Classic Tour of Italy


Classic Tour of Italy, 7 Days

Crete Senesi | Florence | Montepulciano


Explore the endless delights of Tuscany via the gateway of the Eternal city. You will transfer from the capital into one of the most popular areas of Italy. Teaming with olive groves, traditional vineyards, medieval villages, and cities full of art, the combination of good food, history and culture will please any visitor.
Visit the stunning Florence with works of art by the great masters, like Caravaggio, Raphael, and Michelangelo. Sandy coloured Siena and San Gimignano overlook the beautiful, natural Tuscan landscape. On the subject of nature, you will find the perfect, protected areas in the Crete Senesi where you can enjoy some relaxing alone time in the therapeutic atmosphere of the thermal spa. The Cortona countryside is where you will enjoy some delicious Tuscan cuisine and try your hand at making some yourself in your own private villa.


Day 1: From Rome to Val D’Orcia – Via Perugia and Assisi

You will arrive independently in Rome where you will meet your tour guide and transfer to Cortona. On the way, you will stop for an independent visit in Perugia and Assisi.

A medieval-walled town, Perugia is famous for its squares, jazz cafes and Gothic palaces. The music is everywhere within the town and will serve as the soundtrack of your visit. It is also the capital of Italian Art, since Perugino Gentile da Fabriano, Pinturicchio, Lo Spagna, Raphael and lots of others have lived and worked here. The famous chocolate maker Perugina is also connected to the town. If you are a chocolate lover, you must visit the Museum of Chocolate and the factory, although English tours need to be reserved ahead of time, so please let us know if you want to visit.

Continuing your journey, you will arrive in the outstanding village of Assisi, where St. Francis was born. A guide will take you around the town and you will have some free time to explore before arriving in Cortona in the late afternoon. Stay overnight in Montepulciano.

Day 2: Cooking Class in Montepulciano & vineyards experience + Cortona and San Quirico

In the morning, you will join a cooking class and then have a delicious lunch. A short visit of Cortona with your guide then awaits you in the afternoon, and a tour of the Avignonesi Winery and a wine tasting. A small, charming town in the Valdichiana, Cortona is built high up on a hill and is the location for the film, “Under the Tuscan Sun”. Stone walls that date back to Etruscan and Roman times surround the town, and you can see an incredible view of the valley from every corner. After Cortona, you will stop briefly in San Quirico to independent explore and then continue to Bagno Vignoni where you will stay overnight.

Day 3: Crete Senesi – Free Day

Relax and enjoy your own exploration of the Crete Senesi region of Tuscany today, or perhaps instead use your free time to enjoy the Bagno Vignoni Thermal Spa. The name “Crete Senesi” translates to “Sienese Clays”. It is an amazing place to visit if you are looking to relax in a peaceful place where you are surrounded by pure, unaltered nature. The hills, woods, waters, and a semi-desert all break up the emerald Tuscan landscape. There are countless little villages scattered through this beautiful region for you to discover, including Asciano, Buonconvento, Monteroni d’Arbia, Rapolano Terme, San Giovanni d’Asso. Stay overnight in Bagno Vignoni.

Day 4: Siena and Monteriggioni

Meeting your tour guide at the hotel, you will transfer to Florence. Stopping at Siena and Monteriggioni on the way, you will enjoy an independent tour of these charming villages. Enjoy the outstanding views on the drive. The winding Chianti hills are dotted with olive trees, vineyards, cypresses, and castles.

As one of Italy’s most beautiful medieval cities, Siena holds a central piazza at its heart called Il Campo. The piazza is known across the world for its famous Palio, the horse race run there twice every summer. It was featured in the James Bond film, “The Quantum of Solace”.

Driving on to Florence, you will stop in a wonderful Tuscan vineyard and Villa for a cellar visit, wine tasting and a delicious lunch. It will be a fantastic day where you will encounter all the best parts of this glorious region. Arriving in Florence in the late afternoon, you will stay overnight in the heart of town. If there is time, you will take a break in the sweet, little town of Monteriggioni. Stay overnight in Florence.

Day 5: Florence

Join a small group today to discover Florence and learn more about the two thousand years of exciting history that impacted the world forever. Florence is packed with historic sculptures, frescoes, and paintings. During your visit, you will tour three churches – the Duomo, Santa Trinità and Orsanmichele. Before the day is over, you will know how Florence became one of the best arts centers in the world, and was home to da Vinci, Lippi, Michelangelo, Botticelli, and Brunelleschi and many more.

Walking through the medieval center of the city, you will pass the Bell Tower, the Baptistery, the Gates of Paradise, Brunelleschi’s Dome, Piazza della Signoria, Palazzo Vecchio and the Ponte Vecchio, as well as Medieval towers and Renaissance palaces. After the morning tour, you can enjoy wandering the city or return to explore any of the sites that we have experienced earlier in the day. A relaxing lunch can be had in the city before heading over to the Academia in the afternoon to visit Michelangelo’s the David. Stay overnight in Florence.

Day 6: Volterra & San Gimignano

You will be collected after breakfast by your driver to go on a full day tour to San Gimignano and Volterra. A quintessential Tuscan town atop a hill, San Gimignano is famous for its medieval architecture and towers that sit above all the buildings around them. Building 72 tower-houses, the patrician families of San Gimignano wanted them to represent their wealth and power, but only 14 remain today.

Next you will head to Volterra, another hill town in Tuscany, which remains unspoilt and tends to be less populated by tourists. Volterra has a rich history dating to the Etruscan period and you will see many examples dating back to 4th century B.C. Volterra appears to have avoided the stress of today’s modern world and it gives the impression of stepping back in time. Walking the medieval streets, you will wonder at the beautifully crafted items for sale in the shops that line the streets. The day will finish with a stop at a Tuscan villa estate for a cellar visit, wine tasting and lunch. This wonderous day will give you opportunities aplenty to experience the best that the region has to offer. Finish by staying overnight in Florence.

Day 7: Departure

You will independently transfer back to the airport to return home.


The hotels might be replaced with similar ones due to lack of availability.

Name: Orto delle Terme Or Similar
Place: Crete Senesi
Name: Palazzo Castri Or Similar
Place: Florence
Name: Fattoria Svetoni Or Similar
Place: Montepulciano

What’s Included

• 6 Overnights at centrally located 4 star hotels
• Driver guided tour of San Gimignano and Volterra with lunch and wine tasting
• Small Group Walking Tour of Florence
• Driver Guided tour to Signature “Montepulciano & San Quirico”. Pick up in Bagno Vignoni, drop off in Florence with wine tasting and lunch
• Driver Guided tour to “Siena & Monteriggioni”. Pick up in Cortona, drop off in Bagno Vignoni with wine tasting and lunch
• Cooking Class at Fattoria Svetoni
• Wine tasting and visit of Vineyards at Avignonesi Wine Estate
• Driver Guided tour to “Assisi & Perugia”. Pick up in Rome, drop off in Cortona

Not Included:
• City Tax to be paid locally
• Drinks on meals
• Arrival & Departure Transfer
• Porterage at airport
• Tipping for guide, driver and hotel staff
• Any Insurance
• Any Item, product or service not specifically listed under “Inclusions”

Prices & Optionals

Prices may vary according to dates of travel.

Price From Per Person | Double Occupancy: CONTACT US
Price From Per Person | Single Occupancy: CONTACT US


  • Address: \
  • Country: United States


  • Property ID: VIT-11
  • Property Type: Italy Tours

You May Also Like

Apulia Discovery

Bari | Alberobello | Ostuni | Matera | Lecce

FromUpon Request

Duration6 Days

Book Now

The Best of Italy Tour

Rome | Florence

FromUpon Request

Duration6 Days

Book Now

Northern Italy Gourmet Journey

Bologna | Modena | Pavia | Alba

FromUpon Request

Duration8 Days

Book Now

Alps, Matterhorn & Northern Lakes


FromUpon Request

Duration8 Days

Book Now