Charming Tuscany and Le Cinque Terre
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Private self-drive holidayDeparts Daily

The magical region of Tuscany is explored in this enchanting 9 day itinerary. Featuring remarkable history, incredible wine and food, and a National Park full of stunning natural landscapes, this region deserves a bit more time – and a rental car is the perfect way for you to discover the secrets in your own pace and style.

Day 1: Florence

Upon arrival at either Florence airport or train station you will be met by a local operator and transferred to your accommodation. The remainder of the day is at leisure to unwind from your travels.

Day 2: Florence

Full day in Florence to discover some of the city highlights in your own pace and style. Florence is full of incredible sites: Ponte Vecchio; the famed bridge lined with shops overhanging the Arno River, Florence Cathedral the unique octagonal Baptistery of St John with its stunning East Doors (named “The Gates of Heaven by Michelangelo), Piazza della Signoria and Palazzo Vecchio. For lunch, a visit to one of the city’s markets, Mercato Generale or Mercato di Sant’Ambrogio, is highly recommended. Your visit should definitely include the Uffizi Gallery, with masterpieces of Michelangelo and Raphael, and the Accademia Gallery housing the world famous David by Michelangelo. At the end of the day take a stroll towards Piazzale Michelangelo to enjoy the best view of Florence.

Day 3: Florence – Pisa – Lucca

This morning pick up your rented car and head to Pisa. This site, home of the world famous Leaning Tower which was recently re-opened to the public after a e200m restoration, also contains several other beautiful monuments in the are known as Miracles Square - designated a World Heritage Site by UNESCO. After the visit to Pisa continue to Lucca and your accommodation.

Lucca is Tuscany’s best kept secret. The town has a striking historical centre that preserves intact its medieval aspect - characteristic alleyways are surrounded by noble palaces and ancient towers. At night you can attend the daily concert with the music of the great master Giacomo Puccini (La Boheme, Madame Butterfly) in the city where he was born and lived for a long time.

Day 4: Lucca – Le Cinque Terre – Lucca

Today is spent exploring one of the hidden jewels of Italy’s north west: The National Park of the Five Lands (Le Cinque Terre). The road to Vernazza ends 1 kilometre before the town and walking trails, a train, or boat trips are the preferred options to explore this beautiful area. The Five Lands is a truly special experience; it is an authentic immersion in the magic of historic and colourful villages positioned towards the sea, with steep reliefs and lands sown with vineyards. Enjoy the excellent wines of this land such as the Sciacchetrà, and do not miss the opportunity to taste the exquisite focaccia bread with cheese.

Day 5: Lucca – Volterra – San Gimignano – Siena

Depart Lucca today for Siena passing through Volterra and San Gimignano. Volterra is a fascinating and ancient location, originally an Etruscan settlement dating back to the eight century BC. The walled city has been home to a thriving alabaster industry for almost all of this time and to this day many shops are filled with beautiful objects made of this stone. The town features many beautiful sites and was the inspiration for the home of the Volturi vampires in the Twilight series. San Gimigano is also well worth a break during the drive. This hill town is encircled by 13th century walls and contains many stunning examples of both Gothic and Romanesque architecture.

Day 6: The Orcia Valley

Today begins with a guided tour of the historic wine cellars of Montepulciano, including a tasting of the Vino Nobile di Montepulciano. Continue your itinerary to Monticchiello, one of the least known yet most beautiful villages in the valley. Sites here including Pienza, the Chapel of Vitaleta, San Quirico d'Orcia, and Bagno Vignoni have been the setting for scenes in movies such as The Gladiator and The English Patient. Just outside San Quirico d'Orcia there is a remarkable stand of cypress trees that is the most photographed place in Tuscany. Before returning to the hotel, visit Montalcino, the village of the Brunello wine, and the nearby Abbey of St. Antimo.

