Rome & Sicily with PJ Calapa

Day 1: Rome

Benvenuti a Roma! Your first step onto the Eternal City’s fabled cobblestones is the beginning of a journey through the pages of history—from the awe-inspiring Colosseum, where gladiators once clashed, to the timeless beauty of the Vatican’s Sistine Chapel, where Michelangelo’s genius awaits your gaze, this city is a canvas of exploration.

Before we let the whispers of the past propel us forward, a proper introduction is in order. In the late afternoon, we’ll convene at the hotel for some light snacks and cocktails. Here, PJ will take center stage, sharing his profound love for both Rome and Sicily and setting the table for the incredible journey ahead.

Day 2: Rome

We’ll start bright and early and slip right into the teeming street life of Italy’s capital with a foodie walking tour—we’ll visit and taste at off-the-beaten-path bakeries, covered markets and gelaterias, and try Italy’s finest pizza by the slice (sorry, Naples!) in Rome’s former Jewish Ghetto and Trastevere neighborhoods. Every dish has a story attached, and we’ll look to PJ and our expert guide to fill in the blanks between bites of the city’s finest. Just in case we’re still hungry, we’ll belly up to a local trattoria to officially sate our appetites.

The balance of the day is yours to embellish. Rome simply dazzles with art, history and culture, and this is your opportunity to bask in your own private piece of the capital. See you at breakfast tomorrow.

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 (watch it before you arrive!) and immerse ourselves in the history of the Pantheon, Trevi Fountain, Spanish Steps, and Stadium of Domitian.

After some free time in the afternoon, we’ll dive into two of Italy’s greatest culinary gifts: pizza and gelato. We’ll tackle gelato first, hands-on, learning every step in the process from sourcing ingredients to mixing techniques. While our gelato sets in the freezer, we’ll turn to pizza, crafting and rolling out our own dough and selecting just the right toppings: perhaps a mix of zucchini blossoms and artichoke, or spicy salami and Sicilian peppers — or whatever fresh, delicious ingredients capture our imagination.

We’ll dine together—trading bites of our pizzas—and leave feeling electric and armed with a recipe, so we can recreate this magic at home.

Day 4: Rome to Sicily

We’ll be up bright and early this morning for the short flight to Sicily, landing in Catania on the island’s east coast. After breakfast we’ll head out to visit majestic Mt Etna, an active volcano that towers almost 11,000 feet over the island—and occasionally glows red with lava.

We’ll meet a local shepherd and sample his homemade ricotta, then head to one of the area’s vineyards, I Custodi delle Vigni, on the slopes of Mt Etna, once Sicily’s most important wine-producing region. Heritage vines clamber up the volcano’s slopes to an altitude of over 3,000 feet, producing delicate whites and intense, fruit-forward rosés and reds.

Following our tasting, we’ll pause for a bright and lively local lunch. As the afternoon rolls around, we’ll check into our stunning basecamp for the next two nights. Relax and explore our hotel’s grounds, nestled among the foothills of Mt Etna, before settling in for dinner. Every single dish on the menu, from the wild fennel risotto to the rabbit, features ingredients from the property’s abundant gardens.

Day 5: Taormina

Today is truly special—not only will we explore one of Sicily’s most iconic seaside hamlets, we’ll also be hitting the seas for the freshest local seafood. Our first stop is Taormina, pearl of the Mediterranean, to explore on foot starting with its ancient Greek amphitheater, overhanging the crashing surf below. From our perch at arguably the world’s most famous outdoor theater, the views of the bay of Giardini Naxos to the south, and mainland Italy to the north, are spectacular. We’ll take some free time to get to know the town, even pausing for an espresso at one of Taormina’s vibrant squares.

