Narrow streets, amazing valleys and natural stone carved in the architecture of the old-town houses, churches and cathedrals. That is how Tuscany looks like when visited in this tour, that begins with Montalcino and Montepulciano as the most iconic wine places in Tuscany where you can enjoy tasting the noble wines.

The tour then continues in Bagno Vignoni, San Quirico, Pienza, Chianti, San Gimignano and Siena – and in each of these places you will be able to do different activities and see different cultures. From oil making to cheese tasting and fine dining, this tour lets you explore Tuscany off the regular touristic prism and see every bit of its untouched beauty with your own eyes.

Day 01: Florence Arrival | Welcome to Italy! Upon your arrival at the Airport, our local English speaking representative will be waiting to welcome you. You will be transferred by private car to your hotel in Montalcino. Rest of the day at leisure. Overnight in Montalcino.

Day 02: Montalcino and Montepulciano | Breakfast at the Hotel. Today, you will taste some of the most famous Italian wines: Montalcino and Vino Nobile di Montepulciano. Your private driver-guide will pick you up from the hotel and drive you first to Montalcino. This ancient village is best known for its red Brunello di Montalcino wines, made with Sangiovese Grosso grapes. You will have a private visit to a Brunello producer such as the prestigious Poggio Antico estate. On the way to the winery, you can stop for a quick visit of the stunning ruins of the 9th century Abbazia di Sant’Antimo. At the winery you will tour the cellars, the vineyards and take in the gorgeous views and taste Brunello “Riserva” and also Rosso di Montalcino. Lunch will be in the winery’s restaurant. After the lunch, carry on to Montepulciano, a small village of Etruscan origin and one of the most beautiful hill towns in Tuscany. The Nobile wines of Montepulciano, were the first to be given the ultimate quality level of DOCG certification. You’ll visit a top estate such as Valdipiatta or Avignonesi and enjoy a tasting of Vino Nobile wines. In the late afternoon, enjoy free time on your own in Montepulciano and transfer back to your Hotel. Overnight in Montalcino.

Day 03: Day at Leisure or *Optional Tour: Bagno Vignoni – San Quirico – Pienza | Breakfast at the Hotel. In the morning meet your driver and guide at the lobby. This morning depart for Bagno Vignoni, a little more than a group of houses surrounding one of the most memorable squares in Tuscany. Its exceptional square, made up of a great pool of natural spring water, is completely enclosed by medieval and Renaissance buildings. The hamlet is noted for its thermal baths since the time of the Romans, and was frequented by St. Catherine of Siena and the Medici family. Below the town natural thermal pools in mineral outcroppings are still accessible for swimming and wading in. The town of Bagno Vignoni, with its remarkable original historical center is the perfect Tuscan natural setting. Continue to San Quirico d’Orcia with its original medieval street plan intact, is home to the celebrated 12th-century Romanesque collegiate church of Collegiata. Its façade is abundant with Romanesque symbols, portions from the 12th century. Especially unique to the area is its pleasant and elegant 16th century Renaissance garden Horti Leonini of the Chigi family. You will enjoy a Lunch/Food and Wine Tasting in a local Wine Estate before departing for Pienza. Built on a hill that dominates the Val d’Orcia, Pienza is a completely intact, elegant Renaissance town, proclaimed a UNESCO World Heritage of Humanity site (1996) for its important example of Renaissance urban planning, architecture and monuments. Pope Pius II, a great humanist, commissioned his native village of Corsignano to be transformed from a medieval town to a splendid Renaissance city. The itinerary includes the exceptional Cathedral, Piazza Pio II, Palazzo Piccolomini and Palazzo Borgia’s courtyards. Late afternoon continue to your hotel. Overnight in Montalcino.

