What’s there to do in

Key West?

Key West is only 74 square miles. While it may seem like the activities on this tiny island are limited to the tourist traps and the drinking binges, you can actually entertain yourself with a myriad of culture, shopping and even some adult-themed fun.

You should prioritize walking around the island every day. Key West is filled with history, visible in the architecture from the antique homes to the churches. The island is also overrun with free-range chickens. No, my hipster meat-eating friends, you can not eat these chickens. Like the six-toed cats, they’re treasured residents of the island. You can, however, take home a painting of a rooster wearing high heels, but let’s try to steer clear of that…

The Must See’s

Sunset Festival

Mallory Square
Fee: none, but bring tip money
A festival with street performance, vendors and the sunset

Street theater may be somewhat lowbrow, but you can’t help but experience a childlike awe while watching the fire swallowers, tightrope walkers and other performers. Under their sun-loved skin and croaky voices, there is a powerful ability to captivate an audience. Some of them will perform truly impressive and dangerous looking feats, others will simply provide a laugh. This is a tourist destination, so the crowd is mainly made up of spring breakers, families, old people and couples on anniversary trips. It’s a fun event, especially if you don’t care about taking a picture of the sunset. Walk around with a beer in hand and let yourself loose. The festival starts two hours before sunset.

Eaton Bikes

830 Eaton Street
326 Southard Street
Fee: $18 per day, $55 per week
One of many bike rental stores on the island.

The best way to navigate the tiny island is by renting a bike. It’s relatively inexpensive and you can pretty much get around the entire island in one hour. There are plenty of rental stores to choose from, but supplies may run low during spring break season. We enjoyed our cruisers from Eaton bikes in Old Town, though people taller than 6 feet might have trouble fitting on this style of bike.

White Street Gallery District

Bound by White St, Truman St, Flagler Ave, & Truman Ave.
Fee: Varies
Wander the studios of the island and beware the galleries on Duval.

The majority of the galleries in Key West are tourist traps, with cheesy paintings and rather kitschy sculptures. However. you can find some more interesting art in the studios of the gallery district on White Street. Every first Thursday of the month, I hear you can take a nighttime gallery tour with a little wine. I can’t confirm this, but if you’re heading in to town you should look into it.

Fort Zachary Taylor Beach

Entrance at the end of Southard Street
Fee: $3 per pedestrian or $7 per car
A gorgeous beach beyond a civil war-era naval base.

I try to avoid beaches, because I enjoy my pale, cancer-free skin and I hate sand. Despite my apprehensions, Fort Zachary Taylor beach is absolutely gorgeous. Surrounded by tropical forests and dotted with rock formations. Even a beach-hater like myself had to enjoy a couple of hours by the ocean. While the rocky sand may hurt to walk on, the gravel-like floor made for less sand up in my business. The spring break crowd is mostly confined to Smathers Beach; here you’ll find tourists and cruise ship riders. Amenities include restrooms, rentals cafes, and tours of the historic civil war era fort.

Shopping for Eats

Eaton Street Seafood Market

801 Eaton St
Fresh seafood in the heart of old town

We were lucky to have been located a mere block away from this market. The display case selection is gorgeous, with crab claws, lobster tail, shrimp and other locally caught fish. You’re also able to select any one of these fish, and they’ll fry it up and put it on a ciabatta bun with fixings. We went to town on a snowy grouper sandwich with a side of plantain chips. It’s certainly in the running for one of the best sandwiches I’ve ever had, simply because of that buttery grouper. The store also has a pretty decent beer selection.

Fishbusters

6406 Maloney Ave
A fish market on stock island.

While a ways from the dow town area, Fishbusters offers an array of fresh seafood. If you’re in the area, it’s definitely worth stopping in for some snapper, hogfish, or shellfish. The shrimp is divine!

