Itinerary Help!! Two Day Tuscany Advice


New member

My wife and I planning to visit Florence and the Tuscany region for the first time in September. Unfortunately we are trying to pack a lot into a small amount of time. We will be in Florence for 2-3 days and then plan to rent a car and make a 'loop' that would bring us down through Chianti region on our way to Siena(spend the night?) and then spend the next day making our way back towards Florence with the idea of staying in a nice B&B or hotel outside of the city. So 2 day trip. There are so many great tips and posts about places to see/visit, but what would be great is some candid head is spinning. "If this was your first time visiting Chianti/Tuscany hill side, how would your itinerary look so you could see the countryside, visit some great towns, have some wine and not feel like your running from town to town?"

Basically I am looking for someone to tell me what to do. Ha-Ha.




Well-known member
Travels towards Siena

Hello -

I am guessing at least one vineyard is in the gameplan, so I will offer you one of my favorites which if you go there through Chianti will take you through the beautiful sceneries naturally.

The first place is barely outside of Florence - not very well known and most probably requires an appointment. But in my opinion well worth (if not for the wines ha!) for the views and to experience a Medicea villa.

It is located outside of Giaole in Chianti - so it is a mid point between Florence & Siena and not only is the environment beautiful but they are generous with their tastings. I always take my family and friends here because it is warm and welcoming and I feel like it is a lovely representation of Tuscany.

Both places have a fee for wine tasting, but if you are buying...sometimes they will skip that. Maybe not so much the first, because normally they will include a tour of the villa - which is well worth the entrance.

Buon Viaggio