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Help needed for planning a Trip to Tuscany

My wife and I are planning a trip to Tuscany this summer. We will be celebrating our retirement along with my 70th birthday. I used to be good at putting together an itinerary but am having trouble this time around. We have been to Italy 3 times mainly visiting all the major cities including CT and a short time in Siena. I have never driven in Europe before but I’m not too concerned. Thinking about 10-12 nights with ending in Florence for 2 nights before heading home to Chicago. Thinking about going either at the end of June or August. Figure on after we land spending the night and in the morning either renting a car or take a train to our first destination and renting a car there. We want a relaxing trip, stroll the towns, enjoy wine, food, and more wine. Wouldn’t mind staying in a place that has a pool to take a dip at the end of the day and then enjoy another glass of wine! Instead of spending a night here and there I was thinking of maybe making 2-3 base towns and do day trips. This is where I need HELP PLEASE! Maybe someone can come up with a day to day itinerary or maybe you already did. Someone mentioned that as one of our base towns should be Montepulciano?
Would really appreciate any help!!!!

Posted by
7314 posts

We absolutely LOVED Montepulciano- but it is very very steep- we spent 2 nights there, and I think any more I might have grown to dislike it because of all the climbing!
We visited Pienza during the day and also really liked it there- it is a flat hill town so might be a better spot for a longer stay. Easy access and parking and fabulous views from the town.

Lucca is often mentioned- have not been there myself, it is on our list for next trip.

Have you considered an agriturismo?
This is one we looked at but ended up not staying there, no pool but I am sure there are others that do have
http://www.agriturismomarciano.it:

Here is one just outside of Pienza with a pool
http://www.fattoriafregoli.it/eng/index.html

Driving in Tuscany was quite easy. We picked up our car OUTSIDE the ZTL in Florence and made sure all the places we stayed had easy access/parking outside the walls, etc.
You must get an IDP- AAA offices can do this for you for a few bucks.

Posted by
28435 posts

Tuscany can be very hot in the summer. You might want to consider going earlier than late June or after August. You can see actual, day-by-day historical weather data on timeanddate.com. I've linked to Montepulciano's August 2018 stats, but I recommend checking multiple years to get a better sense of what you might experience.

Posted by
8359 posts

Flights are expensive in mid Summer, and it's hot as a firecracker in Italy in the Summer. Air conditioning is not always up to par with that you may be used to having in North America. May or late September for European travel are preferable.
If you're a good driver, you shouldn't have problems driving in Italy. Roads in Tuscany are well paved and well marked. Just be aware of driving in cities that may have radar/cameras for revenue producing. One camera issued 58,000 tickets the last 60 days. And make sure your rental car company rents to those 70 years of age and older, as some don't.
I cannot imagine you going to Italy without spending time in Rome. We always will spend a weekend there, and take a train up to Orvieto where we pick up a rental car at Hertz across the street from the train station. Orvieto would be a great place to do day trips out of to Assisi and other close by cities like Civita.
I'd also prefer to visit an agriturismo north of Siena--maybe close to San Gimignano or Certaldo--to make day trips to the hilltowns of Tuscany (like Volterra).
Another great central city for day trips would be Lucca, northwest of Pisa. You could hit the Cinque Terre from there too.
Florence is about an hour east of Pisa--an easy drive. (Bologna is 1 hour north of Florence driving.)

Posted by
3961 posts

Although Tuscany is warm in June & August, we've been there in early September (still warm). You've chosen some wonderful locations to celebrate retirement & 70th birthday. Like acraven mentioned, you may want to consider weather in your planning.

Montepulciano is one of our favorite towns. Fond memories of visiting the famous Copper shop & also tasting the wonderful wines of that region. Congratulations!

Posted by
35 posts

We travelled to Tuscany in late September. The weather was great and the crowds of July / August had waned.

We stayed in Montepulciano for 5 nights, but wouldn’t stay there again because of the steep roads and paths in the old town. We are quite fit and easily walked over 15 000-20 000 steps a day, but everywhere we went involved walking down a steep road and subsequently walking back up to return to our accommodation.

We also stayed in Siena for three nights and loved it, plus a night in San Gimignano.

Posted by
2213 posts

Since you are retiring, if there is any way possible to. Wait and go at least in the shoulder months, I’d highly recommend it. There’s a number of Fall festivals that would be a lot of fun.

We went two weeks before Christmas in 2015 and had a wonderful time. There was a little frost a couple of mornings but it warmed up to the high 50s during the day. There was only one day with a little rain.

Driving is not hard, but pay attention and do not speed. ZTLs are well marked and easily avoided. Plan to stay off the road if you are doing wine tastings. We stayed at a winery just outside of Greve. We had a great food and wine pairing and they were very generous with both. Luckily we just toured the grounds and went to our room.

Posted by
4105 posts

Do you have any idea of which hill towns you want to visit? There are hundreds, and without some input from you, it's kind of hard to put together.

You're going to have to research, mine favs may not be yours.

Some of my favorites...
Pistoia. Montecatini Terme/Alto. Volterra. Vinci.
Greve. Montereggioni. Castellina in Chianti. Radda in Chianti. Montalcino. Pienza. San Quirico d'Orcia. Castiglione d'Orcia, Pitigliano.
Bango Vignoni. Radicofani. Montepulciano. And if you like gardens, La Foce.