35th Anniversary trip

My wife hates to fly but has agreed to spend 10-14 days in Tuscany in early October 2018. We're really looking for a relaxing trip, not running around a lot (which is what I normally make her do when we visit a city). So I'm thinking rent an apartment in one of the small hill towns (Cortona, Montepluciano). We don't want to rent a car so if anything, we'd like to hire a private driver for a day at a time but for the most part, we'd like to stroll the town, taste some good wine, cook many of our own meals, and enjoy our time living as much like a local as we can. My questions are: Will we go nuts in one of those towns for that long or would there be plenty to do - we love to walk and would probably walk about 5 miles a day without even trying. Or, should we look at something more like Sienna or Florence for that long? Can you give me an idea of what a driver for a day might cost? Also, what does a good bottle of everyday red wine cost in one of those towns? Any advice would be greatly appreciated!
 
35 years ! celebrating in style

Buongiorno,

OMGoodness, get bored? no way! I mean sure you will have some down time with a good book, but it is so easy to invent something to do! As for a bottle of wine, you can start at 5 Euro and the skies the limit as for price. However, if you are visiting vineyards and buying on site, then you can expect to pay from 8 - 15 Euros per bottle for a quality Tuscan wine. The Reserves will be a bit more expensive. When you are in a restaurant - my suggestion is to always go with the house wine (4 - 5 Euros) as long as it is Tuscan :cool:

I have two places that come immediately in mind in the middle of a small - but charming little town - with lots of land for walking around and exploring a beautiful scenery.

http://www.chianti.com/chianti-bed-and-breakfasts/b-and-b-del-giglio.html (especially nice because they have a small kitchen where you can make a light meal or snack)
http://www.chianti.com/chianti-bed-and-breakfasts/palazzo-malaspina.html

However, I suggest that you consider splitting the trip up into three/four days in Florence or Lucca (several day trips possible without a car) or Siena and then the rest of your time at one of the above B&B.

You can contact this person for more information on a private driver: https://www.discovertuscany.com/tuscany-car-rental/tuscany-wine-and-drive.html

Buon Viaggio,

Donna Denise
 
As Donna has said, you won't be bored for sure! Since you don't want to drive, I do suggest Florence or Siena as a great base - you can do many day trips for either, take a look at some suggestions here:

https://www.visitflorence.com/itineraries-in-florence/top-day-trips-from-florence.html

https://www.discovertuscany.com/siena/what-to-do/day-trips-from-siena.html

Lucca is also a good base, as well as Arezzo. Early October is generally still pretty busy so these two smaller towns will give you a better sense of what Tuscany looks like in the quieter months.

Another possibility is San Gimignano. It does get quite busy during the day but empties out in the evenings. It has many restaurants, bars and shops with lots of easy to reach countryside perfect for walks. You'll need to learn how to handle the bus to get around but it is manageable. With more time on your hands, this might offer a great base and having the best of all worlds. Here's more info on getting there and moving around with public transport: http://www.discovertuscany.com/san-gimignano/how-to-reach-san-gimignano.html

Once you have settled on where to base yourselves, you can start the search for lodging. You can start from http://tuscanyaccommodation.com/ and look for a B&B if you want a more intimate setting that a hotel, or an apartment if you're looking to cook on any of the days you're here as most have a small kitchen included. Depends on what you're interested in.

Let us know if you have any more questions! ;)
 
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