We originally had our sights set on the Dordogne, but at the time we were booking our flights the state of emergency had been called due to the unrest across France. We were using frequent flyer points and did not want to wait to see if the situation would improve or worsen so the decision was made to go to Tuscany instead. It was an easy choice as my sister had just returned from there and had shared her photos and travel stories. This would be my 4th trip to Italy, but my previous experience with Tuscany had been limited to Florence, Pisa and Lucca. The theme for this trip to Tuscany would be “The Hill-towns and Countryside of Tuscany and Umbria”. Umbria was added after I read Tom’s trip report “We didn’t drink all the Vino”.

I would have to say that this was one of the easiest trips I have ever planned. There is an abundance of information on Tuscany both written and on the web. It is clear that people love Tuscany and from all the photos and painting I have seen, it is easy to say why. We purchased the Rough Guide to Tuscany and Umbria and also Touring Club Italiano Central Italy road atlas which was rarely used on this trip.

I have heard some nightmares about lost luggage but in all my years of travel I have never been a victim myself. I was determined to have a back up plan in the event that our 3 connection flight would wreak havoc on our wardrobe. I packed a small 21” soft-sided carry on bag with several changes of cloths for myself and my DH. Our other 24” soft-sided duffle would be checked. Sure enough, our 1 hour connection in Munich was reduced to 40 minutes as a result of a minor delay. Upon arrival in Rome, we waited and watched as the conveyor emptied and finally the reality sank in….our bag did not make it! The lost luggage desk immediately located our bag in Munich and we were given two choices. We could wait 3 hours until our bag came on the next flight or our bag could be sent on to us at our destination. We were advised that delivery could take 48 hours. We were due to stay the night in Orvieto, but were moving on the next day to San Gimignano. We feared that if we didn’t wait for the bag we would not likely see it again until the end of the trip in Rome.

We decided that since we had a few hours on our hands, we would call our B&B in Orvieto to advise of our late arrival and then proceed to pick-up our rental car. I purchased a prepaid calling card for 3.00 Euros which turned out to be a very handy thing to have. We found the Avis counter without too much difficulty. We had reserved an economy car through Autoeurope with a guaranteed upgrade to compact. The Avis agent advised that we were upgraded further to a station wagon. We thanked him for the gesture but we told him that we would rather have the compact car we reserved. We decided that we would be more comfortable in the smaller car and would rather economize on gas. The agent gave us a brand new Ford Focus diesel with only 14 kms…my husband would be the first dirver…this should have been a sign of things to come. We located our car, grabbed a change of cloths and stored our luggage in the trunk. Several hours later, we were reunited with our bag and hit the road towards Orvieto.

We had no trouble finding our way to the ring road and we were immediately greeted by the locals waving their hands at us to get our of their way. The traffic was heavy as our delay put us firming at rush hour. Once we got through a major bottleneck of merging traffic it was clear sailing until Orvieto. I was convinced that somehow we would find our B&B quite easily if we followed the enclosed map provided by our kind hostess Valentina. I would have perhaps been more successful had there been any visible road signs on the way. We made a wrong turn ending up on a one-way street and could not double back to where we needed to go. Instead we had to circle around town a second time ending up in a main square where traffic was clearly prohibited. I bravely set off on foot to find Valentina’s. Upon my return with Valentina, my DH seems to have vanished from the spot where I had left him. Panic set in as my jetjag took firm hold of me. I was sure I had left him here I explained to Valentina!! She calmly explained that Orvieto was not so big and we would surely find him very soon. We walked back towards the B&B into another square and there to my relief was my DH. He explained that he was told to move his car so he had to leave the spot where I left him. Valentina walked us to the private parking lot where we were to park for the night and we then proceeded to the B&B. It was now 7pm instead of the expected 2pm arrival.

