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Must-try waterfront restaurants in Sarasota, Longboat Key, Osprey

Looking for a table by the water? For a close encounter with Florida’s natural splendor, enjoy one of these waterfront restaurants on a nearby key.

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  • | 6:00 p.m. November 11, 2022
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  • Eat + Drink
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In the mood for a meal and a show?

The waterfront restaurants of the keys offer front-row seats to the greatest show on Earth. We’re talking about the life aquatic — the grand spectacle of the Gulf of Mexico, our area’s bays and estuaries, and the wondrous flora and fauna that live there.

These restaurants offer breathtaking views that serve as exquisite backdrops for dining. Food’s still the main attraction, natch. Possibilities range from upscale to down-home.

The five restaurants we’re showcasing here are just a few of the terrific waterside offerings out there. Pull up a seat and enjoy the show!


For a blissful al fresco experience at Mar Vista, grab a waterside table and watch sailboats tie up at the nearby dock. (Photo by Lori Sax)
For a blissful al fresco experience at Mar Vista, grab a waterside table and watch sailboats tie up at the nearby dock. (Photo by Lori Sax)

Mar Vista Dockside Restaurant

760 Broadway St., Longboat Key; 941-383-2391;

At the north end of Longboat Key, the Gulf of Mexico flows into Sarasota Bay through Longboat Pass. The Mar Vista Dockside Restaurant and Pub has faced this idyllic confluence since its founding in the 1940s.

The smartly remodeled, air-conditioned interior is a swell place to beat the Florida heat. But for a blissful al fresco experience, grab a waterside table under the shady trees and watch pleasure boats tie up at the nearby dock. Order a chilled bottle of Pouilly-Fuissé and the smoked fish appetizer, and enjoy the ever-changing view of the floating world.

Mar Vista’s seasonally inspired menu offers plenty of fresh fish, along with a cornucopia of sharable veggie sides grown on the Chiles Restaurant Group’s own Gamble Farm Organics or at one of their many regional agricultural partners.

“There is no other place with this feel,” says Arty Cholminski, Mar Vista’s general manager. “To sit so close to the water, beneath the buttonwood trees, with little white twinkling lights at night — it’s simply enchanting.”

Mar Vista’s smartly remodeled, air-conditioned interior is a welcoming place to escape the heat and rain. (Photo by Lori Sax)
Mar Vista’s smartly remodeled, air-conditioned interior is a welcoming place to escape the heat and rain. (Photo by Lori Sax)

Best seat: Table 501 right on the water.

Best seat for romantic encounters: Table 504 (under a tree in the back) or Table 303 (in its own cove of trees).

Life aquatic: Snook, sheepshead, snapper, manatee and dolphin all make occasional appearances.

Signature cocktail: Blueberry lemonade. It’s made with vodka infused with Jubilee Orchards’ organic blueberries, lemonade puree and soda. (Located in Leon County, Jubilee Orchards’ blueberries have been called the best in the South.)

Signature entree: The Island Trio (Caribbean-spiced scallops, shrimp, fresh catch, mango-lime sauce, and Gamble Farms-grown squash and sweet corn).


Dry Dock’s breathtaking vista provides your own front-row seats to the majestic drama of Sarasota Bay. (Courtesy photo)
Dry Dock’s breathtaking vista provides your own front-row seats to the majestic drama of Sarasota Bay. (Courtesy photo)

Dry Dock Waterfront Grill

412 Gulf of Mexico Drive, Longboat Key; 941-383-0102;

This Longboat Key landmark was established in 1989. When it joined the Gecko’s Hospitality Group in 1992, the new management didn’t mess with the magic formula. Which is? Co-owner Mike Gowan sums it up: “Outstanding views, exceptional hospitality and very fresh seafood.”

Indeed, the views are just as tasty as the food here and don’t just take our word for it: OpenTable recently named Dry Dock one of the “100 Most Scenic Restaurants in America.”

Whether you’re enjoying a cold brew on the dockside patio, or a cocktail upstairs in the more formal dining room, the majestic drama of Sarasota Bay is just before you. Prefer locally sourced fare? You can’t go wrong with the grouper or snapper; they’re caught in area waters.

Here are some of Mike Gowan’s top tips.

Dry Dock’s grilled Gulf shrimp are a favorite. (Courtesy photo)
Dry Dock’s grilled Gulf shrimp are a favorite. (Courtesy photo)

The life aquatic: Check out the jumping mullet hunting for their grub while you enjoy yours. During migrating season, the storied Silver Kings can be seen rolling through the waves as they head south.

Signature cocktail: Dry Dock’s Maple Cinnamon Old Fashioned created with Four Roses Small Batch Bourbon, cinnamon simple syrup and garnished with a cinnamon stick.

