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Base Area for Wk in Tuscan Countryside?

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Thanks again to those of you who graciously commented on my proposed itinerary for this fall. I will not be spending a lot of time in Florence this trip (though I loved it several years ago).

We are planning a week in the Tuscan countryside and checking VRBO listings and TA to try and figure out where we want to be based for the week. Have also been reading guidebooks and the book, 101 Most Beautiful Small Towns in Italy. Alot of the rental places seem to be in the Siena region, and I checked Google maps today to get an idea of where places were in relation to each other, plus I read about the Val d' Orcia, a UNESCO region just south of Siena. Thinking about a day in Montepulciano and Pienza. I'd also like a day in Siena that week as well as one in Chianti for wine tastings, etc. further north.

I am trying to gauge distances to balance activities, driving, and just being there in my route planning. So "Toscanaphiles," do you think renting a place just west of Siena would give us the flexibility we need for our week of wandering? Don't mind spending some time in the car, but I don't want to spend all my time in it. Have always loved bits of serendipity even in my most planned travels. Please let me know what you think or would recommend. TIA.

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    I would settle in the Pienza/San Quirico area. On our last visit the the Val d'Orcia in 2013, we stayed here for 2 weeks:

    From my longer Italy itinerary:

    Tuscany – Val d’Orcia
    My wife & I first visited the Val d’Orcia (around Pienza) in the late ‘80s when we were doing the typical “once over lightly” tour of Italy. On an old map I used at the time, I had scribbled the comment “pretty” on the road running between San Quirico d’Orcia and Montepulciano. We passed though this area again on several subsequent visits – usually staying 1 or 2 days each time. In September ’94, we stayed 4 days at the 5-room Hotel La Saracina near Pienza, and explored the area a little more (using up a lot of film) and then moved on to the Chianti area for 3 days, San Gimignano for 2, Lucca for 2, etc. In September ’96 we met 3 other couples (old college friends celebrating our 25th anniversaries together) for a 4 day stay in La Saracina. One of the couples liked the area so much that they booked a 3 week stay at La Saracina the next year, and then bought a 2nd home in the town of San Quirico the year after that (after exploring Chianti & Umbria to make sure they were buying in the area they liked the most). In ’99 when we retired early so we could travel more, we stayed in their apartment for 3 weeks - taking day trips to other areas in Tuscany & Umbria, exploring the Val d’Orcia, and enjoying Italian village life in San Quirico. That same year we had spent a considerable amount of time in Provence (7 weeks), and when we arrived in the Val d’Orcia, we both commented that this area was the prettiest countryside we had seen anywhere in Europe. I have various books & posters showing the Val d’Orcia in early spring when everything is green. It looks quite different in these spring pictures than it does in September when we had always been there. In March of ‘04 when the airfares were low and our friends were living in their apartment in San Quirico for 5 months, we visited the Val d’Orcia again. We thought that in September the countryside looked remarkable with the fields freshly plowed, exposing the soil with colors ranging from dark rust to light tan, with the cypress trees dancing up hills or running along the crest of a ridge, farmhouses tucked here & there, medieval villages everywhere, castles, vineyards, olive groves, and virtually no ugly commerce to spoil the scene (like elsewhere in Tuscany). Well, March is even prettier. The winter wheat that is planted almost everywhere is bright green and when it catches the late day sun, it is really spectacular with all the rolling hills, cypresses, farmhouses, etc. We returned to the Val d'Orcia for 2 weeks in late March/early April in 2013 when we owned a digital camera and my wife could take as many pictures as she wanted (took 2,500). We did not have a digital camera in '04. Since our 3 week stay in ’99, we have visited Vermont during leaf season, Provence several more times (including poppy, lavender & sunflower seasons), the Dordogne, Alsace, Pays Basque, Scotland, Bavaria, the Cotswolds, and many places in between – but we both feel that the Val d’Orcia is the prettiest open countryside we have seen anywhere. When we were there in March '04, we took several day trips to other sections of Tuscany, and when we returned “home” we always commented “why do we travel anywhere else in Italy – there’s nothing prettier than where we are staying”. So, for the remainder of our 2 week trips in '04 and '13, we didn’t travel anywhere else – we spent all our time finding more nooks & crannies in the Val d’Orcia.

