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Chart a Course to Delicious Dockside Dining

Ophelia’s on the Bay’s sesame blackened big eye tuna with butter poached lobster tail.


Twenty years from now you will be more
disappointed by the things that you didn’t do
than by the ones you did do. So throw off
the bow lines. Sail away from the safe harbor.
Catch the trade winds in your sails.
Explore. Dream. Discover.
—Mark Twain

We feel privileged to live in the City of Sarasota, buffeted by warm breezes and surrounded by white sandy beaches. We love traveling the curve of Mound Avenue and taking in the tranquil beauty of boats with white sails bobbing in the bay; cycling over the narrow bridge that leads to Casey Key; rollerblading along Gulf of Mexico Drive towards Holmes Beach; stopping to admire the reflection of the clear blue sky in the cerulean water that laps against the bridge at Coquina Beach. Of course, there’s nothing quite like taking a leisurely boat trip around paradise. And so we’ve come up with a definitive guide to the restaurants along the way that are “worth the sail.”

“Zero Miles to Happiness” at Casey Key Fish House


Casey Key Fish House has formed its own waterfront entertainment destination on a quiet little cove at the entrance to Casey Key. It features an unpretentious atmosphere and a seasonal specials menu that reads like the menu board at a swanky, white-linen ballroom. There’s nothing like docking your boat at Mile Marker 32, eating a decadent bowl of bouillabaisse, and then wandering over to the much-lauded Tiki Bar to listen to live music (Friday through Sunday) and enjoy a tropical drink mixed up by a friendly bartender. You’ll soon be feeling like an extra from the movie Cocktail and the ready smile of owner Jim Von Hubertzo only adds to that mystique.

Casey Key Fish House: 801 Blackburn Point Rd, Osprey; 941-966-1901;

“Nester” Shrimp & Crabmeat Salad in a potato basket at the Crow’s Nest


“As the crow flies” is an idiom meaning the shortest distance between two points, and in the case of the Crow’s Nest in Venice the shortest distance between hunger and pleasure is the short walk from their 200-foot base dock to the stunning view and tasty fare available from the upstairs dining room. Passing through the cozy dark interior of the downstairs dining room I am reminded of an inn from a bygone era serving whiskey and hearty stews to the likes of Ernest Hemingway. The contrast is striking from the hustle and bustle and convivial atmosphere downstairs to the soothing, tinkling music and large windows upstairs, facing the sparkling waters of the Venice Inlet Channel. The beautiful deck offers outdoor dining and the dinner menu changes to reflect seasonal specials.

Crow’s Nest Marina Restaurant: 1968 Tarpon Center Dr, Venice; 941-484-9551;

Great white shark hanging in front of Phillippi Creek Oyster Bar is a Sarasota landmark.

Renting a Duffy electric boat is the perfect way to enjoy an afternoon or evening at the Crow’s Nest


Check your nautical chart for Channel Marker 6 at the south end of Longboat Key and you’ll find yourself at Dry Dock Grill, a casual indoor-and-outdoor dining experience on ritzy Longboat Key. The fresh seafood is sourced locally and the restaurant’s airy, open dining room boasts unobstructed panoramic views. Dry Dock has a core of devoted regular clientele as well as seasonal rotation of visiting characters—and the staff is as loyal as the customers. Shamron has been working at Dry Dock for over a decade and she’s ready with a recommendation for sinful lobster bisque or the simple perfection of a good grouper sandwich, as well as a wealth of local knowledge. She gestures around her with an expansive smile and shrugs, “This place is the best.” We can’t help but agree as we take in the only live entertainment Dry Dock has on offer: playfully cavorting dolphins.

