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Will these 3 days work when driving through Tuscany?

Will these 3 days work when driving through Tuscany?

Old Nov 15th, 2007, 11:55 AM
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Will these 3 days work when driving through Tuscany?

Hi all,
I am looking for some advice/insight for a first time Italy (2 week) trip. More specifically, advice on our Tuscany part of the trip. We would like to experience some of Tuscany by car, so I'm leaning towards training to Chiusi from Rome and picking up the car.
We then have 3 days (that includes the day of picking up the car, which we will plan on taking the earliest train to Chiusi) to drive through Tuscany.

So, my question is, how do we spend those 3 days?
My initial thoughts were:
1st day: Drive from Chiusi and visit Montepulicano, Pienza, San Quirico d'Orcia, and Montalcino(stay in Montalcino?).
2nd day: Drive to Siena and San Gimignano (Stay in Siena?)
3rd day: Drive through Chianti region, Radda, Greve, Strada (Stay somewhere here, maybe Strada?)
-Of course, I say drive to these areas/towns, but I also mean to take time to experience the towns or vineyards, etc, etc. Not just "drive" straight through.-

My biggest problem here is not knowing how much time it takes to drive from town to town or how much time we will spend exploring a town, area, etc. Google Maps shows the drive time to be very short between day 1 towns. However, is it realistic to visit that many the same day as training to Chiusi and getting the car?
Is devoting an entire day to driving through the Chianti area too much?
Is there a better way to arrange these 3 days?

Some side info, we are both 29 years old and active. Also, we will be moving on to Florence after these 3 days, so time in Florence is not a factor for these 3 days.

Any insight on how to arrange these 3 days would be very much appreciated! I know there are many of you out there who have experienced these areas first hand and could help us out.
Thank so much!!

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Old Nov 15th, 2007, 12:05 PM
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I've enjoyed tow visited to Tuscany/Umbria and am a fairly ambitiour sightseer. However, I do like to slow way down in the countryside. I've found the 2 hilltowns/day rule of thumb about right for me!

Plus, there are interesting things to see and do nearby and in addition to the hilltowns, such as Monte Oliveto and Sant'Antimo (not to be missed). Not to mention all the fabulous lunch and dinner options everywhere!

For the towns you have mentioned, I would plan 5 or 6 days.

Day 1, pick up the car and visit Montepulciano, have lunch and visit Monte Oliveto for the late afternoon re-opening. Take your time and drive on to either of the other towns to stay.

From there on, you have the choice of visiting the other southern Tuscany towns you mention for your original day 1 plan, or proceeding on to SG or Siena.

Day 3 for Chianti will probably work fine. Just know that the driving can be slow due to windy roads.

You could do all you have planned, IF you are a take a quick look and on to the next type sightseer.

Buon viaggio!
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Old Nov 15th, 2007, 12:06 PM
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I think you're trying to see too much. I would not rush through so many towns, but would do just one town a day. Also, I would stay at the same hotel all 3 nights and do day trips from there. Even though the distances and driving times between towns are not great, you need to take time to absorb the atmosphere of the various places. Think "slow travel." Otherwise, when you're through, Tuscany is just going to be a big blur in your memory. Also, do a wine tasting, they're great fun.

So, study your travel books and prioritize, figure out what areas you're most interested in. For me, the Siena/San Gimignano/Volterra area would a be the perfect intro to Tuscany.
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Old Nov 15th, 2007, 12:07 PM
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Sorry, make that "two visits" to Tuscany/Umbria.
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Old Nov 15th, 2007, 12:13 PM
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That can be done but I would stay in one location, probably Siena. You can see Montepulciano and Pienza the day you get the car. Then, one full day to Bagno Vignoni, St. Antimo, Montalcino. The last day in transition to Florence is the day to see San Gim.--it is on the route
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Old Nov 15th, 2007, 12:29 PM
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just a thought but when you leave Pienza for San Quirico take the truning left after about a mile - on the junction is THAT farmhouse surrounded by Cypress trees - the one on all the calenders. go down the road that is signposted Montisi for two miles and you coime to the church at Sant Anna in Camprena - (set of the English Patient) very eerie place but very peaceful.

I would stop in San Quirico (Palazzo Del Capitano) the are 3 good restaurants in the town - it has a great local feel at night - and isn't usually over-run with tourists.


