Stop&Shop Market has the best Cuban sandwiches in downtown St Petersburg. It's at the edge of downtown, at the corner of Fifth Avenue N and 1st St N (432 1st St North) and is very unpretentious. Yet - people line up for their hot pressed Cubans - I like mine "Original", thanks. They make lots of other sandwiches to order, so if you're going in to pick it up at lunchtime, you should call ahead (727) 822-0276. Then take it back to your office, your condo, your hotel, or even better - take it to one of the parks and enjoy the Florida weather and lifestyle.
There are no tables inside or outside Stop&Shop Market so it's Take Out only.
Downtown St Petersburg has lots of waterfront parks, so enjoy your lunch, peoplewatch and boatwatch, maybe get a walk in for a little exercise, and enjoy your Stop&Shop Cuban. Prices are reasonable - I can send Rob to get my Cuban and buy one for each of us for less money than many places charge for just one Cuban.