Have you ever read the “New York Times” Travel Section feature “36 Hours In…” when planning a vacation? I love it! The articles make for such a practical way to get a snap shot of a city before you get there. I even enjoy reading them once I’ve returned from traveling to compare and contrast my experience with the article. While the “New York Times” covered Key West in 2007 and 2011, I’ve also enjoyed mimicking their style in various travel articles. So why don’t we give it a try on the Fury Girl Blog? But instead of 36 hours in Key West, let’s distill it down to two days.
If you’ve only got a weekend to explore paradise, you’ll be surprised at how much ground you can cover on the island of Key West in two days. Let’s get started!
Morning Start by renting bicycles in Old Town at either Eaton Street Bikes or Island Bicycles. Consult a map, but don’t worry too much about staying on course. After all, we’re only two by four miles wide and you’ll know you’ve gone too far when you hit the water! A general boundary to maintain would be to stay on the southwest side of Truman Avenue and White Street. Then, feel free to get lost in our tangle of charming side streets with bright, tropical bougainvillea blossoming, palm trees, and pastel conch cottages. It’s a fun way to get the lay of the land without a traditional tour. Some points of interest include the Key West Cemetery, the Historic Seaport, Mallory Square, and Truman Annex.
Make a breakfast pit stop for cafe con leches, smoothies, and Cuban pressed sandwiches at the Cuban Coffee Queen for a bit of local color.
Afternoon In my opinion, you can’t spend too much time in Key West without getting out on the water. For your first day, opt for a trip that won’t take up too much of your time. Take your pick between an hour-long parasailing adventure or a 90 minute jet ski tour around the island, whichever sounds more fun to you!
For lunch, head towards Caroline Street near the Historic Seaport for a fried fish sandwich at B.O.’s fish wagon. Delicious!
Evening Head to Mallory Square for the famous Sunset Celebration, followed by the classic Duval Crawl. Start at Sloppy Joe’s and Captain Tony’s and work your way up. Spots not to be missed include Fogarty’s, The Porch, and the Green Parrot. But see for yourself. You never quite know what you’ll find on Duval Street!
For a casual dinner with big portions and a fun atmosphere, Caroline’s is a longtime local’s favorite. For something a little more sophisticated and off-the-beaten-path, small plates at Santiago’s never disappoints.
Morning Hit up brunch at the legendary Blue Heaven for lobster benedicts or the rooster special and bloody mary’s or mimosas to wash it down with. The expansive backyard setting is colorful, quirky, and totally Key West.
Afternoon Make a pit stop at Besame Mucho just up the street from Blue Heaven and peruse this adorable boutique with one-of-a-kind jewelry, deliciously scented candles, and home goods. Your destination is the Hemingway House on Whitehead Street where the author lived during most of the 1930s and wrote many of his award-winning novels. Take the guided tour for a glimpse into the life of this great American author and one of the original Key West characters. No Key West weekend getaway would be complete without learning some history about one of the most influential people in Key West’s heritage.
Evening Hurry to the Historic Seaport because you don’t want to miss the 3:30pm departure of the Island Adventure. This is one of our newest trips at Fury and summer is the perfect time to experience it! If you’re accustomed to our 65′ catamarans, this is a much more intimate trip. Step aboard the Cruzan Cat with no more than about 30 passengers. Experience snorkeling at the reef, kayaking through the mangroves, and simply relaxing on a sandbar beach in the middle of the Gulf of Mexico with a cooler full of Coronas. It’s such a great addition to our menu of options at Fury. And the best part about our evening trip is that it concludes with a sunset cruise back to the marina. We’ll serve Cuban sandwiches, chips, beer, and sodas to keep you satisfied.
Still hungry once you’re back in port? The Conch Seafood Republic is located right where the trip departs and makes for a perfect dinner overlooking the marina.
So there you have it, my guide on how to do Key West in two days. What do you think? If you’ve visited us before, would you add or subtract anything to the list? Feel free to comment below or on Facebook and Twitter. Hope to see you in Key West soon!
Shayne Benowitz is a Fury crew member and freelance writer. Email her at email@example.com, and follow the fun on Twitter @FuryKeyWest and @ShayneBenowitz.