Perfect if
You want to take a Caribbean vacation but don't have the funds.
You're a workaholic in desperate need of an "Island Time" intervention.
You need a break from Disney World (and the kids).
Itinerary: A little bit of everything
Believe it or not, there's more to Key West than partying on Duval Street (though that does have its merits). Your options are vast and varied: local art galleries, historical museums, eclectic eateries, water sports, maxin' and relaxin' at five-star hotels, and of course, plenty of places to grab a drink (or seven).
Start out the trip by hopping on the Conch Tour Train on Front Street to get the lay of the land (with the added benefit of cheesy conch-related jokes).
Many artists over the years have made Key West their home — the relaxed atmosphere and picturesque scenery opens up the channels of inspiration. Check out the many galleries that feature local Key West artists from past to present in all mediums including the Audubon House Gallery (205 Whitehead St., Key West, 305-294-2116, audubonhouse.com), Gallery on Greene (606 Greene St., Key West, 305-294-1669, galleryongreene.com) and SoDu Gallery (1100 Duval St., Key West, 305-296-4400).
Delve into the culture of Key West and learn about its colorful history at the Key West Art & History Museum at the Custom House (281 Front St., Key West, 305-295-6616, kwahs.com); The San Carlos Institute, which chronicles the city's Cuban history (516 Duval St., Key West, 305-294-3887, institutosancarlos.org); and the Key West Shipwreck Museum, which recounts how the island came into wealth in the 19th century by salvaging from the many shipwrecks just offshore.
To add a little more adrenaline to this vacation, engage in some of the many forms of water sports available — jet skis, parasailing, snorkeling and shipwreck diving. Just watch out for the sharks.
By this time, you're definitely going to need a drink. Now you could do the typical touristy thing and head to Margaritaville or Sloppy Joe's, but explore Duval and its cross streets for some hidden gems. If wine is what you're seeking, Vinos on Duval will sell it to you by the glass, bottle or to-go (810 Duval St., Key West, 305-294-7568, vinosonduval.blogspot.com). If a cold craft beer is what you need, The Porch has it — 10 beers on draft and plenty more in bottle. It's hidden away on the first floor of a stately home-turned-B&B on Caroline Street (429 Caroline St., Key West, 305-517-6358, theporchkw.com). And if you need a stiff drink and don't feel like wearing a shirt or trousers, head to The Garden of Eden — a clothing-optional bar — located on the roof of The Bull Bar on Duval (224 Duval St., Key West, 305-296-4565).
For the best view of the sunset, take a private ride (dinner optional) on Captain Kelly's Yacht to Sea Key West cruise. He and his wife will give you a sea tour of the environs, keep the complimentary drinks flowing and recount some colorful stories (601 Front St., Slip 3, Key West, 850-225-3069, yachttoseakeywest.com).
End the evening with a bite at one of the Eats spots listed below, then head to one of the many bars on Duval Street and drink until you forget your own name. Stumble back to your lodgings and repeat this itinerary for another day or two (educational and art-related stops optional).
Getting around
Rent a bicycle or scooter to get from place to place. Admire the brightly colored, New England-style Classical Revival homes with tin roofs and "gingerbread" trim that are unique to Key West along the way.
Eats
You simply cannot pass up Blue Heaven. Famous for its outdoor dining, complete with chickens and cats running around your feet and the scent of freshly baked bread, Blue Heaven serves up a mix of Floribbean and Southern cuisine for three meals a day. Get there early to avoid a long wait and be sure to visit the gift shop for unique gifts and homemade bread.
For a romantic sunset dinner, visit SHOR American Seafood Grill at the Hyatt Key West. Chef Daniel Elinan and his crew create sumptuous dishes that utilize fresh local seafood and ingredients. There's a very good chance that your fish dinner was caught just hours before ending up on your plate. (601 Front St., Key West, 305-809-1234, keywest.hyatt.com)
To end the evening, save room for Sex — Better Than Sex, that is. Specializing in desserts (and only desserts), this unique restaurant serves indulgent creations that are big enough to be shared. Start off with a chocolate-rimmed glass of red wine and follow up with one of the naughtily named desserts, like Peanut Butter Perversion, Between My Red Velvet Sheets and Team Cream. Make reservations to avoid a long wait (411 Petronia St., Key West, 305-296-8102, betterthansexkeywest.com).
Lodgings
If you want to splurge a bit, check into the Hyatt Key West Resort and Spa. It's located Gulfside and offers stunning sunset views nightly, as well as a small private beach, pool and spa, and one of the comfiest beds you'll ever sleep in. Duval Street and the downtown attractions are just a block away, but the tucked-away location and privacy wall will make you forget you're in one of the biggest party spots in the U.S. (601 Front St., Key West, 305-809-1234, keywest.hyatt.com)
There are also more bed and breakfasts than you can shake a stick at in Key West. La Mer (506 South St., Key West, 305-296-5611), the Artist House (534 Eaton St., Key West, 305-296-3977, artisthousekeywest.com), and The Mermaid and the Alligator (729 Truman Ave., Key West, 800-773-1894, kwmermaid.com) are within walking distance of the sights without being too close to the nighttime shenanigans on Duval Street.
OR…
If you want to get away, but not that far away, go on a DAYcation!
This article appears in May 12-18, 2011.