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Rome and Tuscany with 90 yr old

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Hi! I am planning a trip to Italy in October. This will be my first trip to Italy. After all my research, I have come up with an itinerary. Could you please help me fine tune our itinerary.

We are going on this trip because our mom who turned 90 this year would like to visit Rome during the Jubilee year of Mercy. The only must do for her is the Vatican tour. She has been to Italy a few times in her younger years. She is mobile but does tire easily. My plan is for us to do one major thing everyday using mostly private tours and vans for transportation. This trip is about having fun and building memories. It is not meant to see all the famous sites nor to see them in depth. We are a party of 8, my siblings and mom. Total number of days - 14 including travel days. Breakdown on trip: Rome - 4 days, Tuscany - 6 days, Rome - 2 days.

Day 1 - Travel day
Day 2 - Arrive Rome - rented an apartment near the Spanish steps. Free day to walk around and food shopping.
Day 3 - Rome City Tour - (6 hours) Private van - we will do a hop on hop off tour of the city. Places we would like to drive by/see: Colosseum - outside only, Forum, Palatine hill, Pantheon, Piazza Navona, Campo di Fiori, Trastevere, Jewish Ghetto.
Day 4 - Sunday mass at St. Peter’s Basilica - walk around Piazza Navona/ Campo di Fiori
Day 5 - Vatican Tour - Booking private City Wonders tour with early Sistine Chapel entry
Day 6 - Rome to Siena with side trip to Assisi - booked at Agriturismo il Castagno Siena. Still looking for best private van for this trip.
Day 7 - Tour Siena City, have lunch and return “home” early afternoon. Some of us would like to go to the Outlets.
Day 8 - Florence (whole day) - Private van for the day. Please help me plan this day. I would like to do Florence by clusters. walk around sites that are close to each other then hop in the van and get dropped off to the next group of sites that are close together. This will eliminate too much walking for mom. Is this possible? Must see sites: Academia, Ponte Vecchio and Piazza Michelangelo (drive to see views). Can you please suggest other places that will be good to visit with clustering in mind. We will skip the Uffizi this trip as I think it would be more pleasant to walk around town and see the City.
Day 9 - Chianti/ San Gimigniano ( 5 hours )
Day 10 - Pienza/ Montepulciano ( 5 hours)
Day 11 - Transfer back to Rome. ( same apartment near Spanish steps) Outlets in the morning and drive back to Rome mid to late afternoon.
Day 12 - Christian Rome Tour ( 4 hours): Basilica St. Mary Major, Basilica St.John Lateran, Holy Stairs, Old Appian Way, Basilica St. Paul, Catacombs St. Calixtus.
Day 13 - Free day or Villa D’Este
Day 14 - Travel Day

Most of our afternoons are free time. This is the time for mom to rest and the others can book optional tours, rest or shop and we all meet up for dinner.

We will be getting a wheelchair for the Vatican tour. Should we get one for Siena and Florence as well?

Thank you all for your patience in reading this long article. I hope that you can help me plan a most memorable trip for my moms last trip to Rome.

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