3 Days In Tuscany

It truly feels like our Italy trip was all just a dream. Almost as if I was just planning it sitting at my computer and here I am, back again, writing about it and enjoying every single memory as it floods back to me. If you missed the first part of our trip, before sure to start with our 3 days in Venice. Today I’m diving into one of our most favorite parts of the trip…Tuscany! We had dreams of rolling hills, vineyards and food..and my oh my — Tuscany did not disappoint! If you’ve been dreaming of a vacation a la “Under The Tuscan Sun”, don’t miss today’s post on our 3 days in Tuscany…! 

3 Days In Tuscany

The train from Venice to Florence was easy and took around 1.5 hours (I think?). I read my book the entire time, so it seemed to fly by! When we arrived, our first order of business was dropping off our bags at the hotel. We were taking a breather there for one night before heading deep into Tuscany with our rental car. Since we arrived in Florence much earlier than anticipated, we didn’t have any set plans and decided to saddle up to a table at a café right beside the Duomo. I had zero expectations, but we ended up eating the most delicious burrata of the trip and the beers were as big as your head. Seriously!

We knew we were spending more time in Florence on the backend of the trip, so we didn’t mind using the afternoon for leisure. I think we sat at the café and ate, drank and chatted with the couple beside us for over 3 hours. It was fabulous! They were from the U.K. and indulged me in conversation on all things royal baby and royal wedding (they LOVE Harry and total me to forget tea and break out the prosecco and strawberries if I wake up early to watch the wedding…HA!).

3 Days In Tuscany

Since we didn’t have tickets for Accademia (where the David statue is) yet, we decided to see what the line was like. YIKES! Over 2 hours long and the man at the front told us that even if we waited, we still might get shut out, because Accademia closes. That didn’t sound promising to either of us, so we continued down the road and stumbled upon a serious gem of the trip – a farmer’s market in Piazza della Santissima. Full disclosure: We tried to go back here with friends later in the week and it was closed, so I’m not sure if it’s there all the time, but if you are planning a trip, please consider going, if only for the cannoli and olive samples.

Every food you think of when you dream of Italy was represented at this market (olives, cannoli, gelato, charcuterie, cheese, wine, olive oil, balsamic, prosciutto, limoncello, fresh pasta…this list goes on) and believe me when I say that even though we had just down two pizzas and burrata, we dove right in.

I wanted something sweet (shocker), so I went straight for the bakery stand. The cannoli was so fresh I am salivating writing this. I’ve never had one so delicious in my entire life (beats Mike’s Pastry in Boston and the Reading Terminal Market in Philly). GAH – I wish I had it in my hands right now. Seriously, so creamy and full of flavor.

We snacked our way right through that square and managed to finally find our way back to the hotel. Napoli was playing Fiorentina that night in soccer (football for any European friends reading!) and we had tried to get tickets (and failed) so we wanted to watch it in our room. This was a solid choice, because with a full belly and a hot shower, I drifted right off to sleep listening to the game.

3 Days In Tuscany

We woke up the next day ready to go full force into our most anticipated portion of the trip – driving the Chianti ring through Tuscany! Our first order of business was picking up the rental car, so we chose to pick it up at 8AM. We got there are 7:45 and seeing a line around the block should have been an omen to us, but we were so giddy we happily trotted up to the door. Rather, Dane did and I waited outside with our bags.

Turns out – Hertz had overbooked over 200 cars and no one was getting a car that day. I am not even going to go into details here with all that transpired (it was not pretty and there were multiple honeymooners in tears around us), but 4 hours later we were in a cab over to the airport where there was hopefully a car waiting for us.

Thankfully, there was and we were on our way, but by the time we got on the road it was well past noon and we had to completely scrap half of the winery reservations we had made. Honestly – it was really upsetting, because it meant not getting to Siena at all during our stay, but we really tried to make the best of it.

The drive to our hotel was 2 hours from Florence and it was advised to arrive during daylight hours since the roads are pretty winding and unpredictable if you aren’t familiar, so we really could only stop at one town en route.

We chose San Gimignano and I’m so glad we did. Sidenote: I’ve sung the praises of these black pants forever, but they proved themselves invaluable again on this trip. Perfect for exploring and so comfy, while also look pulled together thanks to that scallop detail on the bottoms! Also, for those asking: my scarf (doubles has a shawl/cape and now I’ll never travel without it!), bag + button up 🙂

San Gimignano

San Gimignano is a walled city, so seeing it perched on the postcard-inspiring green hills is pretty majestic from afar. Parking (they have public, pay-per-hour lots) can be a bit hairy (and be prepared to walk uphill quite a bit to get to the entrance of the city), but it’s SO worth it. Trust me!

We were pretty hungry and wanted a drink after the headache of the morning, so our first stop was food and wine in the form of panino and Chianti Classico. We spent the rest of our time touring the church and tower, walking in and out of dozens of shops, taste testing at the various macelleria, sampling limoncello, pistachiocello, arancinocello (orange) and grabbing some espresso. This turned out to be the best weather we had during our entire stay in this region, so I’m glad we took advantage and walked all around this town.

After about 2 hours, we hit the road again for our hotel – La Locanda, a luxury retreat nestled amongst the wineries and hills of Volpaia.