    The following is a 1-day driving itinerary through this area, with stops at various villages and sites. If you have more time to spend in this vicinity, by all means drive down some of the dirt roads and even take some walks.

    The best times of day to see this area are in the early morning or late afternoon when the sun is lower in the sky. When the shadows are long, the cypress trees & umbrella pines look more pronounced as they “dance up the hill” (my wife’s term). The farmhouses sprinkled throughout the landscape take on a special look in the early morning and at sunset. The Val d’Orcia can get some morning fog. If so, spend the morning in a village & start your drive when the fog lifts.

    In my opinion, the countryside is the “star” in this part of Tuscany. You “must see” Pienza and there are other interesting villages too, but don’t shortchange the drive through the countryside. If you are behind schedule, skip some villages – not the countryside. You might think that this itinerary seems out of order in places & I’m often taking you down roads that you have already driven. Sometimes, I’m considering the position of the sun when you drive on a road, and other times I’m just trying to extend the time to enjoy the countryside.

    You will need the Touring Club Italiano map of Tuscany to follow this route. Also, obtain the Michelin Green Guide to Tuscany. If anyone wants to take walks in this area, get the Carta Turistica e Stradale – Val di Chiana, Val d’Orcia map. They have it at the bookstore in Pienza.

    If you are doing this tour as a day trip from Siena, leave Siena going south on the N2 (marked SS2 also). It’s actually a pretty drive. Just past the second turnoff to Montalcino and past the bridge, look for a beautiful grove of cypress trees to your right. At San Quirico, take the N146 east to Montepulciano. This is an easy drive. If you leave Siena by 7:00 you should get to Montepulcano by 8:30 or earlier.

    Do not visit Montepulciano at this time, unless it is foggy in which case you should wait until the fog lifts before proceeding on this drive. Take the N146 west to Pienza. The sun will be at your back. When you pass the large domed church of San Biagio (on your right/north) just after leaving Montepulciano, look back towards Montepulciano & you will be rewarded with a spectacular site – the Church of San Biagio in the foreground with Montepulciano cascading down the hillside behind it. This is one of the most photographed sites in Tuscany. Before I retired, I had a giant poster of this view in my office – reminding me why I wanted to retire & spend more time traveling. Don’t take a picture just yet – you will be back over this route later in the day and the sun will be in a better position to shine on the church and the perched village behind it.

    Continue on the N146 to Pienza. This road has some wonderful scenery. You should get to Pienza by 9:00.

    As you approach the “old” part of Pienza and the N146 turns right towards San Quirico, make a sharp left turn and you will find some parking spaces. If these parking spots are filled, continue down this road & look for the blue parking (P) to your left. During tourist season, you have to pay to park in this lot. You can also park south of Pienza below the village, but you will have a slight climb uphill to the center of town.

    Explore Pienza by entering through the Porta al Murello, at the west end of Pienza. Just as you enter Pienza, there is a nice pottery/gift shop on your left (in the large square) which has had a significant impact on my wallet. Most stores open at 9:30 & close for a 1 ½ to 3 hr lunch at 1:00 (typical in Italy). You can obtain a self guided 1 hour audio tour of the town (in English) by renting a headset from the tourist office (closed at lunch time, but open on Sunday). If you want to have a picnic lunch at Sant’ Antimo abbey, pick up some lunch provisions while in Pienza. There is a pizza shop just outside of the Porta al Murello (next to the book store/news stand) where you can pick up a slice of pizza. There is a walking path next to the town walls on the south side of Pienza – don’t miss this. It’s a great place to just sit in the sun & admire the views. Plan on spending 1 ½ hrs in Pienza if you take the audio tour or you’re a big shopper, 1 hr if not. It’s one of the few villages in Tuscany where most stores are open on Sunday, & Monday mornings.

