Things to do in Key West

Have your Key Lime Pie and eat it with our guide to the most vibrant island in the Florida Keys chain...
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Amira Hashish27 December 2018

Key West packs a punch when it comes to entertainment. A long weekend here should revolve around delicious food, late nights in gritty live music bars and a stroll around Hemingway’s home.

Here are some of our favourite ways to soak up the best of this bustling island...

Stroll around the Hemingway Home & Museum

Ernest Hemingway lived and wrote in Key West for nearly 10 years, finding solace in the turquoise waters that surround this tiny island. At the Whitehead Street property, guests can step back in time and visit the rooms and gardens where the Nobel Prize winner spent the most prolific period of his writing career during the 1930s. Standing in his study where his typewriter still sits is quite the experience.

Rob O'Neal/Florida Keys News Bureau/HO

Our enthusiastic tour guide recounted tales from Hemingway’s life as we meandered through the home. Look out for the six-toed cats which are descendants of Hemingway's feline friends. An absolute must visit when you are in town.

Sample the Seafood Lover’s Cultural & Tasting Walking Tour

There are so many food options in Key West so this three-hour walking tour is a great way to try some of the best on the island. It will include at least six stops with tastings in each. It is not just about the food either. You will experience what life is like for a Conch (a native to Key West) with recommendations from the guide of architectural gems, tropical flora and attractions woven in. Groups tend to be small so the experience feels personalised.

All aboard the Wind & Wine Sunset Sail

Cruising along the ocean on a historic Key West schooner is lovely enough. Team that with Danger Charters' wine tasting and hors d’oeuvres and things step up a notch. Friendly and laid-back, the staff will offer a very warm welcome and even play some fun tunes.

The experience culminates in watching the sunset as you sail under the cloud of canvas, glass in hand.

Order the famous Key Lime Pie at Kermit’s Cafe Kitchen

A trip to Key West involves copious servings of its signature Key Lime Pie. There are lots of delicious options with different twists but Kermit has been doing his thing for a long time and is a real staple in the town. Head to the original cafe for a slice in the shaded rainforest patio with its very own koi pond. There is a neighbouring shop which sells every kind of Key Lime goodie imaginable.

Party at Mallory Square’s Sunset Celebration

This nightly affair is an essential part of the Key West visit. As the pink and red sun sinks into the Gulf of Mexico a host of local artists and entertainers take to the streets. From swinging cats to street food stalls, it is a celebration of Key West’s wild nature.

Bob Krist/Florida Keys News Bureau

Take in the marina view at Turtle Kraals Bar & Restaurant

The rooftop of Turtle Kraals overlooks the marina and is a fun spot for cocktails and dinner. Influenced by generations of settlers from the nearby Caribbean Islands, dishes vary from fish tacos to mahi mahi. Casual and lively, this is a great place for mingling with the locals over a Mojito.

Do the live music crawl

There are some (almost) obligatory stops in Key West for live music and drinks. Sloppy Joe’s is an institution, Green Parrot has a very loyal following, Virgilio’s is the place for Martini and Willie T’s guarantees a good crowd. Spend your evenings strolling up and down Duval after dinner to stumble across other buzzing options.

Bob Krist/Florida Keys News Bureau

Spot a star at Lucy’s Retired Surfers Bar

Coastal inspired cuisine and surfer style cocktails are on the menu here. This is the place to eat, drink and mingle On Duval Street. Country superstar Kenny Chesney was propping up the bar when we were in town. The dishes are generously sized with tasty sauces. Try the avocado fritas, blackened fish tacos and pao pao shrimp. For the brave-hearted there are some daring cocktail choices which could result in you winning a T-Shirt.

Have a flutter at The Key West Butterfly & Nature Conservatory

The Conservatory is filled with hundreds of butterflies as well as flowering plants, colourful birds, waterfalls and trees. There is a learning centre on site where you can explore butterfly anatomy.

Stay at the Marquesa Hotel

The epitome of boutique hotel luxury, it is a tranquil and sophisticated retreat that feels like a home away from home. Read the full review here.

Make a night of it at Latitudes

A small ferry will meet you at Key West Marina and transport you to Sunset Key Cottages, an exclusive resort on its own island. After disembarking from this charming little boat, head to Latitudes for a special dining experience with a vista of the Gulf of Mexico. The al fresco restaurant is illuminated by tiki torches that twinkle under the night sky. Even the menu lights up when opened (yes, really, see below). Highlights include the lobster crab cake, yellowtail snapper or seared grouper.

There is an excellent wine list as well. An evening here feels like an occasion.

Get pampered at Nailtini

A local favourite, Nailtini does everything from nails to massages in a friendly and inviting little salon on Duval Street. The spa menu has an accompanying cocktail list for that fun touch. Manicure and a Martini? Yes please.

Brunch at Bistro 245

This casual spot overlooking the marina is great for brunch. Part of the Margaritaville Resort, it attracts the locals too. The generous buffet includes meats, pastas, salads and frittata. Plus, lots of dessert options and free flowing champagne or mimosas. Take your time, indulge and enjoy the view.

Don’t miss these foodie favourites...

There are certain restaurants that keep cropping up from local recommendations that are certainly worth working into your itinerary. Blue Heaven is perhaps the most iconic for a slice of Key Lime Pie and live music in a rustic setting with chickens roaming around. Yes, that’s a Key West thing.

Louie’s Backyard is the place to go for a sea view and upmarket dining. Stop off at the nearby Southernmost Point en route for that picture moment. Pepe’s is a great shout for breakfast and freshly squeezed juice. Say yes to the homemade bread of the day. Then pay a late night visit to Better Than Sex, a dimly lit tongue-in-cheek dessert bar with tempting treats.

For more information on Key West and the Florida Keys visit fla-keys.com.

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