Islamorada is a fisherman’s paradise. Situated between Florida Bay and the Atlantic, the waters of the Florida Straits stretch and creep into the mangroves, creating hidden pools and secluded flats perfect for casting for bonefish, snook, tarpon and redfish. About 10 to 20 miles offshore, the waters deepen and take on the azure hue of the Gulf Stream, and depending on the season, teems with sailfish and marlin, kingfish and wahoo. There’s a good reason it’s known as the sport fishing capital of the world.
We’ve been coming to Islamorada for as long as we can remember. When we started vineyard vines, this is where we took our crew for our first company outings. The people are salty, the sunsets are great, the fish never stop biting and the drinks are cold—what else could you want? Check out our insider’s guide before you plan your next trip.
Lorelei Restaurant
We first discovered the Lorelei during Shep’s bachelor party back in 1999. And while most of that trip was (and still is) a little blurry, we knew that this was a place we’d keep coming back to. Even after all these years, it’s still our favorite spot to go after a day on the water to catch up with friends, enjoy a cocktail and some live music while taking in the sunset as locals and tourists congregate around a high-top table known as “Town Hall.” The drink of choice is always a frozen rum runner (for us, at least). And if aloe vera isn’t cutting it, a 151 floater will definitely take the sting out of your sun-kissed skin. Learn more.
Sandy Moret
Within the fly fishing community, Sandy is held with a reverence typically reserved for the likes of Tiger Woods or Tom Brady—and for good reason: he’s been throwing flies in the Keys, and around the world, for more than 40 years. We’ve known Sandy since we first started coming to Islamorada years ago, and no trip to Islamorada is complete without a visit to his shop, Florida Keys Outfitters. Whenever we get out on the water with him, we end up learning as much about life as we do throwing flies. Read more.