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Old Nov 16th, 2007, 09:36 AM
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Thank you all very much for your suggestions! I do agree that seeing things slower is better, so I'm glad I sought some advice from those that have been there. This gives me a better idea of how much time to allow.
I will read up more on the hilltowns and look to focus more on fewer towns this trip.
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Old Nov 16th, 2007, 09:50 AM
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You'll be travelgin mostly narrow, winding country roads and speeds wil not be high. Also - in each town you need to find the place to park (often outside the walls) then walk in, find spots you want to see, enjoy the town, eat etc).

We've never been able to do more than 2 towns per day (and that's a pretty quick look - not an in-depth visit). And if you're moving hotels every night that will take even longer. (We did each trip using a single hotel in a central town and heading out in a different direction each day.)
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Old Nov 16th, 2007, 09:58 AM
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nytravler (or anyone else for that matter),

It's been mentioned staying in one spot and venturing in different directions from that base.
Do you have any suggestions for where I should base for my particular itinerary?

Since I'll be driving from Chiusi, I figure to spend the first day around Montepulciano and Pienza now. Do I base there and venture up towards Siena and San Gimignano, Chianti? This seems like a lot of backtracking??
Or stay in Pienza the first night and then the next two nights in Siena?

And while I'm at it, since I'm looking to drop some towns/areas... would you save Montalcino/San Quirico d'Orcia or the Chianti area/towns for another trip? Which is more of a must see on a first trip (Montepulicano/Pienza and Siena/San Gimignano I'm going to keep for 2 of the days).
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Old Nov 16th, 2007, 10:01 AM
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My trip report from the last visit might give you some ideas and a better indication of places to stay and what can be done.

If you do a search for "Dayle's Solo Trip to Italy" it should come up. The last 8 days were in southern Tuscany and Umbria, pickin gup a car in Chuisi and dropping it in Foligno. Note that Chuisi pick up location info has changed since then.
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Old Nov 16th, 2007, 10:05 AM
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You might consider skipping Siena if you also plan to spend time in Florence. There are a lot of similarities between the two.

Here is a driving itinerary for the Val d'Orcia. Most people would want to spend more time in the towns I've mentioned - so 2 days in this area would work fine.

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 May 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. Budget at least two rolls of film for this area. 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 http://www.slowtrav.com/italy/tuscany/sant_antimo.htm 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.

Stu Dudley
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Old Nov 16th, 2007, 10:08 AM
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We are just about the same age as you are (I'm 28, DH is 30) and we managed to see Montepulciano, Pienza and San Quirico in one day and had a blast. We were based in Umbria (near Assisi) and woke up bright and early so we would have enough time. Pienza and San Quirico are not very big, so it doesn't take too long to see them. Of course, part of the fun of traveling in Italy is taking your time and just enjoying being there, but we felt that we we gave each town adequate time without feeling too rushed. I should mention that we went in March last year, which is definitely off-peak season.

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Old Nov 19th, 2007, 05:02 PM
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Hi ... having just returned from 3 weeks in Italy and having driven all over Tuscany I can tell you that it takes WAY longer to get everywhere than it tells you! And I truly believe that when they say x # of km ... they mean as the crow flies!!!! The windy country roads are through incredibly beautiful scenery. I found Sienna the most frustrating city to get in and out of!!!! Montalcino looked like a beautiful place to stay ... we only had a short visit there but wished we had longer.

There is no way you can see San Gimignano and Sienna in the same day and actually see anything. San G is beautiful (we stayed there for a week using it as our base to see that part of Tuscany). There is so much to see in Sienna. Radda, Greve, Strada are all easily driveable in one day from San G or Seina ...even allowing for a nice long lunch and walking around.

And beautiful as the whole area is ... driving (with those crazy Italian drivers for a full day when you only have 3 days would mean that you would miss so much of the essence of Tuscany.

We picked up and dropped off our car in Florence and drove to San Gimignao ... it makes a good base. You don't say where you are returning your car to.

If you are going to be living in Florence then so many of the cities that you want to see are close enough to visit when you live there.

Enjoy your trip ... and I am envious that you will be living in Florence ... a totally beautiful city that I wished we had another week to visit!


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Old Nov 20th, 2007, 03:56 AM
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My wife and I stayed in Chianti this summer and it was a beautiful area. We rented a car after our stay in Florence and it was great to be able to drive around to the various hill towns. Here is my Tuscany trip report: http://gardkarlsen.com/tuscany_italy_travelogue.htm . Hope that you can find some useful info there

http://gardkarlsen.com - trip reports and pictures
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