4 Weeks in Italy: Itinerary

20-25/8Milan4 nights
25-27/8Vernazza, Cinque Terre3 nights
27-30/8Florence3 nights
30/8-4/9Colle di Val d'Elsa, Tuscany5 nights
4-8/9Berlin, Germany4 nights
8-10/9Rome2 nights
10-13/9Sorrento3 nights
13-16/9Rome3 nights

20/8 (Mon) Late arrival in Milan
21/8 (Tue) Morning Milan sightseeing. Afternoon day trip to Bergamo
22/8 (Wed) Day trip to Turin or Pavia
23/8 (Thu) Day trip to Lake Como/Lugano
24/8 (Fri) Morning Milan sightseeing. Afternoon train to Cinque Terre. Vernazza sightseeing
25/8 (Sat) Cinque Terre hiking
26/8 (Sun) Cinque Terre and surroundings sightseeing
27/8 (Mon) Morning train to Pisa Airport. Train/coach to Florence. Florence sightseeing
28/8 (Tue) Florence sightseeing
29/8 (Wed) Florence sightseeing
30/8 (Thu) Midday pick-up of car. Drive to Colle di Val d'Elsa farmhouse. Perhaps a sightseeing stop.
31/8 (Fri) Day trip to Siena
1/9 (Sat) Day trip to San Gimignano and Volterra
2/9 (Sun) Tuscany
3/9 (Mon) Day trip to Pienza and Montepulciano
4/9 (Tue) Morning drive to Pisa for sightseeing. Midday return of car. Fly to Berlin.
5/9 (Wed) Berlin sightseeing
6/9 (Thu) Berlin sightseeing
7/9 (Fri) Berlin sightseeing
8/9 (Sat) Morning flight to Rome. Rome sightseeing
9/9 (Sun) Rome sightseeing
10/9 (Mon) Bus to Sorrento. Sorrento sightseeing
11/9 (Tue) Day trip to Amalfi Coast - Positano, Amalfi, Ravello
12/9 (Wed) Day trip to Capri
13/9 (Thu) Bus to Rome. Rome sightseeing
14/9 (Fri) Rome, perhaps a day trip to Orvieto/Assisi
15/9 (Sat) Rome sightseeing
16/9 (Sun) Depart from Rome