Rome & Sicily with Chris & Natalie McDade

October 6 - 14, 2023 | One Exclusive Departure

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Insider's Italy

A culinary and cultural deep-dive with Chris & Natalie McDade

October 6 - 14, 2023

One exclusive departure — reserve your spot!

9 Days, 8 Nights

The very best of Rome and Sicily from Taormina and Mt Etna to Siracusa and Palermo

Price from


per person based on double occupancy; includes internal flight from Rome to Sicily

Questions? Text or call us
+1 (855) 219-8018

You’re on the volcanic slopes of ancient Mt Etna, sipping the finest Carricante and Nerello Mascalese wines alongside a winemaker sharing the secrets of her craft. Yesterday, a shepherd demonstrated the centuries-old traditions of Sicilan cheesemaking. Tomorrow, you’re sailing the sparkling waters of the Ionian Sea, pausing for lunch in a quiet fishing village to explore ancient Greek temples. You’ve sampled Rome’s finest street foods and rolled homemade maccarruni under the benevolent eye of a Sicilian nonna (grandmother) kneading flour into a supple pasta dough. This is Rome and Sicily as few others can experience—a rare inroad to the culinary and cultural secrets of Italy.

With us are Chris and Natalie McDade. He’s the chef and culinary force behind Brooklyn’s Popina and Gus’s Chop House, and author of The Magic of Tinned Fish, one of The New York Times’ Best Cookbooks of 2021. She’s a sommelier and major wine travel enthusiast who’s selected wines at some of New York’s top restaurants including Craft, Vallata, Gotham Bar & Grill and Babbo. Together, the husband and wife duo are ready to share their personal passion for Italy, their love for heirloom ingredients and innovative winemaking in two of Italy’s most delicious destinations.

If you like your food and culture layered over thousands of years of history, this trip is for you. From the buzz of Rome’s markets to starlit nights in the shadow of Mt Etna, serene al fresco picnics to glamorous Belle Epoque palace dinners, we’ll explore Rome and Sicily from every angle, tasting everything as we go.

Go Deeper

With local winemakers, artists and chefs in the heart of Rome and the backroads of Sicily


Ancient Greek ruins, medieval villages, a starlit night under the gaze of Mt Etna


World-class wines, delicate pastas and the freshest seafood — and we’ll try it all!


In the finest accommodations — palatial hotels and noble rural villas, all perfectly located

3 Reasons to Travel with Chris & Natalie McDade

Chris & Natalie McDade share many things: a home, a son, and an eternal love for Italian food and wine. Chris is the author of The Magic of Tinned Fish, and he creates plates of pasta so tasty they earned his Brooklyn restaurant Popina a spot on Bon Appétit’s NYC 100 list and Gus's Chop House on Time Out's Best New Restaurants of 2022. Natalie is a sommelier with a pedigree earned at Valatta, Temple Court and Craft — some of New York’s finest restaurants. Together, they’ll wine and dine us through Sicily and Rome.

Insider Access

Rome’s quinto quarto (fifth quarter) meats. The best restaurants hidden in plain sight. Wine tastings with one of Sicily’s most prominent winemakers. Chris and Natalie know their way around. Travel easy, we’re in good hands.

Amano l'Italia

Chris and Natalie hold a deep love and knowledge of Italian cuisine. They kickstarted their careers in some of NYC’s famed Italian restaurants (Maialino for Chris; Babbo for Natalie). Their first international trip as a couple was to Italy. It’s a place, and a culture, that fills them with joy.

Inspiration to Us All

Girl meets boy, boy cooks for girl, and girl selects the perfect wine pairing to complement the dish. Chris and Natalie's story is charming, and one straight from an Italian fairy tale.

Your Experience

“Italy was the spark for both of us. After Italy, we never stopped traveling.”
Natalie McDade

Rome, Taormina, Siracusa, Palermo

“It's not just Italian people I fell in love with. I fell in love with their relationship to food and wine.”
Chris McDade

Day by Day

Day 1: Rome

Benvenuti a Roma! We’ll slip right into the teeming street life of Italy’s capital on a foodie walking tour with none other than Katie Parla, author of award-winning cookbook Tasting Rome. Together with Katie, 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.

We’ll have time to relax back at our hotel before meeting up for cocktails with Chris and Natalie, followed by dinner at Rimessa Roscioli. This traditional trattoria is run by one of Rome’s famous baking families — and it’s the perfect celebration of Rome’s classic dishes.

We’ll end the day 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 could be more quintessentially la dolce vita than this very special nighttime excursion.

Day 1: Rome Highlights

  • Food tour with Katie Parla
  • Dinner at Rimessa Roscioli
  • Fiat 500 night tour
  • Stay at Anantara Pallazo Naidi

Day 2: Rome

After breakfast, the dolce vita awaits! 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, the Spanish Steps, and even the Stadium of Domitian.

