As part of a 2-week trip to Italy in April/May 2013, my husband and I would like to spend some time in the countryside. This part of the trip would (hopefully!) be the most relaxing. I envision renting a car and driving to check out small towns, stopping for a picnic with wine, bread and cheese, maybe visiting a winery or enjoying some pool time (if our lodging has a pool and the weather cooperates), and having a wonderful dinner somewhere. We might even be up to do some bicycling or walking/hiking, as we love being active outdoors. Probably staying in an agriturismo or B&B in the middle of nowhere, 3 nights or so. We will definitely be on a lodging budget - thinking a max of $150/night.

What are your thoughts on Tuscany vs. Umbria to fulfill our goals? For context, we will probably start in Venice, head to the Bologna/Parma area (to feed our foodie obsession), then this countryside section, and finish up in Rome.

Either would work, but you really should read about the towns/sights of both regions because there are differences. Perhaps a particular thing will tip the scales, like Assisi or the Val d'Orcia of Tuscany.

Three nights (two days) is not much time for relaxing plus all of the other things you mention (exploring towns, wineries, picnicking, pool time, bicycling/walking). You'd be limited to seeing a fraction of either region, but since Umbria is smaller you'd probably feel you'd seen more of it.

FYI, most wineries are not prepared for drop-in visitors, so you'd need to make reservations.

Southern Tuscany - Pienza area (Val d'Orcia). The pictures you see on postcards of Tuscany are mostly this area. I would be surprised if any pools are open in April and perhaps not all of them in May.

I've stayed in this agriturismo outside of Pienza for much less than your budget. They have a pool and bikes.
http://www.agriturismobonellinovecch...farmhouse.html

I've also stayed in an apartment in Pienza. It seems the prices are about 60-70€ per night now.
http://www.ilgiardinosegretopienza.it/

You won't have a problem with your budget.

I may have this wrong. When we stayed at a villa near Pienza last August we were told that in Italy owners were not allowed to have the pool operating before May or after September.

Caze17,
Just my 2 cents:
- April-May doesn't guarantee poolside time in Tuscany and Umbria. The later you can come, the better it woud probably be.
- How one explores towns, visits wineries, walks and relaxes during a 3 night stay still has to be explained to me...
- I would focus on Umbria, mainly because it is smaller. Then I would focus on the Perugia, Assisi, Spello, Bevagna area, because of the short distances between these interesting towns.

I would stay here and explore south Tuscany.
http://www.tripadvisor.com/Hotel_Rev...a_Tuscany.html

Thanks to all for your suggestions. And sorry for the confusion - I didn't mean to imply that we would be able to do all of those things. Those were just the type of things that I was considering, that I was hoping could shed some light on which region may be better suited for my travel. My idea of relaxing is that I don't have to be anywhere on a particular schedule (okay, fine, maybe just one scheduled winery visit!), but can choose to take a right or left turn wherever I feel like it. Maybe stop for a walk where it looks interesting, park and have a snack when the pang of hunger hits, or choose to eat in a corner trattoria when we come across one. I love to drive, especially in a scenic area, so that is far from stressful. No pool time - no big deal - that was low on the list anyway - just trying to illustrate that I didn't always have to be doing something. And I certainly don't need to see all of whichever region I choose - quite the opposite, in fact.

Thanks again for your suggestions. I'm really looking forward to this trip and how the itinerary is shaping up! I'm sure I'll be back with more questions as they come up.