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Trip Report Tuscany Trip Report: 9 day driving tour

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About us
The travelers: Hi there, and welcome to our trip report! I’m K, and he’s J. We’re 31 and married. We work fairly long hours that vacuums up our brainpower and makes us eager for relaxing, escapist vacations by the time they roll around. We’ve lost our taste for roughing it (well, mostly me), so we don’t travel on a budget, but we do pursue good value for our money and (mostly) avoid spending more than necessary to meet our requirements. By choosing small, boutique hotels and quality B&Bs—particularly those run by passionate locals—we gain an instant connection to the people and place.

Our pace is vibrant, yet relaxed. We strive to see a fair bit each day without undue stress. We walk A LOT, as we find it’s the best way to appreciate and embrace a place, but nothing more rigorous than that. Hills and steep inclines don’t scare us, but nothing crazy that involves special gear or fear, like hiking or bungee-jumping, unless we’re feeling particularly ambitious (although to be clear, I will never be ambitious enough to bungee-jump. Never happening). We mostly eat and drink, people watch, and take sips of architecture, churches, art, markets, and shops. We don’t mind driving, as we love to enjoy scenery and see where the road leads us. The more off the beaten path, the better. We don’t do touristy for the sake of touristy, although we occasionally do touristy in spite of touristy. We research to the death before we take off, and these forums are a wealth of information that always enhances our enjoyment of the destination. This trip report is our way of paying it forward, and I hope you find some good nuggets to help with your own adventures.

Why we chose Tuscany
We fell in love with Italy during a 3 week backpacking trip around Western Europe in 2006. We always wanted to come back and do a longer, focused trip in a smaller area. Tuscany was obvious given our interests in wine + food + history + rural scenery + small cities. For this trip, in particular, after coming off of intense work projects, we didn’t want to fight for relaxation. We needed a slice of the world to call home for a week that would beg for us to slow down and enjoy life. If you seek the same, then Tuscany is your ticket!

Our itinerary and timeframe
Our trip took place from October 10-20, 2014. We had almost 9 full days on the ground. We flew from Seattle into Florence, opting not to fly into Rome in order to reduce driving time. We rented a car and drove a clockwise route, mostly through eastern and southern Tuscany. In 2013, we drove 1,000+km through Ireland in 9 days, and vowed we’d do half that for this trip in keeping with our desire to chill out (as the chief navigator, I was particularly keen to avoid panic attacks brought on by hours of keeping us on course through drives that had us hanging off cliffsides, literally, but that’s another trip report for another day!). I hated cutting out more stops (Lucca! Pisa! Orvieto! A day trip to Venice!<--haha, yep, not naïve, that’s just the kind of trip planner I am!), but ultimately I am so happy we committed to a slower pace, as that was the guiding vibe for this trip.

Our itinerary (primary towns visited + where we stayed):
Oct 10: Fly in, SEA to FLR (flight arrives next day)
Oct 11: Florence (1 night, 1865 Residenza d’Epoca)
Oct 12-13: Montepulciano (2 nights, Locanda San Francesco)
Oct 14-16: Val d’Orcia, Montalcino, Cortona (3 nights, Casa Bellavista)
Oct 17: Siena (1 night, Relais Borgo Santo Pietro)
Oct 18-19: Chianti, San Gimignano (2 nights, San Donato in Poggio)
Oct 20: Fly out, FLR to SEA

A note about Tuscan weather and scenery in October:
Considering a trip to Tuscany in October? Let me save you hours of research. Advice is split: (1) Tuscany will probably be beautiful in October because the weather doesn’t get cold and rainy until November or (2) Tuscany will be iffy and changeful in October, and thus you should go earlier in the fall to avoid disappointment. We had no luxury to flex our dates, and I’m glad we went anyhow. Although advice seemed contradictory, I found both sides to be partially true. We had only one rainy afternoon, and a couple of overcast days. We had several clear, blue sky, bright sunshiny days. And the rest were mixed—part cloud, part sun. Temps hovered in the high 60’s and low 70’s most days, and evenings never dipped below 50. We found the weather to be quite changeful, varying from hour to hour and day to day, as well as from town to town—a 15 minute drive could yield totally different conditions. Overall, the weather was very pleasant to us and I wouldn’t dissuade you from going this time of year. That being said, I’m dying to go back in early summer, because Tuscany is stunning all lit up in bright sunshine, and I want to see the poppies (hey, priorities!). Scenery in mid-fall felt a bit dead to me. Doing it over, I’d go in September, but only for better scenery, not better weather. Tuscany was still lovely, but the wheat and grapes had been harvested, and it looked a little barren. I know harvest time varies, but going in September, you’re not going to miss it. If scenery is a priority, consider this as you plan dates.

