With its distinctive red sails flying high each evening as the sun goes down, it's no wonder that the Schooner Jolly Rover II is the most photographed ship in Key West. The captain and crew encourage you to play pirate on the classic 80-foot coastal topsail ship and tell the tales of scallywags, rum runners and privateers. They'll even let you take a turn at the wheel or help hoist the sails. While they only serve water, guests are encouraged to bring their drink of choice and perhaps a light picnic. As the wind fills the sails and you soar around Key West, you'll see sights like Fort Zachary Taylor, the Harry S. Truman Little White House and glamorous Sunset Key. When they fire the cannon at sunset, it's a blast. Find them docked in the Historic Seaport just outside The Conch Republic Seafood Restaurant.