When we conceived this magical group tour through the regions of Tuscany and Chianti, we did so with the firm intention of offering a unique experience. From the beginning, we wanted this group journey to Tuscany to be much more than a simple Italian wine route; we aspired to design a journey that would blend the distinction of the region with the warm hospitality of its people.
This exclusive Tuscan wine route in Italy will immerse you in a world of sensory discoveries, from winery visits and wine tastings to unforgettable excursions to local vineyards and charming villages scattered across the most beautiful Tuscan landscapes. Picture yourself exploring the hills of Chianti, participating in Tuscan wine tastings that will delight your senses, and visiting wineries where you’ll uncover the secrets of winemaking, all while indulging in enchanting landscapes full of serenity that make Tuscany such a special destination.
Every detail of this tour, a unique group journey to Tuscany, has been carefully planned to offer you authentic moments and unforgettable experiences. Our group tour is much more than a mere journey; it’s a unique opportunity to share our passion for wine tourism, strengthen the connection with history, and enjoy the cultural richness of the charming region of Tuscany. Join us on this unforgettable adventure through beautiful Tuscany!
Day 1, Sunday, May 26: Arrival at Florence Airport – Val D’Orcia
Arrival at Florence Airport on your own.
Note: Airfare not included.
Meet and greet by our driver or group tour guide (depending on the group size) at the Arrivals gate of the Airport.
Private transfer in a comfortable luxury vehicle from the airport to Val d’Orcia, in southern Tuscany. Val d’Orcia is a UNESCO-protected region, home to the most beautiful villages in Tuscany, surrounded by bucolic landscapes where cypresses play a prominent role.
Check-in for 2 nights at a delightful 4-star hotel in a double superior room with breakfast included.
Travel duration: approximately 1 hour and 50 minutes.
Dinner and night free to enjoy at your leisure.
Day 2, Monday, May 27: VAL D’ORCIA (MONTALCINO – PIENZA)
You will start the day with a delicious breakfast at the hotel.
Depart in the morning towards Montalcino, a picturesque town globally renowned for its rich winemaking tradition and medieval charm. Here, you will embark on a guided tour of a winery producing the famous Brunello di Montalcino wines, and indulge in a wine tasting featuring their exclusive selection.
We will continue to the beautiful town of Montalcino for a short self-guided tour, allowing you to appreciate the Fortezza or Rocca di Montalcino, the Cathedral of Montalcino, Piazza Garibaldi, and the Sanctuary of Madonna del Soccorso.
After this exploration, you will savor a lunch at a typical osteria, where you can indulge in homemade Tuscan cuisine. The menu includes a starter, main course, and dessert. Beverages are not included.
We will continue this day with a visit to the Abbey of Sant’Antimo, a magnificent example of Romanesque architecture in Tuscany, attributed to Charlemagne around the year 750. This stop proves to be an essential experience, blending history and architecture in a peaceful and serene setting. Admission includes audio guide.
After concluding this tour, we will transfer to Pienza for a visit and tasting of the renowned Pecorino cheeses at a traditional farm. Pecorino cheeses are not only delicious but also represent centuries of cheese-making tradition in the region. Each bite is a direct connection to Tuscany’s rich gastronomic heritage.
Next, a brief stop in the charming Pienza, also known as the Renaissance city, famous for its harmonious urban design and exceptional architecture. Here, you can explore Palazzo Piccolomini, the Cathedral of Pienza (Cattedrale dell’Assunta), Palazzo Comunale (the town hall of Pienza), and Piazza Pio II during a short self-guided visit.
Return to the hotel. Rest time and dinner on your own.
Day 3, Tuesday, May 28: Montepulciano
Wake up to a new morning enjoying a delicious breakfast at the hotel and get ready for a day that promises to explore the best of this region!
After an early check-out this morning, your next (brief) stop will be Montepulciano, a charming Tuscan town renowned for its exceptional architecture. You’ll have the chance to explore Piazza Grande, the heart of the city, where the Town Hall and the majestic tower offer breathtaking panoramic views. We also recommend visiting the Cathedral, the church of Sant’Agostino, and the Sanctuary of the Madonna di San Biagio on the outskirts.
