Itineraries for Your Trip to Key West
2 Days in Key West for First Timers
With two days in Key West, you can relax into the pace of life in the Conch Republic. Whether you’re a lifelong sailor or a devoted landlubber, come to explore mangroves, spot native dolphins, and check out local landmarks, with time left over for island sunsets and umbrella drinks. Here’s what you need to know when planning your escape.
Snag tickets for the hop-on, hop-off bus or open-sided trolley that make the rounds of Key West to get your bearings. If you’re going to continue sightseeing in the afternoon, consider an option with all-day access, which is a convenient way to avoid driving and parking.
Tune into the parts of Key West that interest you most by choosing a guided walking tour focused on food, drinks, or history. Key West has plenty of hidden foodie hot spots, and the tree-lined streets are packed with ghost stories and colorful characters that you’ll encounter along the way.
Kick off the night with a Key West sunset; there’s always a crowd at Mallory Square, or you can board a sunset cruise to catch last light on the water. Sunset cruises in Key West range from laid-back sailing trips to parties with free-flowing drinks, so choose your boat accordingly.
Get a salt-water start with an active morning of fishing, paddling among the mangroves, or parasailing. Back on land, fuel up for an afternoon of exploring with a Key West seafood lunch followed by chilled Key lime pie.
Now that you’ve seen Key West from above water, it’s time to peek beneath the waves. Snorkeling and scuba trips feature coral reefs just off the coast—there are even scuba options for noncertified divers—or you can skip the wet hair altogether by hopping a glass-bottom boat.
Finish your Key West adventure with a taste of the local bar scene, which goes from rustic Hemingway haunts to theme bars with a rainbow of tropical drinks. Pub crawls and bar tours are a fun way to meet fellow travelers while getting a feel for the town’s colorful nightlife.
