There’s no shortage of things to do in Key West, but where to begin? Not to worry, we’ve distilled down the very best of the island’s attractions for you in this handy list. From watching the sunset at Mallory Square to a beach day at Fort Zachary Taylor State Park, read on for the ultimate list of things to do in Old Town by day and night. Enjoy!
By Day
Conch Tour Train
The Conch Tour Train is the perfect way to get the lay of the land in Old Town as they whisk you around the island where you’ll learn about Key West’s fascinating history, the quirky characters that shaped Key West and its eye-catching architecture.
Ernest Hemingway
Ernest Hemingway, the Nobel and Pulitzer Prize-winning author, lived in Old Town throughout most of the 1930s in a beautiful home that still stands on Whitehead Street today. You can visit the home-turned-museum to learn all about the author’s life and times in Key West. You’ll also encounter descendants of Hemingway’s beloved six-toed cat Snowball that roam the property today.
Southernmost Point
The most popular photo op in Old Town is the Southernmost Point where you’ll find a buoy that exclaims ’90 Miles to Cuba.’ You might have to wait in line, but it’s well worth it to have that coveted Instagram of you with this famous landmark.
Mile Marker 0 Sign
Once you’ve snagged your Southernmost Point selfie, head to Whitehead Street and Fleming for a photo by the Mile Marker 0 sign. It marks the end of the road and embodies everything that makes the island such an offbeat, quirky destination.
Key West Lighthouse
The Key West Lighthouse was erected in 1825 to offer ships a safe harbor. Today, you can scale the 88 steps of the steel spiral staircase for one of the best bird’s eye views of Old Town. You can also tour the Lighthouse Keeper’s Quarters to get a glimpse at what life was like centuries ago.
Fort Zachary Taylor State Park & Beach
Arguably the most beautiful beach in Key West, Fort Zachary Taylor is the most convenient beach to Old Town found at the end of Southard Street. You can relax on the rocky beach, hike nature trails and discover the historic fort. The park boasts a concession stand for snacks and a kiosk to rent snorkels so you can splash around and discover fish swimming right offshore.
By Night
Mallory Square
A visit to Key West simply isn’t complete without taking in the sunset. Head to Mallory Square where every night the sunset is celebrated with tightrope walkers, musicians and magicians all with the backdrop of the setting sun. Vendors sell conch fritters and mojitos, and the whole atmosphere is festive and fun.
Sunset Pier
Another great perch to enjoy the sunset is at Ocean Key’s Sunset Pier. This colorful tiki bar serves delicious bar bites (lobster rolls, fish tacos, conch fritters) and frozen cocktails (pina coladas, Miami vice, rum punch) on a spacious deck overlooking the harbor with live music and a chill vibe.
Green Parrot
The Green Parrot is easily Key West’s most iconic and beloved bar. Located on Southard Street just a block off Duval, it’s a brooding biker bar meets tropical oasis. The walls are covered with psychedelic posters and Key West mementos. Order a cold beer and a round of root beer barrels (their proprietary shot made with root beer schnapps and Miller Light) and find your place on the dance floor. It gets crowded with live music most nights and there’s also billiards, darts and free freshly popped popcorn.
Duval Street
A night on Duval Street involves the extreme sport of bar hopping, locally referred to as the Duval Crawl. This mile-long street in the heart of Old Town is Key West’s nightlife and entertainment corridor. From classic spots like Sloppy Joe’s to Rick’s, and Irish Kevin’s to more sophisticated options like The Other Side and Point 5, there are more bars to choose from than we can count. Our best advice is to start at one end and pop into any watering hole that tempts you.
Ghost Tour
You may not realize it, but there are many ghost stories and haunted houses around the island, from Robert the Doll to the Key West Cemetery. There’s even a story involving the Victorian mansion that currently houses the Hard Rock Cafe. The best way to experience haunted Key West is on a Key West Ghosts & Gravestones Tour held nightly.