“Under The Tuscan” Sun day trips in Tuscany

If you’ve seen the movie Under the Tuscan sun or read the book you’re probably wondering about the film locations and settings and have been adding them to your bucket list. While the show takes place near Cortona, there are scenes from Positano along The Amalfi Coast,  Rome and many other parts of Tuscany.

We have a charming collection of villas through out Tuscany. Base yourself  close to Cortona and spend the week exploring these inspiring locations. We can tailor make your 7 day “Under the Tuscan sun” experience.


Explore Cortona to find the tourist office, grocery shops, restaurants, and the nearest coffee bar. On a clear day, you can see all the way to Lake Trasimeno. Visit the Etruscan Museum or the churches of San Niccolo and San Domenico. Or follow the mosaic stations of the cross leading up a steep hill to the church of Santa Margherita. Linger in the double central squares and book an appealing restaurant for dinner.


Spend a full and leisurely day poking around this famous resort town, Positiano. Sometimes still described as a “fishing village”.  Hike up to the cemetery, enjoy the beautiful views, shops, restaurants, and the harbor. Choose any of the many restaurants with a terrace with sea view for lunch.


Visit the Cathedral. Follow the winding brick alleys to the shell-shaped Piazza del Campo to relax and enjoy the scenery as you imagine the spectacle of the Palio that takes place here in July and August.


Take the train from one of Cortona’s two rail stations (Cortona-Camucia or Cortona-Terentola), or if you are up for some hassle, drive and park free at Piazzale Michelangelo. Admire the view from San Miniato and walk into town (30 minutes downhill) or take the bus. Make reservations well in advance to visit the Uffizi. Take in the Duomo and Orsanmichelle, if you have time, and come back another day for the rest. On your way back to the train station, stop at the Farmacia di Santa Maria Novella on via della Scala. We love their potpourri, but this ancient apothecary is worth visiting even if you don’t buy anything. Visit the Accademia to see Michaelangelo’s David, as well as the monk’s cells at San Marco. Other options include the Pitti Palace, Boboli Gardens, the library (and market) of San Lorenzo, Sant’ Ambrogio market, and the Synagogue. Don’t visit Florence on Monday when museums are closed.


Visit the Basilica of San Francesco (Saint Francis) and stroll through Assisi to the Basilica of Santa Chiara (Saint Clare). Continue on to Spello, but if you are there in June for the “infiorate,” when the streets are filled with wonderful works of art all made from flower petals, you will want to go on Sunday, and we suggest you get an early start to avoid the crowds.


Explore the countryside of Chianti by driving the SS222 wine route through Greve, Panzano, Castellina in Chianti and on, using your Chianti vineyard map and stopping at villages along the way. Reserve in advance for lunch with wine pairing at historical Vignamaggio. Reserve a wine tasting at the worldwide headquarters of Antinori and pick up some wine for your villa. If you have time, visit the abbey Badia a Passignano.


Take the train from Cortona directly to Rome. Head to Piazza della Repubblica, visit the the Church of Santa Maria degli Angeli to see its beautiful paintings and statues. Continue along via Nazionale all the way to Piazza Venezia, where you can see the monument Altare della Patria (Victor Emmanuel Monument). From Piazza Venezia, continue to Largo Argentina and the Pantheon. After you see the Pantheon, you can take a break to enjoy a coffee water ice with whipped cream at the Bar La Tazza D’Oro. Continue along Via del Corso, and you will find Via dei Condotti (for designer shopping), which will take you to the Spanish Steps. Don’t forget that in via Dei Condotti, there is the Antico Caffe’ Greco, the first café in Italy

San Gimignano & Volterra

See the famous skyline and walk all the way around the fountain in the Piazza della Cisterna to ensure your return. Continue to Volterra to shop for alabaster artifacts or to visit the Etruscan museum or the Museo Giarnacci, a major archaeological museum. Enjoy a local specialty, cinghiale (wild boar), for lunch.


Visit the enoteca in the fortress atop this classic Tuscan hill town to sample the famed Brunello wine. Stopping to see the Sant’ Antimo Abbey, just down the road. Make reservations ahead of time for dinner at Taverna dei Barbi, with an international reputation for Tuscan country cuisine. (Closed Tues evening and all day Wednesday – 0577 8471 17). If you have time continue on to Buonconvento & Monte Oliveto: The drive from Asciano to the abbey of Monte Oliveto Maggiore takes you through the eerie landscape of the Crete. Shop for unique souvenirs in the abbey gift shop, which specializes in herbal remedies. Have lunch at the restaurant by the gatehouse or continue on to Buonconvento for lunch at the unpretentious Da Mario. If you have time, visit the village of Murlo, one of the oldest settlements in the area.


Explore Orvieto, visiting the Etruscan tombs, St. Patrick’s Well, and the Cathedral, as well as its many shops and restaurants. One of our favorites, Antica Trattoria dell’ Orso which has some of the best soup in Italy. Continue on to Todi before returning via the area of Perugia.

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