Bayshore Boulevard is the longest continuous sidewalk in the United States — four and a half miles of seawall and balustrade along Hillsborough Bay, from downtown Tampa south to Gandy Boulevard. The bay side is famous, photographed, and full sun. The inland side is the one to walk. Through Hyde Park and the Bayshore neighborhood, the inland sidewalk is lined with a planted row of bald cypresses and a few mature live oaks. The cypresses were put in by the city in the late 1990s and are now thirty feet tall — enough to throw a continuous shadow at the right time of day.
The trick is to walk the route south in the morning. The eastern building line — old Hyde Park bungalows and the new mid-rises near Hyde Park Village — throws a building shadow across the sidewalk that augments the cypress cover from about 7:30 to 10:30. After that the geometry shifts and the bayside walk becomes the better bet for the wind off the water. The picks below are all morning routes; we’ll come back to the afternoon ones in a separate note.