Key West Bucket List

Compiled here is a list of unique Key West highlights. I’m purposely not including the major tourist magnets, you’ll find those easily enough on your own. It’s impossible to miss the din of Sloppy Joe’s or the beacon that is the Southernmost Point. This list is comprised of the odd, inspiring, and just plain fun that can be had on this crazy little 2 by 4 mile island.

Peppers of Key West “An Introduction to Scoville”

602 Greene Street

This is one of my favorite group activities. The wrap around bar and towering shelves at Peppers boast an impressive array of spicy sauces with laughter-inducing names. Pull up a stool and the staff will guide you through sample after sample of delights ranging from spicy mustards to tear-inducing hot sauces. Peppers is also BYOB so I recommend stopping by the local grocery store “Fausto’s Food Palace” on Fleming Street to grab some cold beers and any food items that would be enhanced with a dab of hot sauce.

The Southernmost House “Best Kept Secret in Key West”

1400 Duval Street

If you are craving some rays head over to the Southernmost House at the end of Duval. Known by the locals as “The Mansion” this architectural icon boasts a luxurious infinity pool, lengthy list of historical icons who have stayed within its walls and an incredible view of the Atlantic Ocean. For a nominal entrance fee the place is yours during pool hours. Entrance gets you a fluffy beach towel, use of any lounge chair, and a free drink at the bar. This deal is not advertised and many locals don’t even know about it. You’ll be in heaven while the less informed are across the street paying $10 for a single lounge chair on a crowded beach. NOTE: Management has fluctuated over the years, call in advance to assure entrance.

Blue Heaven OR Salute on the Beach “Best Key Lime Pie in The Keys”

729 Thomas Street or 1000 Atlantic Boulevard

Owned by the same proprietors these restaurants are home to the best key lime pie in Key West. It doesn’t take long to realize that Key West is all about key lime: key lime desserts, key lime martinis, and should you go for a teeth cleaning they will even offer you a key lime fluoride treatment! If you want the real deal however, either go to Blue Heaven for a sumptuous dinner under the stars (on the same turf where Hemingway held boxing matches in the 1930s) or head to Salute on the Beach for lunch while watching a volleyball game. After your meal order at least one slice of this famous pie which has been featured on the Food Network and the Oprah Show. The meringue is a feat of architecture and the crust could be a dessert in itself.

West Martello Gardens “Intrigue for your Inner Botanist”

1000 Atlantic Boulevard

One of the few free attractions in Key West (donations are accepted) is the West Martello Gardens. This hidden Eden is nestled inside the walls of the West Martello Fort along the Atlantic. The plants are all donated and maintained by the Key West Garden Club members and volunteers. Perfect for a stroll after lunch at Salute on the Beach.

Conch Republic “Oysters in Paradise”

631 Greene Street

Familiarly known the “Conch Farm” this is the perfect spot for a cold beverage while taking in the happenings at the Marina. Although the menu isn’t anything special their oysters on the half shell are incredible. Order a dozen and slurp them down while listening to the tropical sounds of one of Key West’s local performers. If you have time before perhaps watch the 4:00pm Tarpon feeding around the corner at the Galleon Marina.

Green Parrot “Killer Live Music”

601 Whitehead Street

Not far off the Duval Strip resides The Green Parrot. The place is dark, the bartenders are hairy, and the drinks are strong. Aside from being the spot where locals flock to after work, Thursday through Sunday live music ranging from Blues to Ska fills the building (circa 1890) and gets everyone in the place moving.

Mallory’s Square “World Famous Sunset Celebration”

400 Wall Street

During summer this is hands down the best place to watch the sunset. The energy is enthralling with street performers, vendors, and Cuban music filtering through the warm evening. Mallory’s Square is unique in that it is one of the only events in the US that happens every night of the year. Entertainers are sanctioned by the city and they know how to put on a show. If you are lucky you’ll catch “The Cat Man” whose entire routine is the coordinated performances of trained cats. Stop in at El Meson de Pepe before or after for an exceptional Mojito and perhaps join in with the salsa dancers.

The Porch “Local Favorite”

429 Caroline Street

The Porch is my favorite bar in Key West and the best haunted space in which to grab a brew. The bar is on the first floor of a classic Key West style house in the thick of the mayhem of Duval Street but inconspicuous enough the riff raff seem to overlook it. Pop in for a craft beer or glass of wine anytime (they are open late) and if your bartender isn’t too busy you may hear a story about the paranormal history of this local favorite.

The Dry Tortugas “Isolated History in Paradise”

If you are a fan of history and snorkeling a day trip to The Dry Tortugas will be a highlight of your trip. The National Park sits in the middle of The Gulf of Mexico approximately 70 miles from Key West and is hailed as one of the most isolated sites in the US. The fort is immense, holding the title of largest brick building in the western hemisphere. It’s hard to find better snorkeling or more dazzling blue waters. It is possible to visit the Dry Tortugas by plane but most people opt for taking the high speed ferry. If you choose option #2 bring fun friends and a deck of playing cards!

There are countless restaurants, bars, events, attractions and activities I could add to this list. If you are seeking a famous Key West sunset sail Danger Charters is the way to go. If outdoor activities strike your fancy we have great Paddle Boarding at Ibis Bay, Snorkeling is best in the waters of Fort Zachary Taylor State Park and Kayaking may lead you to discover a Manatee at Hurricane Hole. For a dip into the novelty, Key West boasts The Garden of Eden a clothing optional bar as well as Better Than Sex, a seductive dessert-only restaurant. Brunch is a joy at Azur, El Sibonay has by far the best authentic Cuban food and the marinti’s are flowing at Virgilio’s on Martini Mondays. These are just some of the things I most enjoy about this crazy little island. In conclusion: get lost, try new things, enjoy the plethora of unique restaurants and watering holes, and have a blast in paradise.