The afternoon is ours to explore Rome’s backstreets and caffè-lined squares or to take a bit of riposo back at the hotel. Just don’t wander too far because our tastemakers have curated an incredible dinner this evening. Alongside Italian chef, Sarah Cicolini, Chris will prepare a private meal, thanks to a few of Sarah’s secret recipes. The wine pairing? A vibrant list of local varietals sourced by Natalie just for tonight’s dinner. This is a true unicorn dining experience, and we just can’t wait to see what these three dream up. 

Day 2: Rome Highlights

  • La Dolce Vita walking tour
  • Afternoon on your own
  • Dinner prepared by Chris and Natalie
  • Stay at Anantara Pallazo Naidi

Day 3: 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. We’ll head straight to the market, where fishmongers hawk fresh octopus and other catch of the day from the Ionian Sea. As this is Chris’s happy place, he’ll lead the way as we sashay through the stalls and settle in for a fresh market lunch. 

After lunch we’re off to 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. 

Relax and explore our hotel’s grounds, nestled in Mt Etna’s foothills, before settling in for dinner. Every single dish on the menu features ingredients from the property’s abundant gardens.

Day 3: Rome to Sicily Highlights

  • Flight to Catania
  • Fish market tour
  • Taormina visit
  • Stay at Monaci Della Terre Nerre

Day 4: Mt Etna & Around

After breakfast we’ll head out to visit majestic Mt Etna, an active volcano towering nearly 11,000 feet over the island. We’ll meet a local shepherd and sample his homemade ricotta. After hearing a few tales of life on the mountain, we’ll wander over to one of Natalie’s favorite vineyards, Benanti, where 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 sit down to a family-style lunch under the benevolent eye of Le Mamme del Borgo, a collective of local grandmothers who will teach us how to knead the ancient flours into a supple pasta dough for our maccarruni, a typical Sicilian pasta traditionally rolled by hand. Chris will roll up his sleeves here, and under the loving yet vigilant gaze of these Sicilian grandmothers, he’ll prepare us a meal of epic proportion and historic significance. But it’s not just the pasta that we’ll be writing home about. Natalie, a disciple of Sicilian wines, will dole out carefully selected wines from Mt Etna, to make this experience that much more sublime.  

Dessert is a tasting course courtesy of pastry chef and granita maker Giovanna Muscumeci from nearby Randazzo. Granita is now famous world-wide, but it was invented here, on the slopes of Etna, using ice from the volcano’s summit.

Day 4: Mt Etna & Around Highlights

  • Mt Etna cheese & wine tastings
  • Pasta workshop & lunch
  • Granita tasting with Giovanna Muscumeci
  • Stay at Monaci Della Terre Nerre

Day 5: 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. 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 with Chris and Natalie.

Day 5: Siracusa Highlights

  • Ortigia market visit
  • Olive estate visit and tasting
  • Stay at Baglio Occhipinti

Day 6: Ragusa & Modica

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.

In the afternoon we’re off to Modica. It’s hard to know whether Modica is more famous for its chocolate or its beautifully preserved caves and catacombs — both are stunning. We’ll visit a cioccolateria and sample its wares, picking up a few favorites to add to our stockpile for tonight’s dinner.

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 Chris to craft a menu celebrating many of the market ingredients he’s secretly procured over the past week. Natalie too, has been working behind the scenes, and we’ll enjoy her special pairing with this hyperlocal feast. 

As for dessert? It’s a surprise, but one thing we know for sure: today’s chocolate will make its way into a special cannolu, the quintessentially Sicilian dessert better known to us as cannoli.

Day 6: Ragusa & Modica Highlights

  • Ragusa walking tour
  • Modica chocolate tasting
  • Dinner by Chris and Natalie
  • Stay at Baglio Occhipinti

Day 7: 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 7: Agrigento & Palermo Highlights

  • Transfer to Palermo
  • Agrigento exploration & picnic
  • Dinner at Villa Igiea
  • Stay at Villa Igiea

Day 8: 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 Natalie and Chris, our new friends and our adventure together.

Day 8: Palermo Highlights

  • Capo market & Palermo city tour
  • Farewell dinner at Palazzo Lanza Tomasi
  • Stay at Villa Igiea

Day 9: Palermo

Arrivederci Sicilia! We’re off this morning after nine immersive days of adventure and culinary adventure. After breakfast we’ll say ciao to Chris and Natalie, 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.

Day 9: Palermo Highlights

  • Breakfast
  • Transfer to Palermo's PMO airport

Where We Sleep

Beautifully curated accommodations—we’ll relax under the gaze of a volcano in Sicily, and feel like we’re part of the vibrant story of Rome

Anantara Palazzo Naiadi


More than 2,000 years of Roman history are here in one gorgeous space. Ancient ruins of the baths of Diocletian are visible beneath the property's glass floors, and there’s no more quintessentially Roman setting than the hushed, soaring lobby. The hotel has every comfort you'd expect, and some that are wonderfully unexpected (like sunset cocktails at the poolside rooftop bar).

