Please ensure Javascript is enabled for purposes of website accessibility
Eating with Emma

6 historic restaurants to visit in Sarasota, Longboat and Lakewood Ranch

Michelangelo Pizzeria & Cucina opened in Lakewood Ranch in 2004.
Michelangelo Pizzeria & Cucina opened in Lakewood Ranch in 2004.
Photo by Nancy Guth
  • Arts + Entertainment
  • Eat + Drink
  • Share

Our community has become a mecca for outstanding culinary endeavors, with new restaurants opening doors faster (and some closing more quickly) than ever before. But the success of these newbies stands on the shoulders of the historic eateries that have long prepared the food our stomachs crave and put Sarasota on the map as a foodie destination.

If it weren’t for our past, we wouldn’t be where we are today.

Start the new year off right with a visit to one of the legendary dining spots in our area that make me excited to be writing Eating with Emma.

Harry’s Continental Kitchens

525 St. Judes Drive, Longboat Key; 941-383-0777;

Harry's cocktail selection has really aged like a fine wine.
Courtesy image

History of Harry’s: Harry and Lynn Christensen started their culinary journey in 1979 by making sandwiches for lunch and takeout dinners. In 1982, a deli was built, catering trucks were filled and a catering staff was hired. In 1985, the restaurant that has made many memories opened its doors. In 2009, the expansion of the convenience store came to fruition, and the rest is history. Harry’s continues to make its mark on Longboat Key 40 years on.

Must-Bite: Breakfast and brunch are served from 9 a.m. to 2 p.m. I always order the French omelet ($20) with brie and prosciutto with rye toast and grits. Dinner is served from 5-9 p.m. with an array of starters, salads and soups, but I’m here for the salmon ($42) baked with a macadamia crust and topped with poppyseed sauce, smooth grilled corn polenta and asparagus.

Must-Sip: For a brunch slurp, try the Harry’s bacon Bloody Mary with housemade bacon and infused vodka. For lunch or dinner, order the Pryat Old Fashioned with Pryat XO rum, dry curacao, orange bitters and a black cherry.

Patrick’s 1481

1481 Main St., Sarasota; 941-955-1481;

The Thai chicken flatbread ($16) from Patrick's.
Courtesy image

Patrick’s Past: I used to eat at the Kress Building location as a child where the current Fit2Run store is located. Jim Sullivan, or as locals know him, “Sully,” opened the staple Sarasota restaurant in 1985. I started drinking Shirley Temple’s with my grandfather there a few years later. Patrick's is now located a little farther down on Main Street, and my Shirley Temple is now a Dirty Shirley. The restaurant was recently reopened after renovations, drawing new and old customers with its Sarasota arts-theme decor and scrumptious dishes.

Must-Bite: At some point you should get the burger ($13.50 and up). However, football season gets me craving the chicken wings ($16) served with buffalo-style or housemade sauce with whiskey BBQ as well as carrots, celery and house ranch. My dad’s favorite was the Thai chicken flatbread ($16) with broccoli and red peppers, topped with Thai chili sauce. The latter items are also featured on the daily happy hour menu from 4-6 p.m.

Courtesy image

Must-Sip: Cucumber martini me up! Made with Svedka cucumber, lime soda, fresh lime juice, cucumber and mint, this cocktail is exactly what this eating lady craves.

Walt’s Fish Market Restaurant

4144 S. Tamimi Trail, Sarasota; 941-921-4605;

I can confidentially communicate to you all that Walt's has the best crab in our community.
Courtesy image

Way Back with Walt: The journey of Walt’s began back in 1918 when Claus Wallin came to America with the Ringling Circus. He soon fell in love with not just fishing, but with an Irish immigrant named Irene whose brother was a commercial fisherman. Fast forward to after World War II when the family descendants took their knowledge of fishing, markets and more and opened the first Walt’s Fish Market on Fourth Street and Osprey Avenue. In 2012 the Walt’s we know with the Chickee Bar was created, and live music became a must alongside the freshest seafood in town.

Walt's margarita is spicy, sweet and brings the heat.
Courtesy image

Must-Bite: I can confidentially communicate to you that this is the best crab in our community: steamer options come with two choices of sides. I would suggest corn on the cob and garlic sauteed green beans for the sides. Choose from king crab, snow crab and stone crab (all market price!). Or if you want a treat for you and your date, order Justin’s Pot (priced daily), which includes snow crab, shrimp, mussels, corn and red potatoes. Substitute king crab if you’re feeling up to it.

