Ciao Celestine,
We just want to make sure you and your mom love Italy and Tuscany and have a wonderful trip! Once I realized you were posting various questions here and there, I realized we weren't replying offering the BEST advice for your particular situation and so now that you've told us a bit more, these are MY thoughts:
- Milan and then CT staying at Monterosso sound fine! I think you should be able to get her on the boats and have a good tour of the five towns that way, without any hiking --- the ONLY consideration to keep in mind is that March is off-season for the area, so boat service might be very limited and based a lot on weather conditions. I would suggest you contact the hotel where you are staying at to ask whether they can confirm whether the boats are running in mid-March and whether they can help you arrive at their hotel from the train with your mom and luggage in tow.
- I would suggest 2 nights in Florence
- Once you rent a car to head into Chianti, consider staying put for another 2-3 nights in the same place.
- You can drop off the car in Siena and then take the bus to Rome - you can check the timetable here:
http://www.sena.it/Home/78-1-en.html
An alternative, once you have the car, is to drive down and return the car in Rome.
- Have you considered renting a car from the start and just having it the entire time, from Milan to Rome?
- I would recommend dropping Barcelona off the itinerary, you already have a lot planned for the trip and, to be honest, you'll need more time to move around and see things with your mom. I highly recommend taking the time to soak in the atmosphere of each place, not rushing, and letting your mom enjoy the places without getting too tired. Consider that there are a lot of streets with cobblestones and it will be tough with the wheelchair and, if you can, book hotels close to the main sights in Rome and Florence so that you can also take breaks during the day.
Did I miss anything? Let me know if you still have questions!
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