Thanks to the very helpful people on this forum, the trip to Italy that my wife and I (in our 40's) have planned for next July is taking shape. Itinerary is 3 nights Positano, 2 nights Capri, and 4 nights Tuscany. Plan to leave on the first boat from Capri to Sorento, rent a car, stop at Pompeii in the morning and then drive to Val D’orcia region in Tuscany. Clearly our most ambitious day, but I think it will be ok.

So the question I’m left with is in Tuscany. The first decision point is village vs countryside. Might be nice to have a pool and land, but I think we’re leaning to the convenience of being in a village to offer the ability to stroll around and walk to restaurants. I always see very positive things written about Pienza and San Quirico D’Orcia as places to use a base for the region. For some reason, I seldom see Montepulciano suggested, but I’m not sure why. Like the look of some places to stay in Montepulciano, but it would be helpful to understand the differences among the villages.

One last thing. One day we would like to visit Sienna, and then go on to Monteriggioni and Volterra. While it all may look very close on a map, my sense is that this may be quite a bit of driving. Perhaps we get an early start and stay in Sienna through lunch. Any thoughts about this plan would be appreciated.

You should always get to Siena early, parking fills up very quickly.

I think both driving days you mention are ambitious.

I doubt you could get to Pompeii when it opens (8:30, BTW), and by then you will already have taken a taxi from your Capri hotel, the ferry, a taxi to the car rental and driven almost an hour. If you have only moderate interest in Pompeii, you could wander for 2-3 hours and then look for lunch somewhere. (FWIW, we've spent nearly two full days at Pompeii and not seen the entire excavation.) Then you face a nearly 5-hour drive to somewhere like Montepulciano.

Would it be possible for you to visit Pompeii on your way to Positano?

The second driving day to Siena, Monteriggioni and Volterra would mean lots of time in the car and very little time in the towns. Calculating from a sample base of Montepulciano, you're looking at nearly 5 hours of driving that day, assuming you don't get lost or sidetracked by something interesting and assuming you don't lose much time looking for parking. Factor in that it could be blazing hot by mid-day, and you may not want to sprint around. As SAB pointed out, parking in Siena fills early, and you'll likely have to wait in line to enter the Duomo.

The car rental office in Sorrento probably doesn't open until 8:30/9:00. You'll need a car that can hold all of your luggage in the trunk.

Here are options for you. If Volterra is one of your highlights then I would not stay in Montepulciano---too far.

BOB’S FAVORITE DIGS IN TUSCANY
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
Isabella also has 2 apartments in Castelmuzio for rent—a good option.

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

4. Casanova di Pescille http://www.casanovadipescille.com/ 100E
Rural B&B 3 KM from famed San Gimignano—we loved the views of San Gim.

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

7. New historic B&B north of Pienza. http://www.camprena.it/index.htm
Site of filming for THE ENGLISH PATIENT About 90E for double

8. http://www.borgoargenina.it/index.html A special rural B&B in Chianti.
The lovely owner, Elena, will make you feel like family. 170E for double

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

1. Palazzo del Capitano www.palazzodelcapitano.com 170 to 210E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.tuscany.net/oliviera/ 150 to 200E
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. Politian apartments http://www.politian.com/ Good value apts. with
minimum stay of 3 nights in Montepulciano---helpful host---85E

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

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

nydelifan,
This will give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I stayed in Montepulciano last month for a week. It was our 3rd one-week sojourn in that wonderful town.

We re-visited Pienza and S. Quirico on this trip -- we are very fond of both places.

If you decide to stay in a town rather than in the country, Montepulciano is a very appealing choice. Visually stunning, with great views. The architecture, the restaurants, the shops, the other amenities are remarkable for a community of maybe 25,000.

The other two places are little gems too but I stress the "little": they're quite small. S. Quirico usually gets 1 hr of my time, Pienza 2 hrs.

You might not get tired of them, if you are staying only 4 nights, however.

Restaurant choices might be limited, esp, in S Quirico -- and I don't like driving in the evening to another town for a meal.

The one big advantage of S Quirico is that it is appreciably closer to Siena, hence to Volterra. But we have done Volterra on a day trip from Montepulciano.

(PS: Montereggioni is a 1 hr stopover, IMO)

Here is my commentary on Montepulciano from my recent (Oct 2010) Tuscany trip report.

I've included my para.s on La Foce, a great garden nearby. It is open to visitors on Wed PM. July is likely not as good a month for visiting as May or June would be. But the garden shows well in any season -- even late October, when we saw it:

WEDNESDAY OCTOBER 26:
Today we are staying put. I have one item on my agenda: A visit to the gardens of La Foce, quite near here. Until then, I am simply going to steep myself in the atmosphere of Montepulciano and partake of the amenities of our lovely apartment.

