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Why Fall Might be the Best Time to Visit Tuscany

ITALY – Tuscany & Umbria

by Charlotte Anderson

Earlier this fall, Kate and I departed for Florence, Italy. We were off to visit villas in Lucca, Tuscany and Umbria, and get to know the region and culture along the way. Once we landed and collected our car, we made our way to Lucca, 45 mins north of Florence, and adjusted to the notorious Italian drivers. After making several harrowing 90 degree turns and after several Italians yelling at us (all a part of the charm?), we finally arrived to our hotel, Palazzo Dipinto. Sitting down to pizza and bruschetta at a little sidewalk restaurant terrace nearby, it finally started to sink in that we had made it to Italy.

Italy trip report, vacation in italy, Vacaiton rental, villas in italy

First meal in Lucca

Lucca felt like the perfect place to get our feet wet in Europe. It was small enough to be able to get around without a car yet easy enough to get around without speaking Italian. The hotel was beautiful, comfortable and well located in the city. Lucca is sweet, and full of excellent restaurants, shopping, and local sights. For our WIMCO foodies, my favorite dishes included local tortelli (Lucca-style ravioli-like pasta) filled with meat and in a meat and tomato ragu sauce as well as ravioli filled with ricotta and spinach in a cream walnut sauce – divine! 

Italy trip report, vacation in italy, Vacaiton rental, villas in italy

Strolling through the streets in Lucca

As we started our villa tours the next morning, we kept in mind that guests are often making a special trip to visit Italy, so the importance of the suitability of the house for the group is paramount. We visited about 8 villas that day, ranging in size from 3 to 8 bedrooms. Located on the Fattoria Mansi Bernadini Estate, we visited Casa Maria (SAL MAR) and Il Leccio (SAL LEC)). Only 15 minutes to Lucca and 45 mins to Florence, these villas are well located.

One standout villa was La Sorgente (SAL SOR), a 6 bedroom nestled in the olive grove dotted hills, just 20 minutes from Lucca. The house has beautiful gardens, excellent views through the valley and is well oriented- featuring two separate wings interconnected by an upstairs terrace and large main entrance room below. The classic Tuscan farmhouse was well restored in maintaining traditional aesthetic while featuring modern comforts.

Overall, our experience was very positive and enjoyable. The villas were beautiful and provided an excellent introduction to the classic Tuscan farm & noble styles, and left us excited for what else was in store. 

Italy trip report, vacation in italy, Vacaiton rental, villas in italy

Views from Fattoria Mansi Bernadini Estate

The following day, we checked out of the hotel (feeling far more confident in managing the tight Lucca streets than before) and drove 45 mins to begin our villa tours around Florence and in Southern Tuscany.

The villas I was most impressed with included Simonetta (BRV SNT), Gaia (BRV GAI) and Alfieri (BRV GEG):

Simonetta is a 5 bedroom 19th century town-house located right in the heart of Calenzano, about 20-30 minutes to Florence either by rental car or by easily accessible public transit. The house was a perfect oasis in a bustling Florentine metropolitan suburb: well-decorated with gorgeous 17th-18th century antiques, comprised of elegant living areas, and featuring a small private pool hidden away in the romantic fruit & herb gardens surrounding the villa.

Italy trip report, vacation in italy, Vacaiton rental, villas in italy

Details from Villa Simonetta

Villa Gaia is a spectacular 18-bedroom villa located about an hour south of Florence and 20 minutes northwest of Siena. The villa is secluded, with just a tiny medieval hamlet adjacent to the estate. It has been owned for centuries by a Roman aristocrat family, with whom we had the pleasure of meeting and touring the villa and grounds. I fell in love with the villa’s gorgeous, impeccable grounds and elegant, sophisticated interior design. While the estate dates back to pre-15th century, the villa and annexes are well renovated, modern and very comfortable. This villa is well equipped and would be an excellent location for a fairytale Tuscan wedding or a large family or group vacation.

Villa Alfieri is an absolute dream villa, mid-sized with 5 bedrooms and just a stone’s throw from Siena (20 mins). We were fortunate enough to visit the villa towards the end of the day when it was entirely drenched in gorgeous late day sun. The villa is “U” shaped, composed of a main house with two opposite wings. The courtyard was encircled by fragrant, flowering gardens that led out to the terrace, which looked out onto the rolling olive groves and glowing vineyards leading to Siena. The interior was comfortable and impeccably decorated, as the owner skillfully mixed traditional Tuscan elements with modern comforts and contemporary decor. This would be an excellent retreat for a family looking to disconnect, yet within reach of classic Tuscan sights and points of interest.

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View from the main house of Alfieri on to the terrace and vineyards

During the first few days, we spent two nights in Hotel Cerretani, right around the corner from the Duomo in Florence. The hotel was lovely, modern, and well located for those wishing to be in the center of it all. Coming from Lucca, this was a great shock as stepping out of the hotel meant immediately immersing yourself in one of the most popular and crowded areas of the city.

On Saturday evening, we made our way down to San Casciano dei Bagni, a small medieval town located about 90 mins south of Siena, known for its ancient hot springs. After snaking through the dark, wooded, hilly roads to get to the town, we arrived to Villa Federico. The villa was located right across from the main thermal spa resort and down a gated gravel driveway. It was a cozy renovated 5 bedroom farmhouse surrounded by a large lawn, and had views of the main castle and surrounding hills. Guests who stay in Villa Federico enjoy a complimentary welcome dinner at local hotel and restaurant La Fontanella, which was cozy, similarly decorated to the villa and delicious! Kate and I split two different pappardelle dishes both with meat, one with red sauce and the other with white.

We enjoyed our Sunday off and decided to venture out to visit Montepulciano, a medieval hilltop town about an hour north of the villa and home to our favorite wine! If you are staying in the area, we highly recommend visiting these towns, all known for their delicious wine, cheese, and meat products. They are absolutely worth the drive!

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Montepulciano

After our final villa tours in the area of San Casciano dei Bagni, we drove North East towards Perugia. In the city, we stayed at the Sangallo Palace Hotel, a spacious, clean and well-located hotel. We experienced some of the best dining of the trip in Perugia. A standout experience was at La Taverna, where we shared guinea hen terrine with pistachios and black truffle, as well as candy-shaped ravioli filled with red beets and ricotta in a gorgonzola cream sauce (the best!), and finally a dish of fillet medallions over julienned veggies in a Sagrantino wine sauce. It was absolutely out of this world!

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Dinner at La Taverna

From Tuesday through Thursday, we toured about 13 villas in Umbria. Out of the villas we visited Tuesday, Villa Casa Antica (HII NTI) and Villa Ada (HII ADA) were standouts.

Casa Antica, a 4 bedroom nestled in hills of Umbria and adjacent to an olive grove, was a comfortable Tuscan farmhouse with upgraded modern comforts. What most attracted me to this villa was the beautiful, mature gardens surrounding the house.

Villa Ada is a 7 bedroom perched on a hill with panoramic views and meticulously kept gardens. The interiors were well done, clean and elegant. Like most of the homes we saw this house exhibited the classic Tuscan Farmhouse aesthetic yet what set it apart was the care of the gardens and more luxurious style of the interior design.

For the following two days the best villas we saw were Villa Colonica (HII CNC), a 3 bedroom villa located on Lake Trasimeno, about 15 miles outside Perugia. The gardens and pool terrace were well kept, beautiful and had incredible, sweeping views over the Lake. The interiors were very modern but still were in keeping with traditional farmhouse architectural motifs. The villa was easy to get to and was also within easy reach of Perugia as well as activities available around the Lake.

Italy trip report, vacation in italy, Vacaiton rental, villas in italy

Checking out the pool at Villa Colonica

Another villa standout was Castello Ducale, an incredible 15 bedroom castle about 30 miles Northeast of Perugia. The castle was full of history. Not only did it date back to the early 13th century and in the current owner’s family since the mid 16th century, but the family were also direct relatives of Napoleon Bonaparte. The castle was very private, with about 4km of driveway and sweeping grounds leading into woods and fields. It was furnished with family antiques, paintings and other priceless artifacts.

Once we were finished with our tours on Thursday, we drove about 2+ hours up to Florence to begin our extension through the weekend. We had such an excellent time in the city and were able to experience activities and restaurants that I am so looking forward to recommending. Highlights included doing a wine tour in Chianti where we boarded a small coach bus, toured and tasted wine and olive oil in two vineyards, met some new friends and shipped home some of what we tasted for our families to enjoy. We also spent a day touring the Uffizi Gallery and visiting the David in the Galleria dell’Accademia.

Italy trip report, vacation in italy, Vacaiton rental, villas in italy

Relaxing by the Duomo in Florence

Overall, this trip to Italy completely exceeded my expectations and was a great success. I was so impressed with the villas we saw. Anywhere we visited, it was absolutely impossible to order both food and wine incorrectly. I am proud to say that I am now a huge (Tuscan) wine snob. Not only did we learn so much about the villas, regions and cuisine of Tuscany and Umbria, but we got a really good taste for the Italian way of life. Even the villas themselves were all geared towards enjoying life, together: pool decks and sunning terraces with incredible views of the rolling hills, al fresco dining areas set amidst beautiful gardens, and cozy sitting areas with large fireplaces- all places that draw people together to enjoy nature, good food, wine and conversation. Not only were many villas in easy reach of beautiful, historic cities and points of interest, but many also produced their own olive oil, and in some cases wine. These aspects made one feel truly connected to not only the villa itself but also the surrounding areas boundless natural beauty, ancient Italian heritage and the charms of enjoying the most simple moments of living.

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