Peppers of Key West

602 Greene St
An all-hot sauce shop with a free hot sauce tasting bar.

If you’re a hot sauce fiend, then you’ll adore Peppers of Key West. It’s best to taste the hot sauces after a couple of drinks, which will ease the repeated burn, and purchase a bottle once you’re sober again. While the prices are a little overblown, they have some great sauces. We took home the Ring of Fire Xtra Hot Habenero Hot Sauce, a delicious and smoky treat. This is absolutely a tourist trap, but it’s actually really fun.

The Restaurant Store

1111 Eaton St
A Chef’s Supply store with the absolute best beer selection on the island.

While I often struggled to purchase the right beer from the limited selection of craft brews available, I was delighted to discover the diverse array at The Restaurant Store. While I like to think that Chicago has one of the best beer selections, I discovered several beers that I’ve never before seen in my hometown. Also, I noticed that their wine selection, while quaint, was both fairly priced and higher quality than what I had seen elsewhere. If you love beer, this place is for you.

Gay and Sexy Stuff

Island House

1129 Fleming St
An all gay resort complete with nudity

Key West is known for its homo-friendly attitude, and you gotta love it. At this all-gay resort, men are able to frolic in the nude and relax by the waters. Obviously, they wouldn’t let me go inside, but places like this make me wish I was a gay man.

Leather Master Key West

418 Appelrouth Lane
Get yourself a sexy souvenir.

This place hand makes their leather toys in house. It’s almost like the Kino Sandal Factory of S&M. Discover a variety of accessories toys and costumes for the trip. I wonder if they sell a gay man costume that so I can disguise myself in order to get into Island House…

Spooky Stuff and History

Sloan’s Key West Ghost Hunt

Meet at Kelly’s Carribean Bar & Grill, 301 Whitehead St
Price: $26.88

Key West was originally named Cayo Hueso, Spanish for “bone cay (reef).” Historically, the island was used as a communal graveyard for deceased natives. The city is filled with stories about pirates, shipwreckers and other ghostly tales. While I kept it simple with a book of tales, I highly recommend Sloan’s ghost tour, the city’s original ghost hunt. In addition to receiving a rundown of the otherworldly residents of the island, this 90 minute walking tour conjures and communicates with spirits in the heart of the city. I’m not sure how successful the conjuring is but it’s certainly an educational experience and you get a free book. Tours depart nightly, rain or shine and are limited to 20 people. Please provide 24 hours notice.

Fort East Martello Museum

3501 S. Roosevelt Blvd
Fee: $9
Artwork, antiques and a haunted doll.

There are a lot of little museums in Key West and I didn’t even go to one of them. However, this is the one that repeatedly caught my eye. It might because it’s the current residence of Robert the Doll, a toy who used to haunt the artist house on Eaton Street. Among the relics, the museum also has plenty of folk art and sculptures.

Robert the Doll. Courtesy of Facebook.

Audubon House and Tropical Gardens

205 Whitehead St

This house was owned by Captain John H. Geiger, a “wrecker” who made his living by by salvaging artifacts from shipwrecks. Legend has it that he also engaged in piracy. His spirit is said to still haunt the house as is his daughter Hannah, who died at the age of 10. If you aren’t into the spooky stuff, than it’s still worth viewing the lovely home that’s filled with antiques and complete with a tropical garden.

Hemmingway Home

907 Whitehead St
Fee: $13
Visit the home of a famed author, or just look over the fence.

If you’re interested in home tours, it’s a lovely house and I’m sure the six-toed cats spice things up. This is another one of those tourist-clogged events and you will most likely have to wait in line. I’m not a fan of house tours, so I merely peaked over the fence and felt satisfied.

Key West Cemetary

701 Passover Ln
Fee: none

There is nothing like the juxtaposition of clear blue skies, lively palm trees and gravestones. This cemetery is stunning, with many of the graves decaying, cracked or lying on a slant. It was established in 1847, after a hurricane washed away all of the dead bodies buried in the previous cemetary spot, by the West Martello Tower. Considering the island started out as a graveyard, this is a wonderful visit. The iguanas love it here too!