My wife and I are 69 and early 70's and reasonably fit for travel in late August for 3-4 weeks trip Venice to Rome by way of sail through eastern Adriatic August 2025
I was considering and preferred entering the region by way of Ljubljana for a 3 night stay instead of by way of Milan thereby eliminating the lake regions of Magiorre or Como but the airfare is considerably more expensive from MIA to Ljubjana.
8/20 arrival in Milan MXP
8/20 train to Stresa
8/20-8/21 Stresa, 2 night stay
8/22 train to Venice
8/22 Venice, 1 night stay, brief visit, ready to board Royal Clipper 8/23
8/23 Board Royal Clipper leaving Venice proper 8/23
8/23-8/30 Royal Clipper, 7 nights, tour Dalmatian coast, return Venice 8/30
8/30-9/1 Venice, 3 night stay
9/2 train to Verona, stop in Padova for day
9/2-9/4 Verona, 3 night stay (stay in the loop of the old section or in the Veronetta to the east of core city to enjoy the pedestrian friendly atmosphere) train day trips in Veneto to Vicenza and possibly Padova, Brescia.
9/4 Verona, Arena di Verona, Aida
9/5 train to Bologna
9/5-9/6 Bologna, 2 night stay; day trip by train to Ravenna
9/7 train to Florence (Il Treno Di Dante to Florence, if running 9/7, otherwise slow train to Florence via Brisighella and Marradi
9/7-9/10 Florence, 4 night stay, day trips by train to Luca, ? elsewhere
9/11 rent car Florence (drive through Chianti region from Florence to Siena (through the SR222 Chiantigiana Road. Stop in Greve in Chianti, Radda, or Castellina in Chianti for wine tasting and lunch)
9/11 return car in Siena
9/11-9/13 Sienna, 3 night stay
9/14 Rent a car Siena (from one of the agencies near the Siena train station or just outside the city center (outside the ZTL))
9/14-9/16 Drive Through Southern Tuscany touring Val d’Orcia, Montepulciano, Pienza, and Montalcino, Orvieta (Umbria)
? Where to stay with car on those days and for how long
9/16 drop car Orvieto (Umbria) or Chiusi
This avoids driving into Rome before leaving Tuscany
9/17 Train to Rome from Chiusi of Orvieto
9/17-9/21 Rome, 4 night stay
Suggested stay in Monti neighborhood
9/22 Leave Rome FCO by air to TLV