A Homebody’s Guide To Tuscany & Italy

I went to Italy once and now I’m writing this blog post as if I know anything about being a travel blogger. The truth is, I’m a homebody and I hate flying, but the other truth is, I loved Tuscany. I spent the last six days eating, drinking, and pooping my way through the Italian countryside (my stomach wasn’t built to eat pasta, cheese and cured meats three times a day for a week), and can, without a doubt say that I would go back to do it all over again. Dave and I flew from New York City to Florence with a connecting flight in Zurich. I’d skip the connecting flight next time and fly straight into Rome, spend a night there, and then make the 2 1/2 hour drive to Tuscany. Connecting flights are stressful AF and saving an hour by flying into Florence rather than Rome isn’t worth the added layer of having to go through customs twice. So, without further ado, here is a very non-travel-blogger’s guide to traveling in Tuscany.

WHERE WE STAYED

Montestigliano (Villa Pipistrelli)
We spent the bulk of our time in what is known as a “farm stay”, an estate called Montestigliano with a working farm on the property. Located in the Siena Hills, this estate offers several different villas and apartment options for groups of all sizes. Villa Pipistrelli is one of the largest and most private options on the estate, with a seven-bedroom main villa and a two-bedroom annex at the top of the estate. If you’re not traveling with a large group, you can visit Montestigliano’s main site here for smaller options. The estate hosts a coursed dinner on Mondays and pizza night on Thursdays for all visitors staying on the grounds. There is also an in-house private chef you can hire to cook for you and/or host a cooking class for your group. The dinners at the estate were easily some of my favorite meals we had during the trip.

The staff at the estate were A+, and Francesco, the property manager, was easily reachable via Whatsapp for housekeeping requests, driver bookings, and general information on the area. I’d book a driver a few days in advance of any dinner reservations because the drivers tend to book up quickly and you’ll also want to find someone who is accustomed to scaling the narrow, winding, and steep gravel roads up to the estate. Montestigliano falls somewhere in between an Airbnb and a full-service hotel for me. There was daily housekeeping and a staff on-site, but the fact that we had access to a full kitchen, several bedrooms/bathrooms, and a private pool all felt very much like we were staying in our rich friend’s summer house in the Italian countryside.

 

WHERE I WOULD STAY NEXT TIME

While I wouldn’t hesitate to stay at Montestigliano again, we also had lunch at Hotel il Pellicano and it felt like an IRL version of White Lotus. il Pellicano definitely leans more 5-star resort than your rich BFF’s private Italian estate, but there’s a time and a place for everything. I also got a recommendation from a very well-traveled friend that Castello Banfi Wine Resort is absolute perfection for those looking for a cross between a fully-staffed resort and an intimate farm stay.

 

WHERE WE VISITED

Siena
I’d trade lesser-known Siena for the hustle and bustle of Florence, any day. I’m not even going to try and begin to explain the architecture because I’m sure ChatGPT can do a better job of that than me, but suffice it to say, it was all gorgeous and all so very *Italian*. Head to La Vecchia Latteria for some of the best gelato in Siena, La Taverna del Capitano for lunch, and then post-lunch cocktails at Brasserie Bar Al Mangia in the piazza for some prime people-watching.

Montepulciano
An even smaller version of Siena, this small town in Tuscany is perfect for a day trip after a wine tour in the cellars of De’Ricci Cantine Storiche. If I could go back, I’d spend more time wandering the small shops and art galleries here and more than a few hours at Caffé Poliziano – the perfect mix of a bar and coffee shop where I had the best espresso of the trip.

 

WHERE WE ATE & DRANK

I’m not sure if this is sacrilege, but I took very few photos worth sharing of our actual meals in Tuscany. I say this, because no subpar iPhone photo of mine is going to accurately convey how delicious some of the meals were. If you’re headed that way, lean heavily into pasta, cured meats, cheese, wine, Aperol spritzes, and tiramisu for as much as your stomach will allow. Some favorites were Il Grillo Moro for dinner (get the steak prepared the way they suggest it – ie. still mooing), Podere il Casale for lunch or dinner with a view, Poggio Rubino for a wine tasting of all the Brunellos you could ever want with lunch, and, once again, Hotel il Pellicano for any meal at any time of the day, but call the day before to reserve one of their pizzas. We didn’t know this and had food envy seeing the table next to ours get their deep dish pizza that looked nothing like what you can get from your local pizza joint stateside. And, because I find food pics rather boring, here are some random snaps from the rest of our trip to Italy that won’t make you hungry.

Happy Friday biddies. Wherever tonight leads you, may you all find an Aperol spritz because even if we can’t physically be in Italy, we can drink like we are.

Love,
Your internet hype woman