John Clifford's Tuscan, Umbrian, & Pugliese FIAT 500 Adventure

view of Montepulciano in Tuscany
Photo: Apostoli Rossella/Getty Images

John Cliffordis a member of Travel + Leisure’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. Below is an example of the type of itineraries he creates. To work with John, contact him at


Arrive by train to Cortona and enjoy private transfer to the new, Castello di Reschio, a mystical castle estate, comfortably away from the tourist track. We’ve arranged a vintage FIAT 500 rental for your exciting journey ahead. The next morning, Florian Schaible, the Master of Household, will join you shopping in the nearby village and we’ll tour some of the lovely hillside towns nearby.

We have booked you into one of the 8 private houses on the estate, your own masseria, so you can enjoy privacy, space and the many benefits of this vast, historic property.

Castello di Reschio

At the edge of Tuscany & Umbria is an Etruscan masterpiece in a stunning, off the beaten track locale. Today is to unwind in the ancient cellars, now a chic hammam and spa. The sprawling estate is filled with vineyards, olive groves, an enoteca, two tony restaurants and an equestrian center. While you're here, we've arranged truffle hunting, cooking classes olive oil making and serene horseback rides among the pines. Your cooking class is the next door Accademia di Cucina della Bottega, where you'll source ingredients on site and at the local market.


Your local guide will take you though the important sites and residences of the Medici family including the Palazzo Avignonesi. We’ve arranged a private tour of Tales and Ercolani Azienda Agricola wine cellars to enjoy, firsthand the Nobile di Montepulciano this afternoon.


A valley town on the edge of the UNESCO World Heritage, Val d’ Orcia, Pienza is a stunning walled town with early renaissance palazzi. Your local guide will grant you entrance to the Palazzi and you'll enjoy a Pecorino cheese making class and join the festivities of The Fiera del Cacio, a festival celebrating the famous cheese.

Bagno Vignoni

Today we head south of Montepulciano down the Via Cassia, the old Roman road to the thermal spa down of Bagno Vignoni. Enjoy lunch on the square followed by an all day pampering at Le Terme Spa.


Home to the infamous Brunello wine, Montalcino is also an important Etruscan site surrounded by vineyards, spires and elegant stone walls. We have your private guide reveal Etruscan monuments.

Drive from Castello di Reschio to Paragon 700

Check in to the new Paragon 700 in the White City of Ostuni. Paragon 700 is a new, uber chic boutique luxe property, an 18th century manse, managed by Laura Stopani who’s helmed some of Italy’s finest. You're booked in the best, Paragon Suite, with cathedral ceilings, sunken tub, open fireplace and large terrace.

Best Beach Day

Punta Prosciutto is Puglia's answer to the Maldives. Today is to unwind, relax and enjoy the sand and sea.

Private Yacht Excursion

The P Boat, a 15-meter private yacht, is chartered for you today for an adventure on the Adriatic Sea. Visit the Tremeti Islands and Frascone Natural Park.

Motorbike Tour

Today we have arranged a custom, motorbike tory through the olive groves, seasides and medieval roads. Local guide Valentina, affectionately known as TraVale will guide you through the Valle d’Itria

Apulian Cooking Class

Tonight’s highlight is a hands-on private cooking class with Chef Giacomo Simone. After a visit to the local market to pickup fish, vegetables and staples, the chef shares some generations old family recipes.

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