Best Bars and Drink Spots on Siesta Key

Siesta Key isn’t just about powder-white sand and turquoise water—it’s also about what’s in your glass. Whether you’re craving a sunset cocktail, an ice-cold beer after a beach day, or a tiki drink that’s more fruit than liquor (no shame), this little barrier island has you covered. Here are the go-to spots to sip, savor, and soak up the island vibe.

The Daiquiri Deck

Vibe: Party starts here
An institution on Siesta Key, the Daiquiri Deck is exactly what it sounds like—frozen concoctions galore. Their daiquiri menu reads like a candy store for adults (hello, Electric Lemonade). Grab a yard-long cup, snag a seat on the deck, and let the people-watching do the rest.

Gilligan’s Island Bar & Grill

Vibe: Tiki-meets-tropics
If Gilligan had gotten stuck here, he never would’ve wanted to be rescued. With bamboo huts, islandy cocktails, and plenty of live music, Gilligan’s feels like a mini vacation inside your vacation. Try the rum punch—just don’t try to count how many rums are in it.

Siesta Key Oyster Bar (SKOB)

Vibe: Classic beach bar
Locals call it SKOB, and if you want cold beer, fresh oysters, and walls literally covered in dollar bills, this is the place. It’s laid-back, salty, and the kind of joint where flip-flops are basically required.

The Hub Baja Grill

Vibe: Tequila, tacos, and tunes
If margaritas are your love language, The Hub is your match. They’ve got live music almost every night, an endless tequila selection, and the kind of nachos that disappear faster than your first round.

The Cottage

Vibe: Craft cocktails, island chic
A little more elevated but still beachy-casual, The Cottage is known for its creative cocktails and eclectic bites. Think mojitos with a twist or seasonal craft mixes you won’t find elsewhere on the Key.

Siesta Key Rum Distillery

Vibe: Liquid souvenirs
Okay, not exactly a bar, but worth a mention. This local distillery offers tours, tastings, and bottles of small-batch rum you can bring home (if they make it that far). Their toasted coconut rum basically tastes like vacation in a glass.

Insider Tip

Most places on the Key have live music—plan your night around who’s playing rather than just what you’re drinking. Bonus: sunsets taste better with steel drums.