Key West: The Southernmost Sneak Away

With its rich history and quirky charm, the Conch Republic beckons to those in search of an island vacation鈥攐ne that will transport them to the southernmost tip of the country without having to travel too far from home.

Miles from Naples: 248

The Florida Keys - Florida Road Trip Destinations

Why Go: While Key West has a reputation for attracting visitors prone to overindulgent revelry, rest assured there are many sides to this old town, and they have plenty to offer vacationers beyond the bars on Duval Street.

Danger Charters - Key West Sailing Charters - Road Trip Destinations

Come Sail Away: Explore Key West鈥檚 coastline on a catamaran or schooner sailing tour at Sebago, or sign up for a guided snorkel, kayak, or sail trip with Danger Charters (above).

Rum Barrels at Chef Distilled, Key West's First Legal Rum Distillery

Chef Distilled rum barrels

Top Attractions: Foodies and spirits connoisseurs will marvel at the unique process used to create the delicious rums at Chef Distilled, Key West鈥檚 first legal rum distillery. Owner Paul Menta spent decades as a chef and approaches his rum creations in a similar fashion. Our fave: Vanilla Br没l茅e rum. Be sure to schedule a tour of the quaint facility. Literature buffs will also get their fill at the Ernest Hemingway Home and Museum (below), where tours of the iconic novelist鈥檚 residence include the famous six-toed cats that still roam the grounds.

Ernest Hemingway Home & Museum - Key West Road Trip Destinations

The Hemingway House | Photo by Rob O鈥橬eal Photography

Where to Eat: With nature鈥檚 stunning backdrop, there are many options for dining alfresco. Our picks are both in Victorian homes: Reserve a table at Nine One Five (below), a magnificent restaurant and wine bar in the heart of Old Town. (Don鈥檛 miss the melt-in-your-mouth braised pork tacos.) Another culinary favorite and popular spot, Louie鈥檚 Backyard, offers an oceanfront view.

Nine One Five Restaurant

Nine One Five | Photo by Meghan E. Capozzi

Worth the Indulgence: Take a morning stroll down Eaton Street to satisfy the proverbial sweet tooth. At Glazed Donuts (below), the delectable oversized delicacies resemble works of sweet art, while Old Town Bakery is a long-held local favorite for its homemade pastries.

Glazed Donuts Key West

Treats from Glazed Donuts | Photo by Nick Doll Photography

Where to Sleep: The Gates Hotel (below), a new boutique property with a minimalist flair, is a 15-minute drive from Old Town and offers an intimate escape from the hustle and bustle. The hotel also touts pet-friendly amenities, including a welcome BarkBox of treats, a guide to pet-friendly spots, and dog-walking services available upon request. For those who prefer to be within walking distance of the town鈥檚 boisterous crowds, consider Waldorf-Astoria luxury properties Casa Marina and The Reach, which also offer access to Key West鈥檚 largest private beach.

suite at the Gates Hotel - Key West

Suite at the Gates Hotel

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