We had researched extensively about where to stay during our time in Tuscany and had narrowed it down to a few places, which I was talking with my friend Andrea about (she and her husband are heading there in August). We wound up talking about La Locanda and it seemed serendipitous, so I booked it. It’s an investment, but we were saving money in both Venice and Florence with apartment stays, so we felt okay splurging.

Run by the sweet owner Guido who can tell you nearly anything you might ever want to know about the surrounding towns, La Locanda is quintessential Tuscany. Surrounded by olive trees and grape vines, the inn itself has only a few rooms and every night, Guido hosts apertivo (what we might consider happy hour) on the veranda. It’s pure magic  – the rolling hills, the beautiful views, blooming wisteria, a turquoise infinity pool….I could go on forever and ever, but we (clearly) loved it.

Our room had a balcony, so every morning we could see the sunrise over the hills and hear the birds chirping. He even cooks his guests breakfast every morning, which was so sweet and something Dane and I both looked forward to (his olive oil cake is INSANELY GOOD!). It was everything we wanted for our stay and I would go back again tomorrow if I could.

After we checked in, we had a bit of time on our hands before apertivo and our dinner reservation, so we headed straight for a winery down the road that I had visited on a previous trip. I knew the wine was incredible, so a late afternoon tasting sounded divine.

When we arrived there was a group of folks just finishing up, so our timing couldn’t have been better. The owner was there with his dad and we spent over 2 hours drinking, laughing and chatting about all things wine. The winery is Cennatoio if you’re planning a trip and the wine is delicious…we brought half a case just from there home!

After our tasting, we headed back up the road to our hotel and joined Guido and a few of the other guests for more wine and snacks. Guido makes sure all of his guests have dinner reservations since the villages are a bit sparse and our meals in this region were the best of the trip.

Our first night we headed for La Bottega right in the heart of Volpaia. Florence is known for their beef (bistecca Fiorentina) and it is enormous. Dane had his heart set on getting one and Guido assured us this was the place. All I can say is whoa…Dane admits it was the best steak he’s ever had in his life (or at least top 5) and I loved the truffle pasta. We also shared the cheese board and homemade ravioli with a liter of the house wine. I cannot say enough good things, so if you will be in the area – definitely book it!

The Tuscany portion of our trip was completely work-free for me, so I was excited to take three days to just mosey around and relax. We didn’t have a ton of set-in-stone plans and it was so refreshing to wake up and go where the day led us! We asked Guido where to go on day two and he gave us a few “must visits” in terms of towns and we decided to use that as a rough guide for the day. We ended up driving the entire Chianti wine ring (Greve, Radda, Castellina, Gaiole, Volterra) and several small other towns along the way. One of our favorite stops was Greve, which proved to be a great stopover for us, even though the weather was less than cooperative.

We spent a lot of time in the car on this day, because we were determined to hit every town and while I’m glad we did it, I think that if we had it to do all over again, we would have chosen one or two to stroll through at our own pace rather than a breakneck pace. Ya live and learn, right? At one point we ate a delicious piece of tiramisu in the car and the cocoa powder got everywhere and we were just like…what the hell is going on here?! No regrets (obviously), but next time we are parking it somewhere for the day.

Also – I got lots of questions on the vest I’m wearing throughout our trip and if you were following along you’ll notice I wore it pretty frequently. It was a gift from a dear friend, but it’s invaluable to me + you can snag your own (in a ton of different colors) here.

We finished up at an amazing wine tasting shop and I think given the opportunity would have just rolled out some sleeping bags and stayed the night! We did a few tastings and snagged a couple bottles to bring home. The wine in Italy is like something I cannot describe very well, but it’s free of sulfites which means when you wake up – no awful wine hangover! I think we drank 2-3 bottles a day and functioned just like clockwork. Amazing!

That night, we went to Osteria Le Panzanelle for dinner and each had the exact same meal and OMG – totally mouthwatering. It was a truffle pasta with butter, cream and cheese and right now my mouth is watering just thinking about it. 10/10 recommend for anyone who will be visiting or is planning a trip of their own! It was POURING down rain so the drive home was a little dicey given the hairpins turns and gravel roads, but we saw a bunch of deer and even a fox, which was pretty neat.

We had to return our rental car at 5PM in Florence, so we knew that we had to carefully plot our third day in Tuscany so that we could beat traffic, check into our Florence apartment and return the car in time. Instead of the go-go-go of the previous day, we decided to pick two of our favorite places and just enjoy them leisurely. We chose to return to Radda and San Gimignano, because they were both so beautiful and quaint and had some amazing shopping to offer. Plus, the cheesecake at Le Forchette del Chianti is something I will dream about for ages. It doesn’t have a crust and people come from all over the country to taste it. We kicked ourselves the whole way back to Florence for not buying a whole one to devour, because it was THAT good. My husband (a certified cheesecake snob) said it was the best he’s ever eaten in his life and I would have to agree!

All too soon it was time to hit the road for Florence, but we weren’t too sad, because we knew it meant shopping, eating, climbing the Duomo and meeting up with good friends! Stayed tuned for the third installment of our big Italy trip and I’ve linked all my outfits below for easy access 🙂