    Leave Pienza on the N146 toward San Quirico. This is another stretch of road with fantastic views – perhaps our favorite. Just 2K from San Quirico, there is a splendid view to the south of a very small church and another building with cypress trees & umbrella pines surrounding these buildings. This site is on the crest of a hill. If you have been in Tuscany for any length of time, you will have seen this view on many postcards & calendars. You will pass this church again later in this drive when the late afternoon sun makes this scene perfect for picture taking. As you approach San Quirico, drive into the parking lot behind the Taverna del Barbarossa restaurant (which is associated with the Casanova hotel). The parking lot is at the south end of the complex. Park the car, get out & you will see another of the most photographed sites in Tuscany. In fact, the very first picture that appears in my ’95 Michelin Green Guide to Tuscany, is a photograph of this scene – a farmhouse sitting on top of a hill, surrounded by cypress trees. A “coffee table” book I own has photographs of this site at different times of the year – it’s quite remarkable. This site is even on the cover of that book. I also have a poster (yes, it was hanging in my office too).

    You should get to San Quirico by 11:00 if you stopped for some picture taking along the way. Don’t visit San Quirico now – do so later in the itinerary if you have time (it’s worth a visit).

    Follow the signs at San Quirico and get on the SR2/N2 (same road) toward Siena (north). Just after you leave San Quirico on the N2, you will cross a bridge. If you look back, there is a striking view of the village of San Quirico from the bridge. Unfortunately, I have never been brave enough to get out of the car & take a picture from this bridge. Further along the N2 there is a pretty grove of cypress trees on your left (west). This grove can be seen better traveling south, however. On your right, you will see several cypress trees and umbrella pines dotting the ridge of a hill. You might recognize this site from postcards & calendars you have seen. Turn off the N2 & go to Montalcino.

    As you approach Montalcino, you will get some good views of this perched village. The road will turn a few times & will take you to the south entrance of town, which will be marked with a large “Montalcino” painted on a white background on the stone wall of town, and a “centro” sign will be pointing into town . Do not enter through this entrance - instead turn a very sharp left when you see this town sign and follow the road uphill. Very shortly you will see a round-about. Exit to the right off the round-about to find a place to park. There is a rather large car parking lot near the old fortress (Rocca). Note – When you arrive into Montalcino and encounter this round-about, note the sign to Sant’ Antimo Abbey (marked “S. Antimo”), where you will go next on this itinerary (it’s marked on the round-about). The road to this abbey is a very sharp left (almost a full circle around the round-about). We've taken the "wrong" road from this round-about several times. Look for the sign that says "S. Antimo".

    Visit Montalcino. You should get there by 11:00. Many shops will close by 1:00. You can visit the fortress, but I found it only OK. Budget about 1 hour or less in Montalcino. It has some nice outdoor lunch spots if you want a sit-down lunch (I’m pushing the picnic at Sant’ Antimo). See my later comments about Montalcino if you want to spend a morning & lunch there.

    Follow the signs (and your map) to Sant’ Antimo Abbey. The Abbey is quite lovely, but what I like best about it, is the setting – we’ve used up a lot of film there. It’s located in a valley surrounded by hills, cypress trees dancing up these hills, and a lawn around of the Abbey (where you can picnic). It’s also a good place for a little snooze in the sun. There are Gregorian chants inside the church at various times of the day (posted on the entrance to the church – one chant is at 12:45). See for a full chant schedule and a description of Sant Antimo.

    Continue on your drive through the countryside. You should leave Sant’ Antimo about 1:30. Take the road south-east of the abbey, toward Monte Amiata on your Touring Club map and "signed" Castiglione d' Orcia on the road sign. Pass through Monte Amiata, and at Ost. Ansidonia, turn left (north-east) to Castiglione d ' Orcia. This is pretty countryside. Pass through/beside Castiglione (great views from the road to this perched village as you leave town) and get on the N2 & head north toward San Quirico. You should get to San Quirico about 2:00 or so.

    Continue past San Quirico toward Siena. You will have another chance to see the cypress grove to your left, and the cypresses & umbrella pines running along the ridge to your right. Get off the N2 at Torrenieri. There is a road that runs from Torrenieri to San Quirico, just east of the N2. Find it on the Touring Club map. You want to head south on this road from Torrenieri to the “phantom” village of Bellaria on the map (there really isn’t any village there). When driving through Torrenieri just after leaving the N2, you need to turn right at the first stop sign (in front of a small church) and you will immediately cross a railroad track. As you approach Bellaria, look to your right and you will see more umbrella pines & cypress trees dotting the top of a ridge. These are the same trees you saw from the N2 on your drive to Montalcino and to Torrenieri. When you get to Bellaria, turn left (east) to Cosona (it’s marked at the turn). You will be on a dirt road. It is one of our favorite drives in this area. Continue & go slowly on this dirt road. Lots of pretty sites here. This dirt road will kind of dead-end onto another road (see it on your map). Turn right toward Pienza. When you get to the N146, turn west (right) toward San Quirico. You should get here around 3:00.

