While a half day in Key West will only give you a taste of what the island has to offer, the City View Trolley is a great way to maximize your limited time on the island. They have eight stops, and their hop-on/hop-off format makes for a more flexible experience.
City View Trolley — Photo courtesy of City View Trolley Find one of their open-air trolleys at the depot near the cruise docks, located at Whitehead and Front Streets, across from the Custom House. Settle in and listen to the knowledgeable tour guide give you a brief history of Key West as you pass notable attractions like the Audubon House, Oldest House Museum, San Carlos Theatre and the Key West Cemetery.
At the fourth stop, get off at Higgs Beach, where you can walk the long, concrete White Street Pier for stunning views of the ocean. You’ll also find the Key West AIDS Memorial, as well as the African Cemetery where victims of the Transatlantic slave trade are buried.
Walk over to the Key West Garden Club at the West Martello Tower, where a tropical oasis awaits amid a Civil War-era fort. Their collection of native and exotic trees and flowers - including orchids and bromeliads - is nestled between the crumbling red brick arches. Explore the tunnel under the roots of a massive banyan tree, while splashing sounds of waterfalls echo in the air.
Key West Garden Club at the West Martello Tower — Photo courtesy of Mangrove Mike The plants are all labeled, but friendly volunteers are on-hand to answer any questions you might have. Bonus: It’s free. Watch your time, as the trolleys run every 30 minutes, and it’s easy to lose track of reality in this peaceful hideaway.
Once you're at the sixth trolley stop, you can explore the Ernest Hemingway Home and Museum, where the larger-than-life author lived and wrote during the 1930s. Entertaining tour guides will take you through the two-story house and recount the exploits and adventures of “Papa.”
Over 50 polydactyl (six-toed) cats have the run of the property, and you’ll even find them lounging on display cases and antiques. And don’t miss the urinal from the original Sloppy Joe’s that Hemingway brought home; his wife gamely turned it into a fountain.
If you're feeling energetic, you can climb the 88 winding steps to the top of Key West Lighthouse across the street.
The next trolley stop will be the Key West Bight Marina, where you can lunch on fresh seafood at the Half Shell Raw Bar, while watching the boats cruise through the historic seaport. The open-air restaurant has an informal, old Key West feel, with license plates as the main decor.
Freshly shucked oysters at Half Shell Raw Bar — Photo courtesy of Half Shell Raw Bar Grab a picnic table and dig into some peel-and-eat Key West pink shrimp, conch fritters, steamed middleneck clams, conch ceviche, fish and chips and stone crabs (a seasonal dish) paired with ice cold beer.
After lunch, walk along the harbor past Turtle Kraals, Schooner Warf and on to Kermit’s Key Lime Shoppe for dessert. You can’t beat their Key lime pie on a stick, and you can stock up on souvenirs like Key lime candy, cookies, jelly and sauces.