Key West

At the end of scenic U.S. Route 1, past the pulsing sprawl of Miami and 43 islands connected via bridge to the mainland, you've made it to your destination—Key West. The furthest and most noteworthy Key of them all, Key West has been home to artists like Ernest Hemingway and Jimmy Buffet, President Truman's "Winter White House," and plays host to nearly 3 million visitors each year.

Hotel | 24 North Hotel
3820 N Roosevelt Blvd, Key West, FL
www.24northhotel.com

One of the first sights upon crossing the final bridge onto the island is the glistening sea blue sign for 24 North. Set at the northeastern tip of the island, the hotel is a relaxing oasis away from the hustle and bustle of Mallory Square and Duval Street. Featuring one of the best pool scenes on the island, you'll never want to leave the hotel's cozy confines. While much of your time will undoubtedly be spent soaking in those legendary Key West rays by the pool, 24 North has plenty more to offer. Here's my guide for making the most of your stay at 24 North.

Food & Drink | Duval Street

A chef-picked, four-course lesson in family-style Italian fare, handmade pastas, locally sourced meats and produce grown on premise are brought to your table on the fly, prepared using minimal seasoning to let the delicious, unique flavors of the region shine through. Oh, and there's a view.

sloppy joe's key west florida ben brewster the cuff

Visit | Hemingway House

Lunch in Positano is designed to be a tasty, efficient way to minimize your time spent away from the sun. The array of convenietnly located beachside restaurants serve up Italian basics from fresh anchovies to pizza, and Hotel Puppetto is the best of the bunch. Its pristine, cloud-white dining room overlooks Spiaggia del Fornillo while a glass-encased pizza station at the end of the dining room rolls out my favorite pie of the trip.

hemingway house key west florida ben brewster the cuff

Bike to Smathers Beach

Swing by the concierge desk and rent a bike for the roughly 20 minute pedal over to Smathers Beach. Besides working off the fried seafood, you'll also get a chance to cruise along the exceptionally beautiful palm tree lined bike path. Key West isn't naturally beachy, so sand is imported every couple years from the Bahamas—making it super soft and perfect for laying out.

smother's beach key west florida ben brewster the cuff

Sunset | Mallory Square

24 North offers a complimentary shuttle service all day long to ensure you have access to Key West's best attractions. While Hemingway's house and Duval Street's indulgences are only a few steps from the shuttle stop, make sure you don't miss sunset at Mallory Square. During golden hour each day hundreds of onlookers gather at water's edge to watch the sun set over (appropriately named) Sunset Key in an explosion of color.

More favorites:

words and photos by the cuff