Check out the key areas of Key West, where Front Street bars lead to the waterfront and historic neighborhoods, on a flexible morning of exploring. Leaving your car parked saves you the considerable hassle of finding parking on narrow streets, and a hop-on, hop-off bus tour or trolley tour is an appealing alternative to fighting traffic. Since buses and trams are both open-sided, you can enjoy the sea breeze and snap photos of key landmarks as you cruise by.  

Some of Key West’s most memorable experiences aren’t on land at all, so it’s worth leaving the island behind for some time at sea. Once you’re on the water, you’ll see dolphins, vibrant coral reefs, and mangroves that are home to colorful birds. Checking out the natural world in Key West can be as active or as laid-back as you want, with options that include guided paddling tours, snorkeling trips, and glass-bottom cruises to the coral reefs just offshore. For something that takes in the coast with a side of adrenaline, Jet Ski tours and parasailing are gorgeous ways to get your heart racing.

Catching the sunset in Key West is one of the island’s don’t-miss experiences—and locals and visitors alike make it an excuse to celebrate another day in the islands. Book early if you’re hoping to snag a spot on one of the sunset cruises that ply the shoreline, since the most popular boats can fill up well in advance. There are lots to choose from, and options range from party boats with free-flowing cocktails to schooner cruises where you can unwind to the sound of wind and waves.