I'm taking a train from Venice to Siena and picking up a rental car in Siena which I will use for my 3 day stay in Montalcino. If I'm picking up the car at 2 PM in Siena, do you think I'll have enough time to drive to Chianti, explore a little and still make it to Montalcino before dark? Or do you think it's best to forget Chianti for this trip and perhaps explore a bit of Siena before heading to Montalcino? And then the other days I can spend in Montalcino, and drive to Montepulciano and San Gimignano. Thoughts?

In my nineteen trips to Italy in the past dozen years i've been to the Chiante country only once. I don't find much there. I think you'll enjoy a tour of Siena much more. I'd also take a look at Pienza, too. (Of course you'll sample the Brunello.)

Thanks DRJ. Do you think I'll be able to visit Pienza on the first day on my way from Siena to Montalcino?

Are you returning your car in Siena? What time of year are you traveling?

From the Siena location I would take the road south via Asciano and the Crete Senese and then stop at the fabulous Abbey at Oliveto Maggiore--it is closed from 1300 to 1500. From there take the back roads to Buoncovento and finally to Montalcino, arriving at 1730. Forget Chianti--that drive puts it to shame.

kybourbon - I'm picking up and returning my car in Siena, and I'm travling the first week of June 2010.

thanks bobthenavigator - you've been incredibly helpful on all of my posts

Couldn't agree more with Bob. There are a few very good restaurants and some very, very expensive estate villa rentals in Chianti after that the weather is worse and the landscapes poor compared with south of Siena.

Bob is right on the mark about Monte Oliveto Maggiore, which I affectionately call MOM. Click on the link below (my travel website) and take a look at Day Ten. It tells a little bit about the drive and the abbey. Days Ten and Eleven cover some of the sights in Siena (photos, too). In Day Eleven, Bob's name even comes up in a dinner conversation with a Fodorite we met in Siena. Small world. Have a great trip!!!!

http://web.me.com/tomfielding1/Tom_%...cany_2005.html

dtph,

I just want to caution you for all your plans regarding Italy that beauty is in the eye of the beholder, and you may be surprised when you get to Italy that you react differently to the consensus.

The area of le Crete is to me the most beautiful part of Tuscany near Siena (I think it puts the val d'Orcia to shame), and I too loved seeing the freschi at the Abby of Monte Oliveto Maggiore, so I'm hardly in disagreement with the above. But many, MANY people who don't regularly post on Fodor's love the verdant Chianti, and it is generally agreed to have the better food (since that came up).

If you are interested in medieval anything, Siena is a stunning sight to explore. Some people who give lots of advice on this board about touring scenic Tuscany really dislike seeing the historic cities of Italy and constantly tell people to skip them in favor of scenic driving. Personally, I don't enjoy being in walled cities, but thousands of other people find Siena the highlight of their trip to Italy.

So there you have it, as one poster here likes to say.

There is no "objective" answer to your question. I enjoy strongly expressed opinion, and really dislike reading "IMO" in posts, and I write very strong stuff myself. I only popped in to remind you that, objectively, south of Siena is not more beautiful or interesting than Chianti, nor is a scenic drive more worthwhile than a stop in Siena or a stop at the Abbey. These are just purely subjective takes from everybody.

If you are the kind of person who generally enjoys what other people enjoy or what guidebooks recommend, don't worry about it. If you march to a different drummer, Italy is a great place to head off on your own.

I agree with zeppole. Although we loved southern Tuscany, we thoroughly enjoyed the Chianti area (Tracy's favorite, actually). We had a terrific lunch in a great setting at Ristoro di Lamole and our place overlooking the vineyards of Chianti couldn't be beat. You'll just have to see what area is your favorite, which is all part of the fun and the experience.

maitaitom - i started reading your travel site last night. love it! i would join tom's tuscan tours in a heartbeat! i think the idea of putting your photos and journals online is a great way to document your travels not only for yourself but for others to come and read and learn. thanks for taking the time to put it together and for sharing it. since reading your site was the last thing i did before bed, i happily dreamt about italy all night.

zeppole - thanks for always providing insight on another point of view. i think i'm the type of person who likes to gather enough information to have a nicely planned itinerary and route that i think we'll enjoy before arriving, and then be flexible enough to change it on the fly depending on what we see once we're there. so i definitely appreciate varying opinions and experiences because it helps me figure out a good plan, a back up plan and even be ok if i come up with an entirely new plan with my hubby when we're at our destination with out own two heads and hearts =)

buon viaggi, dtph! You've got your heads screwed on straight, so let your hearts do the rest!

To further provide that broad stoke of information to help you decide what Zeppole has created.

As much as I love Seina I think it would be a good idea to tour through Chianti for a day as the landscape is different between Chianti and Val D' Orcia.

As perspective,in the spring I think Val D' Orcia may be the prettiest spot in the world, to me. Since you'll be headed to Val D' Orcia for a few days, I would tour Chianti as it is also stunning. Chianti has many more hills and steeper hills which are predominately woods and vineyards. Val D' Orcia has more rolling hills and farmlands along with some wooded hills and vineyards. I think a well placed drive to see parts of Chianti would more then make up for not spending a day in Siena.

I would recommend driving to Castlello Brolio. Great wooded landscape with a fantastic fortress to view from afar and close up. Castello Brolio, considered to be the birthplace of the Chianti wine blend. The areas and towns near Brolio are very scenic with the wooded hills and vineyards. It's about a half hour drive to Brolio from Siena.
If you decide to drive through Chianti post again and you'll get some tips on the scenic roads to follow.

Web sire for Castello Brolio

http://www.ricasoli.it/




http://www.ricasoli.it/

http://www.verrazzano.com/en/photogallery/