Chesapeake Resort

One-third down the Florida Keys is Islamorada, known as the sport-fishing capital of the world and home to the Chesapeake, a 65-room property that has grown from an old-school seaside motel into a resort that caters to anglers and families. Two separate charter boat outfits on the property can arrange for a full or half-day outing. Or you can book a package through the resort that includes a room, fishing, and a voucher for a nearby restaurant where the chef will cook up your catch.