Finally, here’s the goods! This is a really long trip report, but I’ve highlighted the cities/towns, hotels, and major sights to help you skim through to the parts that might be relevant to you.

Day 1: Florence
After 15 hours of travelling, we arrive bleary-eyed, jet-lagged and sleep-deprived. All this, confirmation that it was the right move to spend a night in Florence before getting in a vehicle and trying to drive anywhere at all  Nonetheless, we are filled with anticipation to see our beloved Italy again. I spend the taxi ride doing what I always do when we’ve just flown half way across the planet: convincing my precious J that we cannot possibly do the only thing we most want to do—nap. (In addition to navigator, I am also chief jet lag fighter.) Napping is too rife with possibility for error, too risky that we may fall asleep in the afternoon for “just an hour” and find ourselves wide awake at 2:00am, something you just can’t backpedal from. The “stay awake at any cost” strategy makes for a mildly wretched first evening anywhere, even Italy, but the payoff is worth it. Highly recommended, without reservation.

We arrive at 1865 Residenza d’Epoca, a completely charming and perfect choice for our night in Florence. Small, quiet, stylish, historical, and comfortable, with very lovely hosts and a self-serve espresso machine and tea kettle (what more could two sleep deprived peeps possibly ask for?!?). When your only goal is to stay awake until 10pm, it makes it really easy to plan your evening: just WALK, baby, WALK! Keep it moving! We set off with a map, and made it our goal to cover as much of Florence as possible before dinner. Turns out, this is not only a great jet lag strategy, but also a really fine way to (re)acquaint yourself with Florence.

We made it all the way to the Duomo and Ponte Vecchio and back, and then had a truly delightful first meal in Italy at Il Cibreo, a dinner filled with coniglio, budino, and sformatino, things that taste even better than they sound. We sat outside on a street that sees a lot of pedestrian traffic, which made it really fun to people watch. Across the street, we noticed a completely hopping place, stuffed to the brim with locals, spilling out into the street with delicious little appetizery things, and we decided that next time we’re in Florence, we’re going to join that party. The rest of our evening was super eventful: we went back to the B&B and promptly passed out, but not before we heard the beginnings of a completely dazzling thunderstorm, replete with torrential downpours. We were both delighted, as we don’t get much stormy weather like that in the Pacific Northwest. It lulled us to sleep, and we awoke to a perfectly sunshiny day.

Day 2: Florence & Montepulciano

Over a super yum, leisurely breakfast, a very sweet Swiss couple obliged my desire to speak French, as it’s been ages. It was a really fun start to our first full day, and a little bizarre to speak French in Italy. The days to come will prove how much of my Italian has stuck with me! Before we set off for Montepulciano, we wanted to see a new-to-us part of Florence. Since our original plans to go see David fell through (technical difficulties), and the weather was so glorious, we were happy to take the long walk to Palazzalo Michelangelo for the view. Highly recommended! From here, we stopped for lunch, during which we discovered that crostina Toscana is not really for us. But hey, you have to try everything at least once, and it was the only thing we ate during our trip that we didn’t like! We made up for our mediocre lunch with some delicious gelato at Grom, and then headed to the car rental place. When we got there, we realized we screwed up our reservation, but happily in our favor, in that they still actually had a car for us. Although we both double checked the reservation, we botched the pick-up day, probably due to our overnight flight. We were bummed that we overpaid by a day, but super thrilled that an automatic was still available for, as neither of us can drive standard, and I’m not sure what we would have done.

We set off for Montepulciano, and had an easy drive of it on the highway (I researched to death driving in Italy before we left. It was, in fact, overkill. We were fine, although watch for the silent speed cameras…more on that at the end.). Sadly, I did not convince J to stop at the Prada outlet on our way (next trip! #1). We arrived at Locanda San Francesco at dinnertime, after our adventure in following the most excellent but slightly nerve-wracking instructions. Somehow we managed to get there in one straight shot. Locanda wins the award for best-ever turn by turn written driving instructions (apparently, a GPS does not work well in Montepulciano). Pro tip: if you are thinking about staying in Montepulciano, get good instructions to the hotel and have a designated navigator who has read them ahead of time. After our drive, we couldn’t have asked for a more chill arrival. At the wine bar behind the hotel, Cinzia greeted us with two whopping glasses of wine and a snack trio of olives, nuts, and chips while we checked in. We loved relaxing on the patio and were there in time to catch the sunset. Ah, this is why we love Italy.

We spent the evening walking the town and had dinner at Osteria Acquacheta, a very stark contrast to the uber quiet rest of the village. The vibe here is great – low ceiling, brick-walled, family-style tables, filled to the brim and bubbling over with boisterous conversation. This was our cheapest but most satisfying meal in Italy. We ordered the pici with meat sauce – simplicity itself – and a half liter of wine (So cheap! I’ve bought bottles of water at airports that cost more!). We hung out for a long while, not watching the clock and just enjoying being together. I guess we stayed too long, because the server came over and told us they needed the space for more people. We were both surprised because we thought this wasn’t something that happened in Italy. I thought you always had to ask for the bill to signal you’re ready to go, but I totally get it. I still think this place is terrific. We headed back to the wine bar at Locanda for a night cap and to continue the conversation, and then to bed.

Day 3: Montepulciano & Pienza

We spent the morning taking an extensive walk to see the whole town, stopping in little shops and churches. My favorite find was a tiny hole in the wall mosaic shop. I’m still kicking myself that I chickened out of striking up conversation with the artisan working there. I was so curious to learn more, but I didn’t think my Italian was good enough. Travel should push your boundaries and comfort zone…but only if you let it! The restaurants have different “off” days so we weren’t able to eat at our first choice, but ended up sharing a satisfying pizza that was the size of a tire.

For the afternoon, we drove to Pienza, the next town over, and walked some more. Had an espresso. Took lots of pictures of quaint, flower-covered buildings, and marveled at the number of cheese shops one tiny town can support! Not a ton to do/see, but a pleasant place to walk for a couple of hours. Then we went back to Monte to do a little wine tasting. We’re fairly serious wine-tasters, and everyone had said you have to go to Contucci, and we couldn’t have been more surprised. Maybe we caught them on an off-day, but we went in and stood for a solid five minutes, with only one other couple there, and the staff member never acknowledged us. We went next door to Poliziano and had the most amazing tasting and service from Giulia. I will never know if Contucci’s wine was any good, but I didn’t feel we missed out at all. Poliziano makes amazing wine. We loved their vino nobile 2011!

For dinner, we walked to La Grotta, a highly recommended Tuscan restaurant. Our walk was punctuated with frequent lightning flashes and some spritzes of rain that I’ve heard are characteristic of late autumn in Tuscany. A bit eerie, so we scurried along and were happy for the warm embrace of La Grotta. This is a white tablecloth and crystal kind of place, and a bit stuffier than we wanted, but with impeccable service and tasty food. I don’t understand all the fuss, but it is surely a lovely spot for a quiet, romantic dinner with great wine. We huffed and puffed back up the hill to Locanda (welcome to Monte!) and then hit up the wine bar again for a nightcap (we love this place!!). I highly recommend Locanda, given its perch on the top of the hill with views, the lovely historical rooms, and the awesome wine bar right next door. Super happy with our stay here.

Day 4: A day in wine country: Avignonesi

Today we drove to Casa Bellevista, near Cortana, for the next phase of our journey. As wine-lovers, we wanted to visit some wineries and committed to a day-long winery tour and dinner at Avignonesi. We dropped our luggage and our host, Simonetta, had arranged for a driver so we could drink as much as we wanted. It was and added expense to an already expensive day, but was worth it. We had about an hour long tour of the winery and were lucky enough to be there right after harvest. Avignonesi is famous for their Vin Santo, and every fall there is a narrow window during which you can enter the climate-controlled room and see the grapes drying. Very cool, and one of my favorite trip memories, as I appreciate seeing how things are made. Vin Santo is indeed, a very special wine and we heard lots about all the painstaking effort and stringent standards that go into making it, building the anticipation for trying it at lunch!

It was a lovely lunch, and tasty, but the food underwhelmed a bit. We’re not fussy, but we paid 95 euros per person for a three course meal with wine pairings. The wine pours were generous, which helped make up for it, but we agreed it cost too much for what you’re getting. The TripAdvisor reviews for this place are glowing, so we were confused about how the reviews were so outstanding. Maybe it was our expectations—we don’t like to be overly pampered, we like to get good value for our money, and we prefer more laid-back experiences…I don’t know. I’m not whining, I mean, we spent a day leisurely eating and drinking in Tuscany, of course it was amazing! But if you’re thinking about doing it, consider how happy you’re going to be spending all that money, and could you have just as good a time doing something else for half the cost? More on this later…some of my favorite moments of this trip were a far better value…and a couple favorite moments did, in fact, cost a fair amount. We did get to try vin santo at the end of the meal, and to buy a bottle of this would have cost a ton, so maybe that’s part of why the meal cost so much. It was unlike anything I’ve ever had, and I’m so happy I got to try it, especially after seeing how it’s made. I now have the most delicious taste memory. I still prefer port, but gosh, I love to try new things that are so rooted to a particular place. Yeah Tuscany!

As you can imagine, with all that wine, the rest of the day was kind of a wash. We passed out in our room at about 4:30pm, woke up at 7:00pm and spent the rest of the night planning our drive the next day.

Day 5: Sant’Antimo and Sant’Angelo in Colle (Val d’Orcia)
This was one of my favorite days of the trip. Simple, slow-paced, unfussy, and utterly perfect. We drove from Sinalunga down through Trequanda to Palazzone, then to Sant’Antimo via San Quirico d’Orcia. We made it just in time for the 12:45pm prayer/chants. Nestled in an olive tree-dotted little valley, Sant’Antimo is the ultimate antidote for over-busy. I can still feel the cool, Spartan church, so peaceful in its emptiness, and the soothing Gregorian chants washing over me, striking me to the core. We left there calm and refreshed. (Check their schedule online for chants – I read that lauds at 7:00am and vespers at 7:00pm are the longer chants, but they also do 9, 12:45, and 2:45.)

My only other goal for the day was to find Il Lecchio and eat there. I read about it in this NYTimes <a href="">article</a>, and as it was praised for the outstanding food and for being a wine-makers hangout, I knew it was an obligatory stop. GUYS, YOU GUYS! IF YOU’VE STOPPED READING CLOSELY, PAY ATTENTION HERE! I don’t know, not everyone’s experiences are the same, but I just don’t know how you couldn’t have an experience at Il Lecchio ranging somewhere between lovely and extraordinary. We parked our car at the base of the hill and wandered up, stumbling onto the most darling little plaza, looked right, and there it was. We proceeded to lunch on their glorious patio. J made the best choice of the trip by ordering the antipasto misto, which was an enormous, jubilant, color-riot of a platter, each bite challenging the last for being the tastiest. And then we had glorious, melt-in-your-mouth homemade pasta. And no one asked us to leave, even though we stayed for a long while. Of course there was good local wine, Brunello! We capped off the meal with a leisurely wander around the quaint town. For such a small town there sure were two gorgeous viewpoints. We hung out for a while on a park bench enjoying doing absolutely nothing. If there was a more leisurely day in my life to date, I don’t know it.

But wait, there’s more...we drove onto Montalcino and climbed the fortezza. We drove back to Casa Bellavista/Creti via Monticchiello and went to a very local place recommended by the B&B owner – La Lodola – simple, local food. After five days of indulgent eating, we were ready for something light and the risotto di zucca hit the spot. We also finally got to try vin santo with cantucci, a local specialty and delicious!

