Year after year, Key West, Florida is one of the country’s top vacation spots for solo travelers, couples, families, and friends seeking a convenient and affordable get-away. If you’re wondering why, check out this short round-up of the city’s best places to go, things to do, excursions, and dining options. You’ll soon see why this tiny island in the Florida Keys offers a significantly out-sized travel experience for even the most discerning traveler.
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One-Of-A-Kind Events Year-Round
Perhaps you’ve heard of one of Key West’s most well-known events, the annual Hemingway Days that celebrate the time famed American novelist Ernest Hemingway lived here, or the popular sport fishing tournaments that draw visitors from around the world. But Key West also offers an array of theater, food, wine, and arts festivals that stand out. Each fall, Fantasy Fest in October is a sell-out event, and the “Bight” Before Christmas is a warm and delightful way to celebrate the winter holidays and get into that seasonal spirit.
Fishing tournaments are usually on-going for at least several weeks or months, so you can book a trip with All In Fishing Charters for deep water, wreck, flats or reef fishing anytime, and your entry will count. There are multiple marathons and 5K events every year, and even if you’re not a runner, cheering spectators are always welcome and genuinely appreciated by the participants and race organizers. And if your vacation somehow lands during a week with none of these special events, you can still join in the nightly Sunset Celebration at Mallory Square, where the all-ages party is popular with locals and visitors alike. Enjoy street entertainment, food trucks, arts and crafts vendors, and the most spectacular sunsets you can imagine.
Arts and Cultural Events
As with sporting and competitive events, the arts and cultural events in Key West are often annual, so they draw a real following from year to year. It’s worth asking your hotel if there are any festival-related specials when you book your accommodations. Here’s just a sample of what you can enjoy.
Tour elegantly appointed local homes and gardens as part of walking tours of the city during showcase-of-homes events like the annual Key West Home Tours. Not only will you get to see magazine-perfect decor and landscaping, but you’ll also learn so much about the history of Key West and its people.
Explore the culinary delights of local restaurants at the Key West Food and Wine Festival. Activities often include such hands-on tasks as making your own key lime pies, and there are usually multiple food and wine pairings presented by local chefs that you can sign up for.
Each fall, the Key West Film Festival showcases notable films that are recognized for their creativity, diversity, and beauty. Festival events include meet-and-greet programs with the films’ cast and crew members, and you can also participate in special screenings, parties, and similar entertainments.
Sporting Events and Festivals
The low humidity and comfortable temperatures of January in Key West make it an ideal location for the city’s annual New Year’s half-marathon and 5K. Races of all kinds are run throughout the year, including the famous Hemingway Sunset 5K where Papa’s look-alikes make the event even more exciting.
If fishing is more your sport, consider the Redbone Celebrity Tournament Series, the Southernmost Light Tackle Anglers Masters (SLAM) event, and the Key West Fishing Tournament. Tournaments typically offer more than one sport fishing and recreational fishing category, so there’s a way for everyone to compete, even if you’re not a professional angler. Most are catch-and-release tournaments, and many are open to entries for several months so that even fishing charter guests like those of All In Fishing Charters can participate.
For visitors who’d rather soothe their bodies and souls, the Key West Yoga and Wellness Festival showcases yoga and wellness workshops and classes, a dedicated marketplace, spa treatments, informational programs, and educational events.
Family Fun for All
Ocean Fest features touch tanks for kids, community art projects, and fishing clinics for all ages. The Mote Marine Lab at the NOAA Florida Keys Eco-Discovery Center and Truman Waterfront hosts this annual event. Families also enjoy live music and performers, plus foods, arts and crafts, and activities. Other popular family festivals include the annual Key West Mermaid Festival and the Papio Kinetic Sculpture Parade.
Peaceful Beaches and Parks
With multiple local public beaches plus Fort Zachary Taylor State Park in Key West, you can make any day a beach day. Try snorkeling, swimming, picnicking, historic tours, hiking and biking on dedicated trails, and fishing off of area jetties. When you’re getting a food takeout order, such as the famous lobster rolls from Eaton Street Seafood Market and Restaurant, take it to one of the nearby parks or beaches for a convenient, casual lunch or dinner.
Key West has it all when it comes to things to do, and the year-round slate of events, from tournaments to festivals, welcomes everyone, so there’s no need to be shy if you’d like to try something new. Compare your itinerary and travel dates with a local events calendar so you can join in all the fun to be had in this jewel of the Florida Keys.
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