    About half way to San Quirico, there is a dirt road that heads south of the N146 – find it on the map (it’s the only road on the map between Pienza & San Quirico). Watch for a road sign of a "leaping deer" and a "3K" (on the deer sign). There is also a "standard" road sign indicating an upcoming left turn. Prior to '13 there was a sign to the “Agriturismo il Rigo” (famous Agrit/cooking school ). Turn south/left onto this dirt road (there is actually a "Y" entrance on this road). Very soon after turning onto this dirt road, there's a sign for the Agriturismo Cretaiole. Il Rigo is at the "other" end of the road - you'll want to take pictures of il Rigo. We have often driven down this road, parked the car, & started on a hike from here. We've probably taken more pictures along this road (per mile/K) than any other road in the area. Continue on this road until it connects with the N2.

    Continue south on the N2, and after about 2K, head east on the paved road (marked yellow on the touring club map) toward Chianciano & Pienza (well marked). This road passes through another “phantom” town called Spedaletto – find it on the map to make sure you turned at the right place off the N2. This road goes trough the heart of the Val d’Orcia and is quite picturesque. Continue on this road toward Chianciano Terme. You will have a nice view of Pienza perched on top of a ridge, off in the distance to the left (north). There is an “interchange” on this road – pay attention & keep heading to Chianciano Terme. Just before La Foce, you will see a lovely double set of cypress trees to the north, dancing (again) up the hill (another much photographed site). Continue on this road, and shortly you will see a parking lot opposite the Restaurant Oasi la Foce. Pull into this lot & you will get another view of this double set of cypress trees. Continue toward Chianciano, and about 1/2K after the parking lot, take the first left (north) on a dirt road toward Montepulciano (well marked). This will be a dirt road and will pass around a lovely castle. When the dirt road becomes a paved road, turn left towards Monticchiello (well marked). As you approach Monticciello, this road becomes particularly scenic.

    Monticchiello is a very cute village – it’s where my father-in-law says he wants to live. Park the car in the lot outside this village near the refreshment stand (do you need any) & wander around. It’s a 30 min wander. There is a nice restaurant in town called La Porta.

    Look at Monticchiello on the Touring Club map. You will see lots of roads radiating from this small village like spokes on a bicycle wheel. All these roads have fantastic views of the countryside – in my opinion, they offer the prettiest drives in the Val d’Orcia. If you have time to spare, by all means drive down all these roads. We’ve done this quite often at various times of the day when the sun casts different shadow patterns on the rolling hills and from the cypress trees. My favorite drive is the one branching out at 8:00 from Monticchiello. It connects to the road heading directly north to Pienza. Drive down this "8:00" road and then turn right towards Pienza & you will get a fantastic view of Pienza. Just a little south of Pienza, there is a dirt road that heads south-west. Take this road and it will connect with the Chianciano road running east/west. From here you can retrace the drive east towards La Foce where you will head to Montepulciano (by-passing the turn to Monticchiello). When this road hits the N146, turn left to Montepulciano.

    If you don’t have extra time available for this side trip, after visiting Monticchiello head back down hill from the parking lot. Immediately after leaving the lot, go straight at the "fork" (just after the first house on the right) and don't follow the "Tutte le Direzioni" sign - instead angle left/straightish past a "marked" parking area. This will lead to Montepulciano on a paved road that shortly becomes a dirt road and later paved again. There is a nice view of Montepulciano from this road. When this road dead-ends at the N146, turn left towards Pienza, or right to Montepulciano if you want to visit this town (one of my favorites).

    Visit Montpulciano, if you like (1 1/2 hr visit). Use the Michelin Green Guide to find the sites you want to visit. Hike all the way up to the Piazza Grande. It’s a somewhat steep walk through town, however, but the village is very pretty. You can taste some excellent wine at the Avignonesi estate (you will see it – just opposite the tall column in the middle of the main street, just after you enter town). If you need a snack, find a place where you can get pizza by the slice & have a mushroom (fungi) and truffle (tartufi) pizza (only in Italy!!!).

