4 Days in Tuscany & Umbria

Vineyards as far as the eye can see

Structured for those looking for a 3 / 4-day trip to taste some delicious wine with beautiful views

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Central Italy Key Spots: For the visually-inclined

(1) Rome Airport; (2) Borgo Santo Pietro; (3) Montalcino; (4) Siena; (5) Tenuta di Arceno; (6) Borgo dei Conto; (7) San Pietro Pettine; (8) Umbrian Vineyards

Itinerary:

4 Days in Central Italy (the wordy version)
I’m convinced the Italian countryside will never get old with quaint hamlets that look frozen in time around every other bend in the road. And then there’s the food and wine. I could go on and on for weeks about this beautiful corner of the world, but it’s probably best to walk you through how I suggest seeing it!

Now I am always very careful when it comes to wine tastings; I typically arrange drivers through my hotels or make sure one of the travelers we’re with stays sober to get us from one place to the next. For this trip, we arranged drivers through the two hotels and maximized our time hopping from glass to glass. So, with that disclaimer out of the way, let’s get on with it!

Arriving in Italy: coming from the U.S. you can typically take a red-eye getting in during the morning, although, for the purposes of this itinerary, we arrived in Rome mid-afternoon on day 1.

Day 1 (Arrival): Land in Rome’s Fiumicino Airport (FCO) and pick up a rental car for the trip; it’s ~3 hour drive to Borgo Santo Pietro. Upon arrival at the hotel, relax by the pool before heading to dinner at the Trattoria sull’Albero (translated is Restaurant on the Tree) which is designed and built around a large oak tree growing through the floor.

Day 2 (Wine!): After sleeping in, head out to the first stop of the day at Ciacci Piccolomini d’Aragona (an hour from the hotel) in Montalcino. The estate was built in the 17th century and sits on 30 acres of vineyard dedicated to the full-bodied reds produced on site. After a private guided tour through the facilities, enjoy a flight of wine before heading on to stop #2! I reached out to the vineyard directly via their website for booking the one-on-one tour.


Stop 2 will be Tassi Montalcino, a younger winemaker than Ciacci Piccolimini, but equally fascinating as you are guided through a recently renovated storeroom and tasting area for the second stop of the day. For this vineyard as well, reaching out directly was the best way to book our tour and tasting.

The 3rd and final stop for the day is San Filippo Montalcino, and if you’re as lucky as we were the owner Roberto just might be manning the tasting room to walk you through his personal favorites (although as he told us, the wines are like his children so he can’t choose just one)!

For dinner that evening, while we had a few places scoped out in advance (Maramanna in Gavorrano and Taverna du San Giuseppi in Siena), I was ultimately just craving a really good pizza so made the last-minute decision to head to Siena and track down Tigella Emilia for some Margherita pizza and cacio e pepe – it was just what the doctor ordered after a long day of wine tasting!

Day 3 (Wine and Truffles in Umbria): After a leisurely and delicious breakfast at the hotel, we packed our things to check out and hit the road to our next destination: Tenuta di Arceno adjacent to a quaint town San Gusme in Chianti. This winery was a little bit bigger than the Montalcino stops, but also included a light lunch alongside a tasting of five wines. After our tasting and lunch, we made a brief stop in the beautiful town of San Gusme at the winery’s suggestion and it proved a fantastic hidden gem!

After our quick stop, we continued on our way to Umbria, with our ultimate destination being Borgo dei Conti, an ancient fortress turned into a Relais & Chateaux property which did not disappoint! After a quick check-in, we were off once again to San Pietro Pettine for the evening.

Once we arrived at San Pietro Pettine (an hour’s drive from the hotel) we were quickly introduced to our truffle hunting guide for the evening Bruno and his adorable sidekick Puci who guided us through the grounds in search of black truffles. Following a fortuitous hunt, we were seated for a few cocktails and ultimately a delicious dinner featuring the truffles we’d found!

Day 4 (Umbrian Wine): Our wakeup and breakfast at Borgo dei Conti was just as memorable and relaxing as our previous hotel; there’s just something about waking up to fresh Italian air with a view of rolling hills. After a leisurely breakfast, make your way deeper into Umbria for the first wine-tasting stop at DiFilippo, a family-run winery with a cute tasting room.

After the first few wines of the day we departed for Saio Assisi for a few delicious white wines made in the area and a fantastic, local lunch. Umbrian food is very similar to Tuscan food, centered around cured meats and cheeses all of which pair incredibly well with locally grown and aged wines.

For the third stop of the day, and on the way back to the hotel, Monte Vibiano Vecchio was a perfect way to end our afternoon of tastings before heading back to the hotel to freshen up for dinner. Once we were ready to go, we made the 15-minute drive to La Locanda del Busta for some amazing pizza in a lively atmosphere that was very popular with locals!

After dinner, we settled in for a good night’s sleep before leaving town the next morning to make our flight from Rome (FCO) to New York City.

Suggested Packing List:

  • Luggage: 1 roller carry-on, 1 backpack or purse
  • Shoes: comfortable walking shoes, stylish shoes for dinner
  • Clothing: day dresses, or something appropriate for all the wine tasting!
  • Accessories: sunglasses, hat
  • Apps to download: Vivino for keeping track of the wine, Uber if you don’t feel like driving

Bonus Info: