Longboat Key Nightlife & Cocktail Guide

Longboat Key is quieter and more refined than its neighbors Siesta and Lido, but don’t let the upscale vibe fool you, this barrier island still knows how to pour a great drink. From waterfront tiki bars to elegant resort lounges, Longboat Key is all about sipping with a side of sunset. Here are the top places to raise a glass while soaking in those Gulf breezes.

Dry Dock Waterfront Grill

Vibe: Laid-back marina views
Perched right on Sarasota Bay, Dry Dock is a local favorite for its fresh seafood and unbeatable waterfront seating. Pair a grouper sandwich with a cold draft beer or one of their tropical cocktails, and you’ve got peak island living.

Chart House

Vibe: Classic & classy
Known for its upscale dining and panoramic bay views, Chart House is also a solid choice just for drinks. Their martinis and wine list are worth lingering over—especially if you time it for golden hour when the water glows.

Shore Longboat Key

Vibe: Modern coastal chic
Shore brings stylish design and craft cocktails to the water’s edge. Expect fresh, beach-inspired mixes and a lively atmosphere that feels a little trendier than most of Longboat. Bonus: their second-floor deck has stellar views.

Harry’s Continental Kitchens

Vibe: Neighborhood gem
Harry’s is a Longboat institution—part gourmet market, part restaurant, part bar. Their wine list is deep, the cocktails are well-crafted, and the cozy vibe makes it perfect for a relaxed evening.

Whitney’s

Vibe: Retro roadside cool
Set in a converted gas station, Whitney’s is one of the coolest spots on the Key. Bright, airy, and a little funky, it’s the place for daytime drinks, brunch cocktails, and hanging out with a local-meets-vacationer crowd.

The Old Salty Dog (Longboat Key location)

Vibe: Casual & family-friendly
No-frills, waterfront, and full of character. The Old Salty Dog is perfect if you’re craving a bucket of beer, frozen daiquiri, or a rum runner with a side of fried seafood. Bonus: bring your pup—this one’s dog-friendly.

Insider Tip

Longboat is more low-key than its neighbors, so don’t expect wild nightlife. Instead, plan your evening around sunset: start at Whitney’s for a craft cocktail, then head to Dry Dock or Chart House for waterfront views as the sky puts on its nightly show.