Self Drive Italy’s Regions of Tuscany & Chianti

Lucca, Chianti & Siena

Best time to travel

Apr – Oct

Ideal length

7 nights

Perfect for

Couples

From (incl flights)

€2,299 pp

At a glance

International flights from Dublin to Pisa.
7 nights’ luxury accommodation in Lucca and Gaiole in Chianti.
7 days’ pre-arranged car rental, allowing you to explore at your leisure.
Privately guided tours of both Lucca and Siena that will show you the most culturally significant sites of the cities.
Scenic, guided tour of the famous Chianti wine region including a traditional Tuscan village visit.

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Introduction

Known for its landscapes, history, artistic legacy, and influence on high culture, Tuscany is one of Italy’s most celebrated regions. In this suggested itinerary, let us take you on an unforgettable journey as you experience the region’s famous gastronomy and culture in the country’s most beautiful settings. Start north, exploring the renaissance past of Lucca and Florence before heading south to Gaiole in Chianti to visit Italy’s famed winelands. Get to know the area during guided tours of traditional villages and the Gothic city of Siena. During this trip, we want to ensure you experience the most Tuscany has to offer through self-driving, allowing you to explore at your own pace.

View all of our luxury holidays to Italy.

Trip Overview

Depart from Dublin to Pisa.

Upon arrival in Pisa’s Galileo Galilei Airport, pick up your pre-arranged car and drive to your luxury hotel in Lucca. Enjoy a three night stay at one of our partner hotels in the city’s historic centre.

Allow us to arrange a privately guided walking tour of Lucca.

Explore the Renaissance city of Lucca as you stroll along its cobbled streets. Take in the main sites, including San Michele Square and the Cathedral of San Martino. Perhaps take lunch at a local café or quietly sip on an espresso watching the world go by.

Experience the music and art culture of Lucca.

Enjoy an evening show of Puccini e la Sua Lucca, an artistic collective dedicated to composer Giacomo Puccini and his music. Recitals, opera selections and special concerts are held year-round in the Chiesa dei Santi Giovanni e Reparata on Via Duomo. Depending on the night of attendance, delight in a creative performance.

Opera at Chiesa dei Santi Giovanni e Reparata

Drive to Gaiole in Chianti in Italy’s famous wine region.

Just southeast of Florence, Gaiole in Chianti is a delightful, Tuscan village in the Province of Siena. Enjoy a four night stay in at one of our stunning partner properties, a renovated 10th century monastery that exudes feudal history and rustic charm.

Explore the ancient city-state of Siena alongside a private guide.

Stroll the city that celebrates the best of Italian Gothic architecture. Discover Siena’s fascinating history as you explore the different Contrades, walking through famous squares, piazzas. and remnants of Italy’s medieval past

Today you will be privately transferred to the famous Chianti wine region.

On your way, pass by rolling vineyards and olive groves as you journey along the famous “Chiantigiana” wine route. Enjoy free time to explore a typical Chianti village, wandering its streets and local shops. If you wish, your driver will lead you to a local winery to taste the Chianti’s best products.

Drive to the airport and leave your rental car behind before your flight home.

Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

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Accommodation

Where to rest your head

Looking for the best accommodation? We've got the contacts

Castello di Spaltenna Exclusive Resort & Spa

Situated along the rolling hills of Chianti lies Castello di Spaltenna. Set in an historic monastery from the 10th century, the immaculately restored property still retains bucket-loads of historic charm.

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Palazzo Dipinto

Set in Lucca’s historic centre, the Palazzo Dipinto boutique hotel is set within a prestigious 13th-century building overlooking the square from which its name derives.

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What people are saying

Dara at OROKO booked the most fantastic trip for my daughter and I to Athens. It was our first time in Greece. Between Acropolis, museum, and gallery visits, to quiet times at a beachside boutique hotel, it was the most perfect Easter break for us both. Thanks OROKO.

Fiona & Ava – Athens, 2022