The hostess waved us inside with a nod and a smile. She was hard to miss, about 6-foot-5 in heels, legs to the sky, a teal sequined dress hugging flawless ebony skin. And then there was that Adam's apple.
I'd never considered spending Christmas Eve in a drag bar before. But then I'd never spent Christmas Eve in Key West.
A week before, the kids had come home from college for winter break. My wife and I decided we could do without Washington, D.C.'s wind chill and windbags, so we booked the family a flight to Florida. Christmas at home is a delight, but routine. We wanted something different, and Key West delivered.
Christmas week here is many things: loud, open, colorful, kitschy, beautiful - but it's hardly, well, Christmassy, at least not in the spiritual sense. If you need a solemn place to celebrate the baby Jesus, you can do better than Key West. But if seasonal partying is atop the menu, then this is the place.
Secular hedonism rules. There are churches here, somewhere. But the most sacred place seems to be the Ernest Hemingway Home and Museum. It sure has the most worshipers. On Christmas Eve lines snaked outside at all hours to get a glimpse of the alcove where he penned "For Whom the Bell Tolls," "Death in the Afternoon" and others from 1931 to 1939. The pre-Civil War mansion was a wedding gift from his second wife's uncle. Seems Papa knew how to marry as well as write.
The town has some great but conventional annual events, such as the Lighted Boat Parade and Holiday Historic Inn Tour, as well as some happenings that are distinctly Key West - Cowboy Bill's Holiday Charity Hayride and the Holiday Lighted Bike Parade.
The weather did not disappoint: It was in the 80s and sunny every day. And the island offers all the water fun you'd expect - kayaking, snorkeling, water scooters. But if that's all you come here for, you're cheating yourself.
Key West is much more than sun and sea. A rich history, stunning architecture, street theater, and an endless restaurant and bar scene collude to make this a unique winter experience. Duval Street is the white-hot current that powers Key West. Stretching 1.25 miles from the Atlantic to historical Mallory Square, its alive with restaurants, clubs, galleries, bars and T-shirt joints. Throngs crowd the street day and night. And during Christmas, Duval is amped up.
On Christmas morning, Mallory Square was jammed. The square is the center of Key West's waterfront and launch point for most charter boats. We booked an all-day tour of snorkeling and kayaking. The snorkeling was good, not great. Kayaking the mangroves was better, with birds nesting around us. Locals say the Middle Keys offer better underwater visuals. Unfortunately, Hurricane Irma, a Category 3 storm, whacked them in September. The area is still rebuilding, so it's better to stay in Key West, which escaped with minor damage.
A pulsating scooter ride along the silky waters of the Gulf of Mexico rounded out our water adventures. We did spend one day at the beach, which was enough. Small and rocky, the beaches in Key West are pretty average when compared with, say, the white-sand paradise of the Florida Panhandle. Bikes are big here; they're the best way to see the island, and there seems to be a rental shop on almost every corner. The island is a bit more than a mile wide and about four miles long, so you can bike the whole thing in an hour or so.
Dazzling sunsets aside, the most visually appealing thing about Key West is the architecture. Key West was, at times during the 19th century, the wealthiest town per capita in the country, and the largest city in Florida. Its first great fortunes in the early 1800s were built on shipwrecks and scavenging the booty.
Storms and bad navigation often caused ships to wreck on the reefs a few miles offshore. Valuable cargo was there for the taking. Every wreck was like Christmas morning and citizens set up sort of a 19th-century eBay. Buyers came from all over to bid on salvaged stuff, and the locals got rich in the process. Legend has it that some of the more opportunistic natives would move markers and buoys to purposely throw ships off course and cause wrecks.
A happy byproduct of this ill-gotten wealth is the amount of beautiful, 19th-century homes and inns throughout Key West. The deep front porches and louvered shutters of the wooden houses give the town a unique warmth and charm.
"So many tourists are shocked to see all this beautiful architecture and homes just a couple blocks off Duval Street," local historian Sharon Wells said.
The Key West Historic District, also called Old Town, has more than 3,000 wooden buildings in a collage of Bahamian, Spanish and New England-style designs. Most are decorated during the season, and it's worth a nighttime walk or bike ride just to drink in the architecture and listen to the palms lazily rustle.
