Tour Itinerary

Day 1 – Welcome to Italy. Benvenuti!!

Meet at the Florence airport for private transfer to Città di Castello nestled at the foot of the Apennines in the picturesque Tiber River Valley. Meet your guide who will acquaint you with this small historic city, your home for the next four nights. Enjoy your first Italian dinner, an introduction to the local cuisine, for which Umbria is renowned.

Meals D

Accommodations: Hotel Tiferno

Day 2 – Truffle hunting and tasting in the medieval village of Citerna

The truffle, a delicacy selling for up to $450 per pound, has been labeled the diamond of the kitchen. Travel to an enclosed small private wood scattered with oak and hazelnut trees. Hunt for truffles with the aid of dogs trained to detect the scent underground. Then watch and participate as the chef owner of this family business teaches you how to transform those same truffles into a simple but elegant meal.

Meals B, L

Accommodations: Hotel Tiferno

Day 3 – Fine pottery in Deruta followed by wine and olive oil tasting in Montefalco

Visit a small majolica (pottery) workshop in Deruta, where a tradition that began in the early Middle Ages has developed into fine art. The characteristic local style is world-renowned and has a highly collectible appeal. Next travel to an organic vineyard situated across the valley from Assisi. Thirty acres of vineyards and olive groves wrap around the hills of this family farm. Over a delicious lunch, the family will explain the subtleties of their award-winning wines and olive oils. Enjoy stunning views and a delightful lunch.

Meals B, L

Accommodations: Hotel Tiferno

Day 4 – Discovering Città di Castello

Twice a week the medieval piazze come alive with merchants and local families buying everything from pecorino to shoes. This isn’t the typical tourist photo-op, but an interaction with a real market where the residents of Città di Castello live and shop. Today is set aside for you to make your own local discoveries. An optional afternoon visit to a generations old print shop or a short train trip to nearby Sansepolcro are available. Tonight gather for authentic Italian pizza, the kind Italy is famous for!

Meals B, D

Accommodations: Hotel Tiferno

Day 5 – Centuries of Craftsmanship in Anghiari

This morning drive to nearby Anghiari, a medieval jewel sitting atop a hill over the Tiber River in Tuscany. Begin with a visit to a historic weaving mill where the well-known Busatti family has been designing fine linens for over one hundred years. Visit the unique artisan shops that line the narrow cobblestone streets while enjoying the stunning views from town.   After a leisurely picnic lunch, make your way to Arezzo, a treasure-filled city with fewer tourists than its nearby rival Florence, but no less impressive. This will be your home for the next two nights.

Meals B, L

Accommodations: Hotel Portici Arrezo

Day 6 – Arezzo, Tuscany’s Exhibit of Artistry

Step back into history and take a private tour to visit centuries-old frescos, cathedrals, and monuments, all in one of the wealthiest cities in modern Tuscany. Arezzo’s wealth comes from gold, still worked in the many jewelry studios found here. Enjoy lunch on your own in the beautiful Piazza Grande or in another special corner you may have found on our morning tour. Meet in the late afternoon for a short walk either to a small wine-producer (cantina) for wine tasting and food pairing or for an evening aperitivo at a local cafe.

Meals B

Accommodations: Hotel Portici Arrezo

Day 7 – Embracing the Tuscan countryside in Montefollonico

After a leisurely morning in Arezzo, sample local panini at one of our favorite sandwich shops and experience the wonderful cheeses, meats and vegetable spreads Tuscans are known for. Some things are best experienced when savored slowly and deeply, and the Tuscany countryside is one of them. Early afternoon, we wind through the Tuscan hills to a small country village surrounded by breathtaking views of the countryside. Go for a swim, sit by the pool, read a book, take a stroll up and down the quiet village lanes or don’t do anything at all. Just be. This evening enjoy a farewell dinner together.

Meals B, L, D

Accommodations: Relais La Costa

Day 8 – Arrivederci. Until we see each other again.

Take in the views from this hilltop treasure while enjoying a leisurely breakfast. Then private transfer is provided to the train station for connections to Florence, Rome and beyond. Buon viaggio. Have a good trip.

Meals B  

Includes 7 nights accommodations, all ground transportation, all breakfasts, 4 lunches, and 3 dinners and full private guide services. Excludes tips and international airfare.