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Feedback please for Milan/Orvieto car pickup/dropoff and Tuscany Itinerary

Feedback please for Milan/Orvieto car pickup/dropoff and Tuscany Itinerary

Old Jan 19th, 2019, 04:24 PM
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Feedback please for Milan/Orvieto car pickup/dropoff and Tuscany Itinerary

My husband and I will be returning to Italy in late May and are trying to decide how best to spend our travel days before meeting up with the rest of our party in Rome. I always try to pack in way too much and am trying to rein myself in! Please weigh in on whether the ideas below sound feasible, and thanks in advance for your help!

We are active travelers, ages 69 and 72, who usually pack a lot of sightseeing into each day, love beautiful scenery and visiting churches and museums, and aren’t interested in wineries or shopping.

In 2014, we were in Italy for 3 weeks and visited Lake Como (Bellagio, Varenna); Venice; Florence (with day trips to Lucca, Pisa, and Siena); and Rome (with day trip to Orvieto).

Here are our travel days -

Wed, May 25 - Arrive Milan Linate at 5:10 pm; Stay at hotel near Linate airport using hotel points; if not too tired, shuttle or taxi to central Milan for dinner and to walk around Galleria Vittorio Emanuele II

Thurs, May 26 – Shuttle or taxi from Linate to tour the Duomo early (opens at 8 am); walk through the Galleria if not done the previous evening; shuttle or taxi to pick up car at Linate; drive to Volterra to spend the night

Fri, May 27 Tour Volterra and San Gimignano, spend the night in Volterra

Sat, May 28 Drive through Crete Senesi to Pienza; tour Pienza; continue to Montepulciano; spend night in that area

Sun, May 29 Do Heart of Tuscany Drive (stopping for San Biagio Church, La Foce Gardens, San Quirico d’Orcia, Monticchiello; spend night in same place near Montepulciano

Mon, May 30 Montepulciano to undecided (Cortona? Perugia? Assisi?) Spend night in same place near Montepulciano

Tues, May 31 – Leave Montepulciano at 8 am; drive to Orvieto (about 1 hour); turn in car. Catch 11:25 train to Rome

Feedback would be appreciated regarding:

1) Typical time needed for visit to Duomo in Milan. Is it realistic to expect that we can see the Duomo early, shuttle or taxi back to Linate, pick up rental car, and be away by 2 pm?

2) Please share experiences of picking up car at Milan Linate (I read some terrible reviews about the Hertz rental there) and dropping off at Orvieto rail station

3) Pros and Cons of visiting Cortona, Perugia, or Assisi from Montepulciano; suggestions for other places to visit

4) Driving from Montepulciano to drop off car at Orvieto rail station

Again, many thanks for your insight!
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