Must-Sip: Ghost pineapple margarita ($12) with spicy blanco tequila, margarita mix, pineapple juice garnished with pineapple and jalapeno. Ask your server about mocktail options too.

Michelangelo Pizzeria & Cucina

11517 Palmbrush Trail, Lakewood Ranch; 941-739-5656; (West Bradenton location temporarily closed for renovations)

Chronicles of the Cucina: This local, family-run Italian restaurant was founded in 1980, making it a pillar in not only the pizza industry but in Lakewood Ranch’s foodie history. Serving so much more than pizza, the Michelangelo menu includes a variety of soups, salads, appetizers and more, using top-notch ingredients.

Spice pepperoni and hot honey pizza is a new and must item.
Courtesy image

Must-Bite: The gourmet pizza selections range from BBQ Chicken ($4.25 slice, $24.95 whole pie) to the New Yorker with pepperoni, sausage, mushroom, onion and green peppers ($4.95 slice, $23.95 whole pie) to the Northern margherita pizza with pesto, garlic, plum tomato drizzle and a sesame crust ($4.25 slice, $24.95 whole pie). My personal pick of the pie is the chicken parmigiana pizza ($4.25 slice, $24.95 whole pie).

Must-Sip: Although adult beverages are not served here, you can enjoy Wine Wednesday and enjoy a complimentary appetizer when you B.Y.O.B of wine to dinner.

Waffle Stop

660 S. Washington Blvd., Sarasota; 941-952-0555;

That’s the Wonder of Waffles: In 1951 this classic, timeless diner opened its doors and has cooked up waffles ever since. The King himself, Elvis Presley, ate here on Feb. 21, 1956. He ordered three eggs, three pieces of bacon, pan-fried potatoes, two orders of toast and three glasses of milk. He returned the next day and ordered the exact same meal before leaving town after his concert.

Waffle Stop owner Dolly Hollinger has accrued a sizable collection of Elvis memorabilia over the years.
Photo by Harry Sayer

Must-Bite: There are a few everyday specials that bring me back to classic diners that I used to go to with my grandparents when I was a kid: Texas French toast ($6.25), golden waffle ($4.95) or two eggs any style, potatoes and toast, corned beef hash ($9.95).

Must-Sip: I’d love the trifecta any day of the week. Pour me a cup of coffee in the Waffle Stop mug, a glass of water and whatever juice of the day I feel like sipping on. Sorry Elvis, I will not be ordering three glasses of milk like you — chocolate or not.

Hob Nob Drive In

1701 N. Washington Blvd., Sarasota; 941-955-5001;

Hob Nob is also open for breakfast, 7-10:30 a.m.
Courtesy image

History of Hob Nob: Family-owned and -operated since 1957, this historic diner makes you feel like you’ve been taken back in time. The 1950s ambiance, diner delicacies and open-air casual atmosphere bring diners back to a simpler time that in a fast-paced world we tend to forget ever truly existed.

Hob Nob opened March 12, 1957.
Courtesy image

Must-Bite: It depends on the time of day you pull up to the Hob Nob. From 7-10:30 a.m., you’ll want to get your hands on the short stack ($5) with a side of home fries ($2.50) or sausage ($3). After 10:30, the menu is exactly what you envisioned this retro drive-in would dish out. From the half-lb. angus beef burgers like the perfect patty melt ($13) to the standard dogs ($5.25-$7.50) to the o-mazing onion rings — your fried food hankering is satisfied right here on Washington Boulevard.

Must-Sip: Save a significant amount of space in your stomach for sweets. Choose from shakes ($7) or floats ($6.50) to get what your sweet tooth deserves.

To restaurants that have been standing tall since the '50s to the newcomers whose doors have yet to open, we wish you all a very healthy, happy and prosperous 2024!

Correction: This article has been updated to with the correct first location of Walt's Fish Market.



Emma Burke Jolly

Emma Burke Jolly has worked at Observer Media Group since 2018 as the digital fulfillment specialist. Originally from Connecticut, this Gulf Coast transplant loves being by the water, reminiscing about what Longboat Key looked like in 1990, navigating life with her husband and their two Maine Coon cats, and sharing her foodie findings with you.

Latest News