- Spending A Month In Key West 
Like A Local

Spending A Month In Key West 
Like A Local
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A month in Key West. Can you think of anything dreamier? There’s something in the air that makes this laidback, bohemian island so intoxicating. Perhaps it’s the big, bright blue sky with cumulus clouds floating lazily above palm trees, conch cottages and the endless spread of the Atlantic Ocean and Gulf of Mexico from all sides. Whatever it is, the quality of life on the island is dialed way up. If you’re lucky enough to retreat to Key West for a month (or an entire season), here are some recommendations for long term living on island time.


If you’ve rented a Key West Vacation Home in Old Town, the good news is that a car is superfluous. So much of the island is walkable and locals’ favorite means of transportation is by bicycle or scooter. You can get around with ease during your stay by renting a bike for a month or even buying a used one for about the same price.

If you’d like to get off the rock and explore the Upper Keys, there’s a company that rents jeeps fully loaded with beach gear, coolers, paddleboards and whatever your adventure needs may be.

Grocery Shopping

There are dozens of delicious restaurants on the island, but if you’re living in paradise for a month, chances are you’ll want to stock your vacation home with groceries and fresh produce. Fausto’s is Old Town’s local grocery store with two locations on Fleming Street and Truman Avenue.

Fresh caught fish is one of the true joys of dining in Key West and you can head to the Eaton Street Fish Market to purchase fresh grouper, mahi, snapper, spiny lobster and whatever the local fishermen caught that day. For a loaf of fresh baked bread or croissants and brownies so sinful you simply won’t be able to resist, make Old Town Bakery your go-to.

On the Water


Take advantage of the tranquil waters of Key West by diving in! Paddleboarding and kayaking are easy sports for all activity levels. Rentals and tours are available all over the island. It’s a great way to explore mangrove islands and the shallow backcountry of the Gulf of Mexico.

From the coral reef to sandbar beaches, there’s a lot to explore offshore and boat rentals and charters will get you where you want to go. Fishing is a favorite pastime amongst Key West’s locals and it’s one of the biggest draws for visitors as well. The island is filled with charter boat captains who can take you deep sea fishing or to the shallow sand flats in search of the big one.

The southern edge of the island is home to Higgs and Smathers beaches for a lazy day relaxing under the sun. You’ll also find water sport kiosks for sailing, snorkeling and paddleboarding along the beach. Fort Zachary Taylor State Park & Beach is a favorite amongst locals for its beautiful setting amidst Australian pine trees and its tranquil atmosphere.

During your month-long stay, plan a day trip to the Dry Tortugas located 70 miles west of Key West. The Yankee Freedom III fast cat gets you there and you’ll spend the day snorkeling, touring Fort Jefferson and exploring this unspoiled national park.

Off the Beaten Path

One of the best things about living in Key West for a month is the feeling of ownership. It’s slow travel at its best and you can really delve into how locals enjoy the island and get off the beaten path. Old Town is home to the indie art house Tropic Cinema where you can while away an afternoon at a matinee complete with popcorn and a glass of wine, if you fancy. For your beach reading pleasures, swing by indie bookstore Books & Books, which just so happens to be owned by iconic young adult author Judy Blume.

There are many gardens and green spaces to discover including the Key West Tropical Forest & Botanical Garden near the Florida Keys Community College on Stock Island and the Key West Garden Club at West Martello Tower on Higgs Beach near the White Street Pier.

From café con leches at the counter to cozy coffee houses for an afternoon of checking emails, you’ll need to find your favorite local coffee shop. Cuban Coffee Queen, Five Guys and Sandy’s are great for a cafecito on the go, while Coffee Plantation and La Grignote are perfect for setting up shop for a few hours with an iced latte and a scone.