Explore the heart of Italy’s most renowned wine areas, stunning landscapes, and authentic Italian cuisine. This self-drive holiday combines stays in two distinct locations and tastings of Italy's finest wines in unique, authentic settings. Includes car rental, hotel accommodations, and return flights to Pisa.

Get ready to immerse yourself in Italy's renowned wine regions, with breathtaking landscapes and exquisite cuisine on this self-drive holiday. Experience the finest wines in authentic, unique settings.

Day 1 – Arrival in Pisa & Explore the Area

Arrive at Pisa Airport, collect your rental car, and drive to your hotel, Grand Hotel Duomo, ideally located near the iconic Leaning Tower. Spend the rest of the day exploring Pisa at your leisure, visit Piazza dei Miracoli, stroll along the Arno River, or enjoy a relaxed Italian dinner nearby.
Overnight in Pisa.

Day 2 – Montecarlo Visit en Route to Greve in Chianti & Siena

Depart Pisa and make a brief stop in Montecarlo, a charming hilltop town in the Lucca plain. Wander through its historic centre or enjoy a coffee while admiring views of the surrounding vineyards.

Continue your drive to a historic castle in Greve in Chianti, dating back to the 1400s. Explore its crenellated tower and preserved manor houses before enjoying a Chianti Classico wine tasting in the castle cellar, framed by panoramic vineyard scenery.

Later, travel to Siena, where medieval charm awaits. Explore winding streets, admire high brick palaces, and visit landmarks such as Palazzo Pubblico and Torre del Mangia, overlooking the magnificent Piazza del Campo.

Overnight in Asciano.

Day 3 - Monteriggioni & San Gimignano

Begin your day with a visit to Monteriggioni, one of the best-preserved medieval towns in Italy, surrounded by a nearly 600-metre-long wall. Explore its quaint houses and narrow streets, evoking a bygone era.

Continue to San Gimignano, a UNESCO World Heritage site famed for its medieval architecture, which has remained unchanged since the 14th century. End the day with a Vernaccia wine tasting at a traditional farm.

Overnight in Asciano.

Day 4 - Montalcino & Montepulciano

After breakfast, head to Montalcino, renowned worldwide for its exceptional Brunello wine. The town, with Etruscan roots, offers a rich history and stunning views. Next, visit Montepulciano, situated on a high tufa plateau, famous for its Vino Nobile di Montepulciano wine.

Overnight in Asciano.

Day 5 - Departure from Siena

Enjoy a leisurely breakfast before checking out. Spend the morning exploring more of Siena before departing for Pisa Airport.

Tour Includes:
- 1 night in Pisa: Stay at Grand Hotel Duomo in Pisa (or similar) with breakfast.
- 3 nights in Siena: Stay at Hotel Montaperti in Asciano or Hotel Le Colline in San Gimignano (or similar) with breakfast.
Wine tastings:
-At a castle cellar in Greve in Chianti.
-At a typical farm in San Gimignano.

- Car rental for the duration of the trip.
- Direct return flights to Pisa International Airport.

*Hold luggage between 15kg and 20kg can be added at a supplement