Day 6: Cortona and more Val d’Orcia

Hoo boy, this trip report is getting robust, so I’m going to attempt to tighten it up here a bit (although I’m confident I will fail despite my best attempts…)
We did Cortona in the morning…church going, looked into shops, thought about a museum but decided that was too much effort with a sunny square beckoning to sit and people watch. Ate at Pane e Vino for lunch where we had ribollita and this delicious bread/cheese/bacon thing that is one of the top three things we still talk about from this trip. Someday soon, I’ll try to re-create it at home.

We were kind of bored in Cortona, so we decided to drive back to Val d’Orcia, as our previous day there was so lovely. We went by way of Castiglione del Bosco (huge lake) and it was a ghost town so we didn’t get out…yet another reason I wish we’d decided to base ourselves firmly within the Val d’Orcia rather than to the east near Cortona. (next time! #2)

We cut over to Chianciamo, up through Sant’Albino, then drove the road to La Foce, something I was very eager to do given its iconic scenic status. The dirt road really was not so bad, although we didn’t approach closely. It really was striking and unusual and I was bummed our timing did not coincide with the garden tour hours (next time! #3). After that, we drove back to Montichiello which was a complete and total highlight of the trip – and a serendipitous one, too.

Side bar here for tips on seeing the Val d’Orcia. Find some suggested driving routes and get a Michelin map so you don’t have to rely on a GPS. That way you can go back and forth, make unexpected turns, etc. and still know where you are. At this point, I’d like to give a HUGE SHOUT OUT TO STU DUDLEY. His <a href="">trip report</a> on Fodors is amazing. We had several truly beautiful moments thanks to following a few of his suggested drives, rather than just randomly driving around (although we did our fair share of that too). It is a breathtakingly exhaustive guide to the area, and we can’t wait to return and try more of his suggestions with the benefit of more time.

Back to Montichiello…we weren’t going to get out of the car, but I had to use the bathroom, and we ended up at a little café called La Porta, and all of a sudden the most glorious sunset was descending upon us, lighting up the surrounding hills in a foggily crazy brilliance. I got out my camera and went crazy for a few minutes. Then we shuffled over to a table, ordered an espresso, and proceeded to marvel at catching such a killer sunset without even trying. There was a group of 6 people from the U.S. there doing an “off the beaten trail” style guided tour and they were surprised we even knew about Montichiello (we told them we found it thanks to a guy who wrote about it on Fodor’s!), so we knew we found a truly special place. We wandered around the cuter than cute town afterward, then headed back to Casa Bellavista for a delicious, local four-course meal, a tremendous value. The B&B owner, Simonetta, is also a wonderful cook. While you’re there you can take a cooking class or have a private evening dinner. Casa Bellavista was very comfortable and Simonetta was a great host. The only reason I wouldn’t return is location – we spent too much time driving back and forth. Next time we’re going to stay farther west, simply because that was the area we enjoyed the most.

Day 7: Siena, Relais Borgo Santo Pietro
We debated doing Siena given the parking challenges (this was supposed to be a super relaxed trip, after all!) but every single person raved about it, and it was on our way to our next hotel…so we went, and I’m glad we did, as it is unique, memorable place. I had previously mapped our GPS to a particular parking lot, but we missed it and ended up flinging our car aside at the first place we found to park and decided not to even look at the price (part of adhering to the “chill” trip vibe we committed to). We didn’t have a map, but set off uphill – all roads lead to the Campo! J climbed the tower to get the view of the Campo while I enjoyed it from below. With a scoop of pistachio gelato in hand, I chatted with the shopkeeper and felt really pleased at how much my Italian was coming back to me. Italians are such truly beautiful people – generally warm, easygoing, and willing to converse (and ignore all my grammatical mistakes) – they were a huge part of how relaxed and enjoyable our trip was – thanks, guys, for being so awesome! I learned a lot about the annual horse race and the local culture through my conversation – way more fun than a hike up a clock tower, although J got some gorgeous snaps from high up above.

Afterward we visited the visually stunning, one-of-a-kind Siena Cathedral. So. Much. To. Look. At. We were lucky enough to be there during the one month a year they lift the carpets to reveal the spectacular mosaic floors. We slowly lapped the church—twice—and then hesitatingly left. We were really bummed not to have more than a few hours in Siena (next time #4), but had to get onto our next stop before sundown – Relais Borgo Santo Pietro.