Don’t miss: “The citrus grouper is sautéed and topped with our citrus cream sauce, which is made with Florida orange juice and heavy cream and then reduced down to nectar. Pair it with a crisp 13 Celsius Sauvignon Blanc for a delightful meal.”


Cocktail for a Cause

Every time a Dry Dock guest enjoys a Shark Lady cocktail, Gecko’s Hospitality Group donates to Mote Marine Laboratory in support of Mote’s research toward the preservation of the region’s coastal waters.

First concocted in 2018, the cocktail is named in honor of the original Shark Lady, Eugenie Clark, Mote’s founder. It’s a refreshing mix of rum, blue curacao, pineapple juice and sour mix.

Shark Lady sales have now provided more than $30,000 to support Mote’s mission.


The Big Chill Seafood Tower at Deep Lagoon is sure to turn heads. (Courtesy photo)
The Big Chill Seafood Tower at Deep Lagoon is sure to turn heads. (Courtesy photo)

Deep Lagoon Seafood & Oyster House

482 Blackburn Point Road, Osprey; 941-770-3337;

Just a stone crab’s throw from the historic swinging bridge that connects the mainland to Casey Key, Deep Lagoon gives every guest an up-close view of Little Sarasota Bay — whether outside on the terrace or inside the airy dining room.

Fresh seafood is the focus here; the restaurant is owned by Phelan Family Brands, which boasts 22 restaurants in its edible archipelago, including the ever-popular Pinchers.

To satisfy all sizes of appetites, the menu includes “all day” for heartier fare, “light lunch,” and “small plates.” There’s also a raw bar and an extensive wine and craft beer selection.

“It’s a great spot to get away from every day,” says Kevin Rooney, vice president of Phelan Family Brands. Rooney was happy to share a few insights:

The chill factor: Want to make a big impression? Order the Big Chill Seafood Tower. This triple-tiered platter is stuffed to the, er, gills with Maine lobster, peel-and-eat shrimp, chilled king crab, tuna tataki, Moscow-style oysters (with horseradish cream and caviar), and pickled clams, and mussels. Is a seafood skyscraper a bit too much? The Little Chill is smaller but just as tasty.

Check out the art: The walls are adorned with nature photography by Alan Maltz, the official wildlife photographer for the state of Florida.

Don’t miss: The tangy conch fritters, crab Rangoon, Gulf-caught hogfish, or the chili rub tripletail.


Old Florida lives on at The Old Salty Dog on City Island. (Photo by Lori Sax)
Old Florida lives on at The Old Salty Dog on City Island. (Photo by Lori Sax)

Old Salty Dog

1601 Ken Thompson Parkway, Sarasota; 941-388-4311;

Authentic Old Florida thrives at The Old Salty Dog on City Island.

Along with its gob-smacking waterfront views, this iconic eatery serves up seafood in all its forms, beer-battered hot dogs, ice-cold brews and … fish and chips? Right you are, mate. Owners Phil Needs and Judy Fryer are authentically British.

If you prefer all-American fare, manager Amy Blair recommends the Fully Loaded Old Salty Dog — a quarter-pound hot dog, dipped in batter, fried, and topped with sauerkraut, bacon, grilled onions, mushrooms and a medley of cheese. According to Blair, the Old Salty Dog’s regulars are like family.

Looking to start your own tradition at the Dog? Blair shared a few recommendations.

And now for something completely different: Grouper egg rolls stuffed with grouper, black beans, corn, pepper jack cheese, cilantro and cumin — and served with a side of sweet chili sauce.

Wake up to bangers and beans: The Dog offers a complete breakfast menu Friday through Sunday. You can celebrate the owners’ UK origins with The British — a plate heaping with “bangers,” baked beans, an egg, toast and grilled tomato. Or salute the Sunshine State, and get the Florida Cracker with buttermilk biscuits topped with bacon, grilled tomato, poached eggs and sausage gravy.

Best seat in the house: Every last one.


The goat cheese and yellow beet salad is drizzled with pistachio oil at Ophelia’s on the Bay. (Photo by Nancy Gruth)
The goat cheese and yellow beet salad is drizzled with pistachio oil at Ophelia’s on the Bay. (Photo by Nancy Gruth)

Ophelia’s on the Bay

9105 Midnight Pass Road, Sarasota; 941-349-2212;

Ophelia’s on the Bay indulges your taste buds with its creative New World cuisine and legendary wine list. The experience would be heavenly if you dined with your eyes closed.

Ah, but open them, and it gets even better.

