Florence's romantic hotel landscape divides between the grand historic hotels of the river-facing north bank and the more intimate boutique properties tucked into the Oltrarno neighbourhood south of the Arno. Both approaches work, but they offer quite different versions of a Florentine romantic experience.
The river-facing luxury hotels — Portrait Firenze, Hotel Lungarno, the St. Regis — provide the classic Florentine view: the Ponte Vecchio lit at dusk, the hills of Fiesole beyond, and the Vasari Corridor connecting the Uffizi to the Pitti Palace along the south bank. A room with an Arno view is one of the world's great hotel views and worth the premium it commands.
For a more intimate alternative, the Oltrarno neighbourhood across the Ponte Vecchio has a cluster of smaller hotels in converted palaces that feel genuinely Florentine rather than internationally luxurious — Soprarno Suites, AdAstra Firenze, and the various privately-run boutique hotels on Via dei Serragli and Via Maggio give access to Florentine neighbourhood life rather than the tourist-facing historic core.
Dinner is central to a romantic Florence break — the city's osteria tradition, with its shared tables, paper tablecloths, and dedication to Tuscan simplicity, is more conducive to conversation than elaborate tasting menus. La Giostra near Santa Croce, Buca dell'Orafo near the Ponte Vecchio, and Buca Mario (Florence's oldest restaurant, 1886) are all ideal for a relaxed romantic dinner.
The practical romantic Florence itinerary: check in on Friday afternoon, walk to the Ponte Vecchio at sunset (best light at 7–8pm in summer), dinner at a neighbourhood osteria, cocktails at the bar of Portrait Firenze or the Florentine Lounge of the Grand Hotel. Saturday: Uffizi Gallery in the morning (pre-book tickets), afternoon drive to Fiesole for hilltop views, return for Aperol Spritz on a terrace. Sunday: Boboli Garden walk and Pitti Palace before the afternoon train north.