Explore two of Italy’s most delectable regions – Tuscany and Umbria! From the mouthwatering cuisine to the fabulous wines, this tour will make your taste buds sing. Take in the spectacular scenery of rolling hills, sweeping vineyards, waving wheat fields, cypress trees that line the roads like sentinels, and medieval hilltop villages with winding cobblestoned streets.

Savor the incredible Tuscan wines we all know and love as well as some varietals you may have never heard of.  Umbria, though not as well known as it’s neighboring region, also produces excellent wines that will have you smiling as you sip. You’ll have the chance to taste a wide variety of fine Italian wines throughout the trip.

Italian food is one of the world’s most revered cuisines – and for good reason! There is special attention given to the quality of each individual ingredient and the culinary traditions passed down for generations. You’ll not only get to indulge in the fantastic cuisine, you’ll learn how to find the freshest ingredients and make it yourself!


Related blog posts:

Curated Experiences

  • Visit 4 different Italian wineries, ranging from large and modern to very small scale
  • Go truffle hunting and take a cooking class with famous agriculturist Augusto Verando Tocci
  • Learn about the art of coffee roasting and chocolate making at a cafe in Arezzo
  • Sample small-batch family made olive oil
Book Now

Tour Details

Tour Details

Arrival & Departure

We meet in the early afternoon on the first day of the tour at a The Grand Hotel Continental in Siena. The tour finishes in Cortona before lunch on the final day of the tour. Cortona is on the mail rail line connecting Florence to Rome, so you can fly out of either city.

Book Now

What is Included

  • All Local Transportation
  • Double Occupancy Lodging
  • 4 Breakfasts + 1 Lunch + 4 Dinners
  • 4 Tastings at Wine Estates
  • Cooking Class, Olive Oil Tasting, Guided City Walks, Visit to Chocolate Maker/Coffee Roaster
  • Professional Tour Guide

Not Included: Travel to and from destination, wine with some meals, personal expenses, and optional gratuities to local staff and your guide. Travel insurance is also not included, though we highly recommend it.  Check out our Travel Insurance page for more information.

While the general trip itinerary will remain the same, the actual restaurants, hotels, and activities listed are subject to modifications. Changes that are out of our control are common — restaurants close or lose their amazing chef, a winery changes their visiting hours, a hotel gets remodeled, etc. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance.

"What a fantastic trip we had in Tuscany! I can't thank you and Giovanni enough for your kindness, flexibility, and support. It makes for a more relaxing and enjoyable experience." - Dane M.

As is with every Taste Vacation tour, the attention to detail is incredible. Everything from ensuring that participants have enough wine, tasting spectacular wines, visiting exclusive wineries, dining on great food, touring beautiful vineyards, plenty of activities to keep us busy, and enjoying unique restaurants is covered.

Elizabeth & Jake

I was concerned about the limitations of being on a guided tour as well as having to spend the entire time with a group of strangers. What I found was that the tours were extremely well planned and the accommodations, meals, wine tastings, and activities were perfect! And at the end of the trip, the people that began the tour not knowing each other, parted as a group of forever friends planning another adventure together with Taste

Alice T.

Tour Itinerary

Day 1

Fattoria di Gratena Grapes

Your guide Giovanni will meet you at midday in the town of Siena. After some quick introducations, we’ll be on our way to the center of the lovely small city of Arezzo where you can explore the various cafes and restaurants for lunch on your own. We’ll then reconvene to visit Vestri Cioccolato, a chocolate maker that has been producing delicious chocolate and roasting their own coffee for 30 years. They own a farm in the Dominican Republic which provides them with the raw cacao beans and coffee beans. We’ll learn about the chocolate-making and roasting processes and, of course, sample a few of their creations. We then transfer to the center of this lovely small city where you can explore the various cafes and restaurants for lunch on your own.

After, we visit Fattoria di Gratena, a winery located on the outskirts of Arezzo. This organic winery is most interesting because of its creation of a new clone, unique to the property, called Gratena Nero.

After the wine tasting we’ll head to our hotel in Città di Castello, a lovely town in the northern part of Umbria. You will have some time to rest or wander the ancient town. Dinner tonight will be at a local family- run wine bar and restaurant that serves outstanding local cuisine in a casual setting.

