A lot of people think vacation rental success is just about clean sheets and working Wi-Fi. Sure, those things matter, but what really makes guests rave about their stay? Easy access to incredible dining experiences they can’t get back home.
Longboat Key isn’t just another Florida beach town when it comes to food. This barrier island has quietly built a surprisingly diverse dining scene, and if you’re staying in Longboat Key, here are our top picks for a fabulous dining experience that’ll make your vacation truly memorable.
1. Shore
Highlights: Outdoor seating, private dining room, and great cocktails
Shore restaurant is a mid-century, al-fresco coastal eatery serving creative recipes combined with local favorites in an open air dining space. What sets Shore apart isn’t just the waterfront views – it’s their commitment to locally sourced seafood. Locally caught snapper, grouper, and crab cakes are some of the standout entrées, with the colorful beet salad as a must-try and kung pao calamari bursting with flavor.
2. Dry Dock Waterfront Grill
Highlights: Dockside patio, exceptional seafood, and fish-themed decor
The Dry Dock Waterfront Grill is a “polished casual” restaurant overlooking Sarasota Bay (second-floor dining room), located at the south end of Longboat Key. This is where locals take out-of-towners when they want zero risk and peak waterfront – best known for serving fresh grouper and red snapper. The second-story dining area offers panoramic bay views, while the dockside patio provides an authentic Florida dining experience.
3. Euphemia Haye
Highlights: Global fine dining in an inviting atmosphere
After weathering both a brief closure and the 2024 hurricanes, Euphemia Haye reopened in May 2025 under new ownership by Jason and Rachel Ghormley, who are committed to preserving its 50-year legacy as Longboat Key’s most celebrated fine dining destination.
The charming bungalow offers intimate dining with eclectic cuisine, signature dishes like Classic Caesar Salad and Roast Duckling, plus the famous upstairs Haye Loft for casual dining and their legendary dessert room. Perfect to celebrate anniversaries and special occasions.
4. Lo’ Key Island Grille
Highlights: Pan-coastal Southern flair in a laid-back setting
Lo’ Key Island Grille delivers coastal cuisine with island vibes, featuring the best happy hour on Longboat Key with great deals on drinks and appetizers in a relaxed island atmosphere. It’s the kind of place where you’ll end up staying longer than planned, ordering another round while watching the sunset.
5. Chart House
Highlights: Upscale waterfront restaurant – perfect for a romantic date-night
Chart House is a long-running waterfront choice with a big-window dining room and terrace overlooking Sarasota Bay. Go for fresh fish or slow-roasted prime rib; time it for golden hour.
For more than 50 years, Chart House has redefined the ideal dining experience, specializing in dazzling views, unique cuisine, and exceptional service. Must-visit if you’re craving decadent seafood & steak.
Want more insider picks – coffee stops, brunch gems, and date-night ideas across Sarasota’s barrier islands? Explore our site for fresh local guides and browse our Longboat Key portfolio to find a home base that puts the island’s best tables within easy reach.
