The Casa Marina, Henry Flagler’s grand hotel on the south side of Key West, is known as a sort of oasis at the end of the road. In 1912, Flagler arrived in town on his new railroad, and he declared he would build a resort on the island. Though the hotel wasn’t completed until after his death, were Flagler to visit the Waldorf Astoria’s Casa Marina today, he’d likely feel quite comfortable in HMF Sidecar. HMF, the swanky hotel bar re-launched just last month, nods to yesteryear, and it’s currently dressed in evergreen and twinkling lights for the holidays. Maxwell Dean, the bartender five nights a week, is often bedecked in throwback fashion: a cap and suspenders.

HMF has kept the dark wood bar and nostalgic atmosphere, but has amped up the cocktail offerings, with Dean blowtorching orange rinds and even bacon for the libations. A classic sidecar is a wise choice, with boozy Cointreau-infused whipped cream and an orange rind twirled inside the cognac cocktail. My favorite was Dean’s take on the gimlet, using bison grass vodka, lime, St. Germaine, apple juice (!), and a touch of simple syrup. Both cocktails were well-balanced and went down almost frighteningly easily. The menu also boasts seasonal favorites, like the Sweet Potato Pie, with Angel’s Envy bourbon, sweet potato puree, cinnamon and egg whites, which sounds like Thanksgiving in a glass.

HMF Sidecar is a cozy space for a cocktail, with tourists and locals alike chatting at the bar and low leather chairs for quiet conversation. HMF is open nightly starting at 5 p.m. Bring your spare liver — you’re going to want to try everything.

Sarah Thomas
Sarah Thomas is the Editor of Key West Weekly and moved down from her second-favorite island, Manhattan. She has worn many hats: publicist, tour guide, bartender, teacher, and cat wrangler, but this one seems to fit the best.