My entire Italian vacation last summer consisted of advice I received on this board during the planning stages. Once again, I'm looking for any information or direction in planning another vacation for July of 2010.

The first trip last summer was throughout Northern Italy; Summer 2010 I'd like to spend exploring Tuscany (specifically the hill towns). I will have 14 days (not including international travel days) to work with. So far, I've got it narrowed down to Lucca/Pisa, Florence, Siena, Cortona, Montepulciano and Orvieto. I know that 14 days is not enough time to explore all of these cities. Do you have a suggestion on which one/s I should Axe? Am I missing an important hill town?

I don't particularily care to stay in Florence for too long, just enough time to see the Duomo and the Museum. I particularily like cafes', shopping, photography and walking the streets. I'd like to rent a bike and/or Vespa to get around town and maybe a car if needed to go from one place to another. I don't drive a stick...so that may be an issue. I'll also be traveling alone.

My flights are not purchased. Ideally, I'd like to fly in or out of Venice. Even though it doesn't make much travel sense, it was my favorite city and I'd like to spend at least 1 full day there again. If at all possible, I'd like to stay clear of Milan airport (pain in the ARSE, plus the train station scared the beejesus out of me!). That leaves florence or rome as an alternative airport.

I've started looking at Convents/Monastaries as a budget alternative to hotels. Are there any in these towns mentioned above that you could recommend?

This is my starting point (beyond books)...so any advice would be very helpful!

Milan means Malpensa?

Since there are no direct flights back to the U.S. from Malpensa for me, I use Linate instead and end up with a better schedule at no additional cost. Linate is about 15min and 18EU by taxi from the Duomo area.

One drawback for Linate is the fog in the winter. But it is not an issue for a July trip.

I don't know how old you are but I have 3 great travel journies to complete in life. They are in no particular order :

1. Home (NW England) to Greece sailing via the Canal Du Midi
2. ICW from New York to Texas via the Bahamas and again sailig.
3. Tuscan hill towns on a Vespa

I have absolutely no idea whether this is doable or how to plan but by travelling very light - why not? Read Vroom With a View by Peter Moore for inspiration.

I pick up these details on our previous visit - still keep it in favourites for the time when my soon stands on the two feet he as born with.

http://www.tuscanyvespatour.com/

I am not sure about the side trip to Venice - its an awefully long detour for one day. Which Milan airport was a nightmare? We used Malpensa last week and the food experience was one of the best we have had.

Why not connect into Pisa - train bus to Lucca then Florence and try to hire a Vespa in Florence. Use easyjet to connect into Pisa - they offer a very good service and if you book well in advance the prices are too good to be true. We paid 22 euros all in to fly from Malpensa to Catania return.

As far as the hill towns go - Pienza is my favourite followed by San Quirico. Leave Gimingnano to the cruise ship types during the day. Try to stay there as after dark it takes on a totally different life.

Everyone has there reasons for loving Tuscany our best experiences have always been in the quiet country lanes - walking or cycling. Not trailing round Florence with the tour parties.

I am sorry I will struggle with cheap lodgings - ours usually come with fluffy robes and flat screens.

I really liked Volterra, but it is further away from Florence. We drove so I have no idea regarding public transit.

I am curious what is scary about Milano Centrale station? This is not the first time I've heard somone say they hated it. Is it full of pickpockets or scam artists? Or just huge and bustling? Just trying to understand, as we'll pass through there several times next summer. Thanks.

You will not be able to see all of your wish list from one location, and Orvieto is better as a stop in transition. Here are places in my favorite part of Tuscany--the best of the hill towns.

BOB’S FAVORITE DIGS IN TOSCANA

A. RURAL LOCATIONS: All have parking and good food options nearby

1. Relais La Saracina www.lasaracina.it 230 to 300E
Fabulous country home near Montepulciano—helpful owners

2. Cretaiole Agriturismo http://www.cretaiole.it/ Good value for families

3. Terre di Nano www.terredinano.com 100 to 155
Both rooms and apartments at rural Agriturismo near Monticchiello

4. Hotel Pescille www.pescille.it Good value at a rustic hotel only 3 km from famed San Gimignano with great views---100 to 130E

5. Fattoria Tregole www.fattoria-tregole.com 110E to 180E
Has both B&B and apartment accommodations. Near Castellina in Chianti

6. Agriturismo apts. near San Quirico— www.poggiolo.info/ About 110E


B. IN-TOWN LOCATIONS: For walking convenience to shops & ristorantes.

1. Palazzo del Capitano www.palazzodelcapitano.com 130 to 180E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.tuscany.net/oliviera/ 130 to 180E
Nice 4 star hotel at the gate into lovely Montalcino---has pool.

3. Palazzina Cesari www.montalcinoitaly.com 80 to 110E
Lovely small B&B in heart of Montalcino—great value—2 night stay minimum.

4. Locanda di San Francesco www.locandasanfrancesco.it 180 to 200E
New boutique B&B in a lovely location in Montepulciano—great reviews !

5. Palazzo Ravizza www.palazzoravizza.it 130 to 180E
Very nice & popular hotel in Siena with parking.

6. Fattoria Vignale http://www.vignale.it/eng/ Four star hotel in Radda in the heart of Chianti. About 230E for double

Thank you all for the advice. I am considering Sant'Anna in Camprena as a base. There are only 6 reviews on tripadvisor. Does anyone have any advice on this monastery?

Starting the trip in Venice because my mom, who will be joining me the first week has a strong desire to visit. Tentatively, I'll go from Venice to Lucca then onto Florence for a few days and then a "base" to explore Tuscany from. Possibly flying out if Rome.

Santa Anna is a pretty setting but somewhat isolated and rustic. I would stay in San Quirico.

Bob - it's rustic but cheap - as far as I remember (3 years ago) the rooms were around 30 euros a night - looking at the OP the average fluffy robe joint may be a little north of the budget. Sant Anna is also very close to Pienza and San Quirico.

It was in the process of being given a lick of paint since Ralph withered away.

I do like all your other fluffy robe suggestiosn though.

What's the place in Sinalunga called where they clean your shoes when you get out of the car? - went up just to have a look - very pristine!