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Tuscany and Umbria off the beaten track recommendations requested

We're flying into (and out of) Bologna at the end of October and returning to the U.S. on November 19th (so about 19 days in country). We've got 3 nights booked in Bologna, which we visited before and loved years ago, but would like to spend the rest of our time in Umbria and Tuscany. Assisi is the only touristy "must" on our wish list but otherwise we'd prefer to be in smaller towns. We're hard-core food and wine folks and especially interested in experiencing the various manifestations of the sangiovese grape in its more accessible and affordable manifestations (i.e. Chianti, Rosso de Montalcino, Vino Nobile but skipping Brunello and anything else that needs 10 years of aging to be worth drinking).

Spello and Montefalco in Umbria seem appealing, as does spending time in Tuscany on some part of the Chianti route or perhaps using Siena as a base for trips? We were initially planning on just using trains and buses but will rent a car if need be. I've driven the tiny "D" roads in France extensively and have no problem with tiny cars with a stick shift but know that leisurely lunches with wine and driving the vineyard roads are an ill-advised mix.

Any thoughts appreciated!

Posted by
1144 posts

Unfortunately the type of Tuscany adventure you're discussing probably requires renting a car. The rural towns aren't well served by public transportation if you're on any kind of schedule. Most of the towns you associate with the wine trade like Montalcino and Montepulciano require non-public transportation. Greve in Chianti is a good wine destination that is reachable by bus from Florence but places like Rada or Castellina in Chianti are harder to reach.

Here's a train map of Tuscan towns:
https://www.wanderingitaly.com/maps/images/tuscany-rail-map.png

You are correct about not mixing wine tasting and driving so another possibility is staying in a slightly larger place and arranging wine tours and/or transportation to wineries as day trips. Siena is the main focus of this in the northern part of Tuscany but I'm less sure about the southern areas. Also in places like Siena there are wine tasting rooms and sampling many options which is not the same as visiting a winery but also saves driving and offers more variety.

Have a great trip, rural Tuscany is as beautiful as advertised,
=Tod

Posted by
4 posts

Thanks very much to both of you for your very helpful recommendations and wise perspective! The information you've provided is invaluable.

Posted by
11798 posts

Umbria and wine in the same sentence leads me to recommend https://gustowinetours.com/. We toured with the former owner years ago. Looks like the new owner is still doing a great job. A thoroughly enjoyable day with no danger of driving yourself, you!ll visit wineries otherwise difficult to find or get into. The Sagrantino di Montefalco is amazing!

We were staying in Spello and loved our time there in early December. We did not rent a car. Also have visited Assisi successfully without a car, but in Tuscany a car is certainly useful.

Posted by
1592 posts

Thinking about food rather than wine, look at visiting Norcia in Umbria (and also driving to nearby Castelluccio) --- towns that were wrecked in an earthquake and besides the food, it is interesting to see how they are recovering.

Also in Umbria for food, Gubbio, for its charm and its birdcage lift to the top of its hill.

Sorry, I don't have time to give more details right now!

Posted by
3008 posts

For off the beaten path excursions by car I can recommend the guidebook "Back Roads Northern Italy" from DK publishing which you can usually find for just a few dollars (used copies) on Amazon. As the name suggests it's chock full of meandering day trips thru some of the most beautiful scenery in the region ... including many out of the way attractions (and wineries) that other guides don't cover.
We wore out our own copy on a visit a few years ago.

Posted by
4 posts

These excellent replies have helped me clarify what I'm looking for on this trip and made me realize I should've been clearer about that from the outset.

My wife and I are most interested in experiencing classic wine and food of these regions at table, and in doing a lot of tasting of wines in order to better understand the different terroirs (thinking, for example, of the different areas within the Chianti region as well as the gradation from generic Chianti to Riserva to Gran Selezione. I've been poring through the current edition of the Gambero Rosso guide and highlighting wines in both Tuscany and Umbria to try.

