I'd like to help pschwerdt in the most neutral possible way, and although I'm not a Fodor's "expert" (yet!), I do work for the region of Tuscany so I know a few things about the area. I'm also human so I have preferences for certain areas, as anyone does, but I can say that they are all great (and I'm not paid to say that, they chose me for this job because I already thought that).

Intro aside: Tuscany offers a LOT of variety. There are flatlands, hills, hill-towns, mountains, seas, and cities. In 4 days you won't be able to see them all so you are right to ask for opinions. You can, however, get a good taste of what "Tuscany" feels like in that time, and it doesn't really matter if you learn the fine differences between what the hills near Arezzo look like versus those around, say, the Monte Amiata. Everywhere you look there's a little bit of everything - great art, wine, beautiful rolling hills.

Here are some things i'd take into consideration for any place:

-proximity to good roads for where you want to visit on day trips (for example, montevarchi is near the A1 highway which is good, while Volterra is adorable, but the road isn't great nor close to much other than San Gimignano).
-season: the countryside ain't great in winter ;-)
-acomodation: 100 USD won't get you far so it might come down to finding a place that looks perfect; if you fall in love with it maybe you should just go wherever that is.

Anywhere you go it's all going to look rosy to you on your honeymoon, and in general, Tuscany doesn't disappoint.

For inspiration, I suggest you check out photos of Tuscany on Flickr (there's some groups with really good ones) and maybe do some reading on the official website turismo.intoscana.it. I'd be happy to answer other questions for you when you have narrowed things down.
best regards, Alexandra

We love Lucca. Unlike many of the hill towns, every second accent isn't American, Australian or British. Great train service and access to the motorways. Last May we stayed at Apartment La Paolina, a lovely little two bedroom apartment located inside the walls, and only two blocks from the cheapest public car park inside the walls. It cost us 500 euro for three people for 7 nights.
We booked through www.bbplanet.it but you can also contact Chiara and Lee directly on [email protected] They are young musicians who speak English (Lee is American) and very hospitable. Chiara told us she can also recommend other apartments if she doesn't have vacancies.

Sarvowinner - I too love Lucca, and have been back several times. As a city to tay, walk around and absorb the atmosphere, I think it has few peers.

Having said that, I do not think it is a great base for exploring Tuscany as a whole. It is certainly close to Pisa, and the Garfagnana, but it a very long way from Siena (my favourite) and Southern Tuscany. Bob's list is, in my opinion, excellent.

I feel Zeppole can sometimes come across as overly contrarian about other's suggestions. Fodor's is, after all, a travel site and people are after advice and opinion. They may choose to ignore or disagree with it, but it doesn't make it less valid.

Agreed Lucca isn't not the closest to Siena & Southern Tuscany, which is lovely. Just a suggestion on based on the OP's accommodation budget of around USD100 per night, all in three to four days, with easy streets to walk around etc. In May, I found the accommodation in Siena to be very expensive compared to Lucca, also car parking was a lot more difficult & expensive. It took us 1 1/2 hours to drive from Siena to Lucca so a sizeable chunk of time but not out of the question for a day trip.

Interesting post - somewhat informative but also very emotional. I was just weaving my way through recent posts on opinions on day trips. I am staying in a house in NW Tuscany for 2 weeks(small town called Petrognano, closest train station Pescia, about 30 minutes from Lucca). I don't want to spend all day driving or taking a train but am thinking about Lerici, Parma, Modena, Siena and exploring other options. Last year was our first year there and we did the usual Pisa, Cinque Terre, Lucca and some small towns nearby as day trips. Priorities are great food, interesting wine bars or vineyards, great architecture, cooking, food markets, getting lost and not museums - any additional advice while I continue to weave my way through these posts?

Ciao! Fritch

Hi Pschwerdt (kind of rhymes with like Beschert --perfect for a honeymoon-related post)

Congratulations on ur upcoming marriage and honeymoon trip!

I am most definitely NOT an expert, having --other than passing through on a train--last been to this area 4 decades ago,.

so now,I'm seeking similar info as you from the numerous Fodorite helpers, for a trip next June

In the course of research for the "perfect" b and b not too far Florence, San Gimignano, Siena, etc etc, i found this:

http://www.casaledelcotone.com/

It's more than $100/night though. So maybe a bit of a splurge for three days?

For me, a pool is important --not sure how the temp is in September, or if a pool matters to you.

This b and b is 50 km from Florence--its proximity to other hill towns is listed on its website.,

Good luck, and let us all know what you find
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We stayed just outside of Pienza for the Tuscany portion of our honeymoon in 2004.

http://www.ilcastellodispedaletto.com/index2_eng.html

We stayed in one of the farmhouses and ended up having the whole farmhouse to ourselves. We adored the place, and it was a great location for daytrips to Montalcino, Montepulciano, Siena, and Orvieto. Pienza found its way into our hearts - it is the place we talk about most when we talk about our trip to Italy. It's been 6 years, so I don't know what the prices have done in the intervening time, but the rates for the agriturismo was very reasonably priced when we were there.

Lots of good info!

Goodness, quite a pissing match here. Personally I have used the advise from Bob many times and the recommends are great.

We too spend a great deal of time in Tuscany absolutly love Radda. But that being said, Radda is a little too remote for a 3-4 day trip as it takes 30 minutes to get anywhere.

I would recommend positioning yourself in a central area such as Siena. (there is an inexpensive clean hotel just inside the wall by Porto Ovile called B&B San Francesco) You can rent a car via AutoEurope and the pickup is just a couple of blocks away. You can then loop in different direction each day. For example loop north east through the small towns of Castellina, Radda, Greve, Badia a Passignano one day. San Gim, Volterra etc another. Montalcino Pienza another. Bus up to Florence one day. You will get a nice overview of the country that way.

I have a great list of restaurants, drives etc. Just email me [email protected] and I'll get it to you.