Villages in Italy 2022 Itinerary

Productivity Recharge Package:

Dolce Far Niente

Hidden Gems of Village Italy

June 13 - 20, 2022

You most likely won’t recognize many of the village names on here. That’s because they were chosen for being lovely, quiet, hard-to-reach locations that have not changed their shops or way of life in order to please tourists. That’s right, there are no chain restaurants or stores. There of course will be other visitors around, but in a couple of places, it might be so quiet that you’ll be able to hear your footsteps on the cobblestone. Plenty of independent time is built in so that you can visit art, architecture or museums that interest you, and wander in and out of shops or cafes to experience different foods and wines. What a treat!

Dolce far niente is Italian for the sweetness of doing nothing. Most of us are so busy that we have no idea of what that feels like. If you want to discover how to operate more efficiently at work and escape from work in order to enjoy a get-away, this Productivity Recharge Package is just for you! Following our pre-Italy virtual seminar, come join us in discovering the quaint villages of Italy! We´ll enjoy scrumptious food, delicious wine and wandering our way through Chianti and Tuscany.

Each village we’ll visit was chosen because: 1) it doesn’t have a train station; 2) it’s not at the top of bus tour lists because large buses can’t fit there easily; and 3) it graced the Top 10 of multiple “best villages” lists produced by travel writers and enthusiasts. We’ve timed the itinerary so that we miss the major late-June festivals – and the wall-to-wall people and traffic they bring.

Villages of Italy Map_Courtesy Google Maps

Day 1, June 13:  Florence to Monteriggioni

Our driver will pick up our group at 12:00 noon in Florence and head for the countryside. We’ll stop for lunch and wandering time in Greve-in-Chianti. The town square is bordered by stores, restaurants and wine shops that offer tastings. If you’d like to hike off your lunch, there’s a 2km uphill trail from Greve to a castle in the even smaller village of Montefioralli, the birthplace of Amerigo Vespucci. We’ll arrive in Monteriggioni in time for our group dinner.

(L, D) Accommodations:  Monteriggioni

Day 2, June 14: Monteriggioni

The day is yours for exploring. This walled medieval village has 14 towers. You can walk along the top of the wall around the village for wonderful views. The Piazza Roma, Church of Santa Maria Assunta and the Armoury Museum are sites to consider visiting. Or you can meander the streets, strolling through squares and past fountains. You can’t get lost for long – you’re surrounded by a wall!

If you'd like, join us for a late afternoon wine tasting.

(B, Tasting) Accommodations: Monteriggioni

Day 3, June 15: Monteriggioni to Montepulciano

After breakfast, we’ll be picked up for our drive to Lucignano. It was built in ringed streets as was common during medieval times, yet it has hidden picturesque corners in many locations. The town was divided into the poor and rich, and much of the original architecture still standing gives away who lived where. You’ll have free time to explore the town’s landmarks, which include the Collegiata, St. Francis Church and Town Hall, which houses the museum with the Tree of Love (considered a lucky charm for couples). Before arriving in Montepulciano and enjoying a group dinner, we will need to stop at a dairy to refresh ourselves with a cheese and wine tasting.

(B, Tasting, D) Accommodations: Montepulciano

Day 4, June 16: Montepulciano

Enjoy waking up in a village on Market Day! The Thursday morning market is held at the bottom of the hill on which the town sits. The day is yours to shop and saunter around the birthplace of Montepulciano wine. If you don’t feel like visiting the piazza, tower or wine cellars in town, you can hire a local guide to take you out into the countryside for a day of winery-hopping.

If you'd like, join us for a late afternoon food and wine pairing.

(B, Tasting) Accommodations: Montepulciano

Day 5, June 17: Civita di Bagnoregio and Pitigliano

After breakfast, we’ll be picked up for our day trip. Civita di Bagnoregio is called a dying village because all of the younger generations who have left for greener pastures have turned this former hilltop fortress into a near ghost-town. (That and the elements have worn away the earth that used to connect it to a larger village.) We’ll enter the village together via a footbridge, then you’ll have some free time to experience a place where there’s not much to do except enjoy dolce far niente. After our morning stop here, we’ll head to Pitigliano, also known as Little Jerusalem. This village seems to emerge out of the volcanic stone on which it sits. The viaduct, Jewish Quarter, museums, fortified buildings around the town center, Santi Pietro e Paolo Church, Santa Maria and San Rocco Church and The Tempietto all await your viewing, if you choose. If you’re up for a rocky adventure, you can wander through some of le vie cave (excavated roads). We’ll enjoy dinner together when we return to our base in Montepulciano.

(B, D) Accommodations: Montepulciano

Day 6, June 18: Montepulciano to Radda di Chianti

After breakfast, we’ll make our way back toward Chianti, stopping in Siena along the way. Then we'll enjoy a farm-to-table lunch at a family estate. Our destination for the afternoon is a borgo in the countryside near Radda. A borgo is a hamlet that was once almost lost to time, but has been refurbished and revived by a family. You’ll have a chance to explore and unwind before we enjoy a lovely chef-prepared dinner in the olive grove.

(B, Siena Duomo, L, D) Accommodations: Borgo

Day 7, June 19: Borgo

You’ll have the day to lounge and enjoy the Tuscan countryside. You can arrange for a picnic or a private car tour of wineries in the area, adventure around the property surrounding the hamlet, or rest poolside. At mid-afternoon, you’re welcome to join us for a cooking class. In the evening, we’ll eat the fruits of our labor as our group will gather together to feast on our farewell dinner.

(B, L, D) Accommodations: Borgo

Day 8, June 20: Borgo to Florence

After breakfast, we’ll wave goodbye to beautiful Tuscany and be driven back to Florence.

(B) - Fino a quando ci incontriamo di nuovo! Until we meet again!

*Please note: this itinerary is subject to slight modifications due to hotel availability, weather, festivals and other occurrences.*