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—24 North Hotel 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. 



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. 

Hotel  |  24 North Hotel
3820 N Roosevelt Blvd, Key West, FL



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.

Drink  |  Duval Street



Suffice it to say Positano is not the kind of place you vacation if you're looking for a cheap weekend getaway. While accommodations skew toward the extravagant, both in comfort and in cost, there are still options for travelers on a budget. Enter Casa Celeste. A true matriachal Italian household, responsibility trickles down the family ladder as Celeste delegates responsibility for the Inn between her son and grandchildren. Each morning she serves breakfast on a cloud-like terrace overlooking the waking town, and from her front door, a zig-zagging stairway leads you on a 10-minute descent toward Spiaggia del Fornillo. At the chairs on the small balcony a few steps from your bed lies the perfect vantage point to revel in Positano’s cascading silhouette as it plunges calmly toward the misty sea. Casa Celeste is close enough to the center of town to easily enjoy its perks, but far enough away to feel like a local.  

Coffee  |  Cuban Coffee Queen




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.  

Site  |  Hemingway House




Likely the first part of Positano you'll stumble upon before wearily finding your hotel, Positano Centro is home to the vast majority of the restaurants and shops in town. Pass under the arborway of purple flowers and poke around the warren of alleys leading toward Spiaggia Grande. Between the art galleries, boutiques and small mercatos, you never know what treasure you might dig up.

Bar  |  Sloppy Joe's




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. 

Beach  |  Smathers Beach




While most of town is quiet after dark, Le Sirenuse, which seems to have been plucked straight from the set of a Wes Anderson film, with its spiraling staircases, ornate decor and vibrant color scheme, keeps late night cocktail cravers satiated with a decadent champagne and oyster menu and, from its perch above Spiaggia Grande, some of the best views in Positano.

Seafood  |  Clam Shack




The Path of the Gods takes at least half a day to complete, but the soaring views from this ancient Mediterranean highway, running atop the jagged Amalfi coastline, can't be beat.

Restaurant |  Italian




Don't just walk by. Pop into Positano’s iconic golden dome. You'll get some historical perspective and plenty of world class photo ops.

Bike  |  highway




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. 

Sunset  |  Mallory Square




Positano underscores the breadth of Europe's vibrant nightlife, showing even a  small coastal town won't pass up the opportunity to install strobe lights and a dance floor, even if it means carving them into their iconic Amalfi cliffs.

Disco |  Music on the Rocks
Via Grotte dell'Incanto, 51


More favorites:

Restaurant | Chez Black | Via del Brigantino, 19 |
Hotel | La Casa di Peppe | Via Fornillo, 24 |
Beach Bar | Da Ferdinando Bar Bagni |
Restaurant | Da Adolfo | Via Laurito, 40 |
Beach | Spiaggia Grande | Via Marina Grande
Pizza | Il Fornillo | Via Pasitea, 266 |
Beach | Bagni d'Arienzo | Via Arienzo, 16 |
Restaurant | Saraceno d'Oro | Viale Pasitea, 254 |