Tour Tuscany & Umbria

Tour of the Hill Towns and Countryside of Tuscany and Umbria, Italy.

May 9th to 17th, 2024 (Sold Out)
Sep 18th to 26th, 2024 (Sold Out)
Sep 26th to Oct 4th, 2024 (Sold Out)
April 23 to May 1, 2025 (BOOK NOW)
October 25 to November 2, 2025 (BOOK NOW)


Embark on a Tour of Tuscany, Italy for 8 nights! Make lifelong memories in the magical hill towns and countryside of Tuscany and Umbria with Castello delle Serre owners and the Castello di Amorosa wine family. We invite you to join in this intimate collaboration and cultural experience sharing influential perspectives of the food, wine and history of Italy. 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.

Guests explore charming villages, farmhouses, majestic castles and the beautiful architecture of churches and monasteries. You’ll taste some of the world’s finest olive oils, wines, learn how the Italians cook, and eat meals you’ll remember for a lifetime.

$5,595 per person

Tuscan Countryside

Day 1 – Chianti and Sleep at Castello delle Serre:

Salvatore, our host, will meet us in Florence in the lobby of the Hotel River (time will be specified via email for your tour). 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.  We will get our first taste of the sweet life with the best gelato in Tuscany before visiting 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 tasting on premises. Castello delle Serre will be our home for the next six nights. A welcome dinner and music will complete the first day of our tour.

San Gimignano

Day 2 – San Gimignano and Sleep at CDS:

Today we will traverse the Chianti region on our way to San Gimignano, “Delle Torri” (of the beautiful towers).  This is one of the bestpreserved 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;  Returning in time for a Castle tour explaining the restoration of this Historic Registry Building before enjoying a local dinner.


Day 3 – Siena and Sleep at CDS:

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 & Pienza, Sleep at CDS:

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 taste some of the famous pecorino cheese produced in this area before we proceed onto the fortified town of Montalcino, situated on the “little mountain” with a 14th century castle. Montalcino was a retreat for the Sienese when the Emperor Charles V captured their city. We will enjoy lunch with the local wine in the village before visiting our favorite producer of Brunello di Montalcino, the king of Italian reds. We will enjoy a fine dinner at a local restaurant on the way back to the Castello.


Day 5 – Montepulciano and Sleep at CDS:

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.  After a wine tasting of Vino Nobile in the beautiful town of Montepulciano, we’ll have lunch in one of the historic cellars in the center of town, followed by time to shop.  Later we’ll return to Castello delle Serre for a casual pizza party night with the Castello family!

Duomo Italy

Day 6 – Orvieto & Cooking Demonstration and Sleep at CDS:

We will board the bus for Orvieto, famous for their much celebrated Duomo. The Duomo is thought to have Italy’s most beautiful Gothic facade and there we will view the fascinating Signorelli frescos.  We will stroll though Orvieto with a local guide and taste the local wines during our lunch. We will return on the early side to pack for our departure early the next morning. A cooking demonstration will take place before dinner at the Castello.

Deruta Italy

Day 7 – Deruta for Ceramics and Sagrantino Winery and Sleep at Assisi


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 dinner before we retire to Assisi for the night.


Day 8 – The Day Exploring Assisi and Sleep at Assisi:

After breakfast, we will tour with a 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. Our farewell dinner will be in Assisi after we pack for our departure on Sunday.

City View

Day 9 – Florence / Departure

Early departure for Florence. The first drop-off will be at the train station around 12:00 pm, if needed. The second drop off will follow immediately at the Hotel River in Florence. Travelers may not schedule departing flights to USA on last day of tour.  It is advised that travelers either extend their trips throughout Italy and Europe following the tour or book at least one night’s hotel room close to the airport of their departure following the Tour.

The Tuscany Tour will Include

  • All meals (continental breakfast, lunch and evening meal)
  • Beverages included with meals and select outings
  • 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

The Tuscany Tour does Not include

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


“We were with Salvatore and stayed at the Castello dele Serre and then San Crispino. What an absolutely fantastic tour!!! Salvatore was wonderful. What an amazing guy! He was so entertaining and knowledgeable about the areas, the wine, the churches, the people, the history, the food, everything. It could not have been better! And hearing all the stories about the castle and all the trials and tribulations he went through to bring it to its present glory was amazing. Wow!! The trips to wineries, churches, restaurants, everything were awesome, the bus was comfortable, the travel times were do-able. I confess, we stayed at the castle one day instead of venturing out with the group on account of me just not sleeping at all one night, no fault of the tour. So that relaxing day at the castle was nice too. What an awesome place to stay, the history, the stories, the colorful past that Salvatore regaled us about! He was so entertaining and such a wonderful guide to have. I give the tour and Salvatore 5 stars!!! Thanks so much for the opportunity to enjoy this. We certainly had fun with our group of 14 total. This was a perfect number, as it was supposed to be 16, but one couple was a no show. Too bad. What an amazing experience they missed. It was also nice that we started our tours daily at about 9 or 9:30 and not too early. We were all in our 50’s and 60’s, maybe a few younger and a few older, but you know….we need our sleep to thoroughly enjoy the sights, the activities and all the walking. This way we had time for breakfast, which I’ll admit could have been a little more varied. It was pretty much the same every morning at the castle. There’s something about bacon and fried eggs in the morning that we all missed, but lunches and dinners were so good, it was fine. And the wine at all of our meals was delectable!  All the people were so friendly, Antonio and his family, Salvatore’s wonderful sister, the staff. Very well done, all! Thank you! Arrivederci!!”Melissa Canfield