Our room at Valentina’s was large, clean and charming. After quickly freshing up, we headed out to see the cathedral before the 8pm closing. Unfortunately, the guidebook was inaccurate and the cathedral had closed at 7pm. Although deeply disappointed that we could not go inside, we enjoyed the façade which had a magical glow as the sun was now sinking. We found a park off to the side of the cathedral with lovely views of the countryside. I took a deep breath and sighed….we’re finally in Italy!! After a walk about we decided it was time to find a place for dinner. I had the names and directions to several places that were recommended from various sources. We found our way to Trattoria del Moro. Upon entry we were acknowledged and told to wait just a moment. We watched for almost a half hour as the waitress served, got cutlery, took orders and made countless trips to the kitchen. The place was not full so I couldn’t understand why we could not be seated to wait. Another kind lady came out of the kitchen and saw us still standing there. She seemed clearly annoyed that the other waitress had not taken the time to seat us…I think she was the owner. Our first dinner was not very memorable but at 42.00 Euros we were full and content.

On the way back to our B&B, we found a Gelati shop and had our first of many…but it turns out this gelati would not be beat anywhere on our trip. I would dream about the Pistachio that night the faint hint of salt and sweet still lingering on my lips.

Next….our new rental car gets broken in…literally.

ooooo... conflict...the plot of any good story!

Keep it going Crazy!

Thank you for the encouragement Suzie. This is my first ever trip report and after reading some of the pros like Tom...it is sure to be quite dull in comparison...I am hoping that it may have some useful information.

Day 2

We woke at 5am…unable to sleep any longer I dragged my husband out of bed. Since we had missed most of the previous day in Orvieto, I wanted to make the most of the early morning hours. The town was sleepy and watching the sun come up over the beautiful countryside was really something special.

The guidebook said the cathedral was open from 7am so we thought we would have time to visit inside before our prearranged breakfast at 7:30am. Unfortunately, that information also turned out to be inaccurate. We decided it was not meant to be….or was it?

Our breakfast at Valentina’s was a non event of a single croissant and American style coffee. I am not much of a coffee drinker at home but love to have a cappuccino or café latte when I am in Italy so it was rather disappointing for a bed and breakfast. I thought the room was still a good deal at 65.00 Euros per night.

We decided to get on the road early so we could be in Siena by late morning. My DH was being very careful not to hit the tree he was wedged next to and as a result completely discounted the car parked on the opposite side of us. The crunch that came next did not sound good and we were now directly snuggled to the car. My husband carefully unwedged the brand new rental car and moved back so we could assess the damage. To my surprise, we had a very small dent which was difficult to see unless you were looking from a certain angle…and a very superficial scratch. I tried very hard to see where the other car was damaged. There was a very visable dent in the front rear bumper but we had not hit the car in that area…that damage was clearly from a high impact collision. We walked back to the house to let Valentina know what had happened. She was not there and was not answering her cell phone so we left a note with the phone number and email of our B&B in San Gimignano where we would be for the next two nights.

The A1 is fast and efficient and we reached Siena in good time. We found Porta Ovile without any difficulty but there was no available parking. We drove a short distance further and found ample parking at the lot called San Francesco. There was a series of escalators that take you to the top of the city just below the Church of San Francesco. This turned out to be a nice stroll from the centre and was very convenient for getting in and out of town.

We headed first to the Duomo to get ahead of the bus tour crowds and it seems that we had as the line was reasonable. It is the first time I’ve paid admission to see a cathedral. The outside was covered in scaffolding but the inside was magnificent. I made the error of not purchasing the combined admission ticket that would allow entry to the Museo dell Opera as well…a 6.00 Euro error (or 2 more gelati I could have bought!!). I chalk the error up to lingering jetlag, as I had read about the dual admission in our guide book. After our visit to the Duomo, we headed over to the Museo Della Opera to climb the tower. The Museo is interesting in its own right but the real attraction is the climb to the top for the views over Siena and the surrounding countryside. It was a glorious day and the bonus is there are no lines here and you pretty much have the views to yourself. We sat for a long while admiring the views and taking countless photos. On to the Il Campo which is an interesting and lovely square. I used the video function on my camera to take a 360 panorama which turned out really great. It was about this time that gelati was calling my name. We spent some time wandering the quiet back streets in search of an outdoor spot to have lunch. We found a restaurant on a side street in back of the Duomo appropriately called Il Duomo. We enjoyed our Crosini and the Caprese Salad but we were not all that impressed by our pasta dishes. It was a nice day to sit outdoors so we enjoyed our lunch of 35.00 Euros even if the food was not memorable. We wandered around some more after lunch, purchased a bottle of wine then set our sights for San Gimignano.

