Small Group of 22



September 29 - Overnight Flight to Rome. Depart the US and arrive in Rome the next morning.

September 30 - Welcome to Umbria. Upon arrival in Rome, we'll be met by our private transfer for the journey to Umbria where we will spend three nights in Castello di Postignano (or similar).

We will have the afternoon to relax and enjoy the surrounding village and amenities the hotel has to offer. In the evening, we'll gather for our Welcome Dinner at La Casa Rosa. (D)

Castello di Postignano
Castello di Postignano
Spoleto's Tower Bridge
Spoleto's Tower Bridge

October 1 - Full Day of Medieval Towns

We depart after breakfast to discover the medieval town of Todi. Set upon a hilltop, this quiet little village is much as it was in the 13th century, when Jacopone, the Franciscan poet wrote his verses there. With one of the most photographed piazzas in central Italy, we will enjoy a tour of the main sites and Renaissance architecture, followed by free time to explore on our own and find some lunch as we stroll.

We will head to Spoleto, our next medieval village after lunch to explore it's charms. Located at the intersection of several trading routes in Roman times, it has a long history of power struggles. From the Tower bridge, a large structure used both as an aqueduct and a walkway, you can enjoy a view of the town and Monteluco, the ancient sacred pagan wood. Be sure to note the Roman remains and architecture as well as the beautiful cathedral with is ornate rose windows.

Next we'll go back to our hotel for some relaxation time before transferring to our third medieval town of the day, Norcia, for dinner at a local restaurant. (B, D)

October 2 - Assisi, Our First Winery & Free Time in Castello di Postignano 

After breakfast we will be transferred to the town of Assisi, birthplace of Saint Francis, patron Saint of Italy. This is a medieval pilgrimage site and has a majestic Basilica that is a UNESCO world heritage site. We will have a tour of the town and it's main sites, with some free time to wander.

This afternoon, on our way back to our hotel, we visit our first winery. Vini di Filippo is a small boutique winery that enjoys a beautiful view of Assisi and amazing wines from the valley below. We will be enjoying a wine tasting and lovely light lunch at this special vineyard.

After our winery visit, we'll head back to the hotel for free time to enjoy the town and hotel amenities before saying goodbye in the morning. Dinner will be on our own at La Casa Rosa or for a light snack, Vini & Oli. (B, L)

October 3 - Orvieto & Our First Cooking Class

After breakfast we head west to Orvieto. This medieval town is set high on a cliff overlooking the western part of Umbria. We'll drop our belongings off at our hotel, Palazzo Piccolomini (or similar) where we'll stay for two nights, and then enjoy a guided walking tour of the town. The winding cobblestone streets will transport you back in time and the Duomo will surprise you when you turn the corner.

We'll have some free time for lunch and to wander or relax as we want.

Later this afternoon, we'll head to our first cooking class. We head to Casa Segreta where we meet our chef and learn how to cook authentic Umbrian cuisine. We will enjoy wine from their vineyards as we eat what we've cooked. (B, D)

October 4 - Montepulciano & Montalcino with Vineyard Visits.

This morning we head down the hill and into Tuscany for a day of more medieval towns and vineyard explorations. Winding through the hills and valleys, our first stop will be in Montepulciano. A Renaissance town that stands in the center of the Tuscan hills, we will stroll the streets laid out in medieval times. The surrounding area provides the exact qualities needed to produce the famous red wine with the same name. After exploring the town, we head to our first vineyard.

We will visit the Donatella Cinelli Colombini winery. We will enjoy learning about the famous Brunello wines on a vineyard both owned AND run by an all female staff, which is rare in the world of fine wines. We will enjoy lunch and a wine tasting before moving on to the next town on our tour.

We will be enchanted by the medieval walled city of Montalcino. With its 14th century fortress and hilltop vantage point, we can understand why it was an important theater of several wars in history. As Montepulciano is famous for its wine, Montalcino is famous for the surrounding vineyards production of Brunello wine. We will end our afternoon with a wine tasting at Montalcino Agricola Bellaria  This small, family owned vineyard is important in the story of Brunello wine and we will be tasting some of their finest.