Did I mention drink? There's plenty of that here - and some food to go along with it.
"Hell week" is how bartender Erin Wagoner laughingly describes the days between Christmas and New Year's. Wagoner works the bar at the Smokin' Tuna Saloon just off Duval Street, where her husband and Key West guitar legend "Caffeine" Carl Wagoner and his band, the Buzz, rock the place most nights. "It's crowded but a lot of fun," she adds. "Christmas here is special, even if the temperature's in the 80s." If you want live music, this is the place to be.
Happy hours here are legendary and they seem to start early afternoon and end early the next morning. Commodore's on the Key West waterfront is a favorite - most things are half price. Conch fritters, a Bahamian delicacy, are local staples. They are fried dough balls of mollusk meat, peppers, onions and whatever seems to be lying around the kitchen. Bartenders push the sweet stuff here - mojitos and Key Lime shooters, the tasty but ultimately vile concoctions of rum, cream, lime juice and whatever the bartender feels like throwing in. This is dangerous stuff; it goes down too easy then stays with you way too long. One is enough, then do yourself a favor and go to dinner.
Key West's diverse history is reflected in its restaurant scene. Cuban food is big - a legacy of the 19th-century immigrants who brought the cigar rolling business here. Wherever you eat, you have to try the giant Key West pink shrimp. It's local and to me, a shrimp snob, the best I've eaten.
After dinner, we ambled toward the south end of Duval Street. It's a bit quieter than the north end, and home to a number of drag bars whose smiling hostesses beckoned to us. We looked inside, tempted, but it was late on Christmas Eve and, Key West or no Key West, we had somewhere to be. We went back to the hotel and watched Midnight Mass on TV.
IF YOU GO
Where to stay
- Casa Marina Key West
1500 Reynolds St.
Built in 1920, this is a high-end, luxury resort from Waldorf Astoria. Rooms are bright and spacious, and two large pools overlook the ocean. Location is near restaurants and nightlife. Room rates in offseason start at $300, but can go as high as $600 during holiday season.
- Truman Hotel
611 Truman Ave.
This is the perfect place for travelers on a budget in a terrific location, just a block off Duval Street. There's also a large pool in the hotel's courtyard. Rooms from $199.
Where to eat
- Blue Heaven
729 Thomas St.
A must stop, Blue Heaven offers Key West-style alfresco dining. Expect Caribbean-influenced cuisine while being surrounded by tropical foliage in a distinctly funky setting. Live music is frequent. Come early, as there's typically a wait. Dinner entrees from $21.
- Alonzo's Oyster Bar
700 Front St.
This waterfront restaurant is a local favorite, and is known for a loud, fun happy hour. Offering both indoor and outdoor dining, it's best known for its cold and warm water oysters, as well as Key West pink shrimp. Entrees start at $12.
- Michaels Restaurant
532 Margaret St.
If you are looking to get dressed up, this is the place to go. Expect a sophisticated and elegant dining experience at this classic steak and seafood house. Entrees start at $22.
What to do
- The Ernest Hemingway Home and Museum
907 Whitehead St.
Informed guides spin tales of Hemingway's Key West years. The home is full of photos and mementos from the writer's life. Expect a wait to get in. Open 9 a.m. to 5 p.m. daily. Admission costs $14; $6 for children ages 5 to 11; free for younger children.
- Smokin' Tuna Saloon
4 Charles St.
Located just a block away from busy Duval Street, this is the quintessential Key West roadhouse. It is an open-air establishment, and there are two bars and a courthouse stage where you can listen to live music. Bonus: There's never a cover charge. The restaurant is open 5 to 11 p.m. daily, and the bar is open from 11 a.m. to 2 a.m.
- Key West Shipwreck Museum
1 Whitehead St.
This is a fun and interactive museum for children, with actors relaying stories of Key West's legendary shipwrecks. Make sure you climb the lookout tower. Open 9:30 a.m. to 5 p.m. daily. Admission costs $15; $8 for children ages 4 to 12; free for younger children.
- Fury Adventures
Various spots around Key West
Fury offers water scooters, snorkeling and just about every watersport you can imagine. It's open all year, with various locations around town. Call ahead for prices.
Carden is a writer based in Bethesda, Maryland. His website is bobcarden.com.