2025 Tuscany Tour 


Spring: May 1, 2025 – May 9, 2025 (Only 1 room left!)
fall: October 17 – October 25, 2025 (SOLD OUT)

Castle Owners' Tour

For eight nights, you can have the exclusive opportunity to be escorted through the most magical parts of Tuscany and Umbria by the Gangale Family and Castle delle Serre owners, our extended Italian V. Sattui family.  We invite you to join in this intimate collaboration and cultural experience with their expert team as they share their influential perspectives on the food, wine, and history of their native country of Italy.  Based on over forty years of experience, we assure you that you will relish in the most authentic meals and local experiences during this stay, effectively capturing the essence of la dolce vita only as a true Italian could.

Day 1 – Chianti for Vineyard Tours and Lunch

Our host will meet us in Florence in the lobby of the Hotel River at 9:00am.  At 9:30 am our group will depart on board our deluxe air-conditioned private motor coach and head south exploring some of the hidden treasures of the enchanting Chianti countryside. We will drive through Chianti’s rugged hills of unspoiled forests, beautiful vineyards, castles, stone churches, monasteries, and farmhouses to visit the quaint village of Greve and Radda in Chianti.  Next, we’ll be visiting the top Super Tuscan winery to the south of us.  At the winery we will have a private vineyard and cellar tour followed by lunch and a tasting on the premises. Castello delle Serre will be our home for the next eight nights. A welcome dinner and music will complete the first day of our tour.

Day 2 – San Gimignano for Wine Tasting and Gelato

Today we will traverse the Chianti region on our way to San Gimignano, “Delle Torri” (of the beautiful towers).  This is one of the best-preserved medieval towns in Tuscany, where 16 of the 70 original towers of San Gimignano remain today. The towers were originally used to watch for invading enemies and later became a symbol of power for many of the richest families.  If you choose you may want to climb up one of them to get a sense of history and to enjoy the beautiful view.  We will then taste some of the best local Vernaccia (white wine) with a light lunch and get our first taste of the sweet life with the best gelato in Tuscany.  We’ll return in time for a Castle tour explaining the restoration of this Historic Registry Building before enjoying a local dinner.

Day 3 – Siena for Rich History and Lunch

After enjoying our morning espresso we will then depart with a local guide for the medieval city of Siena, most famous for its horse race, the Palio. Our tour guide will lead us through this charming city unspoiled by time.  We will visit the Medici town hall, the magnificent Piazza del Campo (town square), the spectacular sculpture-studded Duomo (church) and its museum with works by Pinturicchio, Pisano and Michelangelo, and visit the most important parts of the city.  We will then lunch in one of the most authentic local restaurants of Siena, eating as the contra’s (rivaling neighborhood factions) of Siena do just before their traditional Palio horse race.  After lunch we will be on our own to shop and explore the city of Siena.  We will return to Castello delle Serre for a casual dinner with wine.

Day 4 – Montalcino and Pienza for Wine & Cheese

We will travel to “Picture Perfect Pienza”. This little gem of a city was created by Aeneas Silvius Piccolomini, who became Pope Pius II. He transformed the farming village where he was born into his personal renaissance utopia. We will have lunch at the local Pecorino di Pienza Cheese producer before proceeding to the fortified town of Montalcino for a tasting of the famous Brunello di Montalcino wine (“the king of Italian reds”).  Montalcino is situated on the “little mountain” with a 14th century castle. It was a retreat for the Sienese when the Emperor Charles V captured their city. We will enjoy a fine dinner at a local restaurant on the way back to the Castello.

Day 5 – Montepulciano for Wine Tasting and Shopping.

Today we will tour the unknown countryside of Tuscany. We’ll explore the byroads and quaint villages not in the tourist books; the places that are still unspoiled. Our first stop will be a new facility of one of Montepulciano’s most historic wine producers with a unique sensory experience. You will enhance your wine knowledge and sharpen your sensory skills in a fun, interactive wine education and lunch. After this wine tasting of Vino Nobile, we will venture in the beautiful town of Montepulciano to visit the historic center including one of the most ancient wine caves of Italy. This will be followed by time to shop. Later we’ll return to Castello delle Serre for a casual pizza night. with the Castello family!

Day 6 – Visit Deruta for Ceramics and Sagrantino Winery

In the morning we will travel to Deruta, the center of Italian maiolica ware (pottery) since the 14th century.  We will observe “Ceramisti” modeling the clay in a pottery factory where we can purchase the wares and have them shipped to our homes.  Next, we’ll be visiting Sagrantino Winery.  Sagrantino is the Italian grape of the Umbria region.  Known for its high tannic levels, this fruit produces wines that are inky purple with an almost-black center.  The bouquet is one of dark, brooding red fruits with hints of plum, cinnamon and earth. This wine has a relatively small production and is not widely known outside Italy!  Then it is time for another delicious local dinner before we retire back to the Castello for the night.

Day 7 – Assisi for Piazzas, Basilicas, Temples and Shopping.

After breakfast, we depart for Assisi. We will tour with an authorized local guide this beautiful medieval town, with lovely views and fountains-splashed piazzas. We will visit the Basilica di San Francesco with its beautiful frescoes, the Temple of Minerva, the Basilica Santa Chiara and stroll through the streets where St. Francis walked.  We will shop at our leisure with a light lunch.  We will return back to the Castello for another great local dinner night. 

Day 8 – Truffle Hunting and Italian Cooking Class

For our final day, we will show you the Tuscan countryside with a once in a lifetime experience, truffle hunting! Arrive at a local agriturismo farm and first learn about the wine produced here. Afterwards, we will learn all about truffles. Following an informative lesson, venture out into the woods with the award winning truffle dogs to find some for yourself!

Once our hunt has concluded, we will then return to the kitchen to enjoy lunch made with the very same truffles we found along with the farm’s homemade wine.

We will return on the early side to pack for our departure early the next morning. Dinner will be provided at the Castello.

Day 9 – Florence/Departure

Early departure from Castello delle Serre.  The first drop-off will be at the train station around 11:30 am, if needed.  The second drop off will follow immediately at the Hotel River in Florence.

Note: Tour will begin and end in Florence.

Complete reservation form to secure your spot(s) on this tour.

Email: ali@vsattui.com for reservations.


$5595 per person double occupancy plus applicable taxes.


  • All meals (continental breakfast, lunch and evening meal)
  • Bilingual local tour guides
  • Bus transportation
  • Eight nights lodging in a premium Italian Castle and a Historic Inn
  • Accommodations based on double occupancy
  • Sightseeing, tours, museums
  • Wine and olive oil tasting
  • Cooking demonstration


  • Air transportation and Travel insurance
  • Laundry and Room Service
  • Telephone charges
  • Gratuity to local tour guides and bus drivers