The world famous Anna’s Deli expands its business, adding hot items to menu
By Jane Bartnett
Siesta Key’s Anna’s Deli will soon be bigger and better than ever.
With construction underway, fans of Anna’s can look forward to a larger and even more welcoming space at Southbridge Mall. Construction has begun and is expected to be completed in a matter of weeks.
“We’re shooting for an October opening,” said Anna’s co-owner Dave Havill.
As Siesta Key’s oldest eatery, the landmark deli traces its roots back to 1971. It has a loyal fan following that reaches far beyond the borders of the Key and Sarasota. Known for its Surfer sandwiches and many other favorites, Anna’s is expanding into the space formerly occupied by the Things You Like women’s resort boutique.
Dave and Denise Havill, who have owned Anna’s Deli since 1998, are overseeing the expansion that will double their current space.
“This will create better flow — we’ll have more room for those eating in,” said Denise.
Dave echoed her enthusiasm.
“Our customers have been so understanding, even when the line sometimes stretches to the street and around the block,” he said.

Their daughter Ashley Paynter will continue to manage the Siesta Key Anna’s.
“It’s going to have an old-Florida feel,” said Dave. “We’re going to add some beautiful new photos of Siesta Key to the walls, but it will continue to be Anna’s Deli.”
In addition to the expanded retail space, Dave and Denise are both very excited about the new hot sandwiches and soups that will be added to the menu offerings.
“’The hots,’ as I call them, are going to be a big new addition,” Dave said. “Of course, all current Anna’s items will continue.”
He noted that their acclaimed Surfer sandwich still makes up 50% of their business.
“We’ve wanted to add hot items for a long time,” said Denise, but “we never had the space or ample electricity.”
“We’re adding Reubens and our version of the classic Italian sandwich that we call ItaliAnna,” she added. “Our version of the Cuban sandwich that we call the CubAnna is another reason to look forward to the fall opening. Both the ItaliAnna and the CubAnna can be found on the menu at Anna’s Deli University store, located near the UTC mall.
“The Siesta Key space simply lacked adequate space for these specialty offerings.”
The Anna’s new space was designed with extensive input from the employees.
“We wanted to create a positive atmosphere for our employees,” said Dave.
With the counter space running horizontally, the line will run from right to left. Customers will be able to watch the sandwiches being made and all the seating will be in the front of the store.
“We’ll have a greatly expanded and better kitchen, prep space, more freezer space, a new oven and much more kitchen equipment,” Denise said.
Once completed, Anna’s will expand from its current 875 square feet to 1,760 square feet.
A separate dining area will allow more space for those dining in and create a better flow. Dave pointed out that in the new space, bench seating will remain. Customers, he explained, will enter though the current doorway and exit through the door that had been the entrance to the Things You Like space.
“We’ll have two cash registers — one for orders and one for pick-ups. We’ll also maintain our 10:30 a.m. to 4 p.m. hours,” he said. “We’re not the restaurant that tries to be everything to everybody. We want to be 100% all the time. It’s a 50/50 deal. The customers and the employees have to be happy.”
As one of Siesta Key’s longest-running businesses, Dave and Denise have found a true formula for success.
“We have about 100 years of experience between us,” said Dave as the couple looked back on their careers and what led them to Anna’s Deli. The Bloomington, Indiana natives met while working together at a corporate franchise.
“We figured out what works best,” said Denise, explaining how they came to the decision to maintain Anna’s Deli at the Crescent Beach location as well as their second store in the University Town Center area.
“The Crescent Beach community is such a family-oriented place,” said Dave. “Our landlord does a great job with this center and the new development in this area of the Key is very beneficial.”
Both also spoke warmly of Anna’s customers.
“We have a ton of regular customers — families, workers, construction guys,” said Denise.
Added Dave, “We are adding to our staff. We’re looking for a good attitude and reliability.”
Visit annasdelis.com for updates on opening day.