Ask for an outside table overlooking Little Sarasota Bay. Your tensions will dissolve at the sight of water birds, small water crafts and the sun, before it sets, splashing the sky with colors worthy of the French Impressionists. (Hint: This is a perfect time and place to pop the big question.)

Along with Ophelia’s opportunities for ritual and romance, the restaurant’s daily-changing menu boasts regionally sourced seafood, meats and produce. Even Shakespeare’s lovelorn damsel might change her mind about her fate with this ultra-romantic setting.

Don’t miss: The jumbo lump blue crab cakes placed pertly atop fried green tomatoes; the eggplant crepes with mascarpone and ricotta; or the Vermont goat cheese and yellow beets drizzled with Yuzu honey and pistachio oil. Oh — and the yellow fin tuna with lobster tail fried rice is enough to share.

Best seats: C’mon. Sure, it’s nice inside with plenty of window tables. But if you don’t sit outside, you’re missing Florida’s spectacular waterside drama. If it’s rainy, ask for a table in the covered roof area and enjoy the raindrops splattering on the water before you.

Is Ophelia’s named after Shakespeare’s soggy heroine? Nope. The restaurant is named after the original owner’s aunt.



Ed Chiles

This island entrepreneur fights for natural Florida. His love for Sunshine State ecology runs in the family.

Ed Chiles is son of the legendary “Walking” Lawton Chiles, Florida’s famously ecologically minded governor. Chiles keeps his father’s values alive in his commitment to sustainability.

As the owner of Chiles Hospitality, the parent company behind the Mar Vista, Beach House, and Sandbar restaurants on Anna Maria Island and Longboat Key, he makes sure these venues keep the smallest possible ecological footprint.

Chiles Hospitality also operates Gamble Creek Farms — which grows certified organic produce for its own restaurants and others throughout Southwest Florida. On top of that, Chiles recently launched the “All Clams on Deck” initiative to restore the estuaries of Charlotte Harbor, Sarasota Bay and Tampa Bay.

All of these eco-friendly ventures lead to an obvious conclusion: Chiles is committed to sustainability. We decided to ask him why — and how he’s making it happen.

As the owner of Chiles Hospitality Group, Ed Chiles is committed to sustainability.  (Photo by Lori Sax)
As the owner of Chiles Hospitality Group, Ed Chiles is committed to sustainability. (Photo by Lori Sax)
Why is sustainability so important to you?

Short answer: Because I’ve got a new grandson.

Long answer: Because I grew up in paradise — and I don’t want it to turn into Paradise Lost for future generations.

Florida has more national estuaries than any other state except California. We’ve got four, and three of them are right in this area. Each is a nursery for the Gulf of Mexico. Sea grass is so important, and its acreage is going down in unprecedented numbers. It’s up to all of us to turn that around.

Whether you were born here, or chose to come here, I believe if you live here, you’re taking on a responsibility as stewards of the Florida environment. What do you want our legacy to be? Will we be remembered as the guys who didn’t leave this region better than we found it? I hope not.


Tell us about the way your restaurants have been experimenting with cooking wild-caught hogs.

Wild boars are wreaking havoc on local golf courses, sensitive environmental lands and wild life. They’re a devastating invasive species — but they also happen to be delicious!

These wild boars are descended from the Iberian pigs that Hernando de Soto brought over from Spain — and they’re the finest pigs in the world. Their meat isn’t all washed-out like a pig that’s been penned up all its life; it’s pink with 40 pounds or so of beautiful fat.

Just killing them is a waste. I grew up hunting pigs. You know, we didn’t shoot him to leave him.

David at Shogun Farms shares that philosophy. He humanely traps the pigs and brings them by helicopter to his farm. He pens them in good living conditions and feeds them with grains from local microbreweries and corn from his landscaping company. You wind up with super healthy, artisanal meat from Florida. It’s a win-win for the environment, for health and for everybody.


You ever thought about following in your father’s footsteps and taking your fight for wild Florida into the realm of politics?

I didn’t just think about it, I did it. I ran for the Florida State Senate back in 1990. I lost in a close race and got rid of my guilt about being unwilling to serve. It was a great experience — and it got politics out of my system. Nowadays, I confine my work for natural Florida to the private sector.


During peak season, we’ve thought about camping out to get a seat at Mar Vista. Is there a magic word to secure a table?

There’s no magic word. Getting there first is the only magic that’ll work. It’s first-come, first-serve. That’s how we’ve always run our restaurants.


Mar Vista’s fish dip is in a league of its own. What’s the secret behind it?

Well, the secret is, we cut the fillets for our great fish — and all the leftover edges and scrap goes into making our great fish dip. Our guys cure it and smoke it, and it seems to get great reviews.


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