We found our way quite easily and managed to find an empty spot in the main parking lot closest to Porta San Giovanni. We were told by Palazzo al Torrine to go to the Tabachi on via S. Giovani to collect our keys. It was only a short walk and easy to find. The son of the owner followed us to our car and brought us to another parking lot a little further down the road. We paid 3.00 for the few minutes we were in the other lot so I would shutter to think of what it would cost to park all day. The provided parking was a minimal charge of 5.00 Euro per day. He then took us and our luggage in his vehicle and drove us directly to our B&B. It was located on a street parallel to via San Giovanni which is the main street. We were very happy with the location and the room. The room was clean, nicely decorated, spacious, with a nice large bathroom. We had a lovely terrace with garden furniture where we could enjoy our wine after a day out sightseeing. Palazzo al Torrine was a steal for 70.00 Euros per night. We decided we would not take their breakfast in light of our experience with Valentina.

San Gimignano is magical at night after the bus loads of day trippers leave for the day. We spent the remaining day light wandering the medieval streets and taking in the beautiful scenery that the town surrounds. We had a very nice meal at Restaurant Beppone in their garden terrace. The pizza with truffle cream was delectable and the tiramisu was really good as well. We had been stuffed from lunch so the meal was a light and tasty bargain at 30.00 Euros.

Next…Lost in Chianti and loving it

Those rental cars can get you in a lot of trouble. Looking forward to more.

My husband sleeps like the dead at home but when he’s on vacation he loves to get up early as do I. Although I had been taking Airborne for almost a week, I woke with a terrible cold which would unfortunately stay with me for the remainder of the trip. I was not going to let it dampen my spirit though. San Gimignano is wonderful in the early morning hours and we pretty much had the town to ourselves. We retraced our steps from the day before to find the street that leads to the panoramic views. We decided to see what was on the other edge of town and discovered the path that leads around the walls. This turned out to be one of the most beautiful walk I have ever taken. I can not describe the scenery that unfolded before our eyes but it was truly breathtaking. I think this is likely the side of San Gimignano that many of the tour bus passengers never get to see as the guides tend to take them to only the major points of interest….what a shame.

We had delicious cappuccino and yummy pastries at a café on the main street. We paid close to the 10.00 Euros it would have cost for the breakfast at our B&B but I can not imagine it would have been as good.

As we headed back to Palazzo al Torrione the owner met us at the door with an email from Valentina to call us about the car incident. Finding a public phone was not easy…it was clear on the other side of town hidden in a building on a side street. The phone card I purchased earlier came in very handy. Valentina explained that the person we hit wanted her to pay for the damage. I asked about the damage and said that it must be very minimal as I could not see anything visable on the car. Valentina was very sweet and did not want to trouble us while we were on vacation but the women said terrible things to her and wanted her to pay. I told her that we were fully insured and she certainly did not need to pay that we would pass through Orvieto on our way to Spoleto and clear things up. We told her to make an appointment with the owner of the other vehicle for the day we were passing through. With that settled, we were off for a drive through Chianti.

As we were leaving town, the first groups of tour bus passengers were arriving. It was like a tide washing in with the tour leader charging ahead with her little white flag. We were happy to be going in the opposite direction out of town. We took the minor road that twists and turns its way through the countryside stopping many times along the way to take photos of the beautiful countryside. We stopped in Castellina which was of no real consequence other than the monster self cleaning public bathroom in the parking lot. I had never seen such a contraption and hope to see them outlawed in the future. I paid my money and the door opened. It was completely wet instead with bits of toilet paper plastered on every surface. There was no dry toilet paper and it dawned on me that I had no tissue with me. I could not imagine how I was going to even get near the soaking toilet to do my business. Apparently after you leave, high powered water jets spray the whole interior down. I find it hard to believe that the inventor was rewarded for this idea.