The day will continue with a unique wine experience. We will proceed to the first winery of the day for a private guided tour where you’ll learn about the vineyard and winery operations, followed by an aperitif with sparkling wine from this prominent wine group. Afterward, enjoy a lunch at the winery, paired with four magnificent wines, allowing you to taste traditional Tuscan cuisine. The menu includes a selection of typical starters served at the center of the table, a main course, dessert, and coffee.
Once this experience is concluded, we will continue the journey to the Chianti Classico region, where winemaking tradition comes to life exceptionally. You will be transferred to one of the prestigious wineries in Chianti for a guided tour and a tasting of some of the finest wines from this renowned wine region.
After the visit, and to cap off this day on a high note, you will head to an exclusive 4-star hotel for a 3-nights check-in in a Superior double room with breakfast included.
Dinner and night free to enjoy at your leisure.
Day 4, Wednesday, May 29: SIENA – MONTERIGGIONI
You will start your day with a delicious breakfast at the hotel, preparing to immerse yourself in a unique experience!
The day will begin with a wine tasting at the hotel’s winery, where you can delve into an atmosphere of sophistication and learn about all the secrets behind the production of their exceptional wines.
Once this experience is concluded, you will continue this day to the beautiful city of Siena, where you will have a private guided walking tour with a local guide.
Siena, a historical gem in the region of Tuscany, is known for its distinctive Piazza del Campo, a shell-shaped square that hosts the famous Palio event, and for its Cathedral with an impressive facade and interior adorned with artistic masterpieces of Italian Gothic art. Duration of the tour: 2 hours and 30 minutes. Entrance to monuments not included.
After this tour, you can recharge with a delicious lunch at an authentic osteria, indulging in homemade Tuscan cuisine. The menu includes a starter, main course, and dessert. Beverages not included.
On the way back to the hotel, we will make a brief stop in the picturesque village of Monteriggioni, known for its stunning medieval wall that completely surrounds it. The walls, adorned with well-preserved towers, create an impressive panoramic view and transport visitors to medieval times. Monteriggioni is also known for its connection to Dante Alighieri’s famous literary work “The Divine Comedy”, which mentions the fortified city.
Return to the hotel to take advantage of its facilities and enjoy your free time. Dinner on your own.
Day 5, Thursday, May 30: VOLTERRA – SAN GIMIGNANO
After recharging with breakfast at the hotel and once ready, we will start the day heading to Volterra for a visit to a more traditional-style winery, which, at the same time, maintains elegance and simplicity. Here, you will have a private guided tour of their vineyards and winery, followed by a guided tasting of some of their most exclusive wines.
Once this experience is concluded, we will transfer to the town of Volterra for a brief self-guided visit. This small city stands out as one of the medieval towns that still maintains its essence and walls. Here, you will have the opportunity to enjoy lunch at a traditional Osteria, based on high-quality, locally sourced ingredients, skillfully prepared according to ancient recipes of Tuscan tradition. The menu includes a starter, main course, and dessert. Drinks are not included.
After lunch, with recharged energy, we will continue the journey to the beautiful and picturesque town of San Gimignano, where you will have a private guided walking tour with a local guide. This iconic medieval city, declared a UNESCO World Heritage Site and known as “The Town of Fine Towers”, stands out for its distinctive skyline of towers that rise majestically above the Tuscan hills, as well as its churches and narrow cobbled streets. Duration of the tour: 2 hours. Entrance to monuments not included.
Return to the hotel to take advantage of its facilities and enjoy your free time.
Day 6, Friday, May 31: CASTELLO DI BROLIO – FLORENCE
Breakfast at the hotel and check-out.
Departure from the hotel in the morning and transfer to the first stop, the charming municipality of Gaiole in Chianti, a town surrounded by fortifications and castles.
Here, you will make a stop for a guided tour of Castello di Brolio, a medieval castle that has been part of the Ricasoli family since 1141. Enjoy a private guided tour of the castle and its different wine production spaces, as well as a wine tasting in a private room. This visit concludes with lunch at their Osteria, where you will savor Tuscan cuisine, both traditional and innovative, in a relaxed and welcoming setting surrounded by a wooded park just below the castle. Menu without drinks.
