Tour description

Tuscany is a region where past and present merge harmoniously, often renowned for its art, history, and idyllic landscape. Enjoy the quintessential Italian experience and dive deep into its rich culture among medieval hill towns, rolling green hills, and thriving vineyards. The cities of Siena, Pisa, Lucca, Cortona, and Arezzo contain some of Italy’s most famous works of art and historical treasures, while villages such as San Gimignano, with its iconic towers, or Pienza are tiny Renaissance jewels that sit at the heart of this gorgeous landscape. The Tuscany region is sought after by wine lovers and foodies alike. Famous for its Chianti, Montalcino, and Montepulciano wineries and delicacies like truffles, mushrooms, and cured meats that please any palette. 

Get your hands dirty with an authentic Italian cooking class, winery tours, UNESCO World Heritage site visit, and more on our small group tour to Tuscany. Experience everything this alluring region has to offer like a local.

Read what our friends have to say about this fantastic tour over on Tripadvisor



  • Over 10 sightseeing tours & cultural experiences
  • Walking tours of magical cities like Florence, Lucca, San Gimignano, Cortona, and Orvieto, with their historical treasures & popular markets
  • Visit popular UNESCO World Heritage Sites
  • Wine tours and tastings
  • Hands-on cooking classes
  • Cultural concert


  • Small group tour of 12-14 participants
  • Knowledgeable English-speaking tour director
  • Entrance fees for all sites
  • Tour transportation in a private air-conditioned motor coach
  • Local guides in the outlined cities and towns
  • Hotel city and service taxes at all accommodations and restaurants are included
  • Transfers to the Airport or Train station at scheduled times
  • Baggage transfers and porters are included
  • All breakfasts, two lunches, and three dinners are covered. Main meals include wine, mineral water, espresso, or tea
  • Activity level: Light/Moderate
  • Terms & Conditions/single supplement and FAQ

Not Included

  • Travel insurance and visa fees/Trip Interruption & Cancellation Insurance
  • Any charges for extras not listed in the itinerary
  • Room services, telephone charges, laundry fees
  • Gratuities for the tour director and local driver
  • Single room supplement


Welcome to Tuscany! Today, you’ll arrive at Florence airport or train station and travel to the city center for a fascinating guided walking tour at 09:30 am to explore the city’s architectural highlights such as Ponte Vecchio, Piazza della Signoria, the Duomo Square, San Lorenzo market and Piazzale Michelangelo. Afterward, you’ll visit the Uffizi Gallery on a self-guided tour to see one of Italy’s leading art galleries up close. In the afternoon, we’ll head to LUCCA, an exemplary Tuscan town, for your first two nights at the central “The Tuscanian Hotel(or similar). Tonight, we’ll take you to our favorite local restaurant for a traditional Tuscan dinner. 

Meals: Breakfast and lunch on your own, dinner included

Accommodation: Overnight in Lucca


This morning, we will discover the beautiful town of Lucca on foot with a local tour guide. This magnificent city is surrounded by massive walls completed in 1504 to help the city’s defenses. On our tour, we’ll explore nearly every era in Italian history: a Roman amphitheater, superb Romanesque churches, and delicate Art Nouveau facades. Our stroll takes us to the Duomo di San Martino, Lucca’s main church built in Romanesque style, its peaceful narrow lanes, the medieval buildings, tiny piazzas, and many other reminders of the city’s long history. Afterward, we’ll visit an 18th-century Mansion House with its delightful gardens. We’ll enjoy a delectable street food experience and have the rest of your day at your leisure. This evening, we’ll take in an eventful Puccini Concert at a local church

Meals: Breakfast included, lunch and dinner on your own

Accommodation: Overnight in Lucca


Leave the city and head through the colorful rolling hills of CHIANTI to visit the rural town of Radda in Chianti, which has maintained its charm intact from time immemorial. In the 50s, its land and farmhouses were abandoned. Still, with its rediscovery in the 70s, the old terraced olive groves and vineyards, which had fallen into disuse, gave way to more intensive and extensive farming. We will head to a stunning ancient Castle for a hands-on cooking class, followed by a delicious lunch. Afterward, we’ll drive to the charming hill town of SAN GIMIGNANO, known as the “Manhattan of Tuscany.” It is an astonishing example of a walled Medieval hilltop town, also known for its dry white wine, Vernaccia, and its colorful local crafts: hand-painted pottery, alabaster, olive wood items, and much more. We’ll stay here for the next two nights at the charming “Relais Santa Chiara” or similar, with breakfast included.