Day 04: Montalcino – Chianti | Breakfast at the Hotel. In the morning meet your driver at the lobby. On route to your Hotel in Chianti you will take you a Tour of the Chianti little towns:, your English-speaking driver will take you through the scenic hills of Chianti before transferring you to your Hotel in Chianti. Only a few regions in Italy can offer such a beautiful and rich panorama as the Chianti wine region. This is the classic Tuscan countryside – Green hills with miles after miles of vineyards producing some of Italy’s best marketed wines, olive groves, gentle rolling hills, ancient walled villages and panoramic roads like you have never seen before. Chianti Classico spreads from Florence to Siena and includes the small municipalities of Castellina, Greve, Panzano, and Radda in Chianti. The splendid Romanesque churches, farmhouses, villas and castles dotting the landscape complement the region’s enchanting natural beauty. Lunch/Food and Wine Tour in a local Wine Estate. In the afternoon continue to your hotel in Chianti.

Day 05: Day at Leisure or *Optional Tour: Oil, Cheese & Wine in Impruneta and Chianti. | After breakfast at the hotel, meet your driver/guide in the lobby for a Private Tour of the Tuscany countryside, on route to your Hotel in Tuscany. This excursion begins in the heart of the Tuscan oil kingdom: the hills around Impruneta, were you will visit the Torrerossa oil farm. Here the olives are still collected by hand with the help of wood ladders leaning against the olive branches. Torrerossa still owns an old oil press, the oil is stored in antique enormous terracotta jars. After lunch in a characteristic local restaurant continue on to San Casciano hills. In the Chianti DOCG production area you will visit the Corzano e Paterno winery and cheese farm, specialized in the production of cheeses with traditional methods, using the milk from the farm’s sheep. You will also taste their excellent wines. Late afternoon return to your hotel in Chianti.

Day 06: San Gimignano – Siena | After breakfast at the Hotel, meet your driver and guide in the lobby. Today enjoy a Private Tour of the Tuscany Countryside. You will first visit San Gimignano, a fantastic example of medieval architecture declared a World Heritage Site by UNESCO, famous for its medieval skyscrapers. These tower houses were built by local families at the height of the Guelph-Ghibelline conflict. As you stroll around this compact hill town, your Private Guide will introduce you to the life & times of Medieval San Gimignano. Spend some time here at leisure before meeting with your driver and heading to the Chianti Hills to enjoy a Food a Wine Tasting Tour at Fattoria Sant’ Agnese, a family-run Winery. Here you will be warmly welcomed by its passionate winemaker and after the guided tour of the cellars and the lovely aromatic garden; a delicious tasting of different wines and local products will be waiting for you to make you a lovely Tuscan Lunch. In the afternoon together with your Guide visit Siena. Walking along the narrow medieval streets, you will admire the splendid Cathedral where you can visit the marvelous interior including the Libreria Piccolomini. You may continue to Piazza del Campo, where the famous Palio horse race is held twice a year, overlooked by imposing Palazzo del Comune. Siena was a very remarkable City-State in the Middle Ages, most of its important monuments were built between the XIII and XIV century, today we can still admire these artistic and architectural wonders and much more. There are so many hidden spots within the city walls where past and present blend together. They are off the tourists’ beaten paths and can be discovered only with a Private Guide. Late afternoon return to your hotel. Overnight in Chianti.

Day 07: Chianti – Perugia – Assisi | Breakfast at the Hotel. In the morning meet your driver at the lobby. On route to your Hotel in in the Umbrian countriside, meet your private guide in Perugia, capital city of Umbria, for a morning Private Guided Tour. You will see the recently restored 13th century Fontana Maggiore, the Palazzo dei Priori which houses the National Gallery of Umbria and the Collegio del Cambio with its frescoes by Perugino and amble along Perugia’s elegant main street, Corso Vannucci. Lunch at leisure. In the afternoon you will head for the city of Assisi known throughout the world as the birthplace of Saint Francis. We will take a guided walking tour of the city and see the many important sights, including the spectacular Basilica of Saint Francis with its frescoes by Giotto. Late afternoon continue to your Hotel. Overnight in the Umbria countryside.

Day 08: Day at Leisure or *Optional Tour: Spoleto – Montefalco – Bevagna – Spello | After Breakfast a the Hotel meet your driver and guide at the Hotel Lobby. Today visit three of the most characteristic Umbrian towns: Montefalco, Spello and Bevagna. The tour starts with Montefalco. known as “the balcony of Umbria” because of the panoramic views it enjoys. After a brief walking tour of the town you will get some free time. We will then visit Bevagna, another prosperous Roman settlement, where Roman aristocrats used to build their villas, which is nowadays a tranquil town whose streets are lined with lovely crafts shops, delicatessens and trattorias. Our last stop is the hilltop town of Spello, a former Roman colony where large parts of the Roman fortifications remain intact. In Spello we will visit the church of Santa Maria Maggiore with its magnificent frescoes by Pinturicchio in the Cappella Baglioni. Late afternoon return to your Hotel in the Umbria countryside.

