Struggling to come up with a logical plan to tackle Northern and Southern Italy in 18 days. Arriving last week of May 2018. This will be a trip with me (very active) along with my fairly active (yet slow) parents. I've been to Italy a number of times as well as my parents. We've already seen Rome, Florence, Venice, Assisi, Pisa, and Santa Margherita (we were only there a couple of hours). In addition to these towns, I've personally been to Amalfi Coast/Capri, Naples/Pompeii, Lake Como, and Sienna. So you will see some repeats on my end in the itinerary, but that's ok because I want to show them these places. Mom really wants to go to Venice, but she's been there on two very quick days trips in the past and is trying to spend a couple of days there. But as you will see from my tentative plan it kind of doesn't fit in there anyway. I'd happily pass on Venice (I've been three times already). Anyhow, would appreciate some feedback on my proposed list. Our airline tickets are purchased, we fly into and out of Milan (was the cheapest option).
May 29: Milan (I will arrive late the night before, they arrive at 8 am. So we will have a pretty full day here)
May 30: Milan
May 31: Day trip (Bergamo, Veronna...?; initially thought of Stresa, but with Como I suppose it's redundant)
June 1: morning train to Varenna/Como
June 2: Como
June 3: Como, afternoon train to Cinque Terre (I think we're going to have to stay outside of CT. Perhaps Levanto or a little north. Santa Margherita is nice, but I don't like that it's an hour away from CT. After reading some of the hotel/apartment listings in the RS guidebook we definitely want to avoid lots of stairs). Also, still unsure if we want to leave for CT in the morning or afternoon (either way, a long train ride).
June 4: CT
June 5: CT
June 6: CT to Tuscany (arrive morning to midday). Here's where I'm having a hard time. Ideally would like to base in Florence considering it's close to a major train station (which will make transport to our next stop easier). But are there other good options?We would like to focus our time on Sienna and Tuscan hill towns. I would like to rent a car, perhaps one or two days (I know parking in Florence might be difficult) and do at least the Heart of Tuscany Drive in RS book and see some other towns. Would really appreciate feedback on how to plan out this leg of the trip.
June 7: Tuscany
June 8: Tuscany
June 9: Tuscany
June 10: Tuscany
June 11: Morning train to Sorrento (technically Naples, will figure out later if we take the commuter train or pay big bucks for private transport).
June 12: Amalfi
June 13: Amalfi
June 14: Amalfi (Not 100% sure, but dad may want to see Pompeii. If that's the case should we drop one day from Tuscany and add it here?)
June 15: Amalfi/train back to Milan (unsure if we will want a little more time in Milan. If so, we would leave in the morning. Otherwise, afternoon train and stay in a hotel near the airport)