When Dave Havill first visited Siesta Key as a tourist in the summer of 1997, little did he know he’d be taking a big bite out of the place.
“I just by chance walked into Anna’s in the Village,” he recalled, “and I saw the hours and thought, ‘Only 10:30 a.m. to 4 p.m.?’ Then, I noticed the only thing for sale were cold sandwiches. I wondered, ‘How in the world do they succeed?’”
But then, he sunk his teeth into a roast beef on rye.
“It was the best sandwich I ever tasted,” Havill said. “It really was.”
He studied the place during the remainder of his stay at the nearby Tropical Breeze Resort, noticing the long lines that sometimes reached the parking lot. And he noticed repeat customers, often daily.
As for the location, it was in the heart of the action.
Were these things that made him curious as someone looking for a new business venture in life?
“Not really,” he said. “All that mattered to me was that sandwich. It was that good.”
He also began to believe in fate. After all, when he called the Tropical Breeze Resort on a whim, the owner asked where he lived and next thing they knew they were sharing stories about living in the same region of southern Indiana.
“It was the first place I called, and we had all these things in common with our time at IU (Indiana University),” Havill said. “I booked my trip right away.”
He also just so happened to have recently entered the corporate world as a vice-president of food operations. He knew the restaurant business.
Finally, a year later, he got wind of a private listing for two eating establishments that were on the selling block.
“When I heard it was Anna’s, I couldn’t believe my ears,” Havill said.
So, in the fall of 1998 he obtained a $200,000 loan and purchased the two Anna’s locations on the Key – one on Avenida Messina in the Village and a second in the Southbridge Mall. Also, part of the deal was the neighboring Marcella’s ice cream shop.
“This was destiny. I had to get these,” he said.
But he also paid an emotional price. The deal took months to coordinate and the closing itself lasted a grueling 17 hours.
“I remember it well – Hurricane George was approaching and the guy I bought the business from hadn’t boarded up any of the stores,” Havill said. “I was sweating it out.”
Step one for the new owner was striking a balance between a laid-back scene that everyone knew and the need for an influx of professionalism.
“I had the corporate knowledge and it needed some of that. For starters, there were a bunch of those negative novelty signs all over the walls. And the menu had a drawing of a girl in a bikini,” said Havill, who now shares ownership with his wife, Denise.. “As for the employees, I made it known they would be treated professionally and would have a positive work environment.”
In fact, Havill’s daughter Ashley Paynter holds the title of director of operations and personnel training and development. That’s not what you expect to hear at a family-owned mom and pop operation.
“We needed to get more organized and develop a brand,” Havill said. “We’re not a sub shop, we’re a specialty sandwich shop. We make them liked grandma used to make them, but we are also serious about what we do as a business.
“We also came up with the ‘Often imitated, never duplicated’ slogan for our shirts and ads, as well as the cool logo of the Surfer sandwich on a surfboard.”
Otherwise, tradition has ruled the roost.
“We’ve mostly left things alone and things look the same, which people like,” Havill said. “They want Anna’s to stay Anna’s.
“Now, we could have expanded our hours into the evening, but we want our employees to have lives. We have added some condiments – back in the day, all they had were cucumbers and onions – and some salads and coleslaw, but nothing that would be a surprise to customers. We’ve also added a couple of what we call signature sandwiches but have done it slowly and pretty much based upon request.
“Oh, and I decided to quarter the sandwiches. Although, to be honest, I still only let them cut mine in half. Beyond that, if it ain’t broke, don’t fix it. That’s been my mentality.”
The remarkable longevity of many Anna’s employees points to that emphasis on teamwork.
“When you work in that type of proximity to one another, you can’t help but feel you’re a family,” Paynter said.
It starts with Pat Salerno, who worked there for 34 years between 1978 and 2012. She was 80 when she hung up her apron and never missed a beat despite the often pressure-packed assembly-line atmosphere in the store.
“We always tried to come up with a slogan for her, like ‘a million served,’” said her daughter, Lisa Salerno, who now helps her mother out as she approaches 90. “Think of all the sandwiches she made.
