A First-Timer’s Guide to Key West

Explore the best Key West has to offer visitors with this action-packed list. From great food to state and national parks known the world over for their stunning natural beauty and unique shopping, landmarks, and cultural attractions, you’ll fill your days with enjoyable activities that showcase the best Florida has to offer.  Discover the great reasons that this small island city in the Florida Keys remains such a popular vacation destination, year after year. 


Tour the Island Your Way


Begin your stay in Key West by booking a walking or biking tour for an overview of everything the island offers visitors. For a special view of Key West, book a sunset cruise, many of which include live music, light snacks, and an open bar. Ride the touristy yet popular Conch Tour Train; it makes several stops at some of the most well-known landmarks near Mallory Square and Duval Street. Passengers can hop on or off at any of the stops, making a convenient way to spend a little more time in places that capture your interest. Regardless of the type of tour you choose, you can expect engaging tour guides to share stories, locals’ tips about exploring Key West, and insight into local history and culture to enrich your experience. 


You can also get tickets for a fishing charter, which also allows you to take part in one of the most well-known reasons people visit Key West–the fishing–while you also get to see the city from fresh angles. The catch available changes depending on the time of year but tarpon, trout, grouper, and mackerel are common. Book with All In Fishing Charters for a great experience where all you need to bring is sunglasses and sunscreen plus your lunch if heading out for a full-day trip wreck, reef, flats or deep water fishing.


Travelers can also tour Key West independently. Like many American cities, Key West has a public transportation system of buses to help visitors and locals get around. This is also a bike-friendly community, so ask about rentals from your hotel; some hotels even offer loaner bikes without a fee.


Swimming, Snorkeling, and More


While the beaches in Key West are relatively small, they make up for it in amenities. Visitors to Fort Zachary Taylor State Park can also swim at the park’s beach. This state park, in addition to the historic tours of the fort, has biking and walking trails, fishing spots, and picnic areas to enjoy. From food and beach chairs to snorkeling gear, you could spend a whole day as the city’s own Smathers, Higgs, and South Beaches with ease. Accessible only by ferry, Dry Tortugas National Park is world-famous for its snorkeling. Here, guests can also go kayaking, birdwatching, and swimming; tours of this park’s historic fort are available, too. 


Key West Shopping and Culture


Even though Key West may not be the first place you think of when it comes to upscale and unique shopping opportunities, the boutiques and shops that dot Duval Street offer locally sourced and one-of-a-kind art, clothing and accessories, jewelry, cigars, liquors, and more. Take a break from shopping with a stop at one of the many cafes, jazz clubs, and live music venues in the area, which light up after dark. You can also find a couple of movie theaters that show first-run and classic films. Don’t miss the nightly Sunset Celebration at Mallory Square, where tourists and locals gather for an enthusiastic send-off to the day. Enjoy food vendors, street performers, boardwalk musicians, and more. Be sure to check the calendar to see what festivals may be on during your visit; Key West is home to dozens of annual events that stand out for their character, from Hemingway Days to the New Year’s Eve conch shell drop, food, and wine festivals, home and garden festivals, and more. 


Fine and Casual Dining


No matter what you enjoy eating, you’ll find it in Key West, where flavors from around the world mingle with success. For some of the best house-made pizzas in Key West, visit Duetto’s Pizza and Gelato, and of course, you can’t skip dessert. Find lobster rolls that rival any New England version at Eaton Street Seafood Market and Restaurant in Old Key West. Make sure you try the conch fritters, too. And if your fishing charter trip was a huge success and you have fish for dinner, take it to Dante’s where you can get it prepared and served family-style. Browse restaurants that showcase global tastes from Mediterranean to Spanish, French, Southern American, Chinese, Japanese, and more. And no trip to Key West would be complete without key lime pie; make it a homemade slice from Kermit’s Key West Key Lime Shoppe for the perfect sweet-tart flavor. 


Whether you choose to visit Key West for a long weekend or take a few extra days to fully explore all the island has to offer, adding these ideas to your itinerary is a great way to ensure you get a taste of the highlights. Come see why visitors to Key West rave about the activities, restaurants, shopping, and local attractions. Solo travelers, couples, and families will find there’s so much to see and do, even a week won’t feel long enough and you’ll be planning your return trip before long.