Things to Do in Key West

A Key West Sunset

A Key West Sunset

We already talked about where to stay and what to do en route to the southern most point in the U.S.A., so what do you do once you’re there? From exploring Old Town by bicycle to visiting historic sites like Ernest Hemingway’s house and experiencing the nightlife on Duval Street, Key West is a quaint but lively destination with plenty of things to do. Here are our top 10 things to do while there!

1. Stroll Through Mallory Square
At the heart of Key West’s harbourfront is Mallory Square. It’s a bustling place filled with street vendors and performers, open-air bars, and sidewalk cafes. Every night the Sunset Celebration begins on the dock, with local artisans, mines, jugglers and musicians and the like, entertaining the crowds. It’s a fun place to take in the atmosphere as you watch the sun sink into the Gulf.

2. Take a Sunset Cruise
After you watch the sunset on land, plan to see it also dip below the horizon on water. Dream Chaser Charters offers a private 2-hour cruise with magnificent views of the Gulf of Mexico and the Atlantic Ocean with refreshments and appetizers too for $65US/person (with a minimum 4-person booking). For a more luxurious experience try the Sunset & MOET cruise with Catamaran Eco, where you can sip champagne while watching the sun go down.

Ernest Hemingway's House

Ernest Hemingway's House

3. Visit Ernest Hemingway’s House
Literary lovers shouldn’t miss the chance to see the home of author Ernest Hemingway who wrote and lived at this address for over 10 years. You can self-guide yourself through his house and the property, or take a tour to learn more about this legendary author. Cat lovers take note, there are about 60 felines wandering the grounds (we saw one sleeping on the master bed!).

4. Dine on Fresh Seafood

Nine One Five on Duval

Nine One Five on Duval

When you’re this close to the ocean you can’t leave without dining on fresh seafood. Nine One Five bistro and wine bar on Duval Strett is set in a century-old Victorian home, and features a tapas-style menu. Their signature dish, the Tuna Dome, is outstanding and we highly recommend it. For mains you’ll find local fare like lobster, grouper and prawns. And if you want to continue after dinner, head upstairs to their wine lounge Point5 with DJs spinning on the weekends.

5. Day Trip to Fort Jefferson & Dry Tortugas National Park

About 420 kilometres off the coast of Key West is Fort Jefferson and the Dry Tortugas National Park. The Dry Tortugas are a group of islands surrounded by coral reefs, perfect for snorkelling, swimming and kayaking. Best done as a day trip (it takes about 2 hours each way), the islands can be reached by ferry, seaplane or catamaran. We suggest taking the Yankee Freedom at $165US/adult. It’s a high-speed boat with plenty of amenities including refreshments, a continental breakfast, picnic lunch and snorkeling equipment. Upon arrival you’ll have the option to take a guided tour of the fort. Even if you’re not into snorkelling it’s a fantastic place to explore, birdwatch or just relax on the sandy beaches.

Fort Jefferson at Dry Tortugas National Park

Fort Jefferson at Dry Tortugas National Park

6. Rent a Bike
One of the best ways to see Key West is by bicycle. When you arrive by car you’ll notice how challenging it is to find a parking spot and many of the streets are super narrow. Walking is a great way to see the town, but to maximize your coverage, a bike will let you see everything in half the time! Many hotels let their guests borrow bikes, but if that’s not the case consider renting. Eaton Bikes has a huge variety, plus they’ll deliver, pickup and provide any roadside assistance.

7. Eat Key Lime Pie
keylimepie_optYou can’t leave Key West without eating a piece of key lime pie. You’ll see a couple of popular chains including Blond Giraffe and Kermit’s on Duval and around Mallory Square. But our favourite was from the Mom-and-Pop shop, Sweets of Paradise, a delicious candy store that also sold mouthwatering fudge and ice cream.

8. Sit in the Sand at Fort Zachary Taylor Historic State Park

The beach at Fort Zachary Taylor.

The beach at Fort Zachary Taylor.

Key West isn’t exactly known for its beaches, but if a little lounging by the water is a must-do for you then opt to visit Fort Zachary Taylor. Onsite you’ll find a refreshment stand, picnic tables and grills, and nature trails for walking or biking. The Fort also offers guided tours at noon and 2 p.m. daily.

9. Ride on the Conch Tour Train
If you can get over the cheese-factor, the 90-minute Conch Tour Train ride through Old Town is actually pretty informative. There are two short stops along the way, including a 10-minute pit stop at Station Depot and at the second stop you can disembark to check out the sights and catch a later train if you’d prefer.

10. Have a Drink on Duval
At night Duval Street changes from a shopping and eating mecca into a lively scene with rowdy characters, more than a handful of gay clubs with drag shows, and people looking to party, so don’t expect a lot of classy clubs here — think Sloppy Joe’s and Cowboy Bill’s Honky Tonk Saloon. But if a party time is what you want, this is the place to be. Want class, but a bit of flavour? Try Virgilio’s martini bar, which is on Duval, but away from the drunken crowds. They have a nice garden patio in the back with live music.