Travel Guide: Greve in Chianti

Buongiorno amici! I’m writing to you from…. well, from East Boston. But my heart (and stomach) is still in Italia! We recently spent ten(ish?) glorious days in the motherland, and I have been dying to tell you all about it.

It was truly unbelievable. I’ve been wanting to travel to Italy since I was a little girl, when I learned that my grandma was taking a trip there with a friend. She promised I could go with her the next time she went, but unfortunately hasn’t been back since (it sounds like we need to plan a family trip, if you ask me). So when our friends, Dave & Jill, told us that they were planning a trip there, Peter & I jumped right on board — along with my bff/lifeguard barbie/sporty spice, Jodi. Peter & I had never traveled abroad with friends before, and this was the perfect fivesome with which to pop our friend+travel cherry!

(Disclaimer: all five of us were complete scatterbrains throughout this planning process for a variety of reasons, and it’s basically a miracle we were able to put together a cohesive, thorough trip in the first place. especially since most of our planning sessions were fueled by lots and lots of wine… how many days were we in Greve again? I don’t even know. #thestruggleisreal).

We found some flight deals for mid-September — right in the middle of harvest time for most of the wineries! We would be away for both Peter’s birthday and our anniversary, and would arrive home a mere seventeen days before Dave & Jill tied the knot (cue: my own anxiety at the thought) — we all had lots of things to celebrate, to say the least!

Our trip was divided into three separate parts: five days in Greve in Chianti, in the heart of Tuscany; bopping around in Florence for less than twenty-four hours; and then a handful of days in Positano, on the Amalfi Coast. Plenty of vino, a quick stop in the city and then ample beach time during which to relax before heading back to the insanity of real life — it truly was the perfect trip (thanks, Dave & Jill, for selecting the most fabulous places)! To avoid a novel, I’m breaking up this itinerary into three separate posts for you.

You’re welcome.

Day 1: Montepulciano

We flew into Rome midday on September 17 — Peter’s birthday! After a hilarious and very American (#MAGA) trek through the airport — and what might have been the longest wait time at Europcar, ever — we began our three hour drive north to Greve in Chianti, our home for the next few days. We drove, sleep-deprived and hungry, towards the rolling hills, vineyards and endless bottles of wine. I mean, wouldn’t you?

We decided to make a pit stop around dinner time and took a little detour out to Montepulciano for some vino and a snack. Jill did some expert googling and found an adorable little place called Sax Wine Bar. In an attempt to sample different items on the menu, we accidentally ordered enough food to feed a small army — an antipasto board with pears, local cheese, walnuts and honey; a cheese & meat platter that included wild boar (!!); and the most delicious plate of fresh bread drizzled with amazing Italian olive oil. As expected, everything was delicious — the perfect first meal!

We obviously ordered a bottle of wine to wash down our delicious snacks — and to cheers to Peter’s birthday! We were interrupted at first by a kind old man who conversation raped Peter for fifteen minutes and then generously offered to sell us cocaine. But he eventually lost interest (i.e., got cut off by the waitress) and wandered outside, leaving us to enjoy our wine & snacks in peace.

Montepulciano was the first Italian wine I distinctly remember trying and loving, so I was thrilled that we got a chance to visit this hillside, cobblestoned village — as brief as our visit was. It had started raining as soon as we arrived, so we didn’t really get to explore too much. After our snack, we ducked into a nearby wine shop for a quick look (and taste!), then scurried back to the car to continue our journey up to Greve. It was still drizzling, but Mother Nature decided to dazzle us with a brilliant rainbow, lighting up the towns below. Or maybe it was just my mom, wishing Peter a happy birthday from heaven.

We arrived in Greve just after dark, and drove around for a bit trying to find our villa (props to Dave for navigating those narrow, windy roads!). We met our host (and new best friend), Paolo, who showed us our space and left us to enjoy a couple bottles of wine before retiring for the evening.

Day 2: Exploring Greve in Chianti

When we arrived the previous night, it was too dark to see much besides a smattering of lights in the distance. The next morning, we awoke to find the most beautiful view from Paolo’s villa — we were nestled high among the rolling hills, overlooking neighboring villas and vineyards. We sat outside with our coffee, in awe of the incredible vista and gorgeous weather, mumbling nonsense to each other as we tried to adjust to the time difference.