We found a café where I was able to purchase water and cough drops and I was able do my business in a clean washroom for free. Radda our next stop is a very cute town with lovely views of the surrounding countryside. We had a nice picnic lunch there is a small park. I think after more than 3 hours in second gear, my husband was starting to get tired when we reached Greve. There was a lot of traffic and we did not see the immediate charm so we decided to head back to our home base. We wanted to somehow get to the N2 which was easier said than done. I used my trusty touring club atlas to map our route. The first road we turned town did not look promising as we encountered some speed bumps followed by dirt road which narrowed to one lane. I asked my husband to turn around and we would try another route. The next move turned out to be a mistake as after driving 15kms we came to a road closure. We turned around and headed back to the one lane dirt road and sure enough it seem to be leading in the right direction. Maps seemed of little use in this region except when you were really lost in the middle of nowhere. I was able to navigate us back to the N2 by finding the towns on the atlas. None of them were major towns so we had no idea where we were. But if I had to be lost, this was the place to do it as every inch of Chianti is beautiful.

We decided to stop at Pietrafietta on our way back to San Gimignano. My sister stayed on this winery in one of their gites several months before and I wanted to see it. The house has a wonderful view of the countryside with the towers of San Gimignano in the distance…what a spot! After purchasing a bottle of their wine, we headed back to town.

We had reservations at Chiribiri which was just around the corner from where we were staying. The pumpkin ravioli is something I will never forget. We had a 3 course meal with wine (no desert as we were stuffed) for 45.00 Euros. You must make a reservation to dine here as there are only a dozen or so tables and they accept cash only. It was the best deal of the trip…good food and very attentive service. We ended the day with a stroll around town…what a magical place at night!!

Next: Monks, Montalcino and the famous Brunello

Finding our way out of Poggibonsi towards Siena was not as easy as it should have been. We got confused by the signs referring to the A1 which we did not want to be on…or did we? I guess we did as once we took the turn that said A1 we found the signs which pointed towards Siena.

We made a short visit to the walled town of Monteriggioni which again looks over some magnificent countryside. It was only 10am but I figured there is no wrong time to have gelati…especially since I was too full the day before to have any which is breaking some unwritten rule.

Keep in mind that all driving distances on Mappy.com are a guideline only. You have to take getting lost, stopping for photos and slow traffic into consideration. We hoped to arrive at Mont Oliveto Maggiore by 11am, but it was closer to noon by the time we pulled in. We had only 15 minutes to visit the Abbey prior to the lunch closure. The monk on duty was nice enough to usher us to the library and refectory to see the lovely frescos and carvings. The gift shop which is opened during lunch has quite a variety of herbal medicines, olive oil, liquor and honey made by the monastery. Mont Oliveto Maggiore sits atop one of the most beautiful tracts of countryside and it is glorious in the spring with the fields of wild flowers in bloom.

We had a quick and tasty lunch outside of Buonconvento and found Altesino winery just a few miles outside of Montalcino. The winery is located on a very pretty hill with views of Montalcino in the distance. The owner, who speaks very good English, gives tours by appointment only. There is an 8.00 Euro testing after the tour where you are able to sample the Rosso di Montalcino, A supertuscan blend, and last but not least the Brunello di Montalcino. The Brunello is very tasty but I liked the Rosso di Montalcino just as well. We purchased a bottle of each and headed towards town to find the Hotel Dei Capitani.

The hotel was easy to find, but the hotel parking lot down a very steep grade looked treacherous. Thankfully the person on duty allowed us to park in a spot directly in front of the hotel. The reason I booked this hotel was for the views of the countryside and it did not disappoint. The room was clean and spacious with a small balcony with a view. The balcony is too small for chairs but the hotel has a larger terrace with pool with that same million dollar view. Here you can sit and drink wine and it is also where the breakfast is served in the morning…lovely!!

After a nice glass of wine, we left the hotel to explore some of Montalcino. It is two very steep blocks from the hotel to the main square but a convenient location none the less. The Medieval tower at Piazza del Popolo was covered in scaffolding which was a shame. We visited the Fortezza whose walls are impressively intact and now house an enoteca where you can sample and purchase wine from the region. The churches we entered were pleasant but simple. We did not find Montalcino overly enchanting but it would prove to be a good central base for seeing the area. We had a late lunch which proved to be quite filling so we were not overly hungry. We wanted a light dinner so we decided we would have salad and pizza. We had a very forgetful 35.00 meal that evening at a pizzeria restaurant on via Mazzini where the service was terrible. We agreed that it did not ruin our next to perfect day anyway.

