On your way down to the Florida Keys, make your first stop at Islamorada (at Mile Marker 88, if you're driving that luxe convertible!), most notably at the newly refurbished Amara Cay Resort. This is a delightful place to break your journey if you’re headed to Key West, since it’s almost halfway. Forget the shell-ridden Florida kitsch of the many roadside motels you’ll pass along the way.
Amara Cay Resort is upscale, contemporary, and has been completely renovated sparing no expense. Many suites feature their own living areas, with big-screen TVs and balconies that offer pool or ocean views. The resort is spacious and boasts its own palm-fringed waterfront. Laze on a lounge chair and watch the pelicans frolic—or frolic yourself in the huge pool. Enjoy a tropical cocktail at Sparrow’s Rum Bar, poolside, and for lunch sup on Florida favorites such as fresh fish tacos, grilled jumbo shrimp, and Key lime pie. In season, an outdoor massage is also available.
This resort has it all, but it’s fun to take the complimentary Mercedes-Benz Sprinter to nearby Pelican Cove, which has a private beach and floating dive platform; the use of the facilities and amenities such as paddle boards and peddle boats is included in the Amara Cay resort fee. At sunset, cocktails at Pierre’s at Morada Bay across the highway is a must. There, you’ll see locals and visitors alike converging to witness the stunning sunsets across the Gulf. It’s tempting to stay on for dinner, but you really should head back to Amara Cay Resort’s Oltremare, a fine-dining restaurant with a hip vibe, lively atmosphere, friendly and knowledgeable staff, and trendy cocktails, too. The food here is delicious and the menu has been created with great care by Chef Dario: fresh local seafood with a Mediterranean twist, but also flatbreads, pastas, braised short ribs, duck breast, and Veal Saltimbocca. It’s also the place to tuck into the deluxe and freshly prepared breakfast before you check out and head on your way.