From $797 per person for 5 nights in Puglia, flights from New York included.
Puglia in late November is the Italy you actually want. The tourists cleared out weeks ago. The olive harvest is wrapping up, the wine is fresh, and the Salento peninsula feels like it belongs to you. Temperatures hover in the low 60s. Cool enough for long walks through whitewashed villages, warm enough to sit outside with a glass of Negroamaro.
Here's the exact trip.