My wife and I are looking to go in the first week of October. We are both big cyclists and would like to stay in a nice small town where by the end of the week, we recognize everyone. Visions of an old chateau of some sort would make it awesome also. This is not a budget trip as we wont be going back for some time so nice is better.
Which town do we stay in?
I’m recommend staying on the outskirts of Sienna. Lots to see there, and it’s fairly easy to see the rest of Tuscany and the Chianti countryside.
Also on your short list to look into should be Fiesole (if you prefer to be near Florence) or if you want to really get away, Montalcino, Monte Oliveto, or San Gimignano.
It sort of depends on what the purpose of your trip is. If you just want to ride, eat well, and be familiar with the locals, I’d suggest finding an agriturismo in a small town - an agriturismo is basically a farmstead bed-and-breakfast which may or may not have a family living there as their home. If you want to ride but also see some of the sights, be sure to stay somewhere with easy access to major public transportation (preferably the train line that connects Pisa to Florence or Florence to Siena), probably on the outskirts of Siena or Florence. There’s more to do besides ride, but the food is good everywhere.
Siena, from the clocktower:
http://i3.tinypic.com/w9w787.jpg
Check the view from Fiesole:
http://i3.tinypic.com/w9w9si.jpg
Or the countryside near Monte Oliveto:
http://i3.tinypic.com/w9waxx.jpg
Perhaps Lucca?
http://i3.tinypic.com/w9wcwl.jpg
Was all over that area last June. Unfortuately, I didn’t get much cycling done. However, I have to HIGHLY recommend Cinque Terre which is on the coast northwest of Tuscany near La Spezia. Unbelievably picturesque area with tons of hiking. If you’re dead set on Tuscany, I would still recommend at least a day trip there.
For Tuscany (and Umbria which is very similar and also worth considering), Arezzo, Orvieto (must see the duomo there!), and Todi are all great moderately sized towns that are beautiful and very easy to get to from Rome. A little time on the internet will get you good info on timeshares which will probably be reasonably priced since its the off season.
You’ll have an amazing time no matter what you choose. Feel free to send me a pm if you had any more specific questions.
Sam
If yout want to assimilate into the tuscan life then I recommend the Rick Steves guidebook above any of the regular ones. He always has some good off-the-beaten-path places. BTW, he LOVES the Cinque Terre as well as Lucca.
San Gimignano is really beautiful, but touristy. It is pretty much the must-see quintessential tuscan village - which makes it one you may choose to miss. My guess is that October is a good time to go, though. Siena - and the surrounds - is bigger than i expected.
There is nothign better than getting lost in the alleys within the medieval walls of Siena and finding some great restaurant or cheese shop,or whatever that no tourist know is there.
Lucca is very cool, and very pretty.
The food’s better in Siena, I think. And there’s more to see in Florence. But in October Lucca should be quiet and beautiful, plus you can ride laps on the walls, which is definitely worth doing. It’s only an hour from Florence by train, though… so why spend the whole time there? I’d split my time if I was there more than a week.
restaurant.
You guys rule…thanks. This gives me lots to Google.
Jeff
That’s why I love Siena - I had one of my best meals in Italy there (and I was there for about 3.5 months!) wandering along with my girlfriend.
It was just a mom and pop kind of place. They seated us downstairs, all by ourselves. Typical Italian less-than-mastery of atmosphere… and then the food came! I doubt a better cinghiale in umido has ever been prepared. Homemade pici. Prosciutto di cinghiale. Amazing.
Oddly enough, San Gimignano was the one place I skipped. I hear it’s nice - but I never wanted to take the bus there and battle the tourists. Lucca’s towers are cool enough, and I saw other medieval hill towns.
Rick Steves books are good - but you have to buy into his schtick for it to suit you. I always preferred a book with good recommendations for food, and a highlights list for sites to see. Then I went exploring and referred back as needed (eg when I got hungry). Let’s Go served me very, very well for food from Florence all the way to Amsterdam.
if you can be there October 1st try this event:
http://www.parcociclisticodelchianti.it/eroica.htm
The Eroica. It’s a 200k ride over the “white roads” (i.e. dirt roads) of Chianti that takes all day and is usually done by old men on 20+ year old bikes (who will probably school you… haha). I did it about 5 years ago (it’s much bigger now) but Gaiole is a nice spot for cycing as well since there are some SWEET routes and lots of climbing going both North and South. It’s just not a super high-energy village. cute but small.
I would go with Lucca, San Gimignano or Volterra. Lucca is my favorite, but I’m not sure about the cycling in the area. If I remember correctly, it’s more flat up there You will get the typical Tuscan landscape (rolling hills, gorgeous views in every direction) further south near San Gimignano or Volterra. I also enjoyed Montalcino and the cycling there would be great as well.
Dawn
We were lucky enough to be in Lucca for one of Italy’s national holidays. The place was packed with locals and we had one of the best days and nights of our trip. We rented bikes two different times that day to ride along the wall. What a great little city!
Lucca looks and sounds beautiful, but we’d love the small town atmosphere. We stayed in Casares, Spain (Andalucia area, Costa del Sol) this past summer, and it is a tiny town…we prefer this. ANy suggestions on little towns outside of Lucca.
I really wouldn’t call Lucca big. It’s nowhere near the size of Siena, Florence or Pisa. It’s a very quaint town and I think you will like it. It’s certainly not touristy, but the locals do go there for vacations and holidays. That’s where I would stay if we went back. You might want to look into Terme. If my memory is correct, it’s also a nice town, but it has a natural thermal spas as well.
The other small town that I really liked was San Gimignano, but we were there in May (pretty much off-season), so it wasn’t very busy. It sounds like it gets much busier in high tourist season.
The other town you might want to look into is Empoli. Close to Lucca and I’m pretty sure the guidebooks recommended it. I didn’t go there, but it’s something you should look into.
Good luck! Vacation planning is so much fun!!
radda-in-chianti is very small and a classic hill top town in chianti. we’ve rented an apartment there a couple of times. it was part of a house with a pool and a kitchen for about 85$/night. last time we stayed a week an just did day trips from there. it’s about a 40 min drive to siena and you can make a nice loop through san gimignano and other classic towns. the house is in an olive grove and 800m from town. you can walk from one end of town to the other in a couple of minutes. near Radda are Castellina and Volpaia which are also hill top towns. in the valley nearby is Greve which has a great weekend market and a bike shop.
If you want a small town - and only Firenze and Pisa are what I’d call “big” places - I love Fiesole. I lived there for a bit. Really a nice place, and close enough by bus that you can take advantage of all that Florence has to offer.
Lucca really isn’t that big - it’s a town, rather than a city. Check the picture I posted earlier this thread. There’s a view of Lucca from one of its medieval towers.
Siena is slightly bigger than Lucca; still walkable from one side to the other with no trouble, and it’s quite pleasant. If you really like tiny, though - look for an agriturismo, as that will get you countryside. Or try Montalcino, which is about 5 blocks long. Much less to do, though.