Day 7: The Siena Clays and Cortona

Let yourself be enchanted by the clay-coloured hills dotted with isolated farmhouses and cypress-lined lanes. Standing in this lunar-like landscape is the Abbazia di Monte Oliveto Maggiore, a stunning red-brick monastery - one of the most striking monuments of this area. In the afternoon reach Cortona where the film Under the Tuscan Sun takes place, and where legend has it that Crano (one of Noah’s descendants) founded the settlement 273 years after the Great Flood. The town preserves intact its artistic and historical heritage with many stunning sites.

Day 8: The Chianti Wine Region

Explore the wine region of Chianti starting from the Brolio Castle which appears as though out of a fairy tale. Continue to Gaiole in Chianti, named “the most idyllic place to live in Europe” by Forbes. Here you will visit a farm producing organic wine before departing to Castellina in Chianti. It is worth getting to La Badia a Passignano, an abbey where Galileo Galilei taught, surrounded by an intense cultivation of vines and olive trees. The abbey surprises with its crenellated towers which were created by a private owner following the expulsion of the monks in 1866.

Day 9: Siena - Florence

One last chance to explore Siena today before the approx. 90 minute drive back to Florence. If you haven’t yet done so, we recommend you explore sites such as Piazza del Campo with the Palazzo Pubblico and the Torre del Mangia, the Piazza Duomo with the Cathedral, the old Spedale and the remains of the "new" Duomo. Also be sure to try the excellent delicacies of the city such as panforte, ricciarelli, and cantucci with Vinsanto. As you drive back to Florence, a visit to the Fortress of Monteriggioni surrounded by a wall and 14 towers is recommended.

Upon arrival in Florence return your rental car and continue with your own arrangements.

Tour Inclusions:

  • Private transfer from the airport or train station to the hotel in Florence
  • 2 night accommodation in a boutique hotel in Florence in a double room with breakfast
  • 7 day rental of C group car (in case of 2 people travelling) or D group car (in case of 4 people) – unlimited kilometers – air conditioning – manual – basic insurance
  • 2 nights in a boutique hotel in Lucca in a double room with breakfast
  • 4 nights in a country hotel in the countryside near Siena in a double room with breakfast
  • Shared guided tour in a small group of the historic cellars of Montepulciano with tasting of 2 wines (duration 2.5 hours)
  • Private visit to a winery producing organic wine in the Chianti region with tasting of 5 wines olive oil cold cuts and cheese (duration 1 hour)
  • Private guided tour of the Badia a Passignano

Tour Exclusions:

  • International airfares
  • Optional tours and excursions
  • Tourist tax to be paid to the hotels
  • Porterage
  • Tipping/Gratuities (please refer to tour notes for a recommended guideline)
  • Personal Expenses
  • Departure taxes
  • Hotel charges for minibar or any extra charges
  • Visas (unless specified)
  • Any other services not clearly mentioned in the inclusions above

Accommodation based on the below or similar




Palazzo Alexander OR Ilaria e Residenza dell'Alba OR Villa Marta


Relais Laticastelli

Enquire About This Itinerary

Trip prices and dates are correct at the time of the website going live, however all offers are subject to reconfirmation at the time of booking. Note prices usually display available discounted rates if any, (eg. Early Bird Deals if applicable). All featured tour itineraries and offers maybe subject to change due to seasonal variations without notice, or due to local conditions or other conditions. Please confirm all details at time of booking. Travel insurance is mandatory for all Innovative Travel bookings. All passports must be valid for 6 months prior to your return to your home country. Visas are the responsibility of the traveller. Special VIP meet and assist offers are valid for New Zealand passport holders, for other nationalities please check at the time of booking. For full terms and conditions, please refer to our Booking Conditions page.

First Class / 2023 - 2024 / Price on Application
  • First Class
  • 2023 - 2024
  • Price on Application
  • First Class
Travel Date
  • 2023 - 2024
Room Type
  • Price on Application

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