10 Things to Do Around Longboat Key

Longboat Key is the quiet neighbor to the hustle and bustle of Lido Key and St. Armand’s Circle. But don’t ignore it - there are plenty of things to be done in this beautiful strip along the Gulf.

Fresh from the Sea
Dry Dock Waterfront Grill.  Photo Credit: Robin Draper

If you want to eat like a local fisherman, go where the local fishermen are. After a day at sea, it’s time to dock the boat and a well-earned bite to eat at the Dry Dock Waterfront Grill. And if it’s good enough for those whose taste is only for the freshest just-out-of-the-water seafood, it’s good enough for me.

Stay Where You Can Play

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.

Love is in the Air

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.

’Ski’ a Show

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.

Party Like a Local

The Cove is an insider scoop. Located in the waters behind the Chart House, accessible via Gulf of Mexico Drive – or by sea – it’s the perfect place to launch a kayak, paddleboard, or any water-buoyant device. Locals spend hours upon hours boating, rafting, partying, fishing and sunbathing in these shallow waters.

Make the Hard Call

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.

Sharks and Rays and Otters – Oh My!

Mote Marine Aquarium is the only place where you can see manatees that predict Super Bowl winners, touch prehistoric creatures, search for megalodon teeth, witness shark training, and support research and rehabilitation for numerous sea creatures. And be sure to look for the flamboyant cuttlefish for bonus awesomeness.

Take a Breather

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.

Paddle with the Pros

Grab your gang and join a guided "relaxed adventure" with Happy Paddler Kayak Tours & EcoVentures. Enjoy the views of both the bay and the gulf as you scan the surface of the islands expansive shimmering waterways for jumping dolphins, diving seabirds, and lollygagging sea turtles. These guides know just where to spot them!

Best Seat in the House

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. Oh, and they have great food, too.