- March 3, 2026
-
-
Loading
Loading
National Pack Your Lunch Day (March 10) is financially responsible and practical in theory. In practice? I started going out to lunch in high school and I haven't stopped since.
Let's be honest about high school. Back in my day, bringing your lunch in your pail was social sabotage — especially when friends had licenses, cars and zero fear of being a few minutes late to fifth period.
That’s when it started. The habit. The thrill. The “I’ll just grab something quick.”
I’d skip class (sorry, Mom, but it was mostly free periods) to hop in the car with my upperclassman friends and head to one of our beloved Connecticut delis.
That's where we were sure to find breakfast sandwiches the size of your face, chicken cutlet sandwiches that I still swear can’t be replicated, and always, a crisp Diet Coke. We’d roll back into the school parking lot like we’d just completed a very important culinary mission. Then we'd use our free period to eat and joke around in the cafeteria.
Fast forward to my days at Observer Media Group. Not much has changed (especially my Diet Coke addiction). At least twice a week, as noon approaches, the group text lights up, “Where are we going for lunch?”
National Pack Your Lunch Day doesn’t stand a chance against the siren call of the great lunches in our area. These are the places that continue to make it impossible for me to brown-bag it like a responsible adult.
1825 Hillview St, Sarasota; 941-330 -9302; SouthsideDeliSarasota.com
Bread Winner: I did my best to try and recreate Southside's Italian sub ($11.25) for a friend's birthday because when you see her face bite into this sammie, you know it makes her tastebuds and her heart full of joy. When the group text pops up, "Southside Deli?" you know at least one Italian is making the takeout roster — piled high with salami, capocola, provolone, mayo, lettuce, tomato (pass for me!), onion, cherry peppers and sub dressing.
This is What Deli Dreams are Made of: The chicken Caesar Nutmeg State deli loyalists were unwrapping that beauty long before it was trending. Order Southside's take with blackened chicken ($11.95) for that extra kick, grab a Diet Coke and voila, lunch break is complete.
1695 10th St, Sarasota; 941-330-0245; MaximilliansCafe.com
Bread Winner: Every time our crew orders from Max’s, everyone wants to know about the salad, “What did they even put in here?” Whatever magic Max’s is sprinkling, it makes their greens ridiculously addictive. My personal obsession? The Southwestern Caesar ($12.49) with crisp garden-fresh romaine, fire-roasted sweet corn, pecans, tomatoes (no thanks, catching on yet?) bacon and grilled chicken, all with the Caesar on the side so you control your drizzle.
This is What Deli Dreams are Made of: Let me wipe my mouth as I drool while writing about this one. The fantastic Frenchie wrap ($11.99) is rolled up with honey maple turkey, French brie, thinly sliced apples, tomatoes (not for me!), shredded lettuce, honey mustard in a tortilla wrap. After noshing on this one, I can see why the French love, love.
4657 Cortez Road W, Bradenton; 941-896-3333; PRPBagels.com
Bread Winner: If there’s one thing that instantly transports me back to my Connecticut deli days, it’s a perfectly executed chicken cutlet — breaded, crisp, tender and just begging to be stacked into a sandwich. Pork Roll Pete’s gets it so right. Their Milanese sandwich ($12.50 and up) is piled with breaded or grilled chicken (upgrade to cutlet for $5), fresh mozzarella, arugula, pesto, finished with a drizzle of EVOO and balsamic glaze. Nostalgic lunch deliciousness at its finest.
This is What Deli Dreams are Made of: The Red Bank Classic ($12.50) is one for the books! Breaded or grilled chicken, creamy burrata, add Italian long hots (peppers that can be mild, sweet or quite hot!), arugula and a drizzle of balsamic glaze. One bite and you’ll understand why classic deli selections like this never go out of style.
2300 Bee Ridge Road, Sarasota; 941-924-2268; FocacciaSandwich.com
Bread Winner: When this local gem entered the "where should we go for lunch?" chat, it completely rearranged my sandwich standards. Focaccia's avocado ($9/$16) sandwich comes with porcetta, oven-dried tomatoes, sharp white cheddar, bibb lettuce, and a generous swipe of avocado Green Goddess dressing. This is the kind of sandwich that turns a lunch date into a respectfully silent affair. Wen you’re fully committed to the foodie experience, small talk feels like a distraction.
This is What Deli Dreams are Made of: The daily sandwich specials are the main event here. One scroll through their Facebook page and you’ll see what I mean: charred eggplant, prime rib, duck confit, short rib birria dripping in all the right ways, and pastrami that deserves its own standing ovation.
8225 Natures Way Unit 111, Lakewood Ranch; 941-500-1082; LakewoodRanchDeli.com
Bread Winner: My favorite part of this Lakewood Ranch eatery? Breakfast sandwiches served all day! Because sometimes you just want a good old bacon, egg and cheese ($8.95) at noon. Need lunch for lunch? Snag a reuben, made with your choice of corned beef, turkey, pastrami or a combo ($14.95), that means business, or the classic chicken salad sandwich ($12.95) that would have made a brown-bag lunch look cool even in my high school cafeteria.
This is What Deli Dreams are Made of: Daily soups and crisp, fresh green salads and 10-inch subs like the chicken tender sub ($13.95) that gives Publix a run for its money, round out a menu that somehow manages to hit every craving, every time.
![Brian Taylor, who works as executive vice president for Perform[cb], has been working from CoworkLWR since 2021 in order to have a separation between work and home life. He enjoys the opportunities to network with fellow remote workers at the new location.](https://media.yourobserver.com/img/photos/2026/02/27/IMG_1642_r452x360.jpeg?0dd7e9171d3bd5845bc057d4569a0a31ba6981d7)