Rome & Naples with Jonathon Sawyer

Day 1: Rome

Benvenuto in Italia! Our adventure through the world’s premier culinary destination begins in Rome, the buzzing Italian capital that dazzles with unparalleled art, history, and culture.  

We’ll ease into our first day with an unhurried afternoon at the hotel — luxuriating in the opportunity to refresh and get settled after our flights — nestled within one of Rome’s most enviable neighborhoods, and an exquisite ode to the city’s timeless luxury.

It’s also the perfect backdrop for our first bites of the trip—tonight, we’re paying homage to one of Italy’s long-standing traditions: the aperitivo. Over welcome drinks and plenty of bright, local fare, we’ll learn more about Jonathon and his profound connection to the land and its legendary bounty.

Day 2: Rome

This morning, we’re diving right into the heart of Rome with a foodie tour of one of its most treasured neighborhood: Trastevere. As we meander through the former Jewish ghetto and its iconic monuments, we’ll slip into side streets to sample sour cherry tarts from working-class bakeries, fresh salami and cheese from local delis, and glistening carbonara from fabled stalls and markets. Every dish has a story attached, and we’ll look to Jonathon and our expert guide to fill in the blanks between bites of the city’s finest.

Afterwards, the afternoon is ours to relax back at the hotel or wander through Rome’s endless offering of plazas and ancient streets. After some downtime, we’ll begin the evening’s festivities with the ultimate when-in-Rome adventure: zipping around the city in classic, candy-colored Fiat 500s. Some three million of these iconic little beauties were produced between 1957 and 1975, and nothing is more quintessentially Roman than this very special  excursion.

As the triumphant finale to a storybook day, dinner tonight is at an all-time Roman favorite: Rimessa Roscioli. This traditional trattoria is run by one of Rome’s famous baking families and it’s the perfect celebration of the city’s classic dishes.

Day 3: Rome

This morning, we embark on a sensory journey through the eternal city while experiencing the capital’s most storied attractions. As we navigate the winding alleys of ancient Rome, we’ll follow the plot of the famous film, La Dolce Vita (make sure to watch it before you arrive!) and immerse ourselves in the history of the Pantheon, Trevi Fountain, Spanish Steps, and Stadium of Domitian.

The afternoon is yours to embellish—explore Rome’s backstreets and cafe-lined squares or recharge back at the hotel. Just don’t wander too far because an incredible night awaits: in a cozy eatery that’s a favorite among locals, we’ll begin our evening adventures with an intimate pizza dinner, a sumptuous feast so fresh and flavorful it feels like poetry.

Of course, it’s all but an appetizer to the real show later. In an exclusive after-hours tour, we’ll wind through the storied halls of the Vatican, drinking in timeless frescoes and ornate sculptures crafted by history’s most hallowed artists. Bathed in the ancient silence of our reverent surroundings, it’s an otherworldly—and truly unforgettable—visit.

Day 4: Rome

Today we immerse ourselves in the world of Italian organic farming. We’ll visit an estate just outside of Rome that produces all the key ingredients you’ll find in any traditional trattoria: wheat, wine, honey, fresh cheese, and seasonal vegetables. As we meander through the stunning grounds, we’ll learn more about the farm’s commitment to sustainable agriculture and help Jonathon harvest fresh herbs and produce for today’s lunch. 

Vegetables amassed, we’ll move to cheese next, following the resident cheesemaker as he creates ricotta derived from the farm’s own herd of sheep and goats. Afterwards, we’ll carry a few of our favorite formaggi into the farm’s tasting room to savor alongside a flight of the estate’s top vintages—it’s a truly stunning appetizer to the garden-sourced lunch that follows. 

Buoyed by the hyperlocal meal and bucolic surroundings, we’ll drift back to the city for a leisurely afternoon. Dinner tonight is yours to embellish. Jonathon will be happy to recommend some of his favorite places.

Day 5: Rome to Naples

We’re bidding adieu to Rome and heading to Naples, the beating heart of Italy’s Campania region. Our first stop is Pompeii, a UNESCO World Heritage Site and our setting for an unforgettable archaeological expedition. With Mt. Vesuvius towering in the background, our expert guide will reveal the many mysteries of everyday life during the final hours of Pompeii, highlighting not only the relics from the ruins but also the social structure of those who populated this vibrant city. Still awestruck from our learnings, we’ll wander next to an intimate hillside estate to savor a lineup of lively reds and a freshly-sourced lunch. 

Buoyed from our seasonal spread, we’ll sit back to bask in the views on our short drive to Naples—it’s a route made particularly stunning by the golden descent of the late April sun. Once arrived, we’ll settle into our five-star sanctuary then head off to do what every pilgrim to Italy must: learn how to make the finest pizza in the world. At Palazzo Petrucci, we’ll roll up our sleeves and learn from Jonathon and a master pizzaiolo as we roll dough for our very own dinner. Buon appetito!

Day 6: Ischia

After a leisurely breakfast, we depart for a cruise through crystalline waters to the volcanic island of Ischia. Our sleek Itama speed boats will deliver us to the island’s sun-drenched pier, where locals buy gleaming sea bream and scorpion fish directly from the fishermen on the dock.  

It’s the perfect spot to forgo our sea legs for a walk on land, and we’ll discover a stunning display of local art before arriving at the home of an Ischian family for lunch. Here, we’ll roll up our sleeves to help Jonathon and our hosts harvest fresh ingredients from the garden, then learn how to turn our bounty into the makings of a traditional Italian Sunday feast. As we slice handmade dough into the trademark tangles of tagliatelle and season aromatic ragu sauce over a well-worn stove, we’ll partake in the magic of the Italian aperitif with wines aged directly in the family cellar.

After savoring the fruits of our labor with our gracious hosts, we’ll cruise back to Naples, but not before a visit to the unforgettable Castello Aragonese. As we wind through the quiet alleys and breathtaking churches of this ancient fort-city, we’ll learn the stories of the dynasties that populated its castles and drink in views of the turquoise waters beyond.

Day 7: Naples

There’s no better way to round out our adventures through Naples than with an immersive food tour through the city’s historic neighborhoods. With Jonathon leading the charge, we’ll wind through narrow alleyways and rickety market stands, sampling crisp pizza fritta and other local staples. 

As we breathe in the splendor of centuries-old squares and fountains dedicated to the gods, we’ll be treated to anecdotes about the ghosts of Naples’ past and delve into art history between bites of airy sfogliatella.

Afterwards, we’ll return to the hotel and have time to explore on our own or indulge in the beloved Italian tradition of riposo with an afternoon nap. Either way, make sure you find an espresso later because our farewell dinner will be one for the ages. Perched on the hill above the shimmering Bay of Naples, our restaurant tonight is a triumph of dazzling flavors and out-of-this-world views. Here, we’ll be treated to course after course of elevated Neapolitan fare and carafe upon carafe of local wine. Don’t be surprised to hear excessive clinking of glasses and a litany of heartfelt toasts!

Day 8: Naples

Arrivederci! After breakfast, we’ll say ciao to Jonathon and to each other, knowing our experience together won’t be forgotten. It’s been a week to savor and celebrate the true flavors of Italy, with memories to carry with us for weeks and years to come. Until next time!