John Clifford's Tuscan, Umbrian, & Pugliese FIAT 500 Adventure By John Clifford John Clifford For more than 30 years, Clifford has been crafting celebratory itineraries that are anything but cookie cutter. His industry contacts result in benefits like suites in sold-out hotels, tours led by the hotel managers themselves, and guides vetted for their LGBTQ-friendliness, even in places like the Middle East. He also goes to great lengths to arrange unforgettable singular experiences. On a recent trip to Palermo, Sicily, he arranged for his guests to take a cooking class with a countess, who shared her families’ recipes that have been handed down by word of mouth for generations. Clifford is also applauded for his extensive hotel knowledge. He’ll pair clients with hidden gems like a suite from a chic boutique in The Catskills to an ultimate glamping getaway in Luang Prabang. He’s often invited to scout new hideaways long before they’re on the radar of the mainstream, giving his clients an inside track to new experiences long before they hit social media stardom. Travel + Leisure Editorial Guidelines Updated on March 16, 2022 Share Tweet Pin Email Photo: Apostoli Rossella/Getty Images John Clifford is 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 John@InternationalTravelManagement.com. Cortona 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. Montepulciano 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. Pienza 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. Montalcino 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. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit