Italian Self Drive Holiday to Italy’s Tuscany & Umbria

Florence, Chianti, Val d’Orcia & Perugia

Best time to travel

Apr – Oct

Ideal length

11 nights

Perfect for

All

From (incl flights)

€3,899 pp

At a glance

International flights from Dublin to Pisa and home from Rome.
11 nights’ luxury accommodation in Florence, Castelnuovo Berardenga, Val d’Orcia and Perugia.
11 days’ pre-arranged car rental, to explore the surrounding at your leisure.
Privately guided experiences in Florence including an artisanal walking tour and exploration of the Uffizi Gallery by night.
Immersive experiences in Tuscany and Umbria including a guided tour and tasting at a local cheesemaker’s farm and a guided hike and wine tasting in the picturesque Val d’Orcia.

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Introduction

From the artisans of Chianti to the great maestros of Florence’s High Renaissance, Italy’s thriving culture and momentous talent is alive within the central regions of Tuscany and Umbria. On this self-drive discovery, we will take you on an immersive experience, following expert local guides to watch modern-day master craftsmen and artisans at work. As you drive through the winding roads, rest assured that our hand-picked properties and tailored private experiences will promise an unforgettable journey through Tuscany and Umbria’s cities and countryside.

View all of our luxury holidays to Italy.

Trip Overview

Depart from Dublin to the Renaissance city of Florence.

Upon arrival, pick up your pre-arranged rental car and arrive at your luxury hotel in Florence. Check-in for your three night stay and head to the rooftop terrace for a refreshing cocktail and panoramic views of the city.

Set out on an artisanal walking tour of Florence.

In the company of your private guide, explore the Oltrarno Quarter. The home of Florentine artisans, it is carpeted with small workshops set up on tiny side streets. Watch the craftsmen at work and enjoy a private paper demo and savour some wine and cantucci.

Discover the masterpieces of Uffizi by night.

A much quieter time to appreciate the Renaissance masterpieces of Italy’s maestros, we’ve arranged a privately guided tour of the gallery by nightfall. After your tour, dine in a local taverna renowned for its truffled tagliderini al tartufo.

Enjoy a privately guided night tour of Uffizi Gallery

Set out for the Tuscan hills of Castelnuovo Berardenga.

Spend two nights in a luxury property in this southern part of Chianti. Bordered by the rivers of Ombrone and Arbia, this thriving area is a beautiful destination to explore by car. There are also plenty of ancient villas and Renaissance gardens nearby.

Visit a family-owned cheese maker’s farm and enjoy a wine and cheese tasting.

Today, you’ll visit Il Casale Farm, where the owners will introduce you to the animals and the farming techniques used to produce pecorino cheese as well as a variety of other products. Finish with a delicious cheese tasting accompanied by local wine.

Set out for the picturesque hills of Val d’Orcia.

Drive along winding roads until you arrive in your luxury accommodation on the borders of Val d’Orcia’s cultivated hills. Check in to your elegant country house hotel for your three night stay and make use of the garden pool and luxury restaurant.

Enjoy a guided hike of Val d’Orcia.

A landscape defined by rolling hills and vineyards, dotted with Renaissance villages and medieval ruins, this is undeniably one of the most scenic routes to experience in all of Italy. After a day of guided exploration, enjoy a lunch and wine tasting at the Avignonesi Winery.

Enjoy a lunch and wine tasting at the Avignonesi Winery

Drive to the Umbrian city of Perugia.

Stop off in the historic centre for a short stroll before making your way to your luxury accommodation. We’ve arranged a three night stay in an impressive chateau property overlooking Umbria’s Nestor Valley.

Discover the highlights of Perugia with your private guide.

Explore Perugia’s defensive walls, medieval Fontana Maggiore, Palazzo dei Priori and its gothic cathedral, which houses many Renaissance painting and frescos. Then, its time to sample its world-famous chocolate at a historic chocolatier’s.

Drive to the international airport to drop off your rental car and board 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

Antica Torre di Via Tornabuoni 1

The chic boutique hotel of Antica Torre lies within a medieval tower on the upscale shopping street of Via Tornabuoni, situated next to the iconic River Arno.

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Borgo San Felice

The elegant Relais & Chateaux property of Borgo San Felice lies within a beautiful estate amid 140 hectares of vineyards in Tuscany’s picturesque countryside.

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Villa Cicolina

Villa Cicolila lies within an elegant 16th-century country house, the former residence of a noble family of Montepuciano. Set between two centuries-old trees lies the outdoor infinity pool.

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Borgo dei Conti Resort

Borgo dei Conti’s luxury chateau property lies in the hilltops overlooking Umbria’s Nestor Valley. Set within Gothic-style architecture, interiors are authentic and historic.

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What people are saying

Conor in OROKO arranged a holiday this summer for us and our four teenage boys. We were unsure where to go and his advice was fantastic! He took over completely after a consultation about our expectations, taking into consideration our boys’ needs too! He most certainly delivered a tremendous holiday for us all – way beyond what we could have done ourselves, with each of our three destinations better than the last. All incredibly located and absolutely stunning!

Everything was done for us – check-ins/five-star transfers/individual bag tags/ferry transfers with all seats pre-booked! Conor was incredibly helpful, patient, knowledgable and open. It made our trip truly memorable from conception to finish and I cannot fathom planning a trip again without OROKO! Thank you for everything we will never forget it!

Valerie & family – Greece, 2022