Your Tuscan Itinerary for Italy: Part 2

Sharing the top recs from our recent trip this year.

Nov 14, 2024

Hi friends,

Henah here. As you might have noticed, we didn’t have an issue last week given… well, *gestures vaguely around*. While we’re still feeling heartbroken and ready to fight, I wanted to just send a lot of love and hope to this community—I firmly believe that community (and not further individualism) is how we’ll get through this time. 🫂

If you didn’t catch our previous edition, it was all about the magic of Italy, particularly Rome. Today’s edition is all about Tuscany—I’m biased, but this is my favorite region.

Back in the day, I dreamed of getting married in Tuscany—a long table full of our closest friends outside a castle or villa, with rolling hills in the background and twinkle lights shimmering above. We’d devour bucatini and pappardelle in rich sauces, sip on Chiantis, and indulge on a Parmesan factory tour. Then the pandemic happened.

While going abroad to Tuscany wasn’t in the cards anymore, we ultimately got married in Taco Bell onesies in our living room with a full wedding in New Orleans in Spring 2022. It was just as magical, albeit different.

But my dreams of having a romantic trip throughout the Tuscan countryside never subsided, so I decided to make that a priority in 2023. Funny enough, that dream was deferred another year due to a health issue, but this May, we finally got to embark on this long-waited adventure, and it did not disappoint.

So if this stunning region of Italy is on your list, here’s the itinerary we made—bookmark and comment away if you have questions!

A One-Week Guide to Tuscany

Due to my husband’s (lack of) PTO, we only had about a week to explore the area—while stays can swing upwards of weeks and months, I’d recommend at least 8-10 days if you can as you’ll see this itinerary was a little jam-packed.

Day 1

Picking up from our time in Rome, we took a taxi back to FCO so we could pick up our rental car. Now, while I absolutely do not recommend a car in Rome, you’ll need a car to get around Tuscany in this way. There are of course tours or public transit, but I found that this was the best option to maximize our time and preferences. For a compact automatic car for one week with unlimited mileage, we paid €573 (or about $600 USD at the time).

As a side note, remember that most credit cards do not offer rental car protection specifically in Italy, so make sure that if you’re relying on a premium card, you pick one that does like the Chase Sapphire Reserve. And another huge tip: Be extremely careful driving in Italy, as they’re notorious for sending you speeding and parking tickets months after the fact for hundreds of Euros. For both of these reasons, I generally don’t love renting cars here, but it was necessary.

From Rome, we made our way over to our first stay at La Pescaia in Maremma, near Grosseto. It’s on the coastal side of west Italy, and it took about two hours to get there. But wow, was it worth it: It’s easily the most beautiful place I’ve ever stayed (as I’ve nodded to in past editions). La Pescaia is a family-owned hotel within a historic estate, surrounded by six thousand olive trees, aromatic jasmine in all directions, horseback riding trails, and more.

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There are essentially no screens to be seen, it’s incredibly quiet and serene, and the food is delicious. There are also pets roaming the entire property and the team will take care of you like you’re one of their own. And lest you believe this kind of experience costs $600+/night, it was actually only $260 USD. It’s a hidden gem that’s well-worth the price.

Day 2-3

We spent the next two days lounging on-site, devouring their incredible food, and driving to local spots that they recommended. You can also drive the 40 minutes to Porto Ecole and visit beaches like Spiaggia Lunga, or splurge on a stay or dinner at Hotel Il Pelicano.

For La Pescaia’s food:

The breakfast spread is incredible, and such wonderful fresh food and fruit.
Both the pasta and salad options for lunch are wonderful and extremely well-priced. Pair with a nice drink by the pool and *chef’s kiss*.
Knockout menu items for dinner included: asparagus burrata, butter and sage ravioli, baked eggplant, poached pear in a red wine sauce, and so on.

We went to a local winery in the Castiglione della Pescaia region, Le Mortelle, for lunch and a tasting—it was very casual yet beautiful. There’s also the popular Rocca di Frassinello, which I can’t speak to as we didn’t visit, but it’s got a very interesting history.

For a romantic dinner, we went to Conti di San Bonifacio’s Gavorrano. It’s Michelin recognized, vegetarian-friendly, and while rooms are $600 a night here, the food was much more reasonably priced. The Sustinet, a 2016 Syrah, is rated one of the best in the world, and it was delicious to have alongside the food. Plus, the sunsets here are unparalleled.

