Settle into your first night with Dinner at Sostanza in San Frediano, one of those no-frills Florentine spots that feels reassuringly local the second you walk in. It’s a classic choice for hearty Tuscan comfort food, and after arrival it’s exactly the kind of dinner that doesn’t ask much of you: expect around €25–40 per person, and if you’re hungry, this is the place to lean into the house specialties and just enjoy being in Florence. If you’re coming from the center, it’s an easy taxi or a pleasant walk over the river depending on where you’re staying.
From there, wander a few minutes to Piazza Santo Spirito, which comes alive at night in a very Florentine way — relaxed, social, and just busy enough. The square is great for a slow post-dinner loop, and you’ll get your first real feel for the Oltrarno side of the city, where evenings tend to be a little less polished and a little more lived-in. Keep it loose here; there’s no need to rush, and this is a nice moment to simply sit with the atmosphere for 30–45 minutes before heading on.
If you want something sweet, stop at Gelateria La Carraia near Ponte alla Carraia for a scoop or two before crossing the river. It’s popular for a reason, and a cone or cup will usually run about €3–6. Then finish with an easy night walk to Ponte Vecchio, which is especially lovely after dark when the crowds thin out and the Arno reflects the lights. It’s only a short stroll from the gelato stop, and this is the right kind of first-night sightseeing: iconic, low-effort, and just enough to leave you eager for tomorrow.