10 Things to Do Around Longboat Key

Fish doesn’t get much fresher than at Dry Dock Waterfront Grill, where the shrimp and oysters are sourced directly from the nearby Gulf. They’re basically jumping directly onto your plate. The award-winning waterfront restaurant has earned accolades for its romantic, al fresco, and seafood features. Sitting out back under the stars with the breeze from the water and a plate of Florida snapper might be the ultimate evening. 

For the vacation when you want to do something, but not really something strenuous, the Silver Sands Gulf Beach Resort has you covered. Walk the beach. Tread in the pool. Golf the putting green. Take a shot at shuffleboard. Grill up some local fish. It’s the perfect pace at the perfect place.

Dine at uber-romantic Euphemia Haye, and be sure to finish the feast with a trip to the dessert room, the Haye Loft. Here you can enjoy gazing into your date’s eyes with coffee, wine, port, chocolate, or all of the above, all set to the tune of live music.

Since 1957, Ski-a-Rees has been performing their free waterski show in Sarasota Bay. Watch the trickery while also scanning the waters for manatees and leaping dolphins. Shows are held on Sundays at 2pm on City Island during the Spring and Fall seasons.

The Cove is an insider scoop. Located in the waters behind the Chart House, the Cove is an inlet between Sarasota Bay and the Gulf where locals anchor and spend hours upon hours boating, rafting, partying, fishing, and sunbathing. No boat? Access this secret haven from land via Overlook Park on Gulf of Mexico Drive. It’s the ideal place to launch a kayak, paddleboard, tube, or any water-buoyant device to join the Floridan fun. 

In Sarasota, you have got to have a grouper sandwich, ideally overlooking the water as the salty air adds a little something something to the flavor. City Island, just across John Ringling Parkway from Longboat Key, gives you two such choices and it’ll come down to a coin flip to choose between The Old Salty Dog and New Pass Grill. It’s a hard call. If you have time, just try both. Vacation is no time to make hard decisions.

From the thermal experience to the relaxation lounge, wellness shots to champagne, tranquility abounds unlike any other at the spa at The St. Regis Longboat Key Resort. This is not just a massage, a facial, or a body wrap. It is a full day, life-changing event. Extend the stay and take advantage of the lazy river, tropical fish snorkeling, multiple pools, and butler service of this award-winning beachfront resort.

The north end of Longboat Key is home to one of the most popular photo spots in the area: Beer Can Island. Getting to the driftwood-lined shores of this hidden oasis requires a bit of walking or boating, but it’s worth the view and tropical vibes that will put you instantly at ease.

Grab your gang and join a guided “relaxed adventure” with Happy Paddler Kayak Tours & EcoVentures. Enjoy the view of both the Bay and the Gulf as you scan the surface of the island’s expansive shimmering waterways for jumping dolphins, diving seabirds, and lollygagging sea turtles. The guides know just where to spot them along the barrier island.

It’s hard to beat the view from the Chart House. From your seat, you look down and out over at a panoramic view the water, glistening with the light of the sky. Feasting on Sea Bass & Lobster Risotto and savoring a Hot Chocolate Lava Cake while watching the sun set over the water is the idyllic combo of luxury and serenity and it tastes mighty fine.