What's the best way to explore the subtropical island of Key West? Walking, bike and trolley tours offer a number of options — house and garden, pub crawls, culinary and tasting, Florida Keys architecture and even ghost tours led by (what else?) a “ghost host.” Whatever you choose, our gay-friendly island paradise awaits your discovery.
With a unique history as the home of world-renowned authors, and a natural beauty that has inspired generations of artists, the Florida Keys feature cultural offerings that can’t be found anywhere else. And that means you can find a wide range of “only in the Keys” experiences along the island chain this winter and spring — so start exploring!
The siren song of the subtropical Florida Keys can be almost impossible to resist, particularly when winter has much of the world in its chilly grip. The island chain is rich in ways to indulge body, mind and tastebuds while recharging your batteries ... and sparking lasting memories and smiles that just don’t stop.
Trade the winter blahs for the salt air, sweet breezes, and blue sky and water of Key West. Slip away to the southernmost outpost in the continental U.S. to savor the subtropical warmth and irresistibly laid-back vibe.
Karly Venezia, director of sales and marketing at Islamorada’s iconic 22-acre Islander Resort, has spent more than half her life working for resorts in Key West and Islamorada. She also has an unusual paddleboarding companion: her Rhode Island Red chicken, Loretta, whose on-the-water exploits created a social media sensation.
You can reach the Florida Keys via land, air, and sea. First-time travelers should experience the drive through the island chain at least once -- because the 127-mile road trip from mainland Florida to Key West via the Overseas Highway, featuring 42 bridges over blue water, is absolutely breathtaking.
Santa does things a little differently in the holiday-loving Florida Keys -- and he even brings some Keys warmth and cheer to people who can't spend the season in the subtropical island chain. Unless you're on the naughty list, you might just get a visit from jolly old Santa Keys this year!
At noon on New Year's Eve, don't miss the annual Key West Dachshund Walk -- a short stroll for long dogs that has become a beloved holiday tradition. Last year the wacky walk drew nearly 200 dachshunds, many of them sporting whimsical costumes or accessories as they trotted around Key West’s historic downtown area.
Celebrate New Year's Eve in Key West by watching beloved drag queen Sushi, perched in a super-sized red high-heel shoe, "drop" to famed Duval Street in a wacky takeoff on the Times Square ball drop. The Key West event marks its 20th anniversary this year -- and features celebrity guest host Austin Armacost, best known for Logo TV’s “The A-List.”
Despite the Florida Keys' subtropical climate, residents tend to go a little overboard with holiday decorations (for example, an inflatable 10-foot-tall reindeer perched atop a small houseboat!) and throw themselves gleefully into extended merrymaking. In fact, from Key Largo to Key West, the December calendar is packed with events designed to spread seasonal cheer.