When you think about Key West, you may think about famed author Ernest Hemingway, drinking your way down Duval Street, snapping photos of free-roaming chickens https://www.monroecounty-fl.gov/235/Higgs-Beach, or grabbing a selfie at the southernmost point buoy. But as with most anywhere, there is so much more to discover when you venture off the beaten path.

My best friend and her sister moved to Key West last year, and that’s given me reason to head to the southernmost point of the U.S. several times since then. Each time I go, the sisters have discovered something new and different to do, see, or experience as they dig into their new hometown, which means I’ve enjoyed an insider’s look that most Key West visitors don’t get.

Sure, you may still want to swing by The Hemingway Home & Museum or The Key West Butterfly and Nature Conservatory, and check out the buskers at sunset at Mallory Square, but there is still so much more to Key West that you’ll find away from the crowds. Here’s how to do Key West like a local.

Rooster in Key West
Roosters roaming free all over town is a Key West trademark.

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butterfly on a flower
The Key West Butterfly and Nature Conservatory is pretty spectacular. Get up close and personal with countless butterflies, turtles, various bird species, and more.
Busker and audience at Mallory Square in Key West
All ages marvel at the impressive performances by the buskers at Mallory Square.

How to Get There & Where to Stay

While you can drive to Key West (and it’s a BEAUTIFUL drive!), flying into Key West International Airport (EYW) will get you there faster. Nashville, where I live, enjoys a direct flight via Allegiant Airlines at a very affordable price point, but there are plenty of other airline options, so shop around. 

In terms of accommodations, there are plenty of hotels — both big chains and boutique hotels, each with their own Key West spin — spread throughout the island, but I suggest snagging a vacation rental via Airbnb or VRBO so you can enjoy the comforts of home and many times a private pool. One community in particular, called Truman Annex, has the best of both — a shared pool for the community as well as some homes with private pools. Several rental companies can hook you up with a Truman Annex property, and by staying in this area, which is called Old Town, you will be within walking or biking distance to so many things.

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Speaking of bikes, it’s fun to explore the island on two wheels. Eaton Bikes and Key West Bicycles are both good starting points. And if biking isn’t your thing, the Duval Loop Bus runs daily from 8 a.m. to 10 p.m. Find the schedule and more details HERE.

Where to Go & What to Do

Now that you know where to stay, let’s get down to the many fun things to do. Since there are so many different ways to enjoy your time in Key West, and because it largely depends on your interests, I’ll offer several ideas to get your wheels turning, and you can mix and match as you see fit!

Enjoy a Day at the Beach

Place a lunch order to go at Date & Thyme for fresh, healthy fare, or Eaton Street Market, where you will find the BEST lobster roll in town. Grab your lunch order on the way to the beach at Fort Zachary Taylor Park. Once there, rent a beach chair and umbrella, and bring or rent some snorkeling gear to explore the aquatic life in the clear blue water. Or, if you just want to be a beach bum, grab a towel and spread out under a palm tree with a good book. The view and sounds of the surf will likely lull you into a post-lunch slumber. There’s an on-site cafe if you’d rather get lunch there, and there are also picnic tables and grills if you prefer to DIY your food. Just be sure to clean up your mess to keep the park pristine. And make sure to stick around for a spectacular Key West sunset.

Fort Zachary Taylor Park Key West aerial view
The Florida Keys have some absolutely stunning state parks. Pictured here is an aerial view of Fort Zachary Taylor Park — a great place to lay out your blanket and relax. Image: Rob O’Neal / Florida Keys News Bureau

Check Out the Local Markets

If you’re staying in Old Town, a short walk to the waterfront on Thursdays takes you to the weekly Key West Farmers Market. There, you’ll find a wide selection of fresh produce, tasty locally made food and beverages, and handmade creations from local artisans. (A stop at Samosa Mama’s booth is a MUST!) The action takes place from 2 p.m. to 7 p.m. every Thursday along the Truman Waterfront Park. And if you have kids, you’ll want to make sure they wear their bathing suits and you bring towels, because the sprayground is right next to the farmers’ market and is a HUGE hit on hot days. (The playground next to that is great any time!)