Next: How many times can you say pretty?

I'm really enjoying your report. And it's never too early in the day for gelato! On my recent visit to Rome, I sometimes had it for breakfast...

Thank you SusanP. I had promised myself to have gelati twice a day but was I was always so full I had a hard time keeping that pact. The ones I did have were heavenly!! How I wish we had more Italians in Halifax that could share their icecream making skills with us.

Must be even duller than I thought.

Hi Crazy,

No, not dull at all! Don't take it personally, weekends are slow on the board, especially summer weekends!

I had to laugh at your navigating confusion in Poggibonsi. EVERYONE has trouble in Poggibonsi (we did too)!

Please do continue! I'm imagining sipping some Brunello which I haven't had since my visit to Montalcino last Sept.

Thank you for tuning in Dayle. I just want to make sure someone is interested before I go on. I had no idea how time consuming these reports are to write. I have such admiration for the people that can make them entertaining as well as informative.

Stu Dudley was very kind to email his trip report for Tuscany. I can’t say that we followed it to the letter but it was very helpful in planning some of our drives through the Val d’Orcia.

After a good breakfast on the lovely terrace, we hit the road early. We decided to make Montipulciano our first destination of the day. It was a Sunday and we expected that it would be very quiet. We found parking quite easily outside the walls and started our climb to the top of town. I was enchanted by Montipulciano as soon as I clapped eyes on it. It is a lovely town full of vistas, odd squares and corners with dozens of Renaissance palazzi and churches. I was quite surprised that many of the shops were open for business and I was lucky to find a good pharmacy to get drugs to nurse my cold. After a very nice tour and some delicious gelati (is there any other kind!!), we were on our way.

We almost missed our turn off for Montichiello but I just happened to look back and see the sign. We were taking the detour in the opposite direction heading from Montipulciano to Pienza. All I can say is WOW!! It was like walking directly into every painting I have ever seen of Tuscany. I found myself chanting over and over “pretty”…”pretty”…well you get the point. This is god’s country and surely he must have had a hand in creating such beauty. Post card perfect every inch of it!!

We made our way to the town of Montichiello after numerous photo stops. The town is an extension of the lovely countryside…quiet and untouristic. After a short stroll, we stopped at the Osteria La Porta and had a wonderful $45 Euro lunch. Everything we ate was mouth-watering from the Artichokes in melted pecorino to the Gnocchi in Pecorino. I ended the meal with biscotti dunked in Vinsanto.

More of the same beautiful countryside to our next stop Pienza, which turned out to be my favourite town. I knew it was famous for its pecorino, which I had just tasted at lunch, but I had no idea how lovely the town would be. We found a parking spot at the bottom of the hill behind the Catheral. After a steep climb, we reached the top of town. Every corner of Pienza is pristine and neatly kept. We wandered into cheese shops and tasted some more of the local product. Every alley was a delight and the views of the countryside stunning.

Our next and final stop of the day was San Quirico d’Orca, a sleepy town that was equally lovely. We enjoyed a stroll through the rose garden and around the town. It looked like they were getting ready for their famous flag tossing competition. We had seen this on a Rick Steve’s show several years before.
I have a nice photo of the main street with all the flags hanging from the buildings.

When we got back to the hotel, my husband decided he would try and back into the same spot we had the day before. He does not drive a stick at home but used to years ago. We have rented cars in the past in France without too much difficulty. He is quite rusty to say the least and has trouble when on steep inclines. There was a Mercedes parked in front of the hotel. Somehow while backing up he ended up within a few inches of the Mercedes as he had stalled the car and rolled forward. On his second attempt, he was almost touching the very expensive Mercedes. In a panic, I tried to find the gentleman from the hotel front desk. A local waiting to get through with his car could not understand our dilemma but seemed quite patient. I found the front desk clerk and he was very reluctant to help but realized that we would a) probably either hit the other car or b) block traffic all night until the Mercedes driver returned. The nice gentleman got into the car and without the car rolling at all was able to back into the parking spot. The clerk was very reluctant to take the 10.00 Euro tip I offered, but my conscience really needed clearing to relieve some of our embarrassment, so I insisted. It was a rather rocky ending to the most wonderful day….a sure cure though is Rosso Di Montalcino on the beautiful terrace.