We decided to spend the day exploring downtown Greve (which is the CUTEST, in case you were wondering). After maneuvering our car back down the winding hillside roads, we parked and walked over to Caffé S.Anna, a little coffee shop/bakery along the main road. We enjoyed coffee and some delicious pastries, and the owner taught us about a few famous (motor) racing superstars in Italy. Who knew!

There are dozens of restaurants, wine shops and small groceries along Piazza Giacomo Matteotti, which is the commercial center in Greve. On a friend’s suggestion, we stopped at Antica Macelleria Falorni. Part butcher shop, part bistro, this shop was a little slice of heaven on earth, complete with self-serve wine samples by the glass and a cheese cellar. Yup, you read that correctly: a cheese cellar. Prosciutto and garlic hang from the ceiling, and their selection of salami and other cured meats is unparalleled. The smell that hits you upon entering is — for lack of a better word — heavenly. We spotted some aged cheeses that we knew we just could not leave without — one with bits of pistachio and another with pepperoncini. Needless to say, we found our way back to Falorni a couple of times during our stay in Greve.

We stopped into Casa dell’Olio next door — a cute little instagram-worthy shop that sells olive oils produced at Villa Vignamaggio. After purchasing some olive oil and aged balsamic, we decided to drive up the road to their winery so that we could sample some wine. Their Chianti Classico (I think we tried the Gherardino) and Merlot di Santa Maria were both delicious (we might have come home with a few bottles) — and Jodi & I were thrilled that they had grappa for us to try.

(Quick knowledge drop for you guys: grappa is made by distilling the skins, pulp, seeds and stems leftover from making wine. Not only is it incredibly delicious, but it’s also how winemakers ensure there is no waste in the wine making process. It’s quite literally a spirit after my own heart!)

We eventually made our way back to the house, where we snacked, enjoyed some vino and waited for Patrizia to come teach us all there is to know about Italian cooking. and BOY did she come through.

From the moment she arrived (and insisted that she carry all the ingredients, wine and COOKING APPLIANCES up the dangerously steep driveway to the house without help), we knew it was love at first sight. We immediately wanted to pack Patrizia up in our suitcases and take her back to Boston with us. For FIVE HOURS, she told us stories, shared recipes and helped us cook what might have been one of our favorite meals of the entire trip.

Everything we made was incredibly simple — as Italian cooking typically is. We started off with what might have been the most delicious panzanella of my life (are you sensing a theme here?!) — fresh bread toasted to perfection, tomatoes and basil straight from Patrizia’s garden, chunks of red onion and cucumber, all (heavily) drizzled with olive oil that I’d like to bathe in. Then we learned how to make tagliatelle (out on the patio table while the sun set behind us — SOMEONE PINCH ME), which was tossed with fresh tomatoes and zucchini. This was followed by roasted pork with apples and brandy, along with super simple roasted tomatoes.

Dessert was a lemon almond caprese cake, which I literally still dream about (and may need to replicate soon). Paolo came down to visit somewhere in between the brandy sampling and our pasta making, bringing along his sister and a friend (who used to work with TJX and has spent time in Boston — such a small world!). Towards the end of our evening, Patrizia served us each course and took care of the cleanup inside, while the five us sat outside and feasted.

Five courses, five hours and multiple bottles of wine later, we were very happy, a little sleepy and so, so full.

Day 3: “The Food & Wine Experience” at Castello di Verrazzano

We woke up in the morning still full from our marathon feast the night before — no surprise there! However, we had another full day of food & wine ahead, so we fueled up with coffee (and maybe a small slice of leftover cake) and prepared ourselves mentally for another delicious day ahead.

We had booked what is called “The Food & Wine Experience” at nearby Castello di Verrazzano. This involved a tour of the castle and surrounding gardens, followed by multiple courses (along with wine pairings) in their restaurant.

Verrazzano did not disappoint. The views from the winery were stunning and once again we were treated to a rainbow! Peter and I were celebrating our third anniversary, so again, I think this was my mom’s way of sending us love.

Everything we ate and drank was 10/10; there were actually so many courses I’m not sure I remember them all! The meal started off with fresh bread and olive oil, followed by some cured meats and cheeses. We each got a small taste of their aged balsamic, which was out of this world. There was bruschetta made with the freshest tomatoes I’ve ever had (though I think I said that each time I ate a tomato while in Italy), roasted pork with fennel, penne with (more) fresh tomatoes and a side dish that consisted of cannellini beans and about a half gallon of olive oil. There were three or four different wines that circulated around our table, which we shared with a sweet couple from the Midwest.

