When two people pick each other after a Speed Date Tampa night, the next question is always the same: where do we go? Around Tampa the honest answer is the Riverwalk. It runs a little over two miles along the Hillsborough River from the north end of downtown to the Channel District, it is flat and lit, and it has a bar, a park or a bench every few hundred feet. It is the rare first-date location where you can adjust the plan halfway through without anyone noticing. Here is how we would use it.
Start at one end, not in the middle
Pick a meeting point at either end — the park lawns near the museums at the north end, or Water Street and the Channel District at the south end — and walk toward the other. A walk with a destination gives the conversation somewhere to go, and you can always stop short. Meeting in the middle tends to turn into standing around deciding.
Go late afternoon, stay for the light
Tampa heat is real from May to October. Meet an hour before sunset: the river breeze arrives, the bridges and the minarets across the water light up, and by the time you sit down for a drink it is actually pleasant outside. In the cooler months any time works, but sunset is still the best part.
Have the second stop in your pocket
The best first dates here move once. A drink at a patio along the walk, then either a slow loop back or a short hop somewhere else: over the bridge to Hyde Park and Bayshore Boulevard if things are going well, or back to a garage if they are not. Knowing where you would go next is the difference between an awkward pause and an easy “want to keep going?”
What to skip
Skip game nights when the arena lets out and the whole south end is a crowd. Skip anything with a two-hour wait. Skip the big dinner reservation on date one — save it for date three, when you know it is worth it. And check the forecast: a summer afternoon storm usually clears in an hour, but plan a covered spot just in case.
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