The day was not quite over as we had reservations at Grappo Blu. I heard wonderful reviews of this restaurant and it did not disappoint. My main course was Guinea fowl in a lemon sauce…it was yummy. We had good service and the meal was reasonable at 70.00 Euros.

Next: More dead ends and the chanting Monk has a cold too.

Crazt-thanks for the report. Siena duomo was scaffolded when I was there in Feb., a shame I hear the facade is beautiful-keep it coming.

P.S. wet toilets-ICK

"Artichokes in melted pecorino to the Gnocchi in Pecorino"

You're killing me!!! We loved that place. Keep going. Your trip report is great!

CRAZY4TRAVEL I may need to add Pienza to our itenerary. I can't wait to read more, please!

Great trip report! I enjoyed reading it today when I should have been working on yearly statistical information....very good diverson. Please continue!

I am loving your report Crazy and making notes for our upcoming trip in September.

Thanks for sharing your enjoyable report!

Day 6

We awoke to another glorious day of blue skies. Our plans for today included a visit to Sant’ Antimo monastery in time to listen to the Gregorian chants at 12:45pm and lunch at the Fattoria de Barbi winery followed by a tour.

Our morning was free so we decided to follow the route south as far as Monte Amiata then north again to Bagno Vignoni by way of Castiglione d”Orca. The only real snag is the road closure we encounter at Castiglione. We followed a sign towards the Rocca and decided to visit if it was open. Unfortunately it was’t open, but we wanted to see if there was an alternate route. We head out of foot to find out where the road past the Rocca led to. We pass by a lovely hotel with wonderful views and continue down the hill towards a tangle of houses. The road started to narrow and quickly came to a dead end. We started to feel that we were just a tad off the beaten path and are now somehow intruding on the daily life of these good people. We head out of town and follow the road a short distance to discover another route towards Bagno Vignoni.

The small hamlet is clustered around a large pool enclosed on three sides by the town walls and has been unchanged by time. This area has been known for its thermal springs since Roman times, but the town built by the Medici came later. You can bathe in the sulphur pools at the foot of the hillside below the village or simply enjoy the delightful scenery.

We arrived at Sant’ Antimo at noon, which left us plenty of time to enjoy the incredible vistas that surround the abbey. Unfortunately, the exterior was covered by scaffolding but nothing could mar this picture perfect setting. Inside the churches imposing interior it’s silent and the darkness is barely lit by shafts of light that enter the narrow windows. The Gregorian chants began at 12:45pm and I tried my hardest to suppress my cough. One of the chanting monks had a terrible cough too. It got me wondering if they have alternates that stand in when one is sick like in sports or theatre. Experiencing the chants, helps to bring the history of the building to life. You feel as though you have walked into another era.

We arrive at Fattoria dei Barbi for our 2pm lunch reservation. We had requested a table outdoors but none were available. We are seated inside the taverna which is nice also. A group of 4 gentlemen are seats just after we arrive. They are served water, wine and antipasti within minutes of being seated… almost a half hour after being seated, we have not yet seen a wine menu or a waiter. We decide that there is no excuse for such poor service and leave. I felt a little sad about it as I had heard good reviews about the food.

We decided to head back towards Montalcino and have lunch on the edge of town at Boccon Di Vino. This wine bar restaurant is perched on a hill with glorious views of the Val d’Orca. We arrived at 2:05pm, but the waitress was kind enough to seat us anyway. The service was attentive, the food was delicious and the views were beyond compare. It was our most expensive lunch of the trip at 95.00 Euros, but one of the most memorable.

We were still so full from lunch that for dinner we decided we would have some nibbles and do a wine tasting instead. There are several enoteca on via Matteotti with that million dollar view from their back windows. It was a nice way to watch the sun go down and try some of the tasty wine of the region. To end the day, we had some gelati and took a nice evening stroll.

Next: Back to the scene of the crime - Orvieto