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A romantic two weeks: Rome, Tuscan countryside, Florence, and the Amalfi Coast. Mix of historic city hotels and Tuscan villa stays.
Build this tripDays 1-3 Rome at Hotel de Russie or J.K. Place Roma. Vatican + Colosseum with private guides. Day 4 train to Florence 1h30m. Days 4-7 at Portrait Firenze or Hotel Savoy, Uffizi private tour, Duomo climb, Oltrarno neighborhood. Day 8-10 Tuscany: pick up a car, 3 nights at Castello di Casole or Borgo Santo Pietro, vineyard tours in Chianti, cooking class afternoon. Day 11 return car in Florence, train to Naples, private driver to Positano. Days 11-13 at Le Sirenuse or Il San Pietro, private boat day to Capri, sunset aperitivo at Franco's Bar. Day 14 fly NAP home. Book restaurants on the Amalfi Coast 3-4 weeks out.
May-early June or September-early October.