Need help on Tuscany portion of trip
 

My husband and I are taking my first trip to Italy (he went in college) in September. We arrive in Rome on the 19th and plan to head immediately to our first destination. We are flying out of Venice on the 30th and already have a hotel booked there for the 2 nights prior. We plan to be in Florence for 3 nights before that. This leaves us 5 nights at the start of our trip which we are planning to spend in the Tuscan region. The issue is where to base ourselves (one location or two) and which places to try and fit in during that time.

We are not real big into history or art so will probably limit ourselves to just some of the must-sees while we are in Italy. We prefer to experience the beauty of the countryside while also sampling delicious food and wine. We plan to have a car for these 5 days, dropping it off once we arrive in Florence.

We thought about making Sienna our base but are open to something a little smaller and more quaint. I have done a bunch of research but am overwhelmed by all the options. I would love recommendations on how to make the most of these 5 days without running ourselves crazy. Places to stay and must see places to visit would be greatly appreciated.
Thanks.

What a nice problem to have!
With 5 nights I do think I would split my time. I would start south near San Quirico and Pienza for 3 nites---see Siena for half a day as you transition north--- and then the last 2 nites near San Gimignano. I would drop the car at the airport in Florence---do not try to drive in that town.

Look at Palazzo del Capitano in San Quirico.

The rustic hotel Pescille just south of San Gim. is good value.

Locanda di San Francesco in Montepulciano!

chi jen,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

If you hate the tourist crowd then stay away from Siena and San Gim, filled with buses and people and not the real Tuscany. Typical tourist chaos......

Great book, Walking and Eating in Tuscany and Umbria.......want to see little towns, little trattoria's, great eating......follow the book. We have done 1/2 the hikes and found the most wonderful people and food.

Also, San Felice is in the municipality of Castelnuovo Berardenga, in the southern part of the Chianti Classico area, twenty kilometres from Siena. Its location is ideal for excursions to San Gimignano and Volterra, Florence, Arezzo, Montepulciano and Montalcino.

Radda is a wonderful little town. Stayed their twice.....glorious!

Enjoy!

I second the suggestion of Locanda di San Francesco in Montepulciano! Five days in that area would be perfect. But if you decide to stay at this place, book ASAP. There are only four rooms.

http://www.locandasanfrancesco.it/index.php

+1 Locanda di San Francesco in Montepulciano!

I suggest staying in the Val d'Orcia area for the entire 5 days. I feels it's the most beautiful area in Tuscany. I like to stay at Fonte Bertusi, located about 3 km outside of Pienza-

http://www.fontebertusi.it/eng/

The location is beautiful and very central for exploring the countryside and the many lovely towns and villages nearby. The owners are terrific and the breakfast served is great.

Here are some other choices in the area-


http://www.santamariapienza.it/index.php?lang=ing

http://www.agriturismocasalpiano.it/index.html

http://www.cretaiole.it/index.en.php
(Excellent location)

http://www.cretedisiena.com/Casa_Picchiata/english.htm
(Excellent location)

http://www.terredinano.com/pages_eng...o_toscana.aspx

http://www.lafonte.toscana.it/2006/ita/
(Excellent location)

http://www.agriturismosangallo.com/ENG/home.html

http://www.tobruk.it/agriturismo.php?lingua=en
(Incredible views and a beautiful property)

http://www.casafrati.toscana.nu/
(Well priced)

http://www.lupaia.com/location.html
(A beautiful B&B located in the valley below Montepulciano)

http://www.lafoce.com/
(Beautiful apartments/houses/villa/property- very special)

http://www.lacasadiadelina.com/index...t&id=9&lang=en
(A small, lovely B&B located within the small, lovely town of Monticchiello)

http://www.lemaribelle.it/intro.en.php
(3 apartments located in Monticchiello)

If none of the above works for you, consider searching these two websites-

http://www.cretedisiena.com/english/

http://www.vrbo.com/vacation-rentals...cany/valdorcia

Thanks everyone. Locanda di San Francesco in Montepulciano looks amazing but is unfortunately already booked for our dates. Will look at some of the other suggestions and as always open to additional ones.

"If you hate the tourist crowd then stay away from Siena and San Gim, filled with buses and people and not the real Tuscany. Typical tourist chaos......"

There's a reason those two towns draw such huge crowds. Beautiful scenery, among the best of all the Tuscan towns, especially from up in the towers.

You should definitely visit both at least once. Sure the smaller towns are quaint. If you only like rolling green hills with vineyards, then yes, concentrate on the Val d'Orcia.

But if you want to see medieval architecture in that pastoral setting, then you can't miss the bigger towns either. Not to mention you can see some art in those bigger towns too.

Since you will have a car, I would recommend using Siena for your base, morning and evening strolls, etc. when before or after driving to such sights as San Gimignano, Montalcino (Brunello winery, and their Banfi Castle), Pienza, etc. There are so many things to do in Siena that doesn't take much time, such as Del Campo, the Duomo, and their muesums and restaurants, the medieval walls, castles, markets, etc., that you can have your cake (small towns and their charm) along with seeing Siena at your leisure. Have a great trip, a vino and a gelato on me.

I used Siena as a base for 3 days. I stayed at a hotel which was maybe 100 meters from one of the ports and then I had to walk about another 800 meters to reach the Campo.

I found after long day trips, the prospect of walking 1/2 a mile, with that path not level, kind of a drag, to get to a restaurant for dinner.

If you plan on driving to your Tuscany destination directly from Rome, think again. Arriving jet-lagged and then driving for 2 or 3 hours can be dangerous. I know this from experience when our son in law dozed off at the wheel three times on a four hour drive, even though he had several espressos. It's a miracle we were not in an accident!

You're right charnees- it can be very dangerous to drive when jet lagged.

I recently made the trip to Florence from my home in Idaho. I did not sleep on the flight and did not sleep at all my first night in Florence (I arrived at my hotel around midnight). I finally gave up on trying to fall asleep and got up at 5:00am, showered, and went for a walk on the quiet, empty (how strange!) streets of Florence. Well, I was staggering like a drunk down the street! After 15 minutes of staggering (and before I fell or tripped), I headed back to the hotel. I felt better after breakfast and headed to the car rental office.

I drove around the Chianti region all day until I headed to my base in southern Tuscany. I felt fine until around 4:00 when I was about 30 minutes away from my apartment. Jet lag hit me again and in order to stay awake I had to drive with the AC full blast, the windows down (it was raining), and the music turned up loud (and I swear that every station was playing the same one song over and over- "We Are Young" by Fun). I never dozed off, but it was close.

That said, several times I've arrived after the flight from the US, picked up the car, and driven 3 hours and not felt jet lagged at all. You just never know if/when it will hit you. If you can get a good night's sleep the night prior to your drive, do so.