    Leave Montepulciano towards Pienza on the N146 again. Now you get a better view with the remarkable San Biagio Church in the foreground and Montepulciano in the background (you may have to drive a little west on the N146 to get the view). Hopefully you are at this spot about 5:00 or so. Without any further stops, you are less than 1 ½ hrs from Siena.

    Drive along the N146 toward Pienza & San Quirico again (30 min drive). The sun will be in your face, but now the little church with the cypress trees around it will look quite different, as will other sites you photographed when you drove this route in the morning.

    If time allows, visit San Quirico (it’s 45 mins to Siena from SQ). San Quirico is kind of a poor man’s Pienza – but they like it that way. It’s a town where people really live. In fact, I’ve told friends that San Quirico is the type of town we wish our small towns in the US would be like – kind of a River City, Iowa (Music Man). Everyone knows everyone else, people are out strolling, there are stores where locals shop for their everyday stuff, etc. Families congregate at the Bar Centrale (closed Thurs) in the evening, where the men play cards in one room, the younger children are in the video room, and the older children are outside playing soccer in the town square or just hanging out. If you visit San Quirico, have a coffee latte at the Bar Centrale & “people watch”. SQ is a 30-45 min visit. Some stores may be closed Wednesday afternoon.

    Another driving itinerary

    Head south from San Quirico on the N2 (marked SS2 or SR2). This is a pretty drive & you will visit some appealing medieval towns in a hidden corner of Tuscany.

    Take the Radicofani* exit off the N2. As you approach Radiconfoni, look for the "Centro Storico" sign, follow the sign, and immediately park the car. There is one long street that runs through Radicofani, and it is paved with 2' X 3' pavers. Follow these pavers through the entire length of town and don't wander off onto any asphalt roads (a good suggestion for exploring any village in Europe). In the direction of the "tower" (you'll spot it), there are some interesting side streets to explore. These side streets are covered with 1' X 2' pavers.

    After exploring Radicofani, exit (by car) from the Centro Storico and follow the signs towards Rome and re-connect with the N2/SR2 (same road) south towards Rome. About 6K after this "re-connect", turn right where you see the signs towards Piancastagnaio, Abbadia S.S., and M. Amita. You will almost immediately encounter a Y in the road, and head southwest on a small road – it goes through Sforzesca. I think there are signs directing you to Pitigliano & Sorano (this road was blocked when we were there in '13, so I'm trying to recall info from our trip in '04). Follow this road through S. Valentino to Sorano*. Upon arriving in Sorano, pull into the large parking lot on your right (just off the road) and walk to the old fortress.

    Sorano is like a layered surprise. The first part is the massive castle/fortress that looms in front of you when it is approached from the flat parking area. It is a 'bulky' structure surrounded by what may have been a moat with large adjacent arches. This alone is impressive. As you continue your walking visit, you cross a wide "piazza" and from there ascend a broad set of stairs which takes you to a spot offering an expansive overlook. Then comes the second - perhaps even more memorable - part of the visit. Because, from above and spreading out below, you then see a panoramic view of the old village itself which has not been evident when you first approached the castle. Initially, the vista is mainly one of the village rooftops and the bell tower of the large church. You could easily conclude the visit here and feel rewarded by the memorable view, but continuing down into the village brings real treats. Once you have descended into the village, you find yourself in a maze of twisting, turning pedestrian "paths" - none if which is level and none of which seems to follow any particular plan or organized layout - it is a labyrinth which forms the town. You literally ramble and meander up and down the passages. Unobtrusively, small doors often fronted by a short set of stone steps signal the presence of a home. A small terrace tucked into an outward-facing stone wall offers up another clue that somebody lives within. It is easy to believe that "somehow" this town has luckily managed to remain in livable condition over its hundreds of years and that the small stone dwellings have simply remarkably withstood the toll of time. But, just when you think you are walking through a well-preserved time capsule, you see a structure which has literally collapsed into itself or one which more resembles a pile of stone rubble than a dwelling. Then you gain a deeper understanding and appreciation for the effort that has gone

    into preserving and/or restoring the town to its current pleasing condition. While mostly "residential", the passages widen and open up in several spots to accommodate light commerce - a pottery shop and perhaps a small restaurant. While the town has only muted noises, a child's voice is heard in the distance and cats skitter here and there to signal that there is real daily life going on behind the shutters. From the town, you can glance back up to the pizzza adjacent to the castle and to the stairs which brought you down into the village and you realize fully how the town literally tumbles down the hill from the high, protective point of the castle. Budget 10 minutes to just view the lower village from the fortress, and 1 hour to explore all of old Sorano (there is a "new" part).