Montepulciano, BTW, is the most perfect town in Tuscany:

 Fantastic civic architecture, including dozens of historic palazzi still in private hands (though mostly divided up into flats).
 Bewitching views from its hilltop eyrie. The Val di Chiana and the Lago Trasimeno are spread at your feet -- in the distance, snow-capped mountains nearer Rome; closer in, a welter of picturesque hill towns.
 All the infrastructure that a tourist -- no, a traveler -- needs: a super-abundance of good restaurants, shops, wine “cantine” selling the Vino Nobile di Montepulciano. In season, concerts, theatre, even opera performances.

You need good knees and a good set of lungs, however: This is one of the most vertical towns in Tuscany.

It is a wealthy town and a sophisticated one. Yet it never condescends or demeans the visitor. Neither does it demean itself, to get at your money. You are welcome here and you are invited to admire what its residents admire: the rich history and cultural traditions, the town’s stupendous architectural endowment, the overall “douceur de vivre”, as the French put it -- the “sweetness of life”, in a setting such as this.

The apartment we have rented from Margherita and Giorgio has been created from a derelict outbuilding attached to the palazzo inherited from Margherita’s mother. Margherita shares it -- and the rental business -- with her sister Elena. Their brother has the palazzo of their father’s family, much of it now rented out as government offices.

Elena and her husband also have a “terreno” nearby where they grow olives: the harvest is underway this week and will be converted to oil within days.

Our apartment, one of four in the complex, is really a self-contained 2 storey house. The front door faces a street whose other side is a 5 storey brick and stone retaining wall, complete with buttresses. The wall is so high that I’m not sure what stands above -- there’s surely something, as every usable space in Montepulciano is built on.

Margherita’s architect sons took a large hand in re-designing the building. They have been cunning in their use of space. The main floor has a small hall, two bedrooms and two baths, one en-suite. A central staircase in Travertine marble rises to a large open space, with the sitting area and a large open kitchen and eating area.

A columned white marble fireplace has been added. All the floors are authentic Tuscan cotto -- terracotta bricks. With the same fidelity to local materials and building practices, the kitchen counters are built with glazed tiles and the high, beamed ceiling is constructed along traditional lines.

Elena and Margherita’s grandfather, Count Bracci, was mayor of Montepulciano and a great friend of Marchese and Marchesa Origo, who created the house and garden at La Foce.

It was to take refuge with the Bracci, during the final days of shelling and pillage in summer 1944, that Iris and Antonio Origo walked with their two infant daughters and 60 child refugees from Genoa and Turin the 10 miles from La Foce, along a mined road and with the constant threat of aerial strafing.

When they returned, they found the fabric of the house largely intact, apart from a couple of shell-holes in the walls. The retreating Germans had thoroughly vandalized the house, however, and the arriving Allies had likely done their share. Much of the household furniture was tossed into the parterre garden, we learned during our visit.

But La Foce is a miracle of invention and resurrection. That it exists at all is a testimony to the vision, energy and determination of this remarkable and public-spirited couple.

In the mid-20s, the heiress Iris Cutting, half American and half Anglo-Irish, married the illegitimate son of an aristocratic sculptor, Antonio Origo. They chose for their home an unlikely southern Tuscan property, a former inn and hospice on high ground in the crete Senesi. The land around the house was a waterless near-desert -- “a lunar landscape” according to our guide. (“Crete Senesi” are the dry clay ravines the score the bare and otherwise smoothly undulating hillsides of the area.)

Irrigation, the construction of houses and schools and a hospital were funded by Iris Origo’s American inheritance. That fortune also financed the creation of a wonderful garden around the original building, now converted to a handsome villa, at the centre of the huge estate.

The gardens reflect Iris Origo’s cosmopolitan origins: They were designed by British architect Cecil Pinsent, were paid for by Iris Origo's New York-based grandmother and reflect the grand style of gardens at the Villa Medici, the Florence home of her mother, and the Irish country seat of her maternal grandfather, the Earl Dysart.

From the rear courtyard of the villa, you descend a few steps to a small side garden. Here you have you first taste of the garden’s mix of liveability with formal structure. Box hedges backed by a hemisphere of cypresses frame a metal sculpture by Antonio Origo’s father. Across a broad lawn stands a swimming pool, behind which is not a pool house but the villa’s limonaia -- the orangerie into which the potted lemon trees are moved in winter.

You turn left, past a pair of immense shaped ilex trees, to the villa’s front courtyard, where potted lemon trees stand along flagged walkways, with low box hedges framing flower beds.

From here spread out a series of garden “rooms” -- not closely hedged or walled, as they would be in England, but visually continuous, to take advantage of the stunning views of distant Monte Amiata, beyond the broad valley floor. The rooms are defined by low hedges, by balustrades, by changes in level.