Meals: Breakfast and lunch included, dinner on your own

Accommodation: Overnight in San Gimignano


Today, we’ll visit the medieval town of SIENA, once a capital that rivalled even Florence. We’ll begin our tour by exploring the city’s historic center in Piazza del Campo and the surrounding maze of ancient alleys with an included visit to the Duomo, one of Italy’s greatest cathedrals. In the early afternoon, you’ll enjoy a panoramic journey through the Crete Senesi to discover the sleepy MONTERIGGIONI, a true gem of an ancient hilltop town. It is completely encircled by high walls with 14 heavily fortified towers, built to guard the northern borders of Siena’s territory against invasion by Florentine armies. We will enjoy dinner together this evening in a local restaurant. 

Meals: Breakfast and dinner included, lunch on your own

Accommodation: Overnight in San Gimignano


Our adventure starts with a visit to the hill town of MONTALCINO for a tour of the famous Brunello di Montalcino winery. Here, we’ll taste the region’s unique wines with a delectable lunch to go with it. Soak in the atmosphere of the captivating Tuscan scenery. Afterward we continue to the delightful town of PIENZA. This charming town was almost completely redesigned in the 15th century by Pope Pius, and it overlooks the cypress-lined hills of the stunning Orcia Valley. In the afternoon, we’ll stop by the majestic 9th-century abbey Sant’Antimo, said to have been founded by Charlemagne. After our tour, we’ll drive to the romantic town of CORTONA, where we’ll stay at the central “Hotel San Michel” (or similar).

Meals: Breakfast and lunch included, dinner on your own

Accommodation: Overnight in Cortona


CORTONA is a picturesque and one of the oldest Italian hill towns, founded by the Etruscans. Today, it is a charming maze of old streets and medieval buildings situated at 1,800 feet, offering unforgettable views over the nearby Tuscan hills. The day begins with a visit to the Etruscan Museum, packed with cremation urns, vases decorated with black figures, and Bucchero ware burnished to resemble bronze. Afterward, we journey to the “green heart of Italy,” the Umbria region, and the spiritual town of ASSISI. Sitting on the green hillside with the town climbing ever higher behind it, this is a UNESCO World Heritage site that attracts pilgrims worldwide. The skyline in Assisi is dominated by the vast Basilica of St Francis complex, which includes a Franciscan monastery and two churches. We’ll spend the last two nights of your tour in the unique town of ORVIETO, staying at the central, family run “Hotel Duomo” (or similar).

Meals: Breakfast included, lunch and dinner on your own

Accommodation: Overnight in Orvieto


This morning, we’ll enjoy a guided walking tour visiting the mediaeval Duomo, featuring a frescoed chapel by Fra Angelico and Luca Signorelli’s masterpiece, The Last Judgement. Next, we explore the formerly secret passages of Parco Dells Grotte, a labyrinth of underground caves used since the Etruscan times. Then, you’ll have the afternoon to explore Orvieto. This beautiful city is situated on the summit of a high mountain. It has some of the most dramatic sights in Europe, rising above the almost-vertical face of a cliff with impressive defensive walls built of local volcanic stone. Originally populated by the Etruscans, Orvieto is a charming city rich in history and tradition, with lots to see. In the evening, we will gather again to enjoy a celebratory dinner in a local restaurant. 

Meals: Breakfast and dinner included, lunch on your own

Accommodation: Overnight in Orvieto


Today, we’ll have our morning transfers to the Rome airport or train station. If you want to extend your Italian vacation, we highly recommend our tours such as 8 days Liguria small group tour, Sardinia & Corsica or Sicily. While we say Arrivederci to Italy, you’ll soon realize how many magical memories you’re taking home with you!


2025 TOUR PRICE: € 3,800    SINGLE SUPPLEMENT: € 500    currency converter

Prices are per person based on double room occupancy for 8 days/7 nights

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