I'm not sure if it qualifies as an adventure, but we did go cycling in Tuscany last week. We had a couple of rainy days, more like Seattle-rainy days than all out rainy days (wet mornings, some showers, clearing in the afternoon) and then it cleared up to very clear (and very warm) days. The last day we cycled across a valley into a most awesome headwind to finish with a 4km climb ;)
Tuscany's not flat, but it's generally a good kind of not flat (unless you are absolutely allergic to hills of all kinds). There are some sustained climbs, and you can find them easily, but generally it's rollers and there's a lot of either valley riding or riding along the side of hills that means you don't have to just go UP or DOWN (and it's not boring flat). The Sette Ponti road, for example, is pretty well traveled by cyclists and is a great rolling hills route. That said, there are a lot of towns that are on the hill, or the side of a hill, and to get there, well, you have to go uphill. Some of them are up long gradual climbs, some up shorter less gradual climbs, and some of them finish all of that with 200-500m of brutal stand and climb.
We chose to ride with Ciclismo Classico, this is the Assaggio Toscana trip. They were most excellent. Great van support, good route notes, guides that could review the route and point out anything to watch out for, generally good food and hotel choices. If you like your days filled and planned with cycling, food, and a little bit of education, these guys are for you. I have heard other outfitters just do rides part of the day and then you sit around the pool the rest of the day, but this way was much nicer, as far as I'm concerned. Additionally, this trip had a lot of extra mile options that were perfect for my husband and I. He could ride the main loop, take the van for the long/hard climbs at the end of the day, and decide when he was done; I could ride extra miles and still be supported.
This trip is one of their shorter trips, so day 1 is a bike fitting and warm-up, day 2 is a full (and challenging) 40+ mile day, day 3-4 are full days, and day 5 is your last cycling day with more options. This trip was also rated "athletic beginner" (beginner/athletic beginner/intermediate/expert). Long routes are 40-60 miles days 2-5, shorter routes are up to 40 miles, but always over 25. With regards to the bike fitting, you provide measurements ahead of time, bring your pedals (if you have them), and they do general seat post height (usually pretty close), handlebar (I received a "you must ride a lot" comment by my request to have my handlebars lowered to a more aggressive riding position), and comfort (seat angle/reach distance) adjustments. They actually did quite well. The saddles are of course cushy, which is nice at first but I wasn't really a fan. Next time I'll bring one. The bikes were Bianchi aluminum frame with Campy, which was weird for us Shimano Americans, but you get used to it. I didn't really like not being able to shift from the drops, but it was usually not an issue once you adapt (unless you space out, at which point you drop your chain riding hills ;)).
By the end of the trip, we were already ready to plan our next one - the guide recommended Provence, and they have a few other trips rated for "she wants to train, he wants to take photos" in the catalog. We had a great time. I have a complete photo album up on facebook that I hope to transfer to the trip website and/or flickr, but wanted to post a few before I got sidetracked.
You would be proud to know that the head of the group (by a fairly good spread from the rest of the pack) was 2 women and 1 fine gentleman, and our trip was fairly evenly split at 7 men, 6 women (plus one male/one female guide).
We also spent a week split between Rome and Florence, and only took trains/buses while we were there (other than a taxi to the train station on our last day).
Attached are a few photos... had to post one in my ever so appropriate "she loves hills" TE jersey (sorry for the expression on my face, I think I was saying "should I leave on my sunglasses?" with a clearly sarcastic tone :p).
