First-time guide to Key West

Estimated reading time: 3 minutes

Top tips and recommendations for those visiting Key West for the first time

Located at the southernmost tip of the Florida Keys, Key West has a little something for everyone. I found myself in Key West for the first time at my bachelorette party and was not disappointed. Between the sandy beaches, myriad of dining options, and trendy night clubs, I was in heaven. I’ve listed below a few of my favorite Key West experiences as a first-time guest. 


Let’s just acknowledge the elephant in the room. Key West does have some darn good key lime pie. While there are ubiquitous shops claiming that they have the best key lime pie on the island, the top two contenders according to locals and regular visitors are Kermit’s Key Lime Pie and Key West Key Lime Pie Company (Kermit’s seemed a little more tart, while the latter was a touch sweeter). Nearby, local Mexican restaurant, Amigos Tortilla Bar, not only serves up delicious food made with their special molcajetes, but they also offer their guests the chance to sample a half slice of each famed pie. Try a slice covered in chocolate and cast your vote on which one reigns supreme.

Famed key lime pie from Kermit’s

If you’re looking for a unique dining experience that won’t break the bank, check out Mam’s Best Food, located off of Petronia Street. This unassuming shack offers some of the best kosher food around. My favorite menu item was the falafel sandwich that came on a chewy toasted baguette that rivaled the loaves I’ve had in Paris. Carb perfection aside, the hummus is to die for, and the rest of the menu is continued excellence. The best part about the eatery is charismatic Mam herself. You can find her taking orders, preparing the food, and making sure her patrons finish their plates. Trust me, there’s no wasting in Mam’s house.

Another Key West treat is the famed Conch Fritters. I don’t even like seafood but these crispy fried balls of goodness are right up my alley. Meaty conch is mixed with onions, garlic, and an array spices, then deep-fried until golden brown and served to you piping hot. Be sure to get your order with a drizzle of the creamy key lime sauce – a perfect blend of sweet and savory.


Watering holes can be found around every corner on Duval Street, but there are a few that serve up some history with their poison. Captain Tony’s Saloon is a hotspot that holds claim as not only Key West’s oldest bar, but is also rumored to be haunted. Captain Tony’s centerpiece, a large tree rooted in the middle of the bar, is said to be the town’s old hanging tree, where over 75 crooks and criminals met their fate. The curiosity needs not end there as the hundreds of bras dangling from the ceiling are sure to capture your attention. Grab the house special, a pirate’s punch, and come up with your own theories about this local haunt.

Viewfinder Tip: If you like the atmosphere but prefer a more PG setting, the first two levels underneath the Garden of Eden are for clothed patrons only. 

Not to be outdone, the cleverly named Garden of Eden bar offers its patrons a unique, if not brazen, drinking experience. Located on the roof of the Bull and Whistle, this clothing-optional bar is for the extremely liberated. Leave your inhibitions (and cameras) at the door as you step onto the breezy rooftop terrace. Little is left to the imagination as guests to the garden wear as little as they like. If you’re not sure about baring it all, some nights a body painter can be found on site. Just bear in mind that what is seen cannot be unseen.


The best piece of advice I can give to anyone visiting Key West is to rent a bike. We rented ours from the Silver Palms Inn at a bargain rate of under $25 a day. With our new found freedom we took to the streets of Key West and left no nook or cranny undiscovered.

Cycling around the town

We cycled our way to the southernmost point of the continental U.S., made a stop at the Hemmingway House, took a break from our jaunt by eating a few chocolate-covered key lime pies, and then pedaled our way to our favorite beach located inside Fort Zachary Taylor State Park.

If you want to take your adventures off land, I highly recommend any of the sailing adventures found along the pier. There are cruises to fit every desire, although the two that caught my eye were the sunset champagne sail and the snorkel sail excursion. Be advised that unruly weather can call for choppy seas and a rather unpleasant time on the water. Check the weather reports to see which days would be best for you. 

Regardless of who you take with you to Key West, a good time is sure to be had. My advice is to stuff yourself silly with as many conch fritters and key lime pies as possible. A little bike ride around town is sure to burn off those extra calories and have you exploring the subtle intricacies that beckon Key West’s visitors to return time and time again.

Where’s your favorite destination to visit with friends?

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Captain And Clark

Chris Staudinger and Tawny Clark (also known as "Captain and Clark") have spent the majority of their relationship exploring this great big world. After meeting on Kilimanjaro, courting in South Korea, getting engaged at the Taj Mahal, and sealing the deal in the Cascade Mountains, the two decided it was time to add another explorer to the mix. Traveling the world with kiddo-in-tow might alter the way they navigate the globe, but they welcome the challenge with open suitcases.

Chris and Tawny have had articles and videos published on USA TODAY TRAVEL, BBC Travel, Matador Network, as well as appeared as guest stars on TLC Asia's Fun Taiwan television series. When not on the road, you can find Chris and Tawny nestled in their home in Tacoma, Washington fueling up on coffee and cat cuddles while planning their future adventures. You can follow their travels on their blog, Instagram, and YouTube

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