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    by ibobi Fodor's Editor | Posted on Nov 20, 17 at 01:24 PM
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Day trips from Pienza?

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My wife and I are headed back to Italy this September! We are spending 4 days in Pienza at Giardino Segreto, a lovely bed and breakfast inside the city walls. We have stayed here before and loved it.

I am looking for suggestions for day trips from Pienza. Last time we spent several days at Montalcino (loved the wine and we were there for Sagra del Tordo), Montepulciana and Sienna. We just spent a few hours in Sienna (we spent about an hour looking for a place to park) and I would go back in a heartbeat. We also loved Sant Antimo Abbey and would love to stop there again.

We love old, walled cities with ancient cathedrals, museums, enoteche, tuscan food, etc. Off the tourist bus path is a plus.

What other cities would you suggest within several hours drive of Pienza? We are ending our trip at Florence, so that will be our final destination. We are renting a car and I don't mind driving in Italy. I race cars for a hobby and driving in Italy doesn't bother me in the least.


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    La Foce which is a grand estate with lots of history. It is south of Montepulciano and has guided tours on Wednesday.

    Abbazia di Monte Oliveto Maggiore--a beautiful monastery northwest of Pienza with fabulous fresci. Its a very nice drive and there is even a nice restaurant near the parking lot.

    Bagno Vignoni--lots of interest in the hot springs, spa and ancient channeling and controls of the thermal waters.

    Agree with Bob--La Porta is a must if you can schedule it--lunch on the terrace requires a reservation but dinner is also good inside. Great food.

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    Some of my favorite towns/villages to visit in the area-

    Castiglione d'Orcia
    Rocca d'Orcia
    Lucignano d'Asso (have a simple 15 euro lunch of local cold meats, cheeses and wine there at the small alimentari, located at the end of the village near the old church. Especially nice on a sunny day when you can eat outside)
    Trequanda (Trattoria Il Conte Matto is nice for lunch)
    Montefollonico (lunch at Osteria La Botte Piena. Owned by a brother/sister, the food is great and the local wine offerings are expansive)
    Citta d. Pieve (Saturday is market day)

    Further south (1 to 1.5 hour drive)-

    S. Fiora
    Sorano (have lunch at the beautiful and inexpensive Cantina L'Ottava Rima, located within a cave in the town. Open weekends only. Local simple food, cold meats, cheeses, beers, wine- one of my favorite places to eat in southern Tuscany)

    Favorite sights-

    Abbazia d. Monte Oliveto Maggiore
    Abbey S. Galgano (I love it! Located southwest of Siena)
    La Foce garden tour
    Bosco della Ragnaia (an enticing park cut out of the landscape by artist Sheppard Craig, located just north of San Giovanni d'Asso)

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    If you don't want to drive in Siena again, you could park somewhere outside on the train line (Buonconvento?) and take the train. There is an escalator from the train station (across the street in the mall) up to the hill town. Buonconvento is worth a stop also.

    Heading towards Florence, you could go through the Chianti area (S 222) and stop in Panzano or Greve.

    Cortona isn't too far for a day trip either if you haven't been.

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    kybourban, I don't mind driving to Sienna again, I just didn't know what I was doing last time :-) I will do a better job of scoping out parking areas.

    Lot's of great suggestions, Grazie!

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    Here is some help for your Siena day:


    1. Start in Siena and be there by 0930 for best parking. Enter from the Siena bypass at the “ SIENA SUD” exit to the PORTA TUFI gate. There is a large parking garage just inside the gate—a 7 minute walk to Il Campo.

    2. Plan on 4 hours to see the medieval marvel that is Siena and to have lunch. Do not miss the fabulous Duomo, my favorite in Italy, and the special Piccolomini Library near the end of the walking tour in the Duomo. Of course, spend time in the wonderful Piazza del Campo for some first class people watching, home to the famous Palio horse race twice each summer. The Palazzo Pubblico[town hall] is home to a nice museum & worth an hour.

    3. As you exit Siena to the south, divert to #438 to Asciano. The village is nothing special but the terrain south of here along # 451 starts the scenic area known as “LE CRETE”. The topography here is unique with eroded cliffs and a pattern of deeply grooved inclines. Be sure to bring your camera and hope for good light. Your real destination is the Abbey at Monte Oliveto Maggiore[ closed from noon to 1500]. This 14th century Benedictine retreat is home to the spectacular frescoes depicting the life of St. Benedict painted by Luca Signorelli. Plan to spend an hour at the Abbey before starting home.

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    Bobthenavigator, grazie for the help. We did visit the Piccolomini Library last trip which was really neat since we were staying in Pienza one block from the Piccolomini mansion. But we were hurried last time and I plan on a more relaxed visit this year.

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    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. Our friends in San Quirico say it’s even more scenic in late May or early June when it’s still green, but the wheat is taller and blows in the wind. 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, 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 trip, 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 head set 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 that has most of it’s stores 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 have 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 N2 toward Siena (north). Just after you leave San Quirico on the N2, you will be on a bridge. If you look back, there is a nice 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 the 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).