“I know she just loved her co-workers and seeing her customers come back year after year. She watched many kids grow into adults and start bringing their own kids.”
It was Lisa Salerno, while a teenager, who introduced what many customers will remember as the plastic cup on the counter that had the message “Tipping is not just a city in China” written upon it.
“And boy, did they get the tips,” she said. “I should have received a cut, but I did receive free sandwiches.”
Meanwhile, Pat’s sister-in-law Theresa Jones worked by her side for about 15 years, as did Joan Pollack for about 17 years.
“We called Pat and Joan ‘sugar and spice,’” said Havill, who placed a photo of them on the wall of the Southbridge shop as a tribute. “Joan was the lady at the counter when I ordered my first sandwich. I’ll never forget that.”
Speaking of never forgetting, the Anna’s workers have demonstrated an incredible knack for knowing the names of customers. Something as simple as asking for a name at the time of taking an order, and writing it on the ticket so that name can be called, has gone a long way.
“It’s something we emphasize,” Havill said. “I know it means the world to our customers when they are greeted by their name.”
Kelly Foley is among the masters of that skill. She is one of two current employees approaching a decade of service.
“It’s just something I’m good at,” Foley said. “I like learning where people are from and telling them, ‘We’ll see you next year.’ Sure enough, they always come back. And when I remember their name, they’re shocked.”
Said Paynter, “She’ll even tell us what kind of sandwich they order before they get to the counter. And if someone accidentally orders white bread, she might say ‘I thought you liked wheat bread?’ And they’ll say, ‘Oh yeah, that’s right. Thanks.’”
Foley especially remembers those with the unusual orders.
“Chicken salad and roast beef is one of them. A sauce (only) sandwich is another,” she said.
Why is it still called Anna’s and not called Dave’s?
“Because Anna James is no one to mess with,” said Havill with a laugh. “I know better. She’s a legend.”
In just two short years, James became a local icon after opening the original shop in 1971 in an old-world Florida bungalow at 550 Ocean Blvd. Today, that site is home to the Daquiri Deck.
It was her first foray into the restaurant business and was something she hadn’t planned. But there she was, spending $1,200 toward rent, knowing after six months she’d have to pay an additional $200 a month.
The rest, they say, is history.
“Yes, I’m amazed it has lasted 50 years and that it’s the Key’s oldest eatery. It pleases me to no end,” the 89-year-old James said from her home in Tampa. “It just shows I must have done something right. Truth is, I was never that ambitious. At the same time, it never occurred to me that I might fail.”
She was certain there was a demand.
“There wasn’t much of anything at that time. I just wanted people coming off the beach to have a place where they could eat,” James said. “I know I did.”
And boy did she deliver, coming up with an idea to stack the sandwiches higher than most had ever dared with a mountain of freshly sliced cold cuts.
Then, there’s the sauce. It’s something people will forever ask about and the answer that it’s just a “mustard-mayo mix” doesn’t cut it with most. They want details, James said.
“So many have tried to duplicate it, but they never will. And I’ll never give out the recipe in respect to the current owners. It will remain a secret,” James said. “But I will tell you that the person I sold the business to (Jim Harrigan) took out an original ingredient. And it was a major ingredient. And I’ll leave it at that.”
From where did the recipe originate? A family tradition, perhaps?
“Actually, some guy from New York City gave it to me when I was first opening up. I can’t remember his name – actually, I’m not sure I ever knew it — but I do remember him leaving it with me and saying, ‘By the way, you’ll never make it,’” James said. “How about that? Boy, was he wrong.”
A search for the right bread was also on her plate. Knowing her sandwiches were huge and loaded with sauce, building the perfect foundation was critical.
“I had heard about someone who made canned bread in Tampa, creating a round sandwich which I liked because it was different, so I checked it out,” James said. “I wanted something strong yet soft and spongy, and that was it. I was sold on the idea, but I did have to work a long time with that baker to get it just right.”
Havill to this day still values the importance of the canned bread.
“It’s irreplaceable. We have always had to look far and wide for people who can make it to our standards,” he said, “and few places can. Today, we have it shipped down from a baker we found in Largo.”
