Should we stay in Florence or somewhere else?

Hello,

We are planning a family trip of a lifetime for August 2025 and I am struggling to know what to do about Tuscany.

We are a group of four adults (oldest will be 76 at the time youngest 33) and it is my parents first trip overseas. We are coming from Australia so it is possibly a once in a lifetime trip.

Our trip starts with Viking in Amsterdam on the 7th of August and we split from Viking in Luzern on the 18th of August at which point we travel (mostly independently but I am happy to book professional drivers for sections to simplify things) via Vaduz to Chur (one night in Chur) to catch the Bernina Express to Tirano. We plan to spend two nights in Tirano before taking the train to Varenna to spend 2 nights in Varenna. Then we plan to take the train on the 23rd of August to Milan and onwards to Venice where we will spend 2 nights.

The current plan is to take the fast train from Venice to Florence on the 25th of August and have either a taxi or prebooked private driver take us to our accommodation.

The problem here is I don't know if we should plan to stay in Florence or a smaller town - by this point in the trip we will need trees and green open spaces more than museums as we have all lived our whole lives in semi-rural to rural areas and don't do well in cities. My mother hopes to see rolling hills with vineyards and the other typical Tuscan scenery (less interested in actually seeing the towns than the countryside). She fell in love with the movie Under the Tuscan Sun for the scenery.

We have 3 nights to spend wherever we end up but have to fly out of Florence to Iceland on the morning of the 28th to join the next organised tour of the trip and I don't like the idea of having to drive for hours to get to the airport early enough to make the 3 hour before an international flight thing when the flight looks currently like it might be a 10am one.

One of my Aunts insists we "must do San Gimigano or Montepulciano" as they are her favourite Tuscan towns but we would be just as happy with any single day trip which isn't rushed and promises the type of countryside my mother longs to see if we can't find somewhere to stay that looks out onto that sort of view. I would like the option of a simple cooking class but wine tastings are out as none of us drink alcohol.

We won't have a car so wherever we end up needs to be walkable or have the option of half or full board at the accommodation.

I am so sorry for giving you so much information but my brain is in meltdown mode as my "highly recommended" travel agent keeps answering my questions with "I will ask my expert from the area" or "I don't have an expert in that area so can't book anything in that area for you - you will have to organise that part of the trip on your own". At this rate I think I will be doing it on my own as what decent travel agent can't book a hotel in Venice or Varenna?

Thanks for getting this far.

Thanks,

ReneeNicole

Your trip sounds well thought out Given your priorities it might be a good idea to stay just outside Florence rather than right in the city center. I have a few ideas:
Fiesole - small town just outside Florence (15-20 mins by car). It's got lovely views over the Tuscan countryside and Florence itself. It’s quieter, greener, and has some great spots for a peaceful stay.
Chianti region (like Greve in Chianti) - Chianti is the heart of Tuscany’s wine country. The scenery is stunning and exactly what (I think) your mother would love. Look for places that offer shuttles or private transport back to Florence airport (a 45-60 min drive). Some agriturismos provide half-board options, so you can enjoy local food without needing to go out every evening.
San Casciano in Val di Pesa or Impruneta - they're very close to Florence and have gorgeous countryside views. You’ll find plenty of places offering cooking classes and traditional Tuscan meals
And regarding San Gimignano or Montepulciano , they're lovely towns, but without a car, they might feel less practical unless you plan to stay there and take a day trip. Both are charming, but they can also be tourist-heavy in August. If you choose one, I’d lean toward San Gimignano for its proximity to Florence. However the countryside in the Val d'Orcia near Montepulciano is more iconic in terms of the landscape.
All in all, I'd look for places that provide airport transfers or are willing to arrange private transport for you. That way you won’t need to stress about the 10 am flight out of Florence