
Photo courtesy of the Perry Hotel and Marina
Stock Island doesn’t exactly feel like its raucous neighbor. Where Key West’s atmosphere bears more than a passing resemblance to Las Vegas (ahem, Duval Street), Stock Island, which lies just 10-odd minutes east of Key West and is named for the livestock that used to roam the island, channels calmer, more subdued vibes.
The same could be said of the Perry Hotel and Marina. Located on the southern end of Stock Island, just five miles east of Key West’s Old Town, the 100-room hotel is the product of its environment in more than one sense. Although the Perry has a decidedly upscale aesthetic, take a closer look and you’ll find nods to the boat builders, craftsmen, and mechanics who’ve long called the area home: reclaimed boat wood in the lobby, thick fishing line over the banquettes in the in-house restaurant, exposed steel and concrete throughout.

Photo courtesy of the Perry Hotel and Marina
Still, one can’t talk about the Perry without mentioning the waters of the Gulf of Mexico and Atlantic Ocean lapping just outside its doors. Not only does that proximity to the water make for some very fresh fare—the menu at Matt’s Stock Island Kitchen & Bar brims with fresh yellowtail snapper, shrimp, oysters, and more—the 278-slip marina located just past the pool makes for easy access to a host of maritime activities. This means you can start your day with a deep-sea fishing expedition, end it with a sunset cruise, and still make it back to Duval for some late-night revelry (or, y’know, head straight to bed).