Day 09: Citta di Castello – Gubbio |After breakfast at the hotel, meet your driver and guide in the lobby. Today’s journey begins at Città di Castello, one of Umbria’s most visited tourist destinations, a place where ancient and contemporary art forms live side by side in perfect harmony. The tour of the town starts with a visit to Palazzo Vitelli and Palazzo Albizzini. Continue on to enjoy a visit to the Duomo Museum, located next to the cathedral. Last, but not least, there is the Pinacoteca Comunale, which occupies a part of the prestigious Palazzo Vitelli alla Cannoniera and contains important renaissance masterpieces by Raffaello and Ghirlandaio. Lunch at leisure. In the afternoon visit Gubbio, a delightful medieval town, its center brimming with edifices of great historical and architectural importance such as Palazzo dei Consoli, Palazzo Pretorio and Palazzo del Capitolo dei Canonici. Another building worthy of a visit is the Palazzo Ducale, now home to an excellent history museum. Late afternoon return to your Hotel. Overnight in the Umbria countryside.

Day 10: Florence Departure | Breakfast at the Hotel. Unfortunately, it is time to say Arrivederci. At your convenience, we will transfer you to the airport of your choice. Ciao!

  • 3 Nights in Montalcino
  • 3 Nights Chianti
  • 3 Nights in Umbria
  • Assistance and Porterage at Airports, Train Stations and Hotels
  • Private Transportation by Mercedes E or V Class with English Speaking Driver
  • Private Guided Tours with Professional Local Guides | Door to Door Service
  • Entrances to Museums, Galleries, Archeological Parks and other Venues
  • Breakfast at Hotels, All Food & Wine Tours/Enogastronomic and Most Lunches.
  • 24/7 Assistance and Support from our Ground Operational Office in Italy

Private Package Tours Rates

  • Gold: in 4* Boutique Hotels: Starting at 1,000 Euro per person/per day
  • Diamond: in 5* Luxury Hotels: Starting at 1,500 Euro per person/per day.

For Private Small Groups of 4, 6 and 8 + price per person will be lower.

For Custom Made Tours we work with any reasonable Budget

Embark on an unforgettable journey through the beautiful regions of Tuscany and Umbria in Italy with our exclusive tours. Our tours of Tuscany and Umbria Italy take you to the most picturesque towns and villages, giving you an authentic experience of the rich cultural heritage and stunning natural landscapes that these regions are known for. Our expert guides will take you to hidden gems that are off the beaten track, providing you with a unique insight into the local history, art, and culture. From the charming medieval villages of Tuscany to the beautiful hilltop towns of Umbria, our tours are tailored to suit your interests and preferences. Indulge in the delicious local cuisine and wine as you explore the breathtaking scenery, making memories that will last a lifetime. Don’t miss the opportunity to discover the magic of Tuscany and Umbria with our exclusive toursContact us at +1 (855) 539 0045 to book your tours of Tuscany and Umbria Italy and start planning your dream vacation.


The “Tuscany & Umbria Towns and Villages” tour is a captivating journey that takes you through the charming towns and villages of Tuscany and Umbria, offering an authentic experience of the region’s culture, history, and landscapes.

The tour covers a selection of picturesque towns and villages in Tuscany and Umbria, including Cortona, Montepulciano, Pienza, Assisi, and Gubbio, among others.

Booking the “Tuscany & Umbria Towns and Villages” tour is easy. Visit the tour page, select your preferred travel dates, provide the necessary details, and follow the instructions to complete the reservation process.

The “Tuscany & Umbria Towns and Villages” tour offers a curated itinerary, but if you have specific preferences, you can inquire about any potential customization options.

If you wish to extend your stay, please contact our team. They can provide assistance and recommendations for extending your time in Tuscany and Umbria.