7-Day Wine Food Tour of Tuscany from Rome

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You will arrive in Italy’s capital city of Rome, and meet your private driver-guide to take you to the town and commune of Cortona — the perfect start of any Tuscanny food tour. You may customize this tour and add days in Rome to see the city and partake in a Tuscanny wine tour from Rome or go directly to Cortona.

On the way to Cortona, you will first stop in the walled town of Perugia that is famous for its medieval and gothic architecture. Music is also a big part of the town; there are jazz cafes on every corner, and it is rare to be walking anywhere and not be able to hear a live performance.

Perugia is also known for its art, and is renowned for being the home of great artists such as Perugino Gentile da Fabriano, Pinturicchio, Lo Spagna, Raphael. If you’re looking for a culinary highlight however you won’t be disappointed, as there is a chocolate factory and museum that offer tours to tourists.

You will continue your Tuscan culinary tour to the village of Assisi, which is best known for being the birthplace of Saint Francis, an incredibly important religious figure. A guide will meet you in the afternoon for a tour of the town and you will have some free time to explore, before returning to your driver and travelling to Cortona for the night.


After enjoying breakfast in Cortona, you will get to take part in a local cooking class to learn some of the basics in preparing classic Italian dishes, followed by a delicious lunch — meaning that you can take part of your Tuscany food and wine tour home with you.

This will be followed by a small tour of Cortona led by your driver-guide, exploring the small town which is surrounded by high stone walls and full of both Roman and Etruscan history.

Next, you will enjoy a visit to an Avignonesi winery for a guided wine tasting experience. This will be followed by a short excursion to the small village of San Quirico in the countryside, which is incredibly picturesque and feels like a step back into the past.

You will arrive at your final destination for the day by the evening, and stay the night in Bagno Vignoni.


You can make your own plans on the third day of this tour, and we highly recommend a visit to the beautiful Crete Senesi region of Tuscany to visit the Bagno Vignoni Thermal Spa. The countryside in this area is utterly idyllic, with hills, woodland and natural streams amongst the green fields.

On your journey to Crete Senesi, you will pass some of the area’s tiny villages, which are also lovely for a quick excursion and trip to a local restaurant or cafe. You will have the evening to yourself and can choose where you want to enjoy dinner in Bagno Vignoni.


After breakfast at your hotel in Bagno Vignoni, your private driver-guide will meet you and transfer you to the city of Florence. En route, you will get the chance to visit Siena, which is one of Italy’s prettiest cities.

One of the most famous sights in Siena is the central piazza which is known as ‘Il Campo’, which film fans may recognise from the James Bond movie ‘The Quantum of Solace’. Il Campo is also the location of the annual Palio horse race in Siena that takes place every summer, where the city’s seventeen boroughs compete against each other.

The Chianti hills make up the countryside on your drive to Florence, and you will be able to sit back and enjoy views of vineyards and olive groves, as well as tiny historic hamlets dotted around the landscape. For lunch, you will stop again at a traditional Tuscan villa for a delicious lunch and signature wine tasting session.

If there is time during the day, you will also have the chance to stop and explore the small town of Monteriggioni on your journey. You will arrive in Florence in the late afternoon, and spend the night right in the centre of the city.


The majority of your fifth day in Tuscany will be spent as part of a small group tour, exploring the city of Florence and learning about its history.

Florence is famous for its art and culture, and is home to works by masters of painting and sculpture such as Michelangelo, da Vinci, Lippi, Botticelli and Brunelleschi. The city is filled with frescos, statues and paintings which you will pass during the tour, and which can be found in the three churches you will visit in the morning; the Duomo, Santa Trinità and Orsanmichele.

Your tour will take you past some of the most iconic spots in Florence, including Brunelleschi’s Dome, the Gates of Paradise, the Baptistery, the Bell Tower and the Ponte Vecchio. Medieval architecture is abundant across the city, with elaborate towers attached to many buildings and several stunning Renaissance palaces.

After choosing somewhere to have lunch, you will have the opportunity to continue exploring Florence under your own steam, perhaps returning to some of the sights you passed on your tour or visiting an art gallery. You will have the evening to yourself to enjoy a meal in one of the city’s fine restaurants, and spend another night in your central hotel.

San Gimignano Panoramic


After enjoying breakfast in Florence, you will reunite with your driver-guide and travel first to the small, walled village of San Gimignano. A quintessential example of a Tuscan settlement, the village is full of medieval architecture and classic Italian towers, along with the remains of fourteen buildings that belonged to the noble families who once lived in San Gimignano.

From San Gimignano, you will then travel to Volterra, another Tuscan town that is perched on a hill overlooking the valley and offers a location that is not spoiled by tourism. Step back into the past as you learn about its Etruscan history and wander the medieval streets lined with independent shops.

After spending the morning exploring the two historic towns, you will stop at a classic Tuscan villa estate to visit its wine cellar and taste the variety of wines that are produced in the local area. You will also be served a delicious traditional lunch, again enjoying the finest flavours from the region. You will return to Florence in the afternoon for your final night in Italy.


You will depart from Florence independently after a final breakfast in your hotel.

Tuscany Food & Wine Tour Overview

This is an independent Italian food tour that is customized to your dates, level of accommodation and budget. Contact us today to get a customized price for this tour as it is or with your changes.

Journey from the historic capital of Italy to the Renaissance countryside, experiencing the surrounding landscapes and towns as you travel.

This food tour in Tuscanny sees Rome as the starting point for a sensational food and wine tour of both Italy’s favourite city and its most popular region. Tuscany is not only full of beauty and culture, but also brimming with culinary delights that make it one of the best places to visit to try some of Italy’s best dishes and flavour.

Rome’s grandeur and history are matched with the splendour of the city of Florence, known as the birthplace of the Renaissance and a true delight for those who appreciate great artists such as Caravaggio, Raphael, and Michelangelo. Nearby areas such as Siena, San Gimignano and Crete Senesi offer varied experiences of Tuscany, from medieval architecture to untouched scenery.

This is not a fully escorted tour, but on some days you will be met by a private local guide to lead you on sightseeing excursions, and your transfers will be done by a private driver. There will also be 24/7 local assistance on call in case of any issues.

Full Availability

All 2024

Departure Dates & Pricing

This tour is customized to your exact dates. Please contact us for a price for the date you would like to travel.

Prices starting from:

This tour features custom pricing which means you get to pick your departure dates, level of hotels and make any changes to the program and we will then price it out for you. Just email us at info@italy4real.com for a custom quote.

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What’s Included in this food tour of Tuscany?


  • Breakfast each morning at your hotels
  • A driver-guided tour of Assisi and Perugia
  • 1 Night stay in Montepulciano
  • A driver-guided tour of Montepulciano and San Quirico, including lunch and a wine tasting opportunity
  • A cooking class at Fattoria Svetoni in Montepulciano
  • 2 Nights in the Crete Senesi area
  • A driver-guided tour of Siena and Monteriggioni, again including lunch and a wine tasting opportunity
  • Wine tasting and tour of the Avignonesi Wine Estate vineyards
  • 3 Nights in a hotel in Florence
  • A driver guided tour of San Gimignano and Volterra, followed by lunch and wine tasting at a Tuscan villa
  • A small-group walking tour of Florence

Not Included


  • Transfer out of Florence on departure
  • Italian city tax
  • The airfare to and from Italy. We can help you with the airfare for your trip, just ask when booking
  • Travel Insurance. This may be purchased through us or independently, but it is required for travel

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