The institution is a great starting place to learn about Key West’s quirky history and view thought provoking exhibits featuring both local and international artists.

Mallory Square – Gazing out at the sunset as it sinks into the western horizon is a nightly ritual in Key West and you have to experience the view from Mallory Square at least once while you’re in town. Street performers and musicians put on a show for the crowd gathered before the water.


Stop by the Local Hangouts
The Porch & The Other Side – If you want to meet locals, you have to hang out where the locals do. The Porch and The Other Side are sister bars located across the foyer from each other inside a historic Victorian mansion on Caroline Street. The Porch specializes in craft beer, while The Other Side is dedicated to some of the best cocktails you’ll find on the island.

2 Cents Restaurant & Pub – Also owned by the folks behind The Porch and The Other Side, 2 Cents is a chilled out gastropub plating ambitious and craveworthy dishes. It also has a lively, yet laidback bar scene.

Thirsty Mermaid – The Thirsty Mermaid is the newest restaurant behind the team that brought the island Blackfin Bistro. Expect locally caught fish, oysters and a creative chef-driven menu.

Green Parrot Bar – Green Parrot is the ultimate locals bar and the place to hear killer live music on the weekend. It’s a little bit hippy and a little bit rock ‘n roll. Prepare to dance, swig beer and have a great night.


Explore the Rest of the Florida Keys
While you’re in Key West for a month, why not discover all the Florida Keys have to offer? Rent a car, or be adventurous with an open top Jeep, and feel the breeze in your hair as you travel north to Big Pine, Marathon, Islamorada and Key Largo along the Florida Scenic Highway. Each island has its own identity with plenty to explore.

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