Anytime Is A Good Time To Visit Key West
Green Parrot Bar on Whitehead Street
Key West is an island and part of the Florida Keys. Also Florida’s southernmost point, lying roughly 90 miles north of Cuba. Due to the weather and wonderful exploration of shops, bars and restaurants, it is hard to pick a bad place to stay. These are our top three places to stay while in Key West. Each one offers a way different feel of the island. Be sure to spend some time at Mallory Square, see the Truman Little White House, The Ernest Hemingway House and the Southernmost Point. Go to the top of the Lighthouse if you have time. Grab dinner at Mangia Mangia, or Conch Republic Seafood Company and of course breakfast is great at the Southernmost Beach Cafe. We also love the Green Parrot Bar for a drink anytime during the day.
The Key West Lighthouse is one of the island’s most recognizable landmarks and offers one of the best panoramic views in the Florida Keys. Built in 1848 after an earlier lighthouse was destroyed by a hurricane, it guided ships safely through the surrounding reefs for more than a century. Today, visitors can climb the 88-step spiral staircase to the top for sweeping views of Old Town Key West, the Atlantic Ocean, and the Gulf of Mexico. The adjacent Keeper’s Quarters Museum tells the stories of the lighthouse keepers, including several remarkable women who served in the role. Located directly across from the Ernest Hemingway Home, the lighthouse is an easy and worthwhile stop during any visit to Key West.
Key West Lighthouse
Dry Tortugas National Park
The Dry Tortugas National Park is one of the most unforgettable day trips from Key West, located about 70 miles west in the Gulf of Mexico. Accessible only by ferry, seaplane, or private boat, the park is home to the massive 19th-century Fort Jefferson, one of the largest brick forts ever built in the United States. Crystal-clear turquoise waters surround the islands, making them a paradise for snorkeling, swimming, birdwatching, and photography. Coral reefs teem with tropical fish, sea turtles, and vibrant marine life, while the historic fort offers fascinating insights into military history and its role as a Civil War prison. With no hotels or restaurants on the islands, visitors experience an unspoiled, peaceful destination unlike anywhere else in Florida.
The Key West Film Festival has become one of the island’s signature annual events, attracting filmmakers, actors, and movie enthusiasts from around the world. Held each fall, the festival showcases independent films, documentaries, and award-season contenders in intimate venues throughout historic Key West. Beyond screenings, attendees can enjoy filmmaker Q&A sessions, panel discussions, special events, and waterfront receptions that create a relaxed yet exciting atmosphere. The festival’s walkable setting allows visitors to experience world-class cinema while exploring the island’s vibrant restaurants, bars, galleries, and attractions. Whether you’re a dedicated film buff or simply looking for a unique reason to visit, the Key West Film Festival offers an unforgettable blend of culture, entertainment, and island charm.
The Key West Film Festival is scheduled for November 18–22, 2026.
The Key West Fantasy Fest is October 16-25, 2026.
Fantasy Fest is Key West’s most famous annual celebration, transforming the island into a vibrant costume party unlike anywhere else in the United States. Held over ten days each October, the festival features elaborate parades, themed costume contests, live music, street performances, art events, and lively parties that attract visitors from around the world. While the atmosphere is known for its creativity and playful spirit, there are also family-friendly events held earlier in the festival. The highlight is the spectacular Fantasy Fest Parade, where dazzling floats and imaginative costumes fill the streets of Old Town. Whether you participate or simply watch the festivities, Fantasy Fest delivers an unforgettable experience filled with energy, entertainment, and unmistakable Key West personality.
The Saint Hotel
The Saint Hotel in Key West is run by our good friends that run The Saint in New Orleans. This is a very sexy hotel in heart of “Old Town” Key West. There is an attention to tranquil, casual opulence. There are about 35 rooms, all designed in the signature cobalt blue and white color scheme. Great location and an elegant stay.
Ocean Key Resort & Spa
Ocean Resort overlooks the Gulf of Mexico. There is an on-site spa fitness center and fishing boats, jet skis, and glass-bottom boat tours are available. The rooms feature private balconies which is nice an you can enjoy dinner and dancing over the water at Sunset Pier or experience seafood paired with crafted cocktails at waterfront Hot Tin Roof. Mallory Square plaza is a 1 minute walk away.
Eden House Key West
Eden House will give you a taste of old Key West which dates back to 1924. If you want to try a more historical stay in the heart of real Key West residents, this may be for you. A wonderful location on Fleming Street, this will really give you a taste of living like a local.
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