The highlight of this meal (for me, at least) was the dessert – vin santo and biscotti. Jodi had been talking about this combo for weeks, having tried it previously when in Italy. Vin santo is basically a sweet(ish), white dessert-style wine, into which it’s customary to dunk biscotti. The combination definitely seemed odd to me at first — but after the first bite, I was hooked. The vin santo was sweet, yet slightly dry. Biscotti (which comes from the Latin word meaning twice-baked) are crunchy and also very dry. Dunking the cookie in the wine amplifies the sweetness, but not so much that it is overwhelming. Perfection! Now we just need to find some vin santo to keep around for the holidays, because we (stupidly) didn’t bring any home with us… #amateurhour

We headed back to downtown Greve after our lunch, walking around the main piazza to make a few more purchases and eventually stopping at Caffe Lepanto for a snack. Some bar nuts and house-made chips. More wine. Grappa and limoncello. Then dessert (again) — gelato. Finally.

Day 4: San Gimignano 

Dave & Jodi had both talked about how much they loved the medieval, hillside town of San Gimignano (and Peter seemed antsy to check it out for himself), so we planned a trip there on our last full day in Chianti. About an hour southwest of Greve, the drive there was beautiful. For the latter half of our trip, we could see the UNESCO World Heritage site in the distance, sitting majestically atop the tallest hill.

We arrived amidst hoards of tourists — easily the most people we had seen/been around since leaving the airport three days prior. After finding a spot in a tightly packed parking lot halfway down the hill, we trekked up to the city gates, dodging sightseeing buses and tourists with selfie sticks on the way.

The views were incredible, so we couldn’t help but stop and take a few photos (like the tourists we were).

Our first stop was for food, of course. We did a quick scan from the jam-packed center piazza and settled on a feast of personal pizzas accompanied by some local white wine — just enough sustenance to fuel us for a walk through the city. We window-shopped for a bit, then found ourselves in Parco della Rocca. After trekking up to the tippity top of an old medieval tower, sweating from the scorching hot sun, we stumbled upon some more insane views.

Small villages in the distance. Vineyards, cyprus trees and rolling hills for as far as the eye could see.

Italy’s beauty knows no limits, clearly.

After strolling the streets a little while longer and ducking into one too many souvenir shops, we made our way back towards the main gates, where Jodi pointed out Gelateria Dondoli. A small gelato shop jam-packed with tourists, the line wrapped halfway around the piazza. She insisted that it was worth the wait — and boy, was it ever. I settled on two flavors — fig and pistachio. Creamy and satisfying, it was the perfect treat to end our afternoon.

We headed back to Greve, and Paolo stopped by almost immediately. “Do you like pizza?” he asked, in his best English. Do we like pizza?! ….do bears eat beets? YES, of course! He motioned that we would follow him to his son’s restaurant in San Casciano, a few towns over. Peter took the wheel and took years off my life sped off, chasing Paolo down the narrow roads and around dozens of tight turns, bypassing vineyards the whole way there. I’m pretty sure I was white-knuckled the entire fifteen minute drive (and may have kissed the ground after nearly falling out of the car). I’m just thankful we made it there in one piece, because the feast that followed was… next level.

We followed Paolo into Trattoria Pizzeria Antica Calcinaia, and were greeted warmly by his son and a few of the staff. The restaurant wasn’t too crowded yet — after all, it was still early by Italian standards. Paolo found a friend and started chatting away in Italian, and the hostess walked us out onto the back patio. The sun had just set, and we couldn’t see much except for a stunning, watercolor sky and a few houses on nearby hilltops. Then one of us noticed a smattering of lights in the distance… FLORENCE! I knew we were only an hour away from the city, but didn’t realize that we’d get a sneak peak of the city that night!

It dawned on us that our table must have incredible views of the countryside in the daylight, so we squinted for a bit trying to make out different shapes on the horizon. Mostly we were awestruck by the glittering lights of Florence in the distance, and chatted excitedly for a few minutes about our upcoming adventure there the following day.

