Key West Bar Guide: Where to Drink for a Bachelorette Weekend

How Key West Bars Actually Work

Key West has more bars per capita than almost any other US city and most of them are on or within two blocks of Duval Street. The catch is that the best bars change character throughout the day. A spot that is perfect at 11 AM feels wrong at 10 PM. This is how locals and regulars actually string a day together.

Morning and Brunch

Start the day with a bloody mary at Blue Heaven. The whole place is an outdoor garden with chickens wandering around, the food is great, and nobody cares if you stay for two hours. Bagatelle is the slightly more upscale version, on Duval, with a shady second-floor porch that catches a breeze. If the group is moving slow, Cuban Coffee Queen gets you back to life in one shot of espresso.

Afternoon Pool and Beach Drinks

Key West does not really have swimmable beaches, so the middle of the day is best spent at a pool bar or on a boat. Sandbar Sports Grill or the rooftop at La Concha Hotel are two easy afternoon plays. If the group wants more, book a sandbar tour that drops you on a half-submerged flat with a cooler of drinks. Sunset Watersports and Honest Eco both run half-day trips that work for groups up to about 20.

Sunset

Mallory Square at sunset is a tradition for a reason. It is chaotic, free, full of street performers, and everyone in Key West ends up there at some point. Grab a drink from any nearby bar and walk over. The other sunset option is the rooftop at the Waldorf Astoria Top Hat bar, which is quieter and pricier.

Dinner Bars

For a seated dinner with good cocktails, Latitudes on Sunset Key or Louie Backyard are the splurge picks. Both require reservations and a short boat or taxi. In town, Santiago Bodega does tapas-style with a solid wine list and handles bachelorette groups well.

Late Night on Duval

After 10 PM is when Duval turns into its real self. Sloppy Joe and Captain Tony are the tourist-famous ones, and they are fun in small doses. The better move for a bachelorette group is to bar hop. Irish Kevin has live music that is more fun than it has any right to be. Bourbon Street Pub has the drag show that is worth the cover. Rick has the upstairs dance floor that is slightly less sweaty than the ground floor.

If the group wants to slow down at the end of the night, The Green Parrot is the dive bar that has been there since 1890 and does not care who you are. It is where locals go when they are done with Duval.

A Reasonable Itinerary

One proven day: Blue Heaven brunch, Honest Eco sandbar tour with lunch, rooftop drinks at La Concha, Mallory Square sunset, dinner at Santiago, Irish Kevin for music, Green Parrot to close. That is twelve hours of bars without anyone feeling wrecked, if you pace the water and food.