Off to one side, a monumental set of stone steps rises high up the hillside to a distant sculpture set in a niche. We walk under curved-top trellises heavily hung with wisteria -- flowerless now but breathtaking in Spring, as we hear from the well-spoken young woman who leads our English-language tour.

Now we are in the former rose garden: it was replanted a couple of years ago with fragrant plants such as lavender and rosemary. We look down into the triangular parterre garden, in which all the box parterres point the eye toward the prospect of Monte Amiata.

As you move outward in the garden, it becomes progressively simpler and more rustic until finally, it melts into the landscape. Where the nearer trellises held wisteria, these hold grape vines. The grass is rougher, the stone of the walls and paths is coarser.

Finally, we come to the little gate that leads to the walk Iris Origo took to the family cemetery where her son, dead of meningitis at 7, was buried and where she, Antonio and many employees of the estate now lie.

The guide invites us to drive over to the cemetery and to Chiarentana, another of the estate properties, where olive oil production is underway. The estate still sells its wine and its oil, as it did in Iris`s day.

We take our leave of a Melbourne couple, Carol and Karl, our fellow-tenants at Al Poggiolo. At the cemetery, a story-book “contadino” -- the protoype of all weather-beaten Tuscan peasants -- gives us elaborate road directions to Chiarentana.

At this large and immaculately maintained property (now holiday apartments, for rent) we and some ladies from the tour file into the actual production room. Modern stainless steel machinery, all of it spotless and gleaming, surrounds us. A very handsome young man in a coverall invites us to look at the product: He trains a flashlight on the churning screw within the dark vat: something thick, viscous and unmistakably olive-y is churning around with it. It looks icky but smells wonderful.

When it is her turn to peer, each lady leans in very close to the youth with the flashlight. Perhaps they are olive-oil enthusiasts who have always dreamed of visiting an oil mill.

I have an inspiration: Why not carry on from Chiarentana on this fine dirt road? I can see on my map that it leads back to the highway.

The setting sun is turning all the hillsides golden. It is like a gold scrim in which the hills flatten into cut-outs, each paler than the one in front.

We drive along quite happily until the road starts getting rougher. Then it gets very rough indeed. We seem awfully far from any major road. Now the farmhouses we pass are in ruins. These are outlying properties of the estate: the fields are cultivated but no one can be found to live in these remote spaces. No one to help us if we break down.

I’m starting to get nervous with the approach of darkness when -- magically -- we suddenly descend to a fine, flat highway. It carries us, our spirits and confidence restored, smoothly back to La Foce and then to Montepulciano and dinner.

Some excellent ideas here, I'm bookmarking!

nydelifan,

The rule of thumb for the hilltowns is 2 per day. You can't really do more than that unless 2 out of 3 are very small and they are close together!

Remember to leave time for lunch, photo ops, and that the shops close down in the afternoon for a least 2 hours minimum.

Thank you all for the feedback. I will keep in mind the thoughts regarding driving itineraries. Regarding Pompeii, not really practical on our way to Positano as we will be coming from naples after flying in from NY. thinking not more than 2-3 hours as it will be early July and likely quite warm.

Henry and Tedgale, your detailed information is quite helpful. makes me even more enthusiastice about the region, and Montepulciano in particular.

Bob, I had seen your recommendations and actually might stay at Locanda di San Francesco.

Dayle, appreciate your thoughts. Your input here and elswhere has been great.

Now for a brief editorial. I think the hardest thing about being a first time traveler to certain locations is to not go where "everyone" goes. You can do all the research in the world, but there is no substitute for experience. i think of my own limited travel. I would stay in Princeville on Kauai over any place on Maui, simply a magical place. Armies of people head to Vail, yet I strongly prefer Utah or even some place like Jackson Hole. Similarly, Cape Cod is where "everyone" goes, yet my annual summer stays in Ogunquit, Maine have only reinforced my strong feelings for that destination. As I write all this, perhaps it is Capri that falls most firmly in this category. Only a short stay and it certainly looks like a beautiful island, but I go into it with my eyes wide open that the feel may not be optimal, particularly in early July.

Well. . .I was about to weigh in my recommendations but given all the great advice and insight everyone else has provided I would feel foolish.

Simply great ideas presented here and you can't go wrong with any of them.

Have a great time!

Bookmarking

Well, I'm not so fond of Montepulciano as others here. And it's a hilltown with a steep main street. Depending on where you're staying and where the parking is, you'll be climbing up and down that street a lot on foot or by car. Good views though.

Whereas both Pienza and San Quirico d'Orcia are on the flat. They're easy to drive in and out of when doing daytrips by car. See TripAdvisor for hotel reviews for those towns. And Tripadvisor has reviews on 17 restaurants in and around Pienza, 8 for San Quirico. That's enough restaurants for me.