sformby: I like all your itineraries, and like you, play the mileage game (with minimal miles).

On this itinerary, staying in London too, you have 5 stops. For me, that's a lot. I think I would cut to one in Tuscany, making day trips.

sformby,

I also like your latest itinerary. If you would like a recommendation for the Chianti area look at Hotel Residence San Sano****. It's about 20 min, drive north of Siena just off the Chianti hwy in a TINY village of San Sano. We voted it best lodging of a 3 week trip. We were there for 4 nts.

You're going to have a wonderful trip!

Sformby, you certainly received a great deal of good advice. For a great hotel in Siena, I would suggest the Palazzo Ravizza which had been highy regarded by many on this site. Very charming, in town, with great views of the surrounding hills, and with a parking lot below with tight security. You can enjoy the ambiance of being in town with the advantage of quick egress to local roads. Enjoy Italy...

Yes, thank you all for all your advice!

I am going to ask for help again, as I am in "analysis paralysis" mode. I have everything squared away for this trip except for the 4 nights in Tuscany. I can't figure out where to stay to save my life. Outside Siena? Near Pienza or San Quirico d Orcia? Somewhere else? Here's what I envision: a property located close to or in a village/hilltown. Siena is less than an hour away for a day trip. I can walk to restaurants if I don't want to get in the car after a long day sightseeing (or, a 5-minute drive at most). The hosts are helpful and speak English and can suggest sightseeing and make dinner reservations. There is a place to park my rental car. There are two beds in the room or apt (this can be the tricky part). Budget under $250 a night.

Palazzo del Capitano in San Quirico.
The perfect location for day trips and a really cute village.

Okay, good suggestion. I am thinking perhaps 1 night in Siena at Palazzo Ravizza and 3 nights at Palazzo del Capitano in San Quirico. Or 2 and 2. I really want to see Siena at night, but am concerned about driving home from there to San Quirico. Hmmm. What am I missing if I do Siena as a day trip from San Quirico and don't spend the night there?

Not much IMHO.
I do like Siena and we have stayed there, but I lOVE south Tuscany so much I would spend my time there--as we will for a week next May. Have you seen this place just outside of town with great prices? www.poggiolo.info/

sformby,

I think you are obsessing a bit about seeing Siena at night. The hilltowns I've stayed in have all been lovely at night with great views.....Gubbio, Montalcino, Spello, Assisi.

I only spent a 1/2 day in Siena, but I actually have liked all the other hilltowns I've visited for 1/2 days more than Siena, and it's a long list.

Okay, I'm convinced I can do Siena as a day trip if we are so inclined. I'm looking at Residenza il Poggiolo and Palazzo del Capitano. Prices for il Poggiolo certainly seem a good value. Bob, do you know if its an easy walk into the village? Or, I guess that doesn't matter if the parking is easy.

I think you would drive at night--walk is about :10.
But, you do have to park on the perimeter of SQ--it is pedestrian only village--part of the charm.

Here's a vote for staying at least one night in Siena. Inside the walls in the historic center it IS different than other hilltowns at night. Heavy dark masonry shapes loom overhead, few lights to be seen. No cars, just echoing footsteps.

You could stay one night in Siena and pick up your car the next day.

San Quirico makes a good base but it's really a village, not a town. Being able to walk from your hotel to a choice of restaurants means you can kick back after a tiring day sightseeing and have wine with dinner. You can check walkability for hotels on a mapping site like www.viamichelin.com. Select the pedestrian option.

I'm not such a fan of Orvieto and would definitely not take a day away from Rome for a second night in Orvieto.

We are booked now at www.poggiolo.info for the 4 night Tuscany part of our trip, although I had to change our dates around a bit because of work. Bob, are you staying at Il Poggiolo in May? We picked Casa Micciola apartment. So its:

2 nights London - W Hotel Leceister Sq
3 nights Venice - Westin Regina & Europa
4 nights San Quirico d'Orcia - il Poggiolo
4 nights Rome - Navona Garden Suites

Whew! Nice to have that all decided so that I can move on to what we are actually going to see and do on our trip. All that I have booked so far is the Scavi Vatican Necropolis tour. Very excited about that. I think I would like to have a guide for an ancient Rome tour during our time there. I'm getting a new GPS for Christmas, and I want a new camera to take. And I want a new travel coat and walking shoes. And one of those new fangled "spinner" suitcases. And a Rosetta language software for level 1 Italian. And an international data plan for my iPhone and....yeah. I've got a case of the travel gimmees. Need to lie down and let it pass.

Looks great!
We are staying in Montepulciano in May at Politian apts.
Have fun.

sformby,

Make sure those new travel shoes are very well broken in! Wear them every day before you go.....then - I recommend the Disneyland Test. If you can make it thru an entire day at Disneyland on pavement in them - they are ready!

Even then - take moleskin. It will save your trip. Band aids are not sufficient.

So true. I got blisters in Disneyworld in October even with my favorite walking shoes. Put the moleskin on one day too late. I've got to figure out the always tricky "don't-want-to-wear-athletic-shoes-in-Europe-but-want-to-be-comfortable" dilemma.

Sformby,

We are going to be in Italy the same time as you, but we will be in Rome for the full time with one night toward the end in Florence (I haven't decided which yet). I too have a serious case of the travel gimmees, it's hard not to so close to Christmas. Hope you have a great time!

Yes, the gimmees are still with me. I question everything I normally pack and want the latest and greatest. I will say that I figured out how to add PDFs to my iPhone and I already have all my reservations confirmations loaded. That's pretty slick. Add the maps and guidebook apps and it can really save me some space in the suitcase. I will be buying a good roadmap, of course.