“I just wanted to say what a fabulous, meaningful and unparalleled experience the Tuscany trip was. Salvatore was a one in a million tour guide, host, storyteller, friend and ambassador to Italy, with in-depth knowledge of wines, food, history and just about everything else that elevated this trip into a lifetime experience. We loved staying in the castle and exploring each hill town, with the best of eating and wine experiences waiting for us in unique settings in the castle itself and beautiful indoor and outdoor settings in the heart of the cities we visited.  Thank you Castello di Amorosa for offering this trip! It was seamless and well-planned.”Marsha and Bob Mayer

“We have just returned from Italy where we were part of your 2021 Tour of the Hill & Towns Countryside of Tuscany and Umbria. We continued on to the area of Cinque Terre after the tour and just returned to the United States last Thursday. We wanted to thank Salvatore Gangale, Antonio and their staff for an incredible tour and stay. Everything was just perfect – the people we met, the wineries and cities we visited and the incredible food and wine at the castle as well as all of the other ristorantes that we visited! We highly recommend this tour to members considering the tour in future years. The event was very well planned. Restricting the tour to 12 – 14 people is a good size for everyone to get acquainted with their fellow travelers. It also allows the use of the mini bus that can more easily navigate the streets and roads through the towns. I think having a larger bus would have been difficult if not impossible to navigate in the areas we visited. The tour was very well organized and planned. We highly recommend future years of this tour to the other members of the Wine Club.”

Steve and Jan Wells

Terms & Conditions

This is an active, walking tour of Tuscany and Umbria’s hill towns and countryside. Walking is required and is an important part of this excursion. All trip members are expected to be active, to be in good health, to enjoy traveling as part of a group, and to be ready to experience cultural differences with grace and good manners.

Tour Price:  $5,595 per person double occupancy includes applicable taxes.

Passports:  U.S. Citizens must be in possession of a VALID passport. All other nationalities must check with the Italian consulate for proper papers.

ETIAS: The rules of travel to Europe have changed. Starting from 2024, some 1.4 billion people from over 60 visa-exempt countries are required to have a travel authorization to enter most European countries.

Visas:  NO VISA REQUIRED for U.S. Citizens; others check with your local Consulate. This is your responsibility.

Reservations:  A deposit of $2700 per person is required to secure a reservation. Space is limited to 18 travelers and is on a first-come-first-served basis.

Balance Tour Fees:  The balance of the tour cost ($2895) is due 6 months prior to tour start date, specific date specified in tour packet after deposit is received.

Cancellation:  PLEASE READ CAREFULLY, AS WE WILL ABSOLUTELY ADHERE TO THE FOLLOWING CANCELLATION POLICY. Cancellations may be submitted for double occupancy only and must be written and dated, for the proper refund. Cancellations prior to 6 months of tour start date, is refundable, less $500 per person. Less than 6 months prior to tour start date, there will be no refunds.

Validity: TOUR is based on a minimum of 18 participants. In the event the minimum number of 18 participants do not book the Castello di Amorosa Tour, Castello di Amorosa Winery reserves the right to cancel the tour. In the event Castello di Amorosa cancels the tour for lack of participants, a full refund will be given. All rates are based on the current value of the US Dollar and are subject to change without notice.

Insurance:  We strongly recommend that you take out comprehensive insurance. (Health, accident, baggage, and trip cancellation) Castello di Amorosa Winery shall not be responsible for any injuries, damages, or losses caused by any traveler in connection with terrorist activities, social or labor unrest, mechanical or construction difficulties, diseases, local laws, 
climatic conditions, abnormal conditions or developments, or any other actions, omission, or conditions outside the tour agent’s control. By embarking upon his/her travel, the traveler voluntarily assumes all risks involved with such travel, whether expected or unexpected. Traveler is hereby warned of such risks and is advised to obtain appropriate insurance coverage against them.

To book, contact Wine Club at 707-967-6274 or at .

Additional Details

  • Our tour pick-up date time will be specified via email for your tour at the Hotel River, in Florence. We suggest you arrive in Italy at least one day prior, to avoid any delays. Many guests prefer to stay at the Hotel River the night before the tour starts to be well prepared for the early departure the next day.
  • The bus will depart in the morning the day of your tour start date.
  • We wish to remind everyone that on the day of pick-up in Florence, our suitcases will be traveling with us on the minibus. Please keep your luggage to a minimum (one carry on and one checked bag are suggested).
  • Friendly reminder that rural Italy is a land of understated elegance, therefore formal evening attire is not suggested, comfortable walking shoes however are.
  • Regarding what to pack, it would be best to look at the weather forecast for Siena and Assisi a few days before your departure, to decide on proper clothing.
  • To ensure the full enjoyment of our dining experiences, please inform us prior to your arrival if you have any serious food allergies or restrictions, we must be aware of.
  • Travelers may not schedule departing flights to USA on last day of tour.  It is advised that travelers either extend their trips throughout Italy and Europe following the tour or book at least one night’s hotel room close to the airport of their departure following the Tour.
  • As your tour concludes the first drop-off will be at the train station around 12:00 pm if needed. The second drop off will follow immediately at the Hotel River in Florence.

It is IMPERATIVE that you follow your airlines guidelines as they may differ. Everyone must be responsible for knowing the requirements of their airlines and travel itinerary.