    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).

    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. Pass through Monte Amiata, and at Ost. Ansidonia, turn left (north-east) to Castiglione d’ Orcia. This is pretty countryside. Pass through Castiglion & 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 Bellari, 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 and continue on 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 N146 – find it on the map (it’s the only one on the map between Pienza & San Quirico). There is a sign for this road on the N146 and the turn is marked by a direction sign to the “Agriturismo il Rigo”, and before a “watch for deer” sign. Turn south on this road. We have often driven down this road, parked the car, & started on a hike from here. 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. Turn right towards Pienza on this road & 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 N2/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) instead of turning right the way you entered the lot. 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 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.

    Further reading suggestions:
    War in the Val d’Orcia by Iris Origo
    This is a woman’s diary of happenings in this area during WWII. “Non-political, it is an elegantly simple chronicle of daily life at La Foce, a manor in Tuscan no-man’s land bracketed by foreign invasion and civil war. The Marchesa Origo’s faithful record is one of those rare and precious accounts that give the truth of history with the art of a gifted writer, that bear witness nobly to ignoble times.” The preceding was lifted from the back cover of the book. While we were there in ’02, they were celebrating the 100th anniversary of her birth.

    More places to visit:
    Yesterday’s route took you through some of the most scenic countryside in the Val d’Orcia. 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. 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.

    Visit Montepulciano** in the AM. This is a good town to explore. Pick up a slice of pizza for lunch from one of the many vendors

    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.

    Visit Monte Olvieto Maggiore Abbey, This is a working Benedectine Abbey. The setting is pretty.
    Open 9:15 – 12:00 & 3:15- 5:45.

    Visit Murio & the Etruscan museum (west of Monte Olvieto Maggiore Abbey on the other side of the N2). You have probably driven past many advertisements for this town & museum – the ads look like a cartoon character with a cowboy hat (locals joke it’s a caricature of George Bush). The “character” is actually an Etruscan statue in this museum. The town of Murio is interesting to visit and the road that leads southeast through Bibbiano is very scenic.

    Radicofani*– south of San Quirico off the N2 to the east. This is a large medieval fortress perched on a hilltop. You can see it from miles around. The view from the top of the tower is fantastic. The drive down the N2 is pretty too.

    Another driving itinerary:
    Head south from San Quirico on the N2 (marked SS2). This is a pretty drive & you will visit some appealing medieval towns in a hidden corner of Tuscany. Just after the southern most Radicofani exit (see the map) & before the small Pte d. Rigo (marked on the Touring Club Italiano map) head southwest on a small road – it goes through Sforzesca. I think there are signs directing you to Pitigliano & Sorano. Follow this road through S. Valentino to Sorano*. The next three towns you will be visiting are in the Green Michelin guide to Tuscany under “Pitigliano”. The approach to Sorano is very pretty – get the camera ready. Explore Sorano on foot. Not much happening in town, but it’s fun to wander around – several artisan shops. Leave Sorano to the south, drive to Pitigliano*, and get the camera ready again. This is our favorite town of the three. Historic Pitigliano has been beautifully & tastefully maintained. Several lunch spots available in town. Next drive to Sovana* & explore this town (not quite as interesting as the other two). Leave Sovana going west and then take the first road going southwest. This road hits another east/west road that goes back to Pitigliano. I am taking you on this route so you can see the view of Pitigliano from the south. Get the camera ready again as you approach Pitigliano. After the view, head east to Acquapendente. Get there by going through Onano – the N2 south of Acquapendente has some really ugly commerce on it. Take the N2 back to San Quirico/Pienza.

    More things to visit:
    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” being built nearby just outside the center of town that is scheduled to open April 1 ‘04, but when we were there on March 28 it looked like it was months away from opening. Our friends said that this hotel first started the planning process in ’80. 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.

    Siena*** This is our favorite larger town in Italy.

    It is only an hour drive from Pienza, so you can certainly visit it as a day trip from Pienza, but I think it is much better to stay overnight in Siena so that you can fully enjoy one of the most charming cities in Europe. There is nothing quite like wandering through the Campo in the late evening.

    If you decide to do it as a day trip from Pienza, there is a trick to parking. Head north on the Via Cassia (N2/SS2). This is actually a scenic drive most of the way. This will take you directly into Siena (don’t take the interchange to the left as you get near Siena – many cars will be taking this left). Follow the signs to Porta Romana, which is the old town gate. As soon as you see an arch over the road, park the car. This will be a metered area (with parallel street parking).

    If you are staying overnight, the hotel is close to another Porta. This is the Porta Laterina. You can actually drive through this porta, drop off your bags, let the car sit for a short while, & then park it outside this gate. Ask the hotel how to park the car. I did this without difficulty. It will be best to get to Siena early in the morning before it gets crowded.