Next, it’s onto the ethereal blue waters of the Ionian Sea for a fishing excursion. Aboard our chartered vessel, PJ will be in his element, and we’ll look to him for advice on casting and reeling in our abundant (hopefully!) catch of the day. Of course, no fishing trip is complete without a fresh of-the-moment lunch, and today we’ll be treated to a seafood lunch, cooked and curated by chef PJ himself. As dusk descends, we’ll return to Mt Etna for an evening on our own.

Day 6: Siracusa

We’ll head for Siracusa today, wending our way across the island to this 2,700-year-old seaside wonder that’s an intricate blend of Greek, Roman, Byzantine and North African influences.

Siracusa’s ancient heart is the island of Ortigia; we’ll dive in on a walking tour of its cobblestone alleyways — crowded with markets and temples, castles and churches, tucked around every corner. Then we’ll head to Tenuta Cavasecca for a visit to its olive groves and the ancient temple that now houses vats of freshly pressed oil as it rests after harvesting and milling. Finally, we’ll head to the ancient hall for a tasting of this liquid gold, followed by a family lunch straight from the garden.

We’ll have time to rest back at our hotel, and explore the sprawling grounds of this beautifully restored baglio (fortified farm), before reconvening for dinner and a nightcap with PJ.

Day 7: Ragusa

Ragusa, the City of Bridges, is a harmonious jumble of Greek and Roman ruins, Arab neighborhoods, ancient monasteries, Baroque churches and endless beaches. We’ll explore the old town of this UNESCO World Heritage site, squeezing our way into the warren of tiny medieval streets leading up to the magnificent Cathedral Square.

Our next stop is one of the area’s restored ancient water mills. Here we’ll see firsthand how wheat transforms to flour, and before we know it, we’ll be apron-clad and rolling our own pasta for an unforgettable lunch.

We’ll have the option of playing sous-chef for tonight’s feast, selecting vegetables and herbs from the hotel garden, then rolling up our sleeves and assisting PJ to craft a menu celebrating many of the market ingredients he’s foraged over the past week. 

Day 8: Agrigento & Palermo

We’re off to Palermo this morning, stopping along the way in Agrigento. This former Greek colony was established in the 6th century BC and was a leading city-state in the Mediterranean world. Agrigento’s magnificent Doric temples dominate the ancient town, much of which still lies intact among acres of olive, pistachio, almond and fruit trees. We’ll drink in the sumptuous beauty of the gardens over an al fresco lunch.

Palermo, the former capital of the Kingdom of Sicily, is one of the most dynamic cities in the Mediterranean. We’ll have some downtime and then meet for dinner at our hotel, a gracious Belle Epoque space with views of the Tyrrhenian Sea, showcasing timeless Sicilian dishes and flavors. 

Day 9: Palermo

There’s no better introduction to freewheeling Palermo than the colorful Capo market; even better, experiencing it in the company of Nicoletta Polo, a Sicilian duchess who will share stories of Palermo life as we wander the stalls, listening to the singsong calls of vendors and inhaling an intoxicating swirl of aromas: the sharp tang of Sicilian citrus fruits, fragrant sesame-seed loaves pulled from a wood-fired oven, savory arancini (fried rice balls) and thick slices of sfincione topped with  sweet tomato sauce.

We’ll meet the duchess again tonight at our farewell dinner at Palazzo Lanza Tomasi, the last home of Prince Giuseppe Tomasi di Lampedusa, author of the iconic novel The Leopard. Nestled in the heart of Kalsa, the old Arab quarter, this 18th-century palace overlooks Palermo’s stunning seafront, its terraces and courtyards a tapestry of hanging gardens perfumed with subtropical essence. It’s the perfect setting for our farewell banquet, as we raise a glass to toast PJ, our new friends and our adventure together.

Day 10: Palermo

Arrivederci Sicilia! We’re off this morning after nine immersive days of adventure and culinary adventure. After breakfast we’ll say ciao to PJ, and to each other, knowing the memory of our adventure together will live in our hearts forever! We’ll organize a group transfer to Palermo’s PMO airport for flights to mainland Italy and beyond.