Monaci delle Terre Nere

Zafferana Etnea

This exquisite boutique hotel is perched high on the eastern skirts of Mt Etna, forged out of an old palmento (wine estate) lovingly restored to traditional splendor, down to its chestnut flooring and lava-stone walls. The property boasts its own 15-acre winery, and its in-house restaurant draws heavily from the gardens. This is rustic living at its finest.

Baglio Occhipinti


This ancient, family-run baglio (fortified farm) is centered around a gracious manor house and 300-year-old citrus groves. It's a perfect home base to explore Siracusa and beyond. Meals are prepared over open flame in the enormous scullery fireplace, and culinary-minded guests are welcome to roll up their sleeves and join in the fun.

Villa Igiea


This immaculately restored palazzo is a fever dream of turrets, colonnades and classical statues, spilling out onto terraces overlooking the sparkling Tyrrhenian sea. For more than a century the Belle Epoque property has attracted A-List celebrities; today, after a top-to-bottom remodel by renowned interior designer Olga Polizzi, there’s nowhere grander on the entire island.

Everything was done superbly.
Kelly S.
I was blown away by how flawlessly Modern Adventure fulfilled and exceeded my expectations.
Josh S.
I loved the warmth, sincerity and caring of the Modern Adventure team.
Bob Z.

Book Rome & Sicily with Chris & Natalie McDade

Number of Travelers


Reserve your spot today with a $2,000 per-person deposit plus room supplements (if relevant). Full payment is due 180 days prior to your trip departure date. We’ll email you a reminder. If your trip departs in less than 180 days, we’ll collect full payment either 30 days from when we receive your deposit, or 60 days prior to your trip departure date, whichever is sooner. For details read our Deposit FAQs


per person based on double occupancy; includes internal flight from Rome to Sicily

Can't travel on these dates?
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+1 (855) 219-8018


That’s OK, we have answers. Read our FAQs below. Or text or call us at +1 (855) 219-8018 to speak with a Modern Adventure Trip Specialist.

  1. What does the price include?

    Eight nights at unique four- and five-star accommodations; internal flight from Rome to Sicily; private travel for all day trips and excursions; departure airport transfer; private tours with local guides and cultural experts; exclusive VIP access and tastings; guided activities, adventures and expeditions; entrance fees; daily breakfasts, most lunches and dinners; local beverages with meals.

  2. What does the price not include?

    International roundtrip airfare; travel insurance; transportation to the trip’s starting point; activities not included in the trip itinerary; hotel incidentals including room service, laundry service and hotel bar tabs; food and beverages not included in itinerary; gratuity for tour leader.

  3. Where does this trip start and end?

    Our adventure begins in Rome, Italy, at the Anantara Palazzo Naiadi Hotel. The closest airport is Rome’s Leonardo da Vinci International Airport (FCO). We recommend arriving one day early to ensure you’re at our starting point on time. On our last day, the closest airport is Palermo’s Falcone-Borsellino (PMO) airport. Your flight should be scheduled to depart at 12pm or later from PMO airport.

  4. What travel documents are needed?

    US citizens are not required to have a visa for stays in Italy of under 90 days. Just bring a valid US passport. For citizens of other countries, please check with the Italian embassy or consulate for information and requirements.

  5. Do I need to pay a solo traveler supplement?

    For solo travelers, there is a $2,000 single-supplement fee paid at the time of booking to secure a private room. These spots are extremely limited and available on a first-come, first-served basis.

  6. Who is going on this trip?

    Our adventures typically have between 10 and 20 guests, and our Modern Adventure Team. Our experiences are fun and inclusive and you can expect to be joined by a diverse group in terms of age, background and interests—including solo travelers, couples and friends traveling together. This adventure is for travelers age 18 and above.

  7. Who is leading this trip?

    This trip is led by an expert Modern Adventure trip leader. They’re an experienced travel guide, a representative of Modern Adventure and your go-to person for questions or concerns on the trip. We’ll be joined throughout our adventure by local, expert guides who are deeply knowledgeable with respect to local cultures, customs and history and are passionate about sharing that with us.

  8. Do I need travel insurance?

    We highly recommend purchasing travel insurance. Travel insurance allows you to seek reimbursement for your trip costs; if your trip plans change for unforeseeable reasons, or if you need to get medical help, emergency transport, and for theft, loss or damage of items while traveling. For best coverage, always insure the full trip cost within two weeks of your initial trip deposit and note that most ‘Cancel For Any Reason’ policies must be purchased on the date of your initial deposit.

  9. What is the cancellation policy?

    You may cancel on or before June 8, 2023 and receive a full refund minus a $500 per-person service fee. If you cancel on or after June 9, 2023 there is a 50% cancellation fee. On or after August 7, 2023 there is a 100% cancellation fee. We highly recommend purchasing travel insurance as we are not able to make exceptions to this policy in cases of family/medical emergency or cases of the trip being canceled (see our Terms and Conditions for full details).

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