I booked a one night stay at this property as a super-special Anniversary splurge. After all the glorious views in Val d’Orcia, the scenery was underwhelming. That being said, the hotel itself is completely magical, and that is what you are here for. They have created an experience that makes you feel like you’ve arrived at a little country manor belonging to well-off relatives. We sat on the lawn and enjoyed a glass of prosecco under manicured fruit trees, then got lost wandering the labyrinthine property, discovering every manner of fun surprise. We stumbled across a croquet set and played an impromptu game, went through a flowering garden with a small lake at sunset, re-discovered our inner child on a playset, and on the way back for dinner came upon a trampoline set in the ground, which is great fun if you’ve never tried one. Winded and laughing, we went to our room and changed for dinner.

The food wasn’t memorable, but the setting was incredible. I’ve never seen so many candles and twinkling lights everywhere – giant candelabras loaded with tapers, massive lanterns, twinkle lights – completely magical. I can’t imagine what their candle budget is here, haha. Back at our room, there was a bottle of champagne waiting for us. We each poured a glass and decided to go for a moonlight stroll, admiring the stars and ended up on the tennis court, totally a la Sabrina, if you’ve seen that film. We found a candle-lit tent by a fountain and talked some more. I couldn’t convince J to a chess match by an open fire…so we went back to our room and called for them to make a fire in our fireplace (!!!). Sure beats room service!

Next morning was a gloriously sunny, warm day so we played a short match of tennis, trampolined some more, and enjoyed breakfast (although did not enjoy all the wasps around…yikes…might not be a good place for someone with a serious allergy, but I guess comes with the territory of a country house). After checking out, we saw there was a painting class that day and an opportunity to go truffle hunting or hot-air ballooning (!). Next time #5, for sure (we need a little time to accrue a small fortune first, lol). In case you couldn’t tell, we loved it here. Say what you will – it was expensive – but we left here feeling re-connected to each other, energized and super relaxed – worth it.

Day 8: Chianti
Before we set off for the last stage of our Tuscan adventure, we looked in on the Abbazia di San Galgano, just down the road from Borgo Santo Pietro. I’ve never seen anything quite like it, and we enjoyed spending time strolling around here. We hiked up a little hill to go see what’s supposed to be the legit sword in the stone – a little hokey, perhaps, but we had a great view from there!

As a base for exploring Chianti, we spent our last two nights at Bed and Breakfast Del Giglio in the teeny tiny little hamlet of San Donato in Poggio. Of the 5 places we stayed during our trip, this is the one we would return to. The B&B is nestled into part of medieval wall of the town, how cool is that? Two updated, comfortable rooms with brand new modern bathrooms are available for well under 100 euro (!!). But the hosts really make this place, especially Roberto, who gave us the warmest welcome of our entire trip! He was delighted to learn I speak Italian, and from then on, we spoke Italian the rest of the trip – I loved the practice. As true locals, they gave us spot-on recommendations and also a truly magnificent breakfast, the best of our trip, not only tasty and so much food to eat, but also lovingly presented. We really felt at home here.

We were eager to get started on wine tasting nearby, and Roberto recommended we take a walk up the hill to nearby Fattoria Montecchio, just outside San Donato’s walls. We wandered their property, did a wine tasting, and bought a beautiful bottle of Chianti at a bargain price. We went back to the B&B and relaxed in the yard overlooking the valley, watching the sunset and enjoying our just-purchased wine. Dinner was just as easy as wine-tasting – we strolled a few dozen feet out the door of the B&B to eat at Anitica Trattoria la Toppa. Authentic and local, unpretentious and delicious. I’m still thinking about the Stracotto alla Chiantigiana, a beef stew simmered in red wine sauce.

Day 9: Chianti, San Gimignano
On our last day, we drove the SS222 Strada Chiantigiana to get a full taste of Chianti – both visual and olfactory. All the towns here are tiny, with lots of spots to stop and take in the scenery. We had a list of wineries to stop at, but the first two ended up being closed. At Badia a Coltibuono, we were hoping to do a tasting and lunch, but a struggle of a conversation in Italian via intercom yielded a critical fact: they were not open for another two hours. However, we could do an abbreviated tasting at their little shop at the bottom of the drive. I am still rather confused about how wine tasting works in Italy – I think you really do have to plan ahead here. Or just go with the flow. Ah well, we still had such a fun day exploring!

