Getting out on the water at least once is a must in Key West, and there's no better time than sunset, when you can escape the crowds at Mallory Square for your own private sailboat. Your experience starts at Key West Historic Seaport, where you'll board the Java Cat and get out on the open sea.
As you leave the port, look back at Mallory Square's street performers and other Sunset Celebration artists, and pass by the Navy Mole and Fort Zachary Taylor. Look for marine life such as turtles, dolphins, and jumping fish, and watch frigate birds, pelicans, and ospreys flying and hunting for dinner. On board the boat, you can sit on the aft deck under the shaded top or stretch out on the trampolines. When the sun sets, savor the moment before heading back to the seaport, where your tour ends.