14 Days in Southern Italy | A Fresh Take on an Old Favorite

Not far from the bustle of the Amalfi Coast, perched high above the coastline, a series of towns and villages clings to the craggy hilltops of the Lubrense rock outcrop. Looking serenely out over the Bay of Naples, the press of tourists bloating the picturesque alleyways of Positano and Ravello below seems decidedly out of place. After a day spent strolling through the fragrant Limone di Massa orchards and ancient DOC vineyards of the hill country that serve as a backdrop to the world’s most popular coastline, the contrast in tone between the two settings is as evident as the juxtaposition of the before and after of a pandemic.

A Brave New Luxury

At one point, vacations were the way we acknowledged our accomplishments. These precious weeks were designated breaks from work and school specifically earmarked as a time to have fun, spoil ourselves, and build our case for bragging rights on “Best Vacation Ever”. Spoiler alert: They still are! But as a front-line observer of how our travel DNA has evolved, I can’t help but feel inspired by the fresh take on travel that has been sparked by a virus. For me, this looks different for every client, but I have an easy analogy for you…just in case you drifted off on a limoncello-infused daydream and missed the metaphor in the first paragraph. You are Stanley Tucci (or Andrew Zimmern, or Chrissy Teigen) and the vacation is your show. The guides and local insiders might in fact be the same in both versions of the program, but the important thing to remember is that the reason we stay engaged from one episode to the next is that we can’t wait to see what they’ll be doing wherever they’ll be going next time.

Experience Versus Place

For months, the places we’ve been allowed to visit have been so limited that it’s forced us to think less about where we’re going and more about what we can do to try and make it feel special. To top it off, we have been digitized, polarized, and isolated from everyone (certain family members included) who exists outside of our immediate bubble. The result is profound mindfulness in how we approach travel as a function of our leisure time. I define this as a shift towards travel that is experience-forward in nature with an emphasis on a slower pace and moments of connectedness through cultural authenticity. Place will always play a tremendous role in our travel choices, but it’s the chance to have an immersive, connected experience in that place that is driving our travel desire in a way that it hasn’t always done so significantly before. Why? Because we are now so very aware of the meaning of it all.

A Fresh Take on Familiar Favorites

Experience-based private travel IS the new luxury. Sure, the destination is important, but COVID has laid bare what we’ve always believed: Why we travel is as important as where we travel, and if you lead with your vision, the destination will follow. For that reason, re-visiting old favorites with a brand-new attitude will be a big trend for this year and in the years to come. Countries such as Italy, France, Spain, Greece, Ireland, and the UK -going back to see these places again with a more culturally appreciative lens versus going through the motions of seeing the big hits. After the disconnected isolation of the pandemic, being somewhere new now means something quite different. And just maybe, it means seeing something again, but this time as an old friend.


Back on the hill in Schiazzano, my family of 5 gathers with the De Gregorio family after a day of helping to harvest their renowned lemons. Their iconic, vintage Ape Calessino rests languidly in the shade after a busy day carting us all over the property. My three little ones gesture like tiny Italians as they explain with proud gusto how they helped press and squeeze curds from the estate’s dairy farm to shape the fresh mozzarella, warm and salty-sweet, that’s now swimming in olive oil ready for lunch on the plank picnic table. We’ll eventually head back down to the coast at some point, but I’m in no hurry. Right now, whiling away the afternoon over a home-cooked meal, sipping fresh limoncello with the family who makes it, suits me just fine.


Immersive Amalfi-Early Fall

Day 1 – Arrive from BNA in Rome. Private escorted VIP meet and greet-expedited immigrations and customs-porter and assistant for a private transfer to hotel, sightseeing as time allows.

Day 2 – Private family-themed walking tour of Rome-Gladiator and Emperor Focused-Imperial Rome. Private sunset aperitivo at the top of Gianicolo Hill-Family Photo Session. Cocktails and kid-friendly drinks and snacks. Overnight Rome.

Day 3 – Private luxury vehicle transfer to Umbria. Private visit of Madonna del Latte winery. Lunch and wine at the estate-gourmet local fare-5 course lunch with wine pairing-escorted afternoon visit to Orvieto-Dinner in Rome-Overnight Rome.

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Day 4 – On to Sorrento! Private transfer from Rome to Sorrento-Stop off in Pompeii and Naples for lunch and site visit (if desired). Arrive in Sorrento-Champagne welcome at hotel, sightseeing as time allows. Dinner in Sorrento. Overnight Sorrento.

Day 5 – Full day of local activities. Morning visit to a historic, organic lemon farm and estate-guided tour of the property-hands on activities (lemons, dairy farm, olive oil-traditional farming techniques). Lunch on site. AFTERNOON: Fish the Gulf of Naples with local fisherman and local insider guide/expert-learn traditional fishing techniques, explore hidden fishing villages around the Sorrentine Peninsula by boat, and catch your dinner!. Sunset cruise back-cocktails and canapes. Dinner at a local seaside restaurant where Chef will cook your family’s very own catch to your liking. Overnight Sorrento.

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Day 6 – Day trip to Amalfi Coast-Private escorted luxury vehicle drive. Positano to Ravello with stops for shopping, lunch, and exploring as you wish. Driver at disposal for the day. Overnight Sorrento.

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Day 7 - Day trip to Lattari Hills-Private escorted luxury vehicle. Tenuta San Francesco Estate visit with Gaetano Bove himself. Tour the estate, visit the historic chapel amid the vineyards. Five-course lunch with the estate’s best DOC wines paired. Lunch with the proprietor and his wife, Eva. (She also cooks the gourmet meal.) Overnight Sorrento.

Day 8 – On to Sicily!-Airplane transfer to Grand Hotel Villa Igiea, Palermo. Gulf of Palermo seafront. Views of Mount Pellegrino. Arrival champagne and guided property activities. Choice of walks, private yacht tours, coastal or city bike tours, or mountain biking in Madonie Regional Park. Or simply relax in the gardens or poolside. Overnight at Grand Hotel Villa Igiea.

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Day 9 –Private guided exploration of Sicilian street food traditions with a local insider, market tour, and lunch. Afternoon-time at leisure at the property. Overnight Grand Hotel Villa Igiea. 

Day 10 – Full-day tour of the Magna Graecia-Private driver at your disposal for the day. Fresh off the hook seaside lunch or a remote picnic. Overnight at Grand Hotel Villa Igiea.

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Day 11 – Luxury vehicle transfer to Taormina-Option to stop off in the gorgeously charming and very typically Italian resort town of Cefalu along the way OR choose an additional vineyard visit with lunch and tastings at Relais Sant'Anastasia. Check-In Belmond Villa Sant’Andrea.

Day 12 – Private yacht trip in the Gulf of Taormina-marine highlights, Isola Bella WWF nature reserve, Grottta Azzurra, and hidden coves of Mazzaro. Aperitvio in Taormina with local insider. Overnight at Belmond Villa Sant’Andrea.

Day 13- Day trip to Mount Etna and Benanti Winery. Private guided visit of the southern slope of Mt. Etna. Private visit of the prestigious and stunningly beautiful Benanti Winery, Etna DOC. 5 course wine-paired gourmet lunch in the estate’s lava stone cellars.

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Day 14-Private escorted transfer to Catania airport with porterage and assistant for flights home.