Not long after, food became the main topic of discussion once more. Dave, our resident Chianti wine expert, selected the first bottle, and then we basically let our waitress order the rest of our forty-seven courses. The restaurant is known for their pizza, as Paolo had shared with us earlier, so we made sure to start with a pizza appetizer (only in Italy do you order two full pizzas as an ‘appetizer’). We each ordered our own main course, though made it a point to try a bite of each others’ meals. I ordered the cacio e pepe, which I had only dreamed about up until then — and let me tell you, it was well worth the wait! Such a simple meal, but each bite more flavorful than the last. Jodi ordered another amazing pasta dish (with fresh zucchini!), and we switched our meals halfway through to get a taste of both.

Next up was the steak florentine…. my oh my, the steak florentine. Our waitress tried to convince us that it was a meal for one, maybe two people — but at €50, we knew there was just no way. The cook came out to show us the hunk of raw meat, and it was literally enough to feed all five of us. For a week. So we went with just one order of steak florentine for the table along with a couple of sides, which might have been one of our better decisions this trip. It was SO delicious, of course — perfectly cooked, tender — truly mouthwatering. Pretty sure we ordered another bottle of wine (or two?) and then topped it all off with dessert. They had just run out of their tiramisu, but by some miracle were able to scrounge up one lonely serving of it for us to share. As a self-proclaimed hater, I think this was the tiramisu that finally turned me. Of course, it could have been the setting, the company or the copious amounts of wine… but let’s just run with this new theory that I’m a tiramisu lover until proven otherwise.

Oh, and of course we got more vin santo and biscotti (#obsessed). I had actually taken a bomb photo of it (modest, I know) — or so I thought. I realized after we left the restaurant that none of the photos I had taken were saved on my phone. User error, most likely. So shout out to Jodi for the photos above! Thank you for capturing this incredible meal.

Day 5: Wine Detour en Route To Florence

Once again, we woke up full, our heads still spinning from our delicious meal (and terrifying drive) the night before. Sadly, our time in Greve had come to an end; we spent the morning packing up the house and saying tearful goodbyes to Paolo (okay, maybe not. but we really were so sad to have to leave him!). After promising we’d be back, and maneuvered the car down the long stone driveway for the last time.

We had a short drive ahead, and made good time as we left Greve. Right before we got on the highway, we passed a sign for Luiano Winery — that was one of wines Patrizia brought over with her and also one of the (many) places she worked! Without question, we decided that a detour was necessary.

We drove the long, winding road to Luiano and up a final, steep hill to the tasting room parking lot, passing a giant Chianti rooster on the way (check out this story for how the rooster became the official mascot of Chianti wine — which Patrizia told us in hilarious detail). We realized it was a long shot that the winery would be able to accommodate us for a tasting; after all, many Chianti wineries are small, family-run operations and don’t have a ton of extra staff on hand for impromptu tours and tasting. But alas! We lucked out, and Alessandro (one of the owners) set us up with a small sampling.

Of course, we loved every wine we tried, and each of us bought multiple bottles to take home. Alessandro was hilarious, spoiled us with delicious bread & olive oil and even agreed to take a selfie with us (kissy face, per his request). I am SO thrilled that we made this last stop for wine before finally embarking on the last leg of our (short) journey to Firenze!

So there you have it: Greve in a (3,000+ word) nutshell! I’ve summarized below all of our favorite places. Stayed tuned for parts 2 & 3 of this Italy travel guide — Florence & Positano, coming soon(ish).

In the meantime, check out my full Greve gallery here; I’ll be adding more photos as I go through them. Caio for now!

Sax Wine Bar | Montepulciano – wine bar with an extensive menu of meats, cheeses and other snacks

Caffé S.Anna | Greve in Chianti – cafe with typical Italian drinks & pastries

Antica Macelleria Falorni | Greve in Chianti – butcher & bistro, with a cheese cellar and self-serve wine samples by the glass

Villa Vignamaggio | Greve in Chianti – winery; can accommodate walk-in tastings

Casa dell’Olio | Greve in Chianti – Villa Vignamaggio’s storefront in Geve’s city center, offering olive oil & balsamic tastings

Castello di Verrazzano | Greve in Chianti – winery; appointments suggested; highly recommend “The Food & Wine Experience” (!!!)

Caffe Lepanto | Greve in Chianti – cafe (and gelato shop) with full breakfast, lunch and dinner menus

Gelateria Dondoli | San Gimignano – gelateria (easily the best in town!)

Trattoria Pizzeria Antica Calcinaia | San Casciano in Val – delicious pizza (and everything, really!)

Luiano Winery | San Casciano in Val | winery; appointments recommended