For anyone interested, here is a link to our trip report covering three weeks in Italy during Aug-Sep 2019. (Posted in the Trip Reports section of the forum). https://community.ricksteves.com/travel-forum/trip-reports/italy-2019-sicily-sorrento-amalfi-pompeii-rome-orvieto-tuscany-siena-florence-cinque-terre-milan
Itinerary my wife and I followed:
- SICILY - CANTANIA 2 nights, with visit to ORTIGIA.
- SICILY - TAORMINA 1 night.
- SORRENTO 3 nights, with visits to the AMALFI COAST, POMPEII, NAPLES.
- ROME 2 nights.
- ORVIETO 2 nights.
- Near MONTEPULICIANO 3 nights, with visits to PIENZA, MONTEFOLLOCINO, near MONTALCINO, wineries, an abbey, etc.
- SIENA 3 nights, with visits to FLORENCE and SAN GIMIGNANO.
- CINQUE TERRE (Manarola) 3 nights. Visited all five Cinque Terre towns.
- MILAN 1 night.