Dry Dock Waterfront Grill: 412 Gulf of Mexico Dr, Longboat Key; 941-383-0102;

Sunset view at Marina Jack


We’d be remiss if we didn’t include Sarasota’s premier waterfront dining destination, Marina Jack. Located in the heart of downtown Sarasota, Marina Jack affords visitors three different dining options—all with stunning views of Sarasota’s sunsets, which are as unique and exquisite as individual snowflakes but far more colorful. Baskets of tortilla chips and addictive fresh, sweet salsa paired with margaritas and island music conspire to re-create the feel of the leisure deck of a fabulous cruise ship island hopping in the Bahamas. Marina Jack offers dining cruises, private dinner boat excursions, live music, and two restaurant docks located at Mile Markers 8A and 10. Besides all of their private slips, Marina Jack also provides 20 transient slips that can be booked ahead of time for those who want to spend the night in our fair city.

Marina Jack: 2 Marina Plaza, Sarasota; 941-365-4232;

Tuna with Asian noodles at Casey Key Fish House


Ophelia’s on the Bay features a seasonal menu, heavily reliant on fresh, local ingredients, served in an environment that harkens to a simpler, more elegant, time. From the moment you surrender your keys to the solicitous valet drivers and make your way into the cozy interior of this Old Sarasota icon, you’re transported. Wandering through the dark intimacy of the bar and then back out through the dining room and onto the outdoor dining terrace, we can’t help but feel like an honored guest at a private home belonging to a Jay Gatsby or, more likely, a John Ringling. Arriving by boat only adds to the feeling of belonging to another era and increases the already-fragrant aromas of romance and mystery that seem to waft through the air as you sip a handcrafted cocktail and take in the picturesque calm of the bay.

Ophelia’s on the Bay: 9105 Midnight Pass Rd, Sarasota; 941-349-2212;

Relax and unwind with ocean breezes from the Gulf of Mexico at Marina Jack’s Portside Patio


A sign in the water just past Mile Marker 72 warns passersby to slow down for manatees, and the houses situated along the creek can tell you that the peaceful creatures have been spotted here and there over the years. Phillippi Creek Village is home to two of Sarasota’s favorite waterfront dining locations: casual staple Phillippi Creek Oyster Bar and the more upscale, relative newcomer, The Table. Phillippi Creek’s popular menu of fried and grilled fish platters and classic appetizers such as Beer-Boiled Shrimp and Oysters Rockefeller has only been improved by the addition of intriguing, flavor-forward specials such as the Grilled Snapper Tacos, which make Phillippi Creek a good choice for seafood purists and more adventurous foodies alike. There are slips available for both motorized and nonmotorized crafts, so be sure to stop by for a bite as you kayak up the creek.

Phillippi Creek Restaurant & Oyster Bar: 5353 Tamiami Tr, Sarasota; 941-925-4444;

Pull up a chair and enjoy the fun and sun at the Casey Key Fish House Tiki bar.


Pier 22 is located on the Manatee River and offers multiple dining options to suit your every mood. There are private dining rooms, a casual patio, a ballroom, and a waterfront dining terrace.

The restaurant offers catering options for special events such as weddings but embraces the casual diner with the same enthusiasm and hospitality.

The views are breathtaking and the menu is eclectic, featuring everything from fresh game to handmade pizzas and sushi. The Sunday Brunch is fast becoming a local tradition thanks to delicious food and $3 mimosas and bloody marys. The restaurant offers winemaker dinners and Chef Greg offers cooking classes, so be sure to check their website before you plan your boat trip— you may want to plan your cruise accordingly.

Pier 22: 1200 1st Ave W, Bradenton; 941-748-8087;


The Riverhouse Reef & Grill and Riverside Café in Palmetto offer waterfront dining in a casual atmosphere with plenty of patio seating and live music. Located at the Regatta Pointe Marina the restaurant offers an incredibly popular daily Happy Hour from 3 to 6pm featuring discounted drinks and fun and tasty appetizers such as the Cabo Fish Bites and Coconut Shrimp. Not only can you dock your boat for a fabulous meal but the Regatta Pointe Marina offers the opportunity to “live aboard” your boat and take advantage of the myriad hotel-like amenities such as a Health Club Exercise Room and two Captain’s Lounges. The Riverhouse is a popular choice for local events and fundraisers and the restaurant believes in giving back to the community of which they are a focal destination.

Riverhouse Reef and Grill: 995 Riverside Dr, Palmetto; 941-729-0616;


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