    Remember, Siena will mostly close down for a 3 hour lunch, and some stores will be closed on Monday morning (always the ones my wife wants to shop in).

    The Campo*** is one of the most beautiful squares in Europe.

    Visit the Duomo*** This is perhaps our favorite medium sized church in Europe. Get there early in the morning before 9:00am. Once we were the only ones there at this time once, & there were 100s of people there by noon. When visiting, look for some devices where you can insert some Euros & the device will light up the pulpit, mosiac floor, or whatever – it’s worth it.

    Next to the Duomo is the “Museo dell opera Metropolitano”. We have never visited the museum, but the view from the tower on top is the best in Siena. Climb to the top – it is not difficult. You can see all the terra cotta rooftops & the maze of streets below – even the Campo.

    On the other hand, the tower on the Campo is a difficult climb. It is cramped & if you get a little claustrophobic, don’t do it. My wife & I both climbed it & if you don’t mind the narrow & low twisting stairs, the view from the top is fantastic.

    Wander around Siena. Read the guide books to find the interesting streets & sights. Duck into any courtyards you can find – they are usually interesting. Have lunch on the Campo (on the shady side). The shops are great: ceramice, Florentine paper, tassels, linens, leather goods, & simply “pretty” storefronts to enjoy.

    Stu Dudley

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    Got enough information yet?

    Nobody's mentioned Volterra yet (maybe on your way to Florence) or Monteriggioni and San Gimignano only in passing. All are worth a visit.

    Gotta concur with Stu. The Val d'Orcia is special.

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    Stu Dudley, many thanks for the detailed suggestions. We will definitely try several of the drives. We also feel that the Val d"Orcia is a special area. We will be staying at the Giardino Segreto in Pienza, a lovely B&B inside the walls. And we found a public parking lot not far away that is often full but if I wait 10 minutes someone always leaves. La Buca di Enea is in Pienza and is one of our favorite Tuscan restaurants. I will order a Michelin Green Map and the Touring Club Italiano maps.

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    Wow! All such great info, love the driving itinerary from StuDudley. Reading all this info is giving me information overload! My husband and I are traveling to Florence the last 2 weeks of May 2013. I thought I had everything figured out, until I joined Fodor's Travel Forum! After reading all these excellent ideas and helpful hints, perhaps we should modify some of our plans?

    We had planned on 6 nights in Florence (taking a day trip to Lucca during that time), which would give us 4 full days for Florence. Then we drive down to Montalcino, staying for 2 nights. Should we visit Siena on that day as we head down to Montalcino, or should we stay in Siena for 1 night? I read that Siena is super packed during the day, but that one should experience it later in the day and evening..... aaarhg! Decisions! Then we have 2 nights booked in San Gimignano. What exploring ideas are there from San Gimi? Should we stay in Montalcino longer? After San Gimi, we were planning 3 nights in the Cinque Terre (town of Rio Maggiore). Then home :(. If we cover all that we want in Florence after 3 days, we could obviously do another day trip from there (eg. Siena?)

    We do not want to spend all our time in the car, charging around the Tuscan countryside trying to see it all; we want some on-foot exploring time also. Zoecat mentioned some towns further south - they sound beautiful, but I am afraid that is too much. Just means we'll have to come back! StuDudley - would your friends consider renting out their house - we are neat, clean and do not smoke! :)

    Any ideas and suggestions would be most appreciated! We're in good shape and like to hike and walk .
    Mille grazie.......Mtlbabe

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    My wife and I love Florence, if you love history and art you will easily fill 3 days there. The Uffizi is awesome and if you can fit in a tour with the Vasari Corridor, do it. The Academy Galleria is also a must, along with the Pitti Palace and Boboli Gardens. And just walk around Florence: Ponte Vecchio, Duomo, Babtistry, the leather market, etc. Montalcino, Montepulciano, Sienna are all wonderful cities to stay in and explore. Staying there overnight is magical as you get to experience the cities after the busloads of tourists leave. Pick a couple and spend at least two nights in each one. Use Trip Advisor to find local restaurants where the locals eat. Experience il dulce far niente, the art of doing nothing.

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    Racer042: I have just join Fodors forum and started researching places to use as a base while in the Tuscany area.
    I am thrilled to read your post about Pienza ~ it sounds perfect for what we are looking for. (We too love walled cities, red wine and Tuscan food.)
    I plan to Google the B&B your staying at.
    It would be wonderful if you would post again after you've returned from your trip, as well.
    Thank you to the others that have posted info on this thread - so much helpful information. Love it!

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    I've stayed there before. Here's their website.

    Did you want to stay in a town or out in the countryside? I have a list of places to stay if you need other suggestions. Il Giardino is in the old town of Pienza.

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    I stayed in Il Giardino Segreto at end of May 2009 for a couple of nights. Maybe it was off season, but never had trouble finding parking a few blocks away. It really is a beautiful garden and very convenient to walk around town, but very quiet. Buon viaggio!

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