While some cruise passengers arriving in Key West may be content to browse the t-shirt shops, hit the bars and call it a day, that doesn’t make for a very romantic getaway. With a little planning, lovebirds can easily lose themselves among the waterfront cafés, shaded side streets and historic architecture.
Once you disembark the ship, leapfrog over the other passengers (which can sometimes be in the thousands) by taking a pedicab to the opposite end of Duval Street, the main drag.
Pedicabs are human-powered taxis that carry passengers in rickshaw-style carts. Knowledgeable drivers can provide an insider's tour at a leisurely pace. While the pedicab may be more expensive than a taxi, you can usually strike a deal up front for the price of the trip.
Victorian architecture of the Southernmost House — Photo courtesy of Photo by Rob O'Neal/Florida Keys News BureauStart at the Southernmost Point Buoy Marker - the number one photographed landmark in the Florida Keys.
From there, walk a block down South Street to the Southernmost House, a colorful Victorian mansion built in 1896. The three-story home is painted in a froth of pale seafoam, cream and pink with dark burgundy and acres of decorative trim. Its Queen Anne-style turret and wrap-around porches will transport you back in time.
At the corner of South and Simonton Streets, stop for a pick-me-up at the Conch and Cuban Café. Key West has rich cultural ties to Cuba, which is only 90 miles away. Step up to the window and order a colada, an espresso-style brew to share, or a café con leche, a Latin latte with steamed milk.
Back on Duval, explore the 5,000-square-foot, glass-enclosed greenhouse at the Key West Butterfly and Nature Conservatory. You'll be wowed by the 800 butterflies fluttering merrily about the bright tropical blooms and a splashing waterfall. Sneak a kiss under the Victorian gazebo, and wait for a butterfly to land on you: it’s a sign of good luck.
Waterfront dining at Louie's Backyard — Photo courtesy of Claudia MillerOnce your stomach starts growling, head a few blocks off the beaten path to Louie’s Backyard. It’s a peaceful spot for an intimate lunch outside, with breathtaking views of the Atlantic.
Indulge in the fresh island flavors of the Caribbean-American menu, such as conch fritters spiced up with a hot pepper jelly or a fresh snapper sandwich. Finish with a slice of refreshing Key lime pie with a twist - a gingersnap crust
After lunch, walk back down Duval past funky galleries and boutiques to the Rum Bar at the Speakeasy Inn. Note the white gingerbread trim on the porch, which forms bottles and playing card symbols - their way of advertising as a speakeasy during Prohibition. Have bartender Bahama Bob give you a tasting of rums from around the world and regale you with stories from the rum-running days.
Cut one block over to Whitehead Street, where you can stroll hand-in-hand under the bright orange royal Poinciana trees. Enjoy the delicate scent of the yellow frangipani flowers, and watch out for the famous free-roaming chickens.
As your day in Key West winds down, leisurely make your way down Whitehead Street towards the cruise ship. You’ll pass several historic landmarks on the way, like the Ernest Hemingway Home and Museum; the ultimate dive bar, Green Parrot; the original Pan Am office (now Kelly’s Caribbean Bar); and the Audubon House.
If at any point along your walk you find time (or energy) running short, then just call a cab. Five Sixes Taxi is a favorite because of its easy-to-remember phone number and the can’t-miss, bright pink color of its taxis.