    After visiting Sorano, when you leave the parking lot you will immediately see a sign with two different directions to Sovena. One says Sovena/Pitigliano to the left and the other says Sovena/Castell-Azzara to the right. Take the Sovana/Castell-Azzara to the right and get your camera poised. There are some fabulous views of Sorano from this road. Keep following the road through a gorge to Sovana.

    When you arrive in Sovana*, follow the signs to the "center" (acute left turn involved) and park where it tells you to park. As where Sorano was hilly with narrow streets, lots of small passageways, stairs, few "cute shops" or restaurants - Sovana's one main street is flat, wide, with many shops & restaurants (a bit touristy).

    Leave Sovana heading east - the same road you used to get to Sovana from Soreno. After about 3K, follow the signs to Pitigliano. Get the camera ready again, because there are some fabulous views of Pitigliano from this road - but this is the north side of Pitigliano so the village may be silhouetted. Continue to follow the road to Pitigliano around the base of the village to the south side of Pitigliano. Soon you will see a sign directing you left into Pitigliano, and another directing you right towards Albinia. Take this right towards Albinia and you will see some amazing views of Pitigliano. There is a "pull-out" along this road where you and dozens of other cars will park to take pictures. Do a U-turn & go into Pitigliano. Good luck with parking - it is difficult.

    As opposed to Sorano (above), Pitigliano* presents itself in its entirety upon approach! In fact, a gasp is in order when Pitigliano comes into view. Pitigliano does not "tumble" down its textured rock foundation, but rather is a low-slung town stretched along the top of the rock outcropping on which it sits. It offers a distinctly different visual effect from the "traditional" hilltop towns which have more of a vertical orientation vs Pitigliano's horizontal plane. The rock cliffs which form the base for Pitigliano are fascinating in and of themselves, but when the town and its supporting cliffs are considered in combination, the resulting effect is quite remarkable. The buildings straddling the cliffs look literally like wooden building blocks of varying sizes neatly stacked side by side, punctuated by a set of arches which is visible from a distance on the road outside town. Once inside town, these same arches provide a visual landmark which helps to map in your mind the external and internal orientation of Pitigliano. The proportions of the town are quite simple: long and narrow. Namely, there are literally only 3 primary streets that run the length of the town; at some points you are able to look across from a position on one side of town and see through to the other side. The buildings in the town are rather stark overall and the town has a somewhat utilitarian atmosphere, although there is an almost-Baroque style church in town which catches your eye if only because of its architectural contrast with the rest of town. Touring the town on foot is relatively easy because the terrain is primarily flat (not surprising when you consider the town's geographic placement on the cliffs), but the natural setting of the town may be among one of its greatest visual assets.

    The descriptions of Sorano and Pitigliano were written by my wife.

    We have visited Pitigliano twice, and both times we made the mistake of taking the 74 east towards Orvieto, and then north to Onano and Acquapendente. This is a slow, ugly, and very bumpy route. Most of it is in Lazio and the roads are full of potholes. You will notice a significant difference between the quality of roads in Tuscany vs. Lazio. All the cars taking the Lazio roads were constantly steering around these potholes. One person ever steered off the road into a ditch. When leaving Pitigliano, I would instead retrace my route through Soreno back to the N2. I don't know how this road is "signed" - probably "Siena".

    The last time we followed this itinerary, we left San Quirico at 9:00 and returned at 3:30. We did not have a sit-down lunch, and we did not visit any museums or shops. We explored all four villages quite thoroughly, however.


