Best Ways to Spend a Weekend in Key West

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Sometimes, a short weekend getaway is just what you need. After all, life can be stressful and it’s not always enough to have a staycation: you want to go someplace fun and take your mind off of the day to day. Key West is the perfect place to do that. The weather is warm and sunny nearly every day, the people are friendly, and there is so much to see and do! Check out this itinerary for great ideas on how to spend a weekend in Key West, including great places to eat and shop.

Day One: Welcome to Key West

Key West is wonderful for so many reasons but perhaps none is better than the amazing mix of cultures that can be best found in the food here. Kick your weekend off right with the savory and sweet dishes at La Creperie French Cafe. The patio seating is the perfect place to relax and linger over fresh coffee, too. In addition to crepes, the menu features salads, omelets, croque monsieur, and club sandwiches, and if you’re brunching, homemade sangria.

 After breakfast, it’s time to hit the beach. There are four public beaches on Key West, and while they may be smaller than you are accustomed to, they are no less beautiful. Sandy beaches are edged with the familiar tall palms of South Florida, and gentle waves lap at the shore. The clear waters are great for swimming and snorkeling, too. If you haven’t brought gear of your own, many of the beaches have concession stands where you can rent snorkeling gear, as well as beach chairs and umbrellas for a little shade.  

In Old Town Key West, visit Eaton Street Seafood Market and Restaurant for lunch. You can take your meal to go or enjoy outdoor seating. They get freshly caught seafood daily and prepare every dish to order, served alongside their famous house-made sauces. Among the most popular dishes are the crab cake sandwiches, grilled lobster rolls, and fish tacos. For those who don’t favor fish, there are chicken tenders on the menu, too. You’ll love the art deco architecture of classic South Florida as well as the friendly service and great food.

 After lunch, work off those calories by climbing the Key West Lighthouse. What was once a working lighthouse is now a museum and you can take the 88 steps to the top for a panoramic view of the water, where the original essential workers kept ships’ captains from disaster and shipwreck. Just next door is the lighthouse keepers’ quarters, today a museum where you can see just how the lighthouse keepers lived, including the challenges of the job and the seriousness of doing it well.

 Since you’ve spent the day swimming and climbing lighthouses, go easy with dinner at Sloppy Joe’s Bar or DJ’s Clam Shack, two well-known and popular casual dining restaurants. The menu features seafood favorites and a laid-back ambiance that’s perfect to end a day of fun. Afterward, visit Mallory Square in time to see the sun go down. You’ll be there for the nightly Sunset Celebration, where live music, street performers, vendors, and more make it a real party. Plus, it’s the ideal spot for sunset photos!

Day Two: Land and Sea

Most people know that Key West is tops for fishing, but not everyone realizes that anyone can fish here. When you book a fishing charter with All In Fishing Charters, guests of all experience levels are welcome, not just the experts. What makes it so fun is that everything you need is provided, from gear to basic fishing tips.

 Once you’re back on land, visit Duval Street and window shop or pick up something special for yourself. This is where you’ll find the most unique shops, galleries, and boutiques selling clothes, jewelry, art, housewares, and gifts. Have a cold drink at a bar or an ice cream cone, or try a slice of key lime pie to keep you going. Some hotels also offer bike rentals as part of their amenities, so consider biking up and down Duval Street, too.

 Have a wonderful last-night-in-Key-West dinner at Grand Cafe. It’s located in a Victorian mansion on Duval Street, and its elegance is unsurpassed. The Chef’s Tasting Plate is the way to go, which includes shrimp, lobster, and filet mignon. Afterward, drop into the Little Room Jazz Club for a drink and live music, and make your vacation last just a little longer.

 After you head home, you’ll always remember the great weekend you spent in Key West, and you’ll probably be eager to come back soon. There is something about the soft breezes, gentle sunshine, and welcoming atmosphere that feels like home for many people. It’s the weekend vacation spot you can return to again and again.