After concluding this visit, you will continue the journey to the beautiful city of Florence for a 2-nights check-in at a comfortable and centrally located 4-star hotel, in a Standard double room with breakfast included.
Travel duration: approximately 1 hour and 25 minutes.
Dinner and night free to enjoy at your leisure.
Day 7 – Saturday, June 1 – Pisa – Lucca
Wake up on your second-to-last day of this magical trip with a rich breakfast at the hotel. Once ready, you will be transferred to the city of Pisa (renowned for its rich history and UNESCO World Heritage architectural structures) and the city of Lucca to explore these beautiful cities of authentic Tuscan tradition.
The guided tour in Pisa will start in front of the Opera del Duomo Museum, later exploring the Miracle Square, the Baptistery of San Giovanni, and then admiring the Gothic dome and the beautiful Pisa Cathedral. Of course, the famous Leaning Tower cannot be missed, followed by a walk through Via Santa Maria and the Romanesque church of San Sisto.
You will stroll through the alleys of the historic center, reaching the Knights’ Square and walking along Borgo Stretto, one of the most commercial streets. You will also see the ancient Market Square and finally reach the Lungarni, the streets along the Arno River, from where you will admire the view of the Thorns Church and the Old Citadel. Entrance to monuments not included.
Lunch on your own.
With satisfied stomachs, you will immerse yourself in this guided tour with a local guide through the magnificent old town of Lucca, exploring its charming squares and picturesque streets. Among the most notable monuments you will visit are the Amphitheater Square, the Tower of the Hours, and the Cathedral of San Martino. Lucca is also distinguished by its numerous medieval towers and a perfectly preserved medieval wall. Private tour duration: 2 hours. Entrance to monuments not included.
Return to the hotel for dinner and a free night.
Day 8 – Sunday, June 2 – FLORENCE – DEPARTURE
Culmination of this extraordinary group journey with a flavorful breakfast at the hotel.
Check-out and a free morning to visit and enjoy the beautiful city of Florence.
Optional, not included: guided tour of Florence with a local guide.
Private transfer at the agreed time to Florence Airport for the return to the home country.
End of trip and of services.
TOTAL PRICE PER PERSON, IN DOUBLE OCCUPANCY: 4.848,00 EUROS
Extra for single occupancy: 952,00 EUROS
- 7 nights’ accommodation in 4-star hotels as indicated in the itinerary. Accommodation with breakfast included.
- Private transportation in a comfortable luxury minibus for all transfers to all the visits included here, following the proposed itinerary. Note: any additional hours incurred by the client, if any, will be billed separately.Transfers APT-HTL-APT included.
- Accompanying guide from our agency throughout the program, following the outlined itinerary.
- Visits to 5 wineries with wine tastings, as indicated in the above itinerary.
- Wine tasting at one of the hotels.
- Private guided tours with local guides in Siena, San Gimignano, Pisa, and Lucca. Duration: approximately 2 hours each.
- 5 meals (lunches) as clearly specified in the above itinerary. Menus as indicated.
- Self-guided visit to the Abbey of Sant’Antimo. Entrance included.
- Basic travel assistance insurance (please check our terms and coverage before booking).
- Technical coordination and organization of all services included here by our agency.
- Applicable tax (any variation in this tax by state and/or municipal authorities will be reflected in the final invoice)
- Flight or train tickets.
- Transfers not mentioned.
- Touristic city tax (to be paid by the guests directly to the hotels)
- Guided tours by local guide not mentioned.
- Entrance fees to museums or monuments not mentioned.
- Lunches and dinners not mentioned, as well as beverages not mentioned.
- Cancellation insurance (recommended). Please contact us if you wish. In case of contracting cancellation insurance, you must indicate it at the time of booking.
- Tips or porters (luggage handling).
- Extra / personal expenses (e.g. telephone, minibar, laundry, etc).
Any other service not clearly indicated in the “Price includes” section.