    Montalcino* is one of our favorites. It is flatter and easier to walk through than Montepulciano, has more interesting shops, restaurants, and cafes than San Quirico - and is less touristy than Pienza. Of course, there are dozens & dozens of wine shops. Spend the morning and lunchtime there. Arrive at about 10:00 and have cappuccinos at the Caffe Fiaschetteria Italiana on the Piazza del Popolo (main square in town). It has outside tables and also an interesting interior. This is a great spot to people-watch. Don't be surprised if some school kids join you. After a leisurely cappuccino, wander through town. Get a "rustic" town map at the tourist office and follow the paved (not asphalted) streets that traverse town. At about noon, have a "sit-down" pizza at the Belvedere Bar on Via Giacomo Matteotti just off of the Piazza del Popolo. However, do not eat outside at one of the tables set up on the street. Go inside to the "farthest" section of the cafe and dine there. The back of the cafe is all windows with a fabulous view of the Val d'Orcia countryside below. After lunch, visit the Fortress** (access through the wine bar) and admire the views from the Ramparts.

    Head east, then north from Montalcino towards Siena/Buonconvento and get on the SR2 heading north.

    Here are two short drives where you can visit the most interesting Etruscan museum we've ever experienced, see some more scenic countryside, and then visit a monastery.

    From Montalcino, head north on the SR2, and then into the "Centro" of Buonconvento - not the bypass to the east around Buonconvento. Turn left (west) and follow the signs to Muro. This is an extremely scenic road after you get about half-way to Muro. We really enjoyed the Museum** in Muro. It is rated 2 stars in the Michelin Green Guide, has descriptions in both Italian and English, and has a "lift" for handicapped people. We spent 40 minutes in the museum and 5 minutes exploring the small village.

    Return to Buonconvento and then head northeast of Buonconvento on the 451 twoards Asciano and Chiusure (direction signs from Buonconvento). The first site you will want to visit is the Abbezia di Monte Olvieto Maggiore** (check opening times). After visiting the Abbey, follow the direction signs to Chiusure and then to San Giovanni d'Asso - this is a very scenic road. Continue through San Giovanni to Torrenier and then get on the SR2 & back to your hotel/apt.

    Additional sightseeing options
    If you want to drive around on your own and explore a little further out, here is a rough geographical description of the area that I think is the most scenic between Siena and Lake Bolsena to the south:
    Find Monte San Savino on the map. Draw a line from there to about ½ inch west of Sinalunga, to about ½ inch east of Montepulciano, to ½ inch east of Chianciano, and then down the A1 to Orvieto. The area in Lazio just north of Lake Bolsena is not scenic and the roads are full of potholes (compared to the roads in Tuscany) Everything west of this line I have found to be very scenic, and everything east is not so scenic, in my opinion. If you explore the area from Orvieto, to Todi, to Spoleto, and to Trevi, you will find the villages & scenery enjoyable too. Assisi is one of my “must see” towns and so is Perugia, but the area around these cities is not that great (especially around Perugia). As I mentioned earlier, the countryside around Cortona & Arezzo is not scenic (didn’t take the road from Arezzo to Sansepolcro, which is described in my books as nice). As you go from Bibbiena, to Poppi, to Dicomana, the drive is quite pretty. The Strada dei Sette Ponti (Road of 7 bridges) from Pontassieve (just east of Florence) to Vallombrosa, to Reggello, to Castelfranco to Loro (pretty village) is also quite beautiful.

    Drive through the area north of the N146 in the afternoon & see some of the small perched villages:
    Petroio, Trequanda, Montisi, Castelmuzio. This area is very scenic.

    Another drive

    Spend more time in the Val d’Orcia. You should stay at least 4 days in this area (we’ve spent over 2 1/2 months there & we’re still discovering new places).

    Drive to San Quirico from Pienza (if you are staying in Pienza), and when you approach San Quirico, go over a bridge, and the arched town gate is directly in front of you. Immediately turn left in front of the gate (don’t go through the gate - expensive ticket if they catch you). Continue down this road at the east end of San Quirico and park there for a visit (lots of public parking available – free). There is a stairway up to town at the south end (far end) of this car park. There is even something happening on Sundays in San Quirico (many stores close Wednesday afternoon). Have a café latte at the Bar Centrale .

