Tuscany Food & Wine Tour (Public Tour April 28 - May 4, 2019)

Red Wine
White Wine
Olive Oil
Local Food
Overnight Tour (2+days)
Food Tour
Chauffeured Tours
Walking Tour
Pick up
Tour guide
Minimum Drinking Age
/ Person
Beth P
Activity Overview
Tuscany is one of the great destinations of Italy and, indeed, of the entire world. The beautiful scenery comes from the large tracts of agricultural land placed on rolling hills, dotted with cypress tress and crossed with the famous strada bianchior white-colored dirt roads.

It is hard to say whether Tuscany is better known for its food or its wine and this toss-up is what makes this region perfect for a combination Food & Wine Vacation.

We start our tour in Florence, capital of the Medici, and hit major areas including Chianti, Arezzo, Assisi, and Montepulciano, with a side trip into Umbria. Our days are filled with wine tastings, visits to local food producers and sellers, and even truffle hunting in the forests visited by few tourists.

Tuscany is a spectacular region for a vacation and there is no better way to visit than to focus on the local food and wine. (Note: We can cater to almost any food allergy or eating preference on this and all our tours.)

Tour Itinerary

DAY 1 
We meet at our Florence hotel at 1:30 PM and set off on an exploratory walk of the city, focusing on the history and culture of the city through the eyes of a food lover. (If you wish to visit the David or any of the other impressive historical sites, you should plan on arriving to Florence a day early.) Your guide, Giovanni, is a wealth of knowledge about all things Tuscany – food, wine, history, and culture. In the late afternoon, we’ll stop at B.Gallo, a “loungeaperitif” where we’ll toast the waning day with a Prosecco, the famous Italian sparkling white wine.

We’ll then make our way to a quaint family-owned restaurant for a lovely welcome meal. After dinner, we head back to the hotel and rest up for tomorrow’s adventures – our first full food and wine day in Tuscany.

We check out of our hotel and begin our day by exploring the Saint Ambrogia Market.  This diverse market is less touristy than say Mercato Central which means we get a glimpse of how everyday Tuscans shop for their daily meals. We’ll have time to stop and sample the wares of the various merchants along the way.

Next, we are off to one of the most famous wine regions with one of the most famous wine styles in Italy: Chianti. Our first stop is the picturesque city of San Gimignano, a small medieval walled town famous for its dozen or so towers sticking up into the sky. After exploring the town on foot, we’ll head to the local Fattoria Poggio Alloro for a lunch of food products from this farm, such as the Chianina brand of beef and the saffron spice which has been locally grown since the 13th century, paired with the white wine Vernacciadi, also grown on site.

Next on our agenda is the winery Castello di Volpaia, which is located in a fortified village of the same name and where we’ll do a tasting of the famous Chianti Classico wine. We finally head to our hotel for the night, Dievole, an exquisite country retreat on 1000 acres with vineyards that were planted as early as 1090 – over 900 years ago! We’ll visit their cellars and then eat dinner outside in the garden if the weather is good, with wines from the estate paired with our courses

We drive in the morning to Arezzo to visit Vestri Cioccolato, a chocolate maker that has been producing delicious chocolate for 30 years and which owns its own farm in the Dominican Republic. Not only do they make their own chocolate but they also roast their own coffee. We’ll learn about the chocolate-making and roasting processes and, of course, sample a few of their creations.

We then jump back in our vehicle to transfer to the center of town where you can explore the various cafes and restaurants for lunch on your own. After lunch, we visit the nearby small town of Anghiari, famous as the site of the Battle of Anghiari in 1440 between the armies of Florence and Milan. This is also your guide Giovanni’s home in Tuscany.

Next, we’ll visit the world-famous Busatti linen factory, sold in such outlets as William & Sonoma. This family-run business has been based in Anghiari since 1842. The factory tour is extremely interesting and you can purchase products to take home, although they are not cheap!

We head to the walled town of Sansepolcro to check into our hotel for an hour’s rest and then visit a local hotspot, Enoteca Guidi, which is a combination wine bar and restaurant that serves outstanding local cuisine in a casual setting.

DAY 4 
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 Verando Tocci, a botanist famous for his pursuit of the equally famous truffle.

Verando 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 Pasticcera, a local bakery and 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.

Our dinner tonight is at Relais Palazzo di Luglio, situated on 30 acres in the countryside outside Sansepolcro. The owner Giuliano previously owned one of the most successful restaurants in town and produces an elegant, traditional Tuscan dinner featuring whatever is in season.

DAY 5 
Yes, this is a food and wine tour of Tuscany but nearby Umbria is well worth a visit. We’ll start out with a visit to the very small and local olive oil mill of 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.

We then head to Assisi, the city made famous by St. Francis, for a tour of the city and the church where he is buried. Assisi is a great town to walk around on your own, with many shops and restaurants, and we are on our own here for lunch. After lunch, we’ll head to Arnaldo Caprai winery, a leading producer of the wine Sagrantino di Montefalco. If you have never had Umbrian wine before, you will be impressed.

After our wine tasting, our time in Umbria is ended and it is back to Tuscany as we drive to Cortona, made famous by the book Under the Tuscan Sun our home for the evening. We’ll check into our hotel and then walk to dinner at La Bucaccia, rated the top restaurant in Cortona on Trip Advisor (out of 84 restaurants) serving, as one recent reviewer wrote, “wild boar ragu with tagliatelle, pici with an intense tomato sauce, a pecorino flan, seasonal vegetable soup, and bruschetta to die for.”

DAY 6 
The Val d’Orcia is one of the most beautiful sections of Tuscany, which is one of the most beautiful provinces of Italy, which is one of the most beautiful countries in the world. We are in a good place!

We’ll start our tour by visiting 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.) After a quick historical walking tour of the city, we’ll head to a local farm that specializes in making pecorino, the ubiquitous local sheep’s cheese. We’ll learn about the process, have a taste of the fresh cheese, and eat a nice picnic lunch right on the farm.

It is then on to Montepulciano, another famous hilltop town, where you will have an hour to wander the streets on your own. We then gather together again to visit Cantine Gattavecchi for a tour of their barrel room and tasting of the local wine, the outstanding Vino Nobile di Montepulciano. Heading back to Cortona, 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 Tuscan cuisine.

DAY 7 
We’ll take a post-breakfast walk of Cortona, as Giovanni will point out some of the important sites that featured in 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?

Tour Accommodations
Night 1: Antica Torre di Via Tornabuoni, Florence: An incredible hotel located in a tower built in the first half of the 13th century and situated in the center of the city.

Night 2: Dievole, Chianti: An exquisite country retreat on 1,000 acres with vineyards that were planted as early as 1090 – over 900 years ago!

Nights 3 &4: Palazzo Magi, Sansepolcro: Located in a 14th-century residence within the walled town of Sansepolcro, one of our favorite Tuscan towns and rarely visited by tourists.

Nights 5 & 6: Villa Marsili, Cortona: Luxury hotel located in the center of Cortona, which sits high on a hill overlooking the Val die Chiana in central Tuscany.
Practical information
We meet at 1:30 PM on the first day of the tour at our downtown Florence hotel, allowing you to arrive either that morning or the day before. The tour finishes in Cortona before lunch on the final day of the tour. Cortona is on the main rail line connecting Florence to Rome, so you can fly out of either city. One nice option is to fly into Florence and out of Rome, so you can visit both cities.
  • All Local Transportation
  • Double Occupancy Lodging
  • All Meals Except One Lunch
  • All Scheduled Activities
  • Wine During Organized Tastings
  • Professional Tour Host
Not Included
  • Travel to and from destination
  • Wine with meals
  • Personal expenses
  • Optional gratuities to local staff and your Host
  • Travel insurance is also not included
4-16 people
Pricing info
Optional single supplement
Start Time
More Information
More information about the timing
On Apr 28, 201912:00 PMPublic tour
Daily12:00 PMPrivate tour, ask for availability
7 Days
Frequently Asked Questions
Wine Tours: winery visits, vineyard walks, food and wine pairing dinners, blind wine tastings, conversations with vintners, and more Food Tours: cooking classes, cooking demonstrations, shopping at farmer’s markets, and visits to local artisan producers such as olive oil mills, cheese farms, honey bee farms, and more
Our tours include double-occupancy lodging at four-star hotels, meals as indicated in the tour itinerary, local transportation, all organized culinary and drink experiences, and the professional services of a Taste Vacations host and, sometimes, a local guide. Alcoholic beverages at meals are not included in the cost of the tour, allowing you to choose your own wines, beers, or other beverages. Deluxe accommodation upgrades are available for each tour, upon request.
While everything under “What is Included” on the webpage for each trip will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road undergoes construction. 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 (even at the last minute, during the guides’ scout) 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! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.
Our trip prices are based on double occupancy. If you are coming on a trip solo, we will find you a roommate of the same gender. Many tour companies require you to pay a single supplement if they can’t find you a roommate on a public tour. We don’t! If we can’t find you a roommate then you may end up getting your own room at no charge (although this is fairly rare). You also have the option to pay the single supplement to get your own room if you don’t want a roommate. Please see each individual tour page for the single supplement cost.
We select hotels that provide unique and comfortable accommodations while also being conveniently located and providing a casual atmosphere. We believe the best hotels are those that walk the walk by providing outstanding in-room comfort, excellent staff, and complete amenities. We are not impressed by hotels trying to impress. Keep in mind that hotels differ in different countries. We might stay in a modern, upscale hotel in the United States but choose a historical gem upgraded with modern comforts in Europe. Please keep in mind we sometimes have to switch a hotel from what is listed on each tour page due to availability. We eat our meals in a variety of locations from a private dinner at an estate winery to a beer pairing dinner with a brewmaster to a formal dinner at a city’s finest restaurant. Some meals are more casual and some more formal – we like the variety and think you will too. All of our restaurants pride themselves on serving top-quality meals in keeping with the local culture.
Since our tours are focused on wine, beer, and spirits tastings where we encourage long, lingering meals, and may need to travel to get between destinations, our vacations are designed to be enjoyed without children.
More Info
Cancellation Policy
  • Cancellations made at a later date will not be refunded.
3 reviews   0 comments
Overall Experience
(5.0 of 5)
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 ... more adventure together with Taste Vacations.
Overall Experience
The attention to detail is incredible. Everything from ensuring that participants have enough wine, taste 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.
Overall Experience
What a fantastic trip we had to Tuscany! I can't thank you and Giovanni enough for your kindness, flexibility and support. It makes for a more relaxing and enjoyable experience.
Overall Experience
Tastings Nearby
Florence, Tuscany, Italy
3 H
Following an expert, each participant will learn to make handmade gelato and pizza using quality ingredients and putting into practice the principal ideas of these iconic treats.... more

Each participant will learn what is involved in making an excellent pizza from scratch by mastering techniques of dough-making and rolling and sauce-making, while using only the best ingredients.

Following the lesson, the participants partake in the sampling of the pizza, gelato, and sorbet in a cozy cantina

Following an expert, the secrets for making handmade gelato using quality ingredients and putting in practice the principal ideas will be revealed to the participants.

The participants learn the activities involved in pizza making, the creation and the working of the dough.
They have the chance to learn all the types of flour, the amount of ingredients, the manipulation of the dough, and the products used for making the sauce.
Following the lesson, the participants partake in the sampling of the pizza, gelato, and sorbet.

The options of gelato are: vanilla, chocolate, stracciatella, cream, pistachio, etc,

And the options of sorbet are: pineapple, strawberry, and lemon


Small Classes

Professional Chef

Equipment and ingredients included

Learn to make gelato

Learn to make pizza by hand and sauce

Eat what you have made!
Florence, Tuscany, Italy
3 H
DISCOVER HOW TO PREPARE DELICIOUS HOMEMADE PASTA FROM AN ITALIAN PROFESSIONAL CHEF Enjoy a Pasta cooking class with great typical Italian recipes for authentic pasta lovers! ... more

Pasta-making is an ancient Italian tradition and you can find some of the best pastas in the world around every corner in this country, so why not take home the skills to impress friends and relatives with the most famous dishes Italy has to offer? This course includes working with various types of flour, eggs, and other ingredients necessary for making fresh pasta.

Participants learn the techniques of working with pasta, using a rolling-pin and machine, and will be able to master the secrets of a thousand year-old cooking tradition.
This class focuses on preparing three types of pasta with three different sauces to accompany them and also a typical Italian dessert, all of which will be eaten and enjoyed together after the class.

For those who wish to discover the techniques and secrets of the ancient Italian tradition of homemade pasta making.This course includes working with various types of flour, eggs, and other ingredients necessary for making fresh pasta. The participants learn the technique of working with the pasta. Using the rolling-pin and the machine, the participants learn the secrets of a thousand-year cooking tradition. The participants will learn to prepare three types of pasta with three different sauces to accompany them and also a typical Italian dessert.

The menu:

Fresh water pasta – Tagliatelle
Fresh egg pasta – Tortelli di patate
Raw tomato sauce
Mushrooms sauce
Olive oil, garlic and peperoncino
Panna cotta


Small classes

All equipment and ingredients provided

Learn cooking skills with a professional chef

3 types of pasta and sauces

Typical Italian dessert

Eat what you've prepared!
Florence, Tuscany, Italy
3 H
Who doesn't like the Italian cuisine, a plate of delicious pasta or a mouth-watering dessert? Come and learn how to make some typical Italian dishes to impress your date or family ... moreonce you return back home.
Do not miss the opportunity while you are in Italy to get your hands dirty during our cooking class taught by local professional chefs in a real cooking school in Florence.

You will also receive an apron and recipes so that you won't forget a fun and truly delectable experience!


Come and experience how the various regions of Italy each developed a unique taste for produce.Find out where and when some typical dishes were invented (lasagne, risotto alla milanese) and give them a try by cooking and then tasting the delicious outcome!

Learn how to make traditional Tuscan dishes. Tuscany, an amazing region that hosts mountains and rolling hills, well-known for its refined wines, as well as several prominent seaside dishes.


Meet at 2:45pm at our office.
Go to cooking school where you will meet your chef and get to prepare some delicious and typical Italian dishes.
You will also receive an apron and a recipe book so that you won't forget a fun and truly delectable experience!


Professional chef

Free apron and recipes

Real cooking experience

Italian cuisine

Get your hands messy