We then head back to Orvieto, where you are free to enjoy the evening and dinner on your own as "a local" in this special little town before heading to the "big city" of Florence in the morning.(B, L)

Cooking Class
Cooking Class

October 5 - Siena, Florence & Wine Tasting Lunch

Today we say goodbye to Orvieto and the small medieval towns we've been visiting and head into the historic and powerful cities of the Tuscan region.

Our first stop is Siena, a powerful city-state in the Roman and Renaissance periods. The city was instrumental in the development of Italian art. We will walk through the lovely streets and squares of the city, seeing the oldest bank of Europe and the majestic Italian Gothic architecture of the Duomo of Siena. We'll see the famous Piazza del Campo and learn the history of the horse race, Palio, that has been held here for centuries.

After some free time to explore, we will stop to enjoy a wine tasting lunch at Boschetto Campacci winery. Here we will get our first taste of the Chianti Classico wines this part of Tuscany is known for.

Then we head to Florence and 4 nights in the Hotel de la Ville Florence (or similar). After some time to settle in, we'll gather for a group dinner in Florence. (B, L, D)

October 6 - Full Day in Florence 

Today we will expolore the old town of Florence on a full day walking tour. We start the morning in Old Town, visiting Piazza della Signoria with its staues, including the replica of Michelangelo's famous David (the original is safely on display in the Galleria dell'Accademia) and Palazzo Vecchio and on to the famous Ponte Vecchio where you'll learn its history and how it survived the ages.

We will enjoy lunch in a local Trattoria before heading to the lesser known artisan neighborhood of Oltrarno. Here you will find the most authentic artisan products of Florence, including leather works, goldsmith and jewelry making and paper and book binding. We will visit a local artisan workshop and learn about their craft.

The rest of our afternoon and evening will be free to explore Florence and it's culinary delights on our own. (B, L)

October 7 - Day in Chianti with a Local Family & Cookng Class

Today we travel back into the Tuscan wine region of Chianti to enjoy a special day with a local family. We will visit their family farm and learn how they grow olives and produce olive oil and grapes to produce the famous Chianti Classico.

We will have the opportunity to learn about the agriculture of the area as well as the culinary delights produced from their locally sourced items. We will enjoy a cooking class with traditional Tuscan recipes and then share our labors with a lunch paired with their Chianti wine.

After lunch, we can enjoy some free time to wander the farm and then we'll head back to Florence to relax and have dinner on our own.  (B, L)

October 8 - Full Day FREE DAY in Florence & Farewell Dinner

Today we will have a full day to explore Florence on our own. You can choose your own pace and itinerary.

If you would like to visit any particular sites in Florence such as one of the museums, the Pitti Palace or Boboli Gardens, or climb Brunelleshci's Dome, these can be arranged in advance by request for an additional cost.

We will gather again this evening for our Farewell Dinner (tbd). (B, D)

October 9 - Transfer to the Airport & Flight Home

This morning we will head to the airport and bid goodbye to Italy for our flight home. (B)

Chianti Toast
Chianti Toast


PRICE PER PERSON: $4999*/per Person Dbl Occupancy




Pricing Includes: 9 Nights Luxury Hotel, English-speaking Tour Leader, All Transportation & Transfers, Tours, Vineyard Visits & Cooking Classes as Listed, Daily Breakfast, 5 Lunches, 5 Dinners.

Pricing Does NOT Include: Airfare (to be added at add'l cost by November 2021), Gratuities, Meals Not Listed or Travel Protection, which can be purchased separately for an additional cost.


*Pricing is based on small group size of 22 people and today's currency exchange rate. 


Payment Schedule: 

 DEPOSIT $500/person**

January 3, 2022 - 2nd PAYMENT $2000/person

June 1, 2022 - FINAL PAYMENT