    Return to your car & continue in the same direction you were driving (south). The road will turn to the right around SQ, and there is a stop sign at the south entrance to town (where you entered on foot). Continue straight and head to the small town of Ripa d’Orcia (southwest of San Quirico). This road is quite scenic. Ripa d’Orcia is actually a castle with a rustic B&B (It’s in the Karen Brown guide – our friends stayed there when they were buying their home in SQ). You can’t go into the castle unless you are staying there or having dinner there (rustic dinner too). Turn around & drive to Vignoni. They were restoring the largest building in this town when we were there in March ’04 and it will be apartments. Continue on this road to Bagno Vignoni. This is a bath/spa town with old Roman bath ruins that are quite interesting. There is a spa/hotel in town. You can purchase a day pass for the spa even if you don’t stay at the hotel (our friends have done this many times). I’m not a spa person, but the spa complex looks like a resort hotel you might find in Mexico or Hawaii. The “pool” is fed by a heated water source. It has walkways over the pool as it winds around, and there are lots of lounge chairs where people catch some “rays”. We were there on a Sunday on a cold but sunny day in March and there was lots of activity. The actual town was quite nice too with many/all stores open on Sunday. There are lots of restaurants/ delicatessens with outdoor dining tables for picnics. There is another 90 room “super spa” called Adler Thermae just outside the center of town. Our friends said that this hotel first started the planning process in ’80 and finally opened in '04. People in Tuscany like to keep things beautiful and planning is a lot of give & take. The hotel looked very pretty & blended in with the countryside quite well. Great views from the hotel.

    Stu Dudley

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    We have returned to the Chianti are four times. This is the area direcrly north of Siena on 222. Look at Castellina and Panzano.
    We also enjoyed being based outside of Cortona.

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    I think you have to decide just how much time you want to spend traveling from your base and what your destination priorities are. You might want to split the week between two locations, one more north and one more south.

    If you're checking routes on, I suggest you choose the option to "avoid highways, avoid tolls" for better scenery and then add time to the estimates. I usually add 10 minutes to every hour of Google's estimates. You'll also spend some time beyond the Google estimate looking for parking and walking into and out of the towns, so a destination that's "only" an hour away will take closer to 90 minutes overall each way.

    We've encountered lots of traffic in the immediate area around Siena, especially in the morning and afternoon commuting hours. Depending on where "just west of Siena" actually is, you might need to add even more time to get to/from Montepulciano which is pretty far east.

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    We stayed in three different areas of Tuscany for a week each. We stayed at Il Palagio near Panzano in 2001, at the Castello di Proceno in 2002 and at the Podere Lucignano Secondo near Castello Brolio in 2014. We liked them all a lot but you need to read the details about each place to see if they might work for you. I posted a report of our June 2014 trip - click on my name and scroll down to the trip report section. We did a few of the things you mention above and I did not find the driving to be a problem - but then I love to drive through the Tuscan countryside.

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    We stayed at Fonte Bertusi, just outside Pienza, for a week. This is a farmhouse that has been divided into individual apts. We thought the location was great. Took a day trip to Siena one day, Cortona another, Montepulciano another. Lovely hosts, and the breakfasts will keep you filled for most of the day.

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    Will you go out to dinner at night or do you plan to cook (or need a place that provides dinner)? You didn't say when in the fall, but it will be getting dark early.

    >>>Just be aware that Chianti and Val D' Orcia are very different landscapes.<<<

    Many Tuscan postcards you see are of Val D'Orica.

    >>>Montepulciano and Pienza. I'd also like a day in Siena that week as well as one in Chianti for wine tastings, etc. further north. <<<

    For the places you mentioned, I would look somewhere around Pienza. I would also wine taste in Montalcino which isn't far from Pienza. I prefer the Montalcino's Brunello wines to the Chianti wines. Montalcino also has sweeping views. You could still visit Chianti, but it would be a bit of a longer drive.

    There are quite a few interesting towns you can reach from the Pienza area in addition to the ones Stu listed.

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    Many Tuscany scenes from "Under the Tuscan Sun" were also filmed near Cortona and Sansepolcro. The house in the movie, Villa Laura near Cortona, is available to rent mostly to larger groups, but there is one suite that sleeps 4.

    If you remember "Much Ado About Nothing" (Kenneth Branagh, 1993), it was filmed near Greve in Chianti. The property in that movie, Vignamaggio, is a wine estate/agriturismo.

    "Life is Beautiful" (Roberto Begnini, 1997) was filmed in the Arezzo area.

    "Tea with Mussolini" (Zeffirelli, 1999) was filmed in Florence and San Gimignano.

    Hollywood loves Tuscany too!

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