We had read that if you only have time for one castle in Tuscany, make it Castello di Brolio. We’re glad we did – once inside, you can see how magnificently fortified this place is, and you have a lovely view of Chianti from multiple vantage points. We did a wine tasting and then debated how to spend our last evening in Tuscany.

Roberto had enthusiastically recommended we go to San Gimignano, and I’m so glad we did against our “better” judgment that it was too touristy. Thanks to his persuasion, we had such a lovely, relaxed evening. Even though we arrived at dusk it still took a while to park and we had to walk a ways to get into town, but all the better to work off a week’s worth of pasta eating! I can’t imagine a better way to end our trip, and I can’t imagine seeing SG any other time than night – it was magical.

We did a lot in just a few hours. We went to La Rocca and took in the views and the medieval tower “skyline”, went into the Collegiate Church and spent a long while digesting the colorful and expansive fresco stories that line the entire perimeter, did some window shopping at a street art fair on the Piazza del Duomo. Overall, we loved the ambiance. The hardest part was figuring out what should be our last meal! We wandered round and round for about 30 minutes looking at menus. Finally, we walked by a tiny little place where couples were eating giant platters of assorted bruschetta, and it seemed exactly right – simple, light, honest food. We ordered a platter and two glasses of Vernaccia di San Gimignano, which was the perfect counterpoint to a week’s worth of red wine drinking – crisp, bright, and super-refreshing (since getting back to Seattle I’ve sought out and purchased a couple of bottles, as it is inexpensive and makes for an amazing summer wine.)

Although it was getting late, we were looking for reasons to linger just a bit longer, and realized we’d forgotten Roberto’s earnest plea that we must not leave San Gimignano without going to Gelateria Dondoli. Thanks buddy, for an amazing final curtain to a beautiful trip. We sat on the cistern in the Piazza della Cisterna and ate the best of gelato EVER (seriously guys, you truly earned the world champ title!), reminiscing on our trip and talking about what it would take to re-locate to Italy, watching candlelight flickering at the restaurants close by, and listening to a flutist playing in the street. Figuring it wasn’t going to get better than this, we hesitatingly walked back to our car.

Back at our B&B, we polished off the remainder of our bottle of Chianti while packing, and got ready for a very early morning flight back to the U.S. Thank you, Tuscany, for giving us a beautiful place to quiet our minds, stretch our legs, and fill our bellies. We’re very grateful.

I’m a project manager, so of course I have to do a retro here…
What would I do again?
Il Lecchio
B&B Del Giglio in San Donato
Leisurely, random drives through Val D’Orcia
San Gimignano (at night)
Locanda + wine bar

What would I do differently?
In retrospect, I would have stayed right in the heart of the Val d’Orcia. We couldn’t find a place we were happy with that had availability, so we opted for the highly-rated Casa Bellavista. This was too far northeast of where we really wanted to be so we spent more time driving than we wanted. If we’d ended up loving Cortana and the environs, it would have been fine, but we really fell in love with the Val d’Orcia, and kept having to drive west to get there.

We also should have planned ahead on wineries to stop at, especially in Chianti. It worked out fine, but we stopped at a couple that ended up being closed. Also probably would have skipped the tour and lunch at Avignonesi and tried to find a more authentic/humble winery experience. We wanted to meet the winemakers and taste wine in a makeshift little barn or something…next time, we’ll do more research.

For real you guys—DO NOT EXCEED THE SPEED LIMIT! Not even a little. We got a very nice little souvenir in the mail six months after we got back, in the form of a speeding ticket. It was TWO HUNDRED AND TWENTY EUROS. Sheesh. We also had to pay Avis a fee for forwarding us said ticket. Saddest part? We got it at 4:00am the morning we were driving to the airport in Florence to fly home (via camera on side of road, so didn’t even know it at the time). Italy is probably the only place on the planet that can do this and know that they will still get repeat visitors. Maybe just factor it into your trip budget…

Finally…I would stay longer! (Well, that wasn’t really an option, but a girl can dream)

Buon viaggio, tutti!

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