Key West Day Tripping: 10 Activities and 12 Places to Eat and Drink
By Britt Myers
It is no secret that one of the most alluring draws to the Southernmost City is the island’s world famous bar scene. With more than 350 options to choose from, it would almost be impossible for anyone (and their liver) to visit every bar in a single day. For the day tripper, we recommend a simple bar crawl along the Historic Seaport and surrounding area.
Begin your day at Two Friends Patio—a staple on the island since 1967, the historic locale is located along Front Street in the heart of Key West. The bar is legendary, serving as one of Johnny Carson’s favorite hangouts when he visited and it is the same bar where Mel Fisher received his first two chests of gold from the Atocha. In fact, legend suggests that Mel sat the gold atop of the bar for approximately two hours as the celebration commenced. We recommend you begin with their famed Bloody Mary, complete with edible garnishes and topped off with pickled green beans. And the breakfast at Two Friends is one of the best, so you can prepare your day of bar crawling equipped with a full tummy.
Just across the street from Two Friends Patio is the Chart Room Bar, located in the historic Pier House Resort. In fact, the bar was so popular with locals; the resort actually built around the quaint watering hole and included it in the master plans. This is the first bar that Jimmy Buffett visited when he arrived in Key West in the early ’70s. The bar is filled with island memorabilia and the drinks here are great.
From the Chart Room, take a few steps towards Simonton and take a left. When the pavement turns into white sand, you will know that you have arrived at Lagerheads Beach Bar & Water Sports. This newly renovated fish shack and bar has revitalized what was once known to locals as Simonton Beach. This local secret offers draft beer, frozen drinks and fresh seafood, all of which can be enjoyed on the white sand and lounge chairs—so be sure to pack your sunscreen and bathing suits.
For happy hour, you will want to begin a tour along the Historic Seaport. The Tower Bar at Turtle Kraals provides a second story view of the bustling harbor as the day’s fresh catch and boating adventures return to port. Along with one of the best backdrops in the city, Turtle Kraals offers an incredible happy hour. Enjoy half off well drinks, domestic beers and house wines, along with an assortment of affordable food specials to keep your body equipped for the next stop.
No Key West bar crawl is complete without a mojito. As you wind around the seaport and make your way to Mallory Square, be sure to stop by El Meson de Pepe for one of the best mojitos on earth. The outside bar of the Cayo Hueso y Habana building embodies the rich history between Cuba and Key West and their mojito is the perfect way to prepare for sunset—complete with live Salsa music and dancing.
A Key West sunset is the perfect way to wrap up any bar crawl. Located at Ocean Key Resort and Spa, the Sunset Pier is the ideal location for waterfront libations and offers premier seating for all of the sunset celebrations. Known for their live music and nightly entertainment, bar crawlers can indulge in night cap of dancing or simply relax in the southern breeze that flows over the pier.
(Note: The Keys Weekly highly recommends that any day tripper planning a bar crawl in Key West consider a designated driver or a room for the evening. Two ideal locations to spend the night are the Pier House Resort or Ocean Key Resort & Spa).