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Suffice it to say: We ate, slept, and relaxed indulgently these few days—no regrets.

Day 4

Despite my dreams of living on-site at La Pescaia for the foreseeable future, we had to trek on for our next destination. We drove from Maremma to Pisa, for a quick detour to see a Leaning Tower, perhaps you’ve heard of it. Obviously it was fairly touristy, but it was a nice stroll to walk through Cathedral Square.

Then we headed onward to Lucca! Known as a “città d’arte” (city of art), it’s a quaint little city inside Renaissance-era walls—and it’s fairly easy to see the sites quickly. We had lunch at Gigi Trattoria, just outside the city center, and it’s very traditional Tuscan food. I had an incredible gnocchi topped with burrata, and my mouth still waters at the memory. 🥲

We ended the day by driving finally to San Gimignano, where we stayed at Podere la Quercia just outside the city—it’s a beautiful property, low key, and great for a one-night stay.

Day 5

The next morning, we headed into San Gimignano proper. Since it’s a medieval hill town (which gives it that iconic skyline), it’s a bit hilly, but it was totally fine to walk. Of course you’ll want to check out the famous towers, piazzas, and palazzos, but we also did a little shopping and snacking here—picking up glass-blown olive oil dispensers and fairly good gelato near Piazza della Cisterna at Gelateria Dondoli.

From here, we visited Siena for the afternoon. Unfortunately, we got caught in a downpour, so we weren’t able to see as much as we wanted, but it’s a rustic and charming city I’d go back to if I could. There are also beautiful handicrafts here if you want to pick up souvenirs; I picked up an ornament, trinket bowl, and a few gifts.

We drove through Cortona to get to our eventual destination: Precise Tale Poggio Alla Sala, a stunning, sprawling, and secluded resort where we’d stay until the end of our trip. Also reasonably priced, this is a gorgeous property in the middle of the Tuscan countryside (and also Michelin-recognized!).

For our stay here:

Once again, a fantastic dining experience, whether for breakfast or dinner—their spaghetti aglio e olio, pear flambè, wine list, and panzanella salad were all divine.
There are multiple pools throughout the property, as well as a spa, sauna, and fitness center. Laying poolside ~under the Tuscan sun~ was a dream.

Day 6

I’ve always dreamed of seeing the Val d’Orcia—aka the rolling hills and valleys lined with cyprus trees. (And let me tell you, it does not disappoint in person). We drove through that area, stopping whenever possible, and soaked it all in.

Eventually, we made our way to Pienza so we could go to Podere il Casale for a hands-on cooking class. This was, without a doubt, one of the highlights of our trip. We toured their farm, organic gardens, and on-site restaurant to start, seeing how they make the local cheeses and greeting the livestock. We sourced our own herbs, then spent a few hours making a multi-course meal with three different pastas (pici, a Tuscan favorite, gnocchi, and tagliatelle) with various sauces (breadcrumb sauce, arugula pesto).

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We ultimately enjoyed our homemade meal at their local restaurant, overlooking the hills and under the stars—similar to what I had always dreamed.

Day 7

For our last day 😭, we went to visit wineries around the region—as one does when they’re in Montepulciano! We prioritized places with Vino Nobile wines, or wines made locally in the area typically with Sangiovese grapes.

First, we went to Palazzo Vecchio for a Vino Nobile tour and tasting. It was a small group of us (I believe just two couples), and we got to walk through the wine barrels underground as well as see the vineyards sprawling in every direction.

Then we headed to Fattoria Svetoni, a winery producing local wines since 1865. The cellar was awe-inspiring to walk through again, and we loved both the Nobile wine and olive oil here so much that we bought some to bring home.

For our final dinner in Italy, we went to the Michelin-rated Osmosi (just next door to Fattoria Svetoni). They were extremely accommodating to vegetarians, and we did the five-course tasting menu for €85 apiece—at this point, I was a little “Parmesan’d out” so I didn’t enjoy it as much as I wanted to, but that’s showbiz, baby!

So there you have it: A weeklong road trip throughout Tuscany. If you’ve been, I’d love to hear what you’ve done (or would do differently)—as it’s on my list to visit as much as possible again in the future!

Departure

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