We've been lucky enough to spend a great deal of time living in the villages of the Southern Rhône and feel no need to visit more vineyards and don't want to be under any obligation to buy wine from producers on some tour. My career as a professional taster of coffee and tea makes me very comfortable (indeed, very happy) to slurp and spit my way through couple of dozen (or more) wine samples at a sitting. A big focus for this trip is trying to become as familiar with high-value everyday Italian wines and the food that goes with them as I am with their French counterparts.

At this point I'm thinking that Siena would be a good base and that it would probably make sense to rent a car for a few days in order to be able to do some overnights in Chianti villages. For Umbria I'm more inclined based on what I've read both in these comments and in guidebooks to spend a few days each in Assisi, Spello and Montefalco, using public transport to get from place to place.

If anyone has any recommended restaurants with classic regional cuisine (humble just as good or better than fancy for us and hopefully no English language menus) to recommend that'd be most helpful. Thanks again to everyone for the helpful comments!

Posted by
186 posts

My wife and I have been travelling to Europe for around 20 years. In all our travels, the absolute best and most memorable experience was the time we spent in Tuscany with Isabella -- first in their agriturismo, Cretaiole near Pienza and then, two years later, in their upscale villa in the small hill town of Castelmuzio. We also enjoy good food and wine so she sent us to 2 amazing wineries. one of which you absolutely must go to if you are anywhere near Montalcino. It's called Nostravita and the owner is a true Renaissance Man. He hand paints every label that goes on his wine and has several other art hobbies that he shares with you.

I hope you can arrange it!

Posted by
272 posts

I highly recommend taking a winery tour with Gusto. My husband and I have taken three tours with them and have enjoyed all of them. I would note that the original owners have retired, but I trust them to have passed it on to someone who will replicate the experience we had with them.

https://gustowinetours.com/

Posted by
4 posts

Thanks all for the fantastic advice! I'm going to take it to heart and am really grateful for your help.

Posted by
1127 posts

Montalcino will certainly suit you and provide the experience you’re looking for. If can, book a meal at Boccon di Vino. It’s an experience that you won’t forget. This is a foodie/wine town and such a great stop given your goals.

In Chianti I highly recommend a visit to Badia Coltibuono. The cooking classes are amazing, as is a meal. Their wines are phenomenal and the food a wine combinations are one of the top experiences I cherish. You can also stay here.

Posted by
15794 posts

In late March 2022 I rented a car, small 4-door hatchback, and tootled around Tuscany and Umbria for 9 days. I generally prefer more driving and fewer hotel changes, but this trip I decided on changing places every 2-3 nights, which I don't mind with a car, because the places I chose were spread out. This turned out to be the best plan because driving was slower than I expected. There were few tourists in most of the hill towns, partly because it was early in the year, more because Italy has just begun reopening after Covid. My itinerary:

Pick up rental car at Florence airport after visiting Florence
1N in Castiglioni del Lago
2N in Montefalco
4N in Perugia
2N in Greve in Chianti
Drop the car back in Florence (it was about €100 cheaper to do a loop than a one-way rental)

For the details, read my trip report. The part about the rental car begins with my response on March 28

Not in my trip report - I'd planned to drive to San Gimignano for the day from Greve. The road into Greve was so long and I was warned that the limited parking there fills up early, I just stayed in Greve. Greve was my least favorite place to visit. I was expecting beautiful green scenery (after all, that's what March is like in my Mediterranean country) but mostly it was stark - grapevine stumps, and bare trees. The views from the hill towns were better. I only booked hotels that had parking. The only exception was the single night in Castiglioni where there was free public parking very close.

To put a pin in my driving difficulties . . . I've driven the hill towns in Andalucia, the cliffs of the Amalfi coast, the hills of San Francisco. I've driven backroads in France, Sicily, Portugal. I never had a worse time driving than in Tuscany and Umbria.