The other market you don’t want to miss is the Key West Artisan Market, which takes place every other Sunday at Higgs Beach — but only from November to April. There, you can enjoy live music and sip a fruity beverage as you meander among the various vendors. Look for clothing, flags, jewelry, art, home decor, food, and orchids! You’ve GOT to see the orchids!

Key West farmers market
The Key West Farmers Market takes place every Thursday and features amazing local goods.

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Sprayground at Truman Waterfront
The sprayground at Truman Waterfront is a hit on hot days!
The orchids in Key West are unbelievable. You’ll find them strapped to trees all over town. Pick one up at the Key West Artisan Market to take home.

Bring Your Pup

If you’ve never traveled with your dog, make your Key West adventure your first foray into the world of pet-friendly travel. Key West is INCREDIBLY dog-friendly with plenty for pets and owners to enjoy. In addition to several dog parks, there are also puppy parades and dog-friendly boat tours.

The Doggie Day Sail invites you and your pup to enjoy a breezy sail aboard a 75-foot yacht. Tickets are $85 ($20 of which goes to the Florida Keys SPCA) and include treats for your pooch and a lovely lunch for you, with beer and wine available as well as non-alcoholic options too. Limited dates are available for this fun fundraiser, so make sure you book well in advance.

Griffey on the Doggie sail
Griffey enjoyed his first Doggie Day Sail. Image: Lou Kinney

If you want to get a little closer to the water, rent a paddleboard or kayak to share with your pup as you explore the shallower waters of Key West. Lazy Dog Adventures will hook you up with everything you need to explore on your own or opt for a guided tour if you prefer. It’s a nice way to enjoy a slower-paced activity in an unmatched setting.

As for the dog parks, water-loving dogs will love the Key West Dog Beach, where they can run wild among the surf and sand. And when your pup’s all worn out, head to Louie’s Back Yard, a few steps away, for a tasty bite and a cool drink. Other Key West dog park options include Higgs Beach Dog Park, which has separate runs for large and small dogs, or Grinnell Street Pocket Park, which is smaller but shady and perfectly adequate.

Iguana in a tree
Dogs and chickens aren’t the only creatures you’ll find throughout Key West …
Key West sunset celebration
Every night in Key West is a celebration! Crowds gather nightly in Mallory Square to take in performances by buskers, browse local vendors, and applaud as the sun sets below the waterline. Image: Rob O’Neal / Florida Keys News Bureau

Eat Well!

There is no shortage of dining options in Key West. And while there are plenty of loud and vibrant eateries and bars along Duval Street that are always crawling with tourists, I challenge you to think beyond Sloppy Joe’s and Hog’s Breath Saloon. Here are a handful of tried-and-true options worth experiencing and what to consider ordering at each:

  • Blue Heaven for a fantastic breakfast (the lobster Benedict is AMAZING!)
  • Kaya Island Eats for a killer patio and fish & chips
  • Moondog Cafe for brunch and a variety of mimosa flavors (definitely try the blood orange) 
  • The Cafe for pretty much anything — including lots of tasty vegan options
  • Sarabeth’s for fried chicken
  • Nine One Five for the cone of fries

Most of all, enjoy your time in this one-of-a-kind destination. By all means, do Duval Street — it’s kind of a must. With no stops, it takes about 25 minutes, and then you can say that you walked from the Gulf of Mexico to the Atlantic Ocean. Just be sure to start your wanderings down this world-famous avenue with a rum punch in hand from Two Friends Patio. Tell them you’re a friend of the sisters!

If you happen to see “the sisters” (and Bonnie), tell them StyleBlueprint sent you!

All photography by Ashley Haugen unless otherwise noted.


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Ashley Haugen
About the Author
Ashley Haugen

Ashley is a StyleBlueprint contributor who was born and raised in the South. She loves hiking, travel, photography, and spending time with family and friends.