Anna’s Deli – A Legend in it’s Time!

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By Diana Colson

Anna’s Deli has been a Siesta Key tradition for more than 41 years. The oldest eatery on Siesta Key, it is famed for its enormous “Famous Specialty Sandwiches”, especially its award winning Surfer.

Anna’s has continuously received culinary accolades. For six years, it has received the “Reader’s Choice Award for Best Sandwich” from the Sarasota Herald Tribune. For four years, it has received the “Best of the Best Sandwich Award” from the readers of SRQ Magazine. Most recently The Surfer was voted “Best Sandwich” by the readers of Sarasota Magazine.

Anna’s was established in Siesta Village in 1971 by a lady named Anna James. She started this little deli in a funky old house that once stood in the spot now occupied by the Daiquiri Deck. Anna James didn’t keep her deli very long, however:  she sold it to Rita and Jim Harrigan in 1973. Rita and Jim were to own the original Anna’s Deli for eighteen years, adding a second Anna’s in 1978 at the current location just south of Stickney Point Bridge.

In 1991, along came Alex Dragolovitch.  He purchased the two Anna’s and operated them until 1998, when they were bought by Dave and Denise Havill.

Now, Dave was a restaurant man.  For years he had been the Vice President of Operation for a food group in Indiana. Their business was putting up restaurants. Dave had developed approximately forty of them from the ground up—places like Miami Subs, Kenny Rogers, and Checkers. It was long hours and hard work, so he finally left the restaurant business and went into real estate. That field was okay, but he couldn’t help thinking: I’m restaurant, not real estate.

 Time came when Dave decided that he’d had enough of the Indiana winters, and opted take a sunny vacation. He pulled Siesta Key out of an AAA travel book, and phoned ahead to find a place to stay. He reached a man named Bob at Captiva Beach Resort near Crescent Beach, a place which is no longer in business.  Bob told Dave:  “If you’re lookin’ for a party, you gotta go to the other coast. If you want peace and quiet and a beautiful beach, Siesta is it—very family oriented.” Good enough, thought Dave, and down he came.

 While here on holiday, he looked up a broker, Dudley Carson at ReMax in the Village, and asked: “Do you have anything in Restaurants on Siesta Key?” Dudley said that he had two sandwich shops that were privately listed.  Perfect, thought Dave. Sandwich shops are open from 10:30 to 4:00, very civilized hours in the restaurant world.

It took a year and a half to work out the details. At the end of that journey, Dave found himself living in the place he wanted to be, and operating the kind of business that gave him time to enjoy the quality of life.

Dave had known Denise from his Indiana days. They had both been involved in the very same business. Of Denise, he cheerfully says: “She is the best restaurant operator I have ever met, except for myself, of course.”

Dave decided to see if Denise would like to join in on the Anna’s Deli project. “I am going to take the chance,” he told her. “Do you want to get involved in this too?” She did, and they began working together. They also started getting personally involved, and in 2002 they were married on Siesta Beach.

All three of Dave’s kids are in the restaurant business, so it wasn’t hard for Dave to convince his daughter and one of his two sons to move down. In 2003, son Dave opened Anna’s Downtown, located at 128 North Orange Ave., in the heart of our beautiful city.  After managing Anna’s Siesta for several years, daughter Ashley took over the operation of Anna’s Downtown in 2006 when her brother moved on to other things. In keeping with the concept of civilized hours, Anna’s Downtown operates from 10:30 to 3:00 every day except Sunday.

Son, Eric, remained in Indiana, a location he loves, although of course he comes often to visit. Eric bought a restaurant in Bloomington called Opie Taylor’s. It is a sports-related full-service restaurant serving Indiana University.

In 2012, Dave and Denise Havill opened Anna’s University. This newest branch is located at 8207 Tourist Center Dr. in University Park, and is open from 10:30 am to 8 pm seven days a week. At both the Downtown and University locations, “HOTLINE” sandwiches and soups have been added to the menu in addition to the regular sandwiches for which Anna’s is justifiably famous.

Most recently, the Havills reluctantly closed the Village location because of the difficulty of finding parking spaces in the Village. Siesta Key is now served only at the Crescent Beach location—6535 Midnight Pass Rd in Southbridge Mall, where it is open seven days a week from 10:30 to 4:00. When you stop there, say “Hi” to Pat Salerno.  She has been a fixture at Anna’s Deli for 32 years. “She’s the most incredible woman I’ve ever met!” says Dave of this trusted employee.

Check out Anna’s fabulous menus at Party Platters and delivery are available at all locations.

Phone numbers are:  Anna’s Siesta Key 941.349.4888, Anna’s Downtown 941-330-ANNA, Anna’s University, 941-893-5908

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