Day 2

Most tourists don’t make it to the section of Tuscany called the Upper Tiber Valley. Even fewer travel to the hamlet of Badia Tedalda, 40 minutes up into the Apennine Mountains. But it is here we will travel this morning, specifically to visit Augusto Tocci, a botanist famous for his pursuit of the equally famous truffle.

Augusto will take us into the forest with his trusted dog to look for truffles, which can be found in this area at any time of the year. Successful or not, we will return to his home to participate in a cooking class and lunch involving many of the edible plants and roots found in the forest, including the local liquor Spinello.

After lunch, we’ll return to Sansepolcro for walking tour of this adorable village with a stop at an artisanal gelateria. Many gelato stores in Italy do not make their own product but purchase it from a big manufacturer, so this will be a special visit.

Tonight, we’ll enjoy an exquisite renaissance dinner at one of the oldest restaurants in Sansepolcro, another beautiful village. Owner Alessia is an expert of traditional and historical cooking and will explain the history of each dish as it is presented.

Day 3

Tuscany Olive Oil

This morning begins with a visit to the very small and local olive oil mill of our friend Emanuele Ragani and his family. Emanuele will not only show us how the mill, with an actual grist stone, operates but will fire up a wood oven, heat up bread, and pour delicious olive oil on top for a tasting. The olive oil makes a great souvenir from Italy but it is the local experience, watching Emanuele and his family as they continue to run a business serving the locals, who bring their olives by for pressing year after year.

After, we’ll head for a visit to Arnoldo Caprai winery, the leading winery of the region and leading producer of its most famous local grape, the Sagrantino di Montefalco. We will learn all about and taste wines made from the Sangrantino grape, grown in this area for over 400 years.

We then make our way to Assisi, the city made famous by St. Francis, for a tour of the city and the church where he is buried. Assisi’s church is impressive but you will equally enjoy the many winding streets, the views over the valley below, and the multitude of shops and restaurants. We are on our own here for lunch, allowing you to pick your dining option at leisure.

Then it’s time for more wine! We travel to a very different winery, Antica Azienda Agricola Paola Bea. This winery is small, biodynamic, and run by a very interesting (and opionated) owner who will give us a much different viewpoint from the large Arnoldo Caprai.

We’ll continue on our way to the charming hilltop village of Cortona (made famous by the book Under the Tuscan Sun) and check into our hotel overlooking the Chicana Valley. We’ll have dinner at another delightful local restaurant.

Day 4

Tuscan hills

We start our day with a visit to Azienda Agricola Leuta.  This is a relatively new winery in a new region, which only recent has been identified as having good terroir for wine grapes. Leuta specializes in Syrah and Cabernet Franc, two grapes we will not have tried much up until now on this tour.

We’ll then head to the breathtaking Val d’Orcia and stop in the city of Pienza, perched high above the valley and designated a UNESCO World Heritage Site. (The entire valley is designated a World Cultural Landscape.) You’ll have some free time to grab lunch on your own before reconvening to go on a walking tour of this beautiful city.

On our way back to Cortona, we’ll stop in the small village of Bagno Vignoni to see its Roman-era thermal baths located right in the center of the town.  Heading back to Cortona, you’ll have some free time to explore on your own. This evening, we’ll share a final meal together at the Locanda al Pozzo Antico, a fine dining establishment run by the owner Paola where we’ll try to outdo our previous successes with delectable cuisine.

Day 6

Tuscany Food & Wine Tour

We’ll take a post-breakfast walk of Cortona, as Giovanni will point out some of the important sites that featured in the movie, Under the Tuscan Sun. You are then free to take the train or a shuttle onwards to Florence or Rome (Check out Extend Your Stay: What To Do in Italy). Or perhaps you’ll follow the theme of the book and decide to stay in Tuscany permanently?

Tour Accommodations

Tuscany Food and Wine Tour Hotel San Michele

Nights 1 & 2: Hotel Tiferno, Città di Castello: Built in 1895, this historic boutique hotel was once a 17th century monastery and is perfectly located in a quaint square in the center of beautiful Città di Castello.

Nights 3 & 4: Hotel San Michele, Cortona: Enjoy modern comforts in an ancient 15th-century palace, located in the historic center of Cortona. You’ll not only find beautifully and uniquely decorated rooms but incredible ancient artwork in the lobby.