Get ready to immerse yourself in Italy's renowned wine regions, with breathtaking landscapes and exquisite cuisine on this self-drive holiday.
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.
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 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 23kg can be added at a supplement
Pisa is a city and comune in Tuscany, central Italy, straddling the Arno just before it empties into the Ligurian Sea. It is the capital city of the Province of Pisa. Although Pisa is known worldwide for its leaning tower, the city contains more than twenty other historic churches, several medieval palaces, and bridges across the Arno. Much of the city's architecture was financed from its history as one of the Italian maritime republics.
Siena, Italy, is a captivating medieval city nestled in the heart of Tuscany, renowned for its historic charm and vibrant culture. The city’s winding streets and well-preserved Gothic architecture transport visitors back in time, with red-brick buildings and narrow alleyways creating an enchanting atmosphere. At the city's heart lies the iconic Piazza del Campo, a unique shell-shaped square that hosts the famous Palio horse race twice a year. Dominating the square is the Palazzo Pubblico and its towering Torre del Mangia, offering breathtaking views of the city. Siena's rich history, artistic heritage, and delectable cuisine make it a must-visit destination for anyone exploring the wonders of Tuscany.
Tuscany’s beauty is legendary, from the golden hills of Val d’Orcia to the cypress-lined roads of Chianti. Explore Florence, the birthplace of the Renaissance, with its iconic Duomo, Uffizi Gallery, and Ponte Vecchio. Wander the medieval streets of Siena and San Gimignano, or admire t...
The Grand Hotel Duomo in Pisa is a well-established and elegantly styled hotel located just a few steps from the city’s most iconic landmarks, including the Leaning Tower and Piazza dei Miracoli. Its classic Italian décor, warm atmosphere, and comfortable rooms make it an ideal base for exploring the city. Guests can enjoy a panoramic rooftop terrace offering stunning views over the Cathedral and historic centre, perfect for a sunset drink or memorable photos. With attentive service, a welcoming lounge bar, and convenient access to restaurants, shops, and cultural sights, the Grand Hotel Duomo provides a charming and convenient stay in the heart of Pisa.
Set at the top of a hill in the countryside, Hotel Montaperti is only 10 km from Siena. The hotel offers an indoor heated swimming pool with massaging water jets, a gym, a garden and two solarium terraces, perfect for relaxing after a long day of sightseeing. There is also a wellness centre with a sauna, steam bath and sensory shower available at an extra charge. The hotel’s restaurant 1260 serves Tuscan wines and regional traditional dishes made using only the finest seasonal ingredients. All rooms have a modern style and feature air-conditioning, flat screen TV, safe, hairdryer, minibar and free WiFi. Apartments also have a kitchenette. Siena's historic centre is only 7.5 miles away, while the Chianti wine district is a 20-minute drive.