Go to the Globe and Mail homepage

Jump to main navigationJump to main content

A gingerbread mansion in the residential neighbourhood of Key West's upper Duval street area (Wallace Immen/The Globe and Mail/Wallace Immen/The Globe and Mail)
A gingerbread mansion in the residential neighbourhood of Key West's upper Duval street area (Wallace Immen/The Globe and Mail/Wallace Immen/The Globe and Mail)

Say so long to Margaritaville in Key West Add to ...

It's 5 o'clock somewhere, but in Key West, it's 8 a.m. And for the "breakfast club" at the Schooner Wharf Bar, that means it's already happy hour.

At the open-air bar on this southernmost island in the United States, the guy next to me is already hard at work finishing off a bloody mary so he can move on to a beer chaser. Two entertainers from one of the local drag shows are sharing makeup tips and a couple of roosters are staging a noisy impromptu fight. Meanwhile, throngs of passengers off a newly arrived cruise ship are snapping photos of lewd T-shirts that adorn the windows of shops on lower Duval Street, which is to Key West what Bourbon Street is to New Orleans.

That's exactly what you'd expect from a typical morning in downtown Margaritaville, where Jimmy Buffett is the patron saint and drunken escapades in convertibles are an all-day pastime.

But just a few minutes walk from the Margaritaville vibe of Key West is a neighbourhood that's lesser known but quickly becoming an attraction in itself. Upper Duval - or, as locals call it, uptown - is being reborn as an elegant and highly walkable area of unique boutiques and attractions that counter the island's castaway reputation. New shops offer merchandise difficult to find elsewhere and side streets are lined with rows of freshly renovated gingerbread cottages and grand Victorian homes that date to the late 1800s, when Cuban immigrants set up hand-rolled cigar factories in the area.


Many choose just to hoof it because most of the island's sights are within a few blocks of each other. Bicycles are an option and tend to be stately touring models, with upright handlebars and extra-padded seats. They go for about $12 for the first day and $8 for each additional day. You can also rent adult tricycles. The Moped Hospital, 601 Truman, 866-296-1625, www.mopedhospital.com

Electric cars that seat up to four are cute and practical, but don't come cheap: Expect to pay about $70 for three hours. That's enough time to cover most of the streets of the island. If you want one for the day, it will run about $150. Tropical Rentals, 1300 Duval St., 305-294-8136, bellsouthpwp.net/t/r/troprent


You'd never expect that The Flaming Buoy Filet Co., an unassuming restaurant on a residential street, is such a gourmet eatery that reservations are a must. On the outdoor terrace, you'll hear crickets chirping and chickens clucking, but no traffic even though it's right in the city. 1100 Packer St., 305-295-7970, theflamingbuoy.com

The Green Parrot is reputed to be Key West's oldest drinking hole. The sign over the bar reads, "No snivelling." 601 Whitehead St., but you can just ask people where the zero mile sign of U.S. 1 is located. 305-294-6133, greenparrot.com

Executive chef Brendan Orr came to Key West by way of Paris. Every night at the Roof Top Café, he embellishes on what he calls "new island tropical" cuisine based on what's fresh that day. Entrees are so large that a single order of mahi-mahi with udon ($27) was more than sufficient for me and my wife. Don't make the mistake of ordering the Patron margarita, priced at $99. "A lot of people order it, thinking it's 99 cents," the waiter warned. 308 Front St., 305-294-2042, rooftopcafekeywest.com


There's no Fred at Fast Buck Freddie's, just a couple of guys who in the seventies listened to way too much Jefferson Starship and decided the song title would be a heck of a name for a store that features an eclectic mix of home furnishings and objets d'art from palm tree door knockers to seashell lamps. They've never had any notion of expanding off Key West, but the furniture is so popular they've shipped it worldwide to decorate the patios of software millionaires. 500 Duval St., 305-294-2007, fastbuckfreddies.com

Glass Reunions, a museum-quality collection of mesmerizing contemporary art glass pieces by more than 200 different artists, assembled by artist Kim Sprague, could take hours to see and appreciate. There's everything from paperweights, mobiles and jewellery to lighting fixtures to enormous fountains and chandeliers worthy of office atriums. Yes, they can ship any purchase to Canada. 825 Duval St., 305 294-1720, glassreunions.com


Silver Palms Inn This former motel has been renovated into apartments. The refit brought it to the Florida Green Lodging Program's gold level, with energy-saving appliances, insulation that holds in the cold, low-flush toilets and lights and thermostats that turn off when no one's home. From $139, with breakfast. 830 Truman, 305-294-8700, silverpalmsinn.com

The Crowne Plaza-La Concha Restored to reveal its elaborate detailing, La Concha was the posh place to stay when it was opened in 1926. Luminaries who stayed here include Tennessee Williams, who was said to have finished A Streetcar Named Desire while staying in a suite, and Ernest Hemingway, whose home was only a couple of blocks away and who referred to the La Concha in To Have and Have Not. From $130. 430 Duval, 877-660-8550, laconchakeywest.com

Report Typo/Error

Follow us on Twitter: @tgamtravel

Next story




Most popular videos »

More from The Globe and Mail

Most popular