What James does recall with vivid detail are those who helped her get things rolling a half century ago.
“Suzanne St. Clair was a Realtor who pulled people in off the streets for me,” she said. “During the rush, she’d even help in the kitchen on her lunch break.”
It’s the same tiny kitchen that customers would visit when lines got long to take a peek at what was going on.
“They’d take the lid off my soup kettle to see what I had that day,” James said. “People felt at home, and that’s partially because it was literally a house. You couldn’t help but not feel that way.”
Meanwhile, James even remembers her early regulars.
“The two men who were among my first customers, and were there every day, were Bill Shroder and Gil Waters. They were so funny. Gil was the one who suggested I put tables on the front porch,” she said.
Then there’s artist Barbara Barrett, who sketched the building.
“I heard people would buy her drawing for their wall at home,” James said. “That’s how much they loved Anna’s.”
Many artists would take a liking to Anna’s. James recalled a certain table that saw the likes of John MacDonald, the famous crime novelist; Syd Solomon, a renowned abstract painter; and MacKinlay Kantor, a Pulitzer Prize-winning writer.
“That’s when I knew we were on the map,” James said. “I had also added wine to the menu, so it became a real gathering place.”
By the time 1973 rolled around, James had some health struggles and was exhausted. She decided to sell despite her raging success.
“I practically gave it away,” she said, “but I don’t have any regrets. I wanted to do other things.”
Those things included her residing in Ashland, Oregon; Spring Island, South Carolina; the North Carolina mountains; Aspen, Colorado; and Washington, D.C.; Finally, she has returned to the area.
“I’ve had a wonderful life,” she said, “and I’m writing a memoir about it.”
Will Anna’s be part of it?
“Oh, yes,” she said. “That was such a fun time. In fact, I still visit Anna’s whenever I can.”
Harrigan left the original building soon after his purchase of Anna’s, taking the shop to the Avenida Messina location, and then added the Southbridge Mall location in 1978. He called it Anna’s II.
Due to declining health, he sold it in 1991 to Alex Dragolovitch, his neighbor, who would sell it to Havill.
Despite the success of the Village operation, Havill said he ran into constant headaches due to limited parking, troublesome landlords, and unreasonable neighbors. The store’s locale would bounce from one spot to the next and potential customers were known to give up on finding a parking spot and instead drive down to the south shop.
“Did you know that Anna’s had five different locations in the Village?” he said. “In 2012, we finally gave up in the Village but of course kept the Southbridge shop. People were upset, and I had to put a sign on the door here that explained things. I simply didn’t have a choice.”
He had already expanded his business to downtown Sarasota in 2003, closing it in 2016, and took the equipment from the Village shop out to University Park for a new operation in 2012.
Hot sandwiches are now on the menu there, but the Siesta Key site isn’t large enough to accommodate an oven for such a plan, Havill said.
“I am on the lookout for some space down here,” he said of the south end, “and I wish I would have kept that space next door where the ice cream store was located. But I let that go years ago, as soon as the lease was up.”
Speaking of leases, is Anna’s a shop that could lose its cozy spot?
“No way. I’m signed up through 2025. I used to have to go with three-year extensions, but I was able to get it up to six years at a pop,” Havill said. “If I could do 20, I would.
“When we decided to do this, we wanted it to stay with the family. We wanted it everlasting. And the kids have followed – Ashley has her big role and also manages the Siesta Key store, my son David ran the downtown store, and my son Eric runs the University Park store. We’re all in.”
Certainly, the ongoing success is also a motivator.
“It’s incredible – our Surfer has been awarded ‘best of’ for 21 straight years in different publications and magazines,” Havill said.
His Southbridge shop in 2019 was also featured on a “Best Thing I Ever Ate” segment on the nationally televised Food Network.
“We aren’t going anywhere,” Havill said. “It’s funny, but I often get asked, ‘How did you get ahold of this?’
“I’ve also received several on-the-spot offers from people in line. There’s a Canadian guy who, for 12 straight years, has left me a note with an offer when he visits.
“But the answer is always no.”