Tuscany & Umbria - Planning
 

I am traveling to Italy in September for 17 nights. My wife and I would like to do a full tour of Tuscany and Umbria. I'm working on our bases for the trip and can't decide how many to choose. All accommodations will be B&B/Agriturismo in the countryside. We will have car for all 17 nights.

I have three competing trains of thought:

1. Lucca area (4 nights), Pienza area (6-7 nights), Montefalco area (6-7 nights)

2. Siena area (8-9 nights), Montefalco area (8-9 nights)

3. Siena area (5-6 nights), Pienza area (5-6 nights), Montefalco area (5-6 nights)

Any thoughts would be appreciated.

I would divide my time to Umbria (Assisi area?),Chianti and the Val D' Orcia areas. Is this for this September? Many good places are already getting booked. We will be staying at our favorite agriturismo in Greve this September.
I usually stay in Montalcino for the southern Tuscany stays, but Pienza is fine.

I like your #3 option, but let me be specific:

1. Chianti---Fattoria Tregole near Castellina

2. Val d,Orcia---Fonte Bertusi near Pienza

3. Umbria---Genius Loci near Bevagna/Montefalco

Sounds like fun---I am jealous.

#3 is my favorite option as well.

Jabez - Yes, this September. I know. Bookings will be done this week.

Bob - Thank you for the suggestions. I will look into them. My only caveat is that the places I book through must be on Airbnb (which most are nowadays, Ive emailed a ton to ask). the reason for Airbnb is Amex points transfer 1:1.

Great advice from Bob (as always). In 11 years, he's never steered us wrong.

You may be able to find more accommodation options in/around Montepulciano in the Val d'Orcia region. It's really quite close to Pienza

So i have made a little progress...

Booked 6 nights at a B&B steps outside of Greve in Chianti.... This will be the first leg.

Still working on the remainder.

Our itinerary now stands at:

A. Tuscany/Chianti area (6 nights): Sept 7-13 The Chianti Classico wine festival is Sept 10-13 in Greve So excited. Will be staying at B&B Casale Le Masse steps outside of Greve in Chianti.

B. Tuscany/Val d'Orcia area (6 nights): Sept 13-19, looking at B&B La Casa di Adelina in Monticchiello.

C. Umbria/Montefalco area (6 nights): Sept 19-25, looking at B&B Villa Mustafa.

Thoughts?

Looks good !
Be sure to eat at La Porta in Monticchiello.

I went to the Chianti festival a couple of years ago. Try to pick a cooler day. It was 10€ for a glass and holder to wear around your neck, booklet with map/list of participants and space to record your comments. There was a punch card which gave you 7 tastings. Some wines (Riserva for example) cost 2 punches off your card. If you wanted to taste more, you could just buy another card.

Many vineyards have their own booths where you can sample their wines and other products (olive oil, cheese, cured meats, etc.). The consortium has a long tent with a lot of wines. There will also be some IGT wines along with Vin Santo available to sample.

I am much looking forward to the Wine Festival.