Our Local Experts' Top Wine and Cigar Bars in Key West, Florida

Charming, wine lounges and cigar bars with knowledgeable staff offer a change of pace from the rowdy, drinking frenzy that engulfs much of Duval Street. Find a new wine, or enjoy a returning favorite, often served with small plates or cheese platters. Intimate atmospheres invite friends and couples to mingle without Jimmy Buffet’s songs blasting from the speakers. For a relaxing, upscale experience, here are some of Key West's wine and cigar lounges.

Chris Otten (former chef at nine one five) and Chris Schultz (owner of The Porch, The Café) have taken the wine lounge and gastropub scene and exploded it. Their newest concept, 2 Cents, features fresh ingredients and a selection of wines and microbrews in an artistic and inviting atmosphere. They’ve managed to make wine bars a comfortable, laid back place to enjoy the company of others.

Authentic cigar bars like Cork and Stogie are a throwback to Key West’s cigar-making roots, and also offer a unique experience that you won’t find at Sloppy Joe’s. For something entirely different, The Key West Winery serves samples of grape-free wine that is made of berries and citrus produce.

While the nightlife scene on Key West may be changing, it is still holding on to the friendly, island vibe.

Duval Street
Cork and Stogie
Photo courtesy of Cork and Stogie


Shops all over Key West sell "Cuban cigars," however they are typically made domestically because it is still illegal to buy and sell Cuban cigars in the United States. Most cigars in the Keys are made with Cuban tobacco from plants that were...  Read More



Louie's is a gem that locals try hard to keep secret. The food and the view make for an exquisite dinner – if you can get a reservation – or an elegant lunch. This perennial favorite restaurant has been in business for more than 25 years,...  Read More

Duval Street


The staff at The Porch claim that it is haunted by the spirit of Dr. Porter (ask them about the dimes), but the ghost stories aren't enough to scare off those seeking craft beer or a quality glass of wine. Most of their craft beers come from the...  Read More



A wine bar that is dog friendly? Nine One Five restaurant has an eclectic fusion menu, and welcomes pets on the outdoor patio of a historic Victorian home. Starters include bacon wrapped dates (Devils on Horseback) and crab chowder, with mains...  Read More



Part gastropub, part wine bar, 2 Cents offers a nice selection of craft beers and wines, with an ambiance is decades away from the flood of cruise ship passengers. The newly-opened restaurant (January 2012) features funky decor consisting of...  Read More

Duval Street


Located on Duval just next to the Tropical Inn, Vinos on Duval it's a refreshing change of pace. The intimate environment invites conversation, and sharing a bottle and cheese plate is the way to go. They have an extensive selection of reds,...  Read More

Duval Street
Grand Vin
Photo courtesy of Grand Vin


Opened in 1997, this cozy wine bar has been a Duval Street favorite (on the quieter Atlantic side) among locals. Thursday nights are bar game nights, 80s music is the usual selection, and the vibe is laid back and inviting (like so much of the...  Read More

Photo courtesy of D'Vine


The Gardens Hotel features 17 luxurious guest suites set among one of the oldest tropical gardens in Florida with amenities like a Jacuzzi and heated pool, expansive breakfast, trickling fountains, an aviary, and a wine room gallery....  Read More

The Key West Winery
Photo courtesy of The Key West Winery


While not a traditional wine bar, (it is a wine store) the Key West Winery has a unique selection of tropical, fruity wine. What truly sets them apart is that the wines are made with citrus fruits and berries – not grapes. Fruits are squeezed...  Read More

Historic Cigar Alley
Photo courtesy of Historic Cigar Alley


Whether you're cigar smoker, a wine drinker, or just enjoy a different atmosphere, the Historic Alley Bar makes a leisurely stop in Old Town. An extensive micro brew list is available and the staff can help you find a beer, glass of wine, or...  Read More


Meet Amber Nolan

Originally from upstate New York, this restless traveler has a knack for befriending interesting characters. You can usually find her just about anywhere that has a hammock. Amber's favorite...  More About Amber