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 grown in other parts of Latin America. They might not be "authentic" but they are as close as you can get without breaking the law. Although many of the cigar factories are long gone, there are plenty of places to buy cigars and a number of smoke shops to enjoy them in. Two blocks west of Green Street is often referred to as "Cigar Alley," but stores are scattered all over the city including Cork and Stogie, which partnered with the Original Key West Cigar Factory two years ago. The wine list includes international bottles from New Zealand, Russia, South Africa, Argentina, and more. A warm ambiance, selection of fine wines, and friendly staff are a winning combination at this "Southernmost Cigar Bar." Be sure to check their website for coupons.
Local Expert tip: Monday night is game night at Cork and Stogie, and guitarist Paul James plays every Friday and Saturday night.
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, and also features a cocktail and wine bar upstairs and small plates items like focaccia, bruschetta, carpaccio, and roasted clams. Servers are helpful and friendly, adding to an overall friendly dining experience. The upstairs wine bar also offers a flight of cheeses to pair with wine selections. Note that the upstairs lounge is open evening hours from Tuesday through Sunday.
Local Expert tip: If you visit in the evening you will want to plan your meal around the spectacular sunset.
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 New England area – like Shipyard Export Ale from Portland or Dogfish Head 90 Min IPA from Delaware. Order some fine wine (they have an enormous selection), and sit outside on the porch for some people watching, or stay inside in the air conditioning and watch the occasional movie showing. The bartenders are friendly and helpful, and they don't serve any bar snacks, but you're welcome to bring your own.
Local Expert tip: The ghost tours kick off here as well, so arrive early and grab a seat before the spooks take them.
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 like gnocchi with caramelized pears or seafood soup. An international wine list invites connoisseurs, and upstairs the Point 5 wine lounge and tapas bar is open late. The restaurant is also ideal for private parties and special events (including New Year's Eve). Prices are on the high-end (compared with similar venues), but the world-class menu is worth the splurge.
Local Expert tip: Be aware that new city ordinances may prevent pets from dining in the future. Call the restaurant in advance.
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, whites and sparkling wine, and the list is constantly changing to keep things fresh and exciting. Not a wine connoisseur? No problem. This is a great place to find a new wine that you love, and the bartenders will guide you in the right direction. They also offer a sampling of gourmet sandwiches and desserts from Croissants de France. The comfy porch on Duval Street allows you to slowly watch the world go by as you sip on a fine wine. Don't miss their $5 sangria happy hour, and check their calender for other wine tastings and special events.
Recommended for Wine Bars because: This cozy wine bar is a locals fave, serving up an ever-changing selection of top wines paired with delicious cheeses.
Claudia's expert tip: They deliver! From 2:00 p.m. to 1:00 a.m. they offer free delivery on bottles of wine to your hotel. You must provide ID upon delivery.
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 island). The bar staff will hold a bottle with your name on it (ask nicely) and the wine list varies from affordable bottles, to high-end prices from vineyards around the world. True wine lovers find themselves returning more than once during their vacation, and will quickly be on a first-name basis with the cheerful staff.
Local Expert tip: They don't serve food, but just next door you can grab a bite.
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. State-of-the-art dispensers distribute individual chilled or room temperature wine samples of some higher-end bottle selections. It's a small space but visitors can also sit in the lobby area, or wander the grounds. The hotel was voted "The Prettiest Hotel in Key West" by The New York Time's List, and it is also featured in the book "1000 Places to See Before You Die."
Local Expert tip: First you have to purchase a card with a minimum balance of $25.
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 in the parent store in St. Petersburg, Florida. Blends are made with pink grapefruit, oranges, cranberries, tangerines, and other tropical fruit, and their signature is Key Limen, which tastes like - what else - a margarita. Specialty varieties include orange wine with roasted coffee beans, coconut, or chocolate. Tastings are available to shoppers during store hours.
Local Expert tip: The store also sells sauces, cheesecake mixes, and more.
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 cigar that matches your tastes. A glass of wine ranges from $6 to $9, making it an affordable option for those on a budget. If cigar smoke bothers you, there is an outdoor seating area as well. This smoke and wine shop is also home to Duke, the bulldog that runs the show (and has his own "blog").
Local Expert tip: There are more than 50 wine bottle selections at reasonable prices.