Sicily & Naples


Southern Italy's flavors, the birthplace of pizza, world-class wines, the freshest seafood


Ancient Greek ruins, medieval villages and hillside churches, a star-lit night under the gaze of Mt Etna


With local winemakers, artists and chefs at meet-ups and exclusive dinners

Why Sicily & Naples

Sorry New York and Chicago: this is where pizza comes from. You may have heard of Neapolitan-style before, but you haven’t really tasted it until you explore each ingredient’s origin story, smell the fresh mozzarella and San Marzano tomatoes, and feel the elasticity of dough in your hands. Add that to the dreamy beaches, the Greek, Roman, Arab and Spanish influences, and the monumental wines of Sicily. This is Italy seen through a local’s eyes and foodie’s heart.

Moments That Matter

The Italy lesser-seen comes with unforgettable access to superb wines, volcano hikes, street-art walks, private boat rides, Greek theaters and a whole lot of pizza. In between exploring Mt Etna with a local volcanologist, learning the history behind the region’s most admirable medieval sites and gazing across lush Mediterranean vistas, you’ll get a hands-on look at what goes into making Sicily's unforgettable regional dishes.

Your Private Experience

Who It’s For

Our Sicily and Naples is an adventure as flexible as you need: a journey of history and culture, romantic escape, family adventure, a master class in wine.

When to Travel

May, June, September and October offer warm and pleasant temperatures, ideal for outdoor exploration. July and August are busier, and warmer.

Make It Yours

More art and history, more wine, more regional cuisine—or extra days in Tuscany, the Amalfi Coast or Campania, Piedmont, whatever suits your tastes.

Day by Day

Whether you want to explore deeper in Sicily—or explore farther afield in Rome, Tuscany, the Amalfi Coast, Piedmont and beyond—we’ll help craft your ideal experience.

Day 1

Benvenuto a Sicily! Dive into the epic market scene in Catania, sampling the area’s finest street foods as fishmongers hawk fresh swordfish and octopus hauled in overnight. Afterwards, head to nearby Siracusa, a seaside wonder basking in 2,700 years of history. Wander through ancient sites and around dreamy Ortigia, the cobblestone island that still lives like a village, and meet up with locals for an even passeggiata.

  • Catania market tour
  • Guided exploration of Siracusa

Day 2

Start today with a private tour of the hilltop towns of Noto, breezy, walkable and famed for its limestone Baroque buildings; and Ragusa, an unreal mountain-top town with sloping alleyways and sun-kissed cathedrals. Here, get a full-on exposé of traditional Sicilian cheeses at the CoRFiLaC Laboratory, with an expert-led tasting. Next is a meet-up at one of Italy’s most respected tomato growers, Casa Morana, for a hands-on cooking experience and to sit down to a picnic farm lunch.

  • Tour hill towns of Noto and Ragusa
  • Cheese tasting at CoRFiLaC
  • Meet tomato growers at Casa Morana
  • Farm picnic lunch

Day 3

Hike around Mt Etna’s craggy fissures with a local volcanologist who shares the ins and outs of its fascinating history. Move on to one of the area’s most notable vineyards, Tenuta San Michele, set atop the volcano’s slopes. Meet the winemaker, sip juicy reds and rich whites, then lunch on the best charcuterie and aged sun-dried tomatoes under the golden Sicilian sun.

  • Mt Etna hike with volcanologist
  • Lunch at Tenuta San Michele vineyard

Day 4

Rise early with a private boat ride along the Ionian Sea’s breathtaking shorelines, exploring grottos and caves with crystalline waters that glow blue. Enjoy a specially prepared lunch at sea, then dock to explore the lovely historic city of Taormina’s medieval lanes and churches, and its epic hilltop Greek theater, however you choose—we recommend gelato in-hand.

  • Ionian Sea private boat tour
  • Lunch at sea
  • Explore coastal town of Taormina

Days 5 - 6

It’s a short flight to a buzzing Mediterranean capital under the watch of Mt Vesuvius. Jump into Naples’ irresistible energy with a chef-led tour of its most famous creation: pizza! Savor some slices at Naples’ most beloved pizzerias and learn the history of the world’s favorite pie; or be the star guests at one of Naples’ top restaurants, for unforgettable courses paired with regional wines.

  • Flight to Naples
  • Chef-led pizza making
  • Guided street art tour
  • Dinner at Michelin-starred kitchen
  • Explore Naples after dark

Where We Sleep

Authentic, lovingly curated accommodations—we’ll relax and unwind under the gaze of a volcano in Sicily, and feel like we’re part of the vibrant story of Naples


In Sicily, even post offices are palaces. You’ll feel that fully, entering this magnificent, palatial former post office from 1920 in the perfect spot in historic Siracusa. It’s a joy to stay here. Sprawling rooms are decked with fine Italian designs, lounges have expansive views of the Mediterranean coastline.


Set at the foot of Mt Etna, your hotel is a luxurious mansion dating from the early 1700s. The chic rustic feel benefits from wood beam ceilings in its alluring interiors—the perfect place to set up while exploring the area’s best wineries and a hike up an active volcano.


Filled with antiques, modern art and Liberty stained glass, this 19th-century, neoclassical villa is the perfect spot right in the historic center of Naples.

People Love MO/AD’s Italy

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.


  1. How many people is this itinerary suitable for?

    We can plan a custom, private departure for any group size. Our custom trips are perfect for a couple wishing to travel on their own, a family, or a multi-generational group. If you’re looking to travel on one of our group departures on a private basis, a minimum number of travelers may apply.

  2. Can you curate an itinerary for a larger group?

    Yes, we can craft an unforgettable milestone celebration or company retreat for groups as large as 40 or more.

  3. What makes a MO/AD experience different?

    Our level of curation, care, and in-country connections. We handle everything, overseeing your experience from beginning to end with the highest levels of ownership and responsibility. We support you every step of the way with comprehensive itineraries, detailed day-by-day descriptions, insider destination info, and 24/7 dedicated support.

  4. How far in advance should I plan my trip?

    Preferably six to nine months in advance and earlier for holiday travel. We stay in unique, in-demand boutique and luxury hotels where advance reservations are important to secure the best accommodations possible. We can help with last-minute travel planning, however availability may be limited.

  5. What is typically included?

    We curate your MO/AD Private Departure to ensure the experiences are authentic, immersive, and included in your trip price. Your itinerary typically includes accommodations, airport transfers, private transportation for all day trips and excursions, privately guided tours with local guides, exclusive VIP access and activities, and meals as detailed in your itinerary.

  6. How much will it cost?

    MO/AD Private Departures typically cost $750 to $1,500 per person, per day, and vary by destination, time of year, number of people in your group, and types of activities you prefer.

  7. What's not included?

    MO/AD Private Departures do not include roundtrip airfare to/from your destination, travel insurance, gratuities for local guides, hotel incidentals, and any activities and meals not included in your itinerary.

  8. What deposits are required?

    After learning more about you, your interests, preferred style of travel, dates, and budget, we will present you with initial ideas and examples of what we can plan for you. In order to design a detailed itinerary and check availability, there is a $500 non-refundable planning deposit due. This will be applied to your final trip cost. Once your itinerary is perfect, we require a 25% non-refundable confirmation deposit to start confirming all of your arrangements. Many of our local partners and hotels require additional advance deposits to secure the best accommodations. The balance of your trip cost is due 90 days prior to travel.

  9. What travel documents are needed?

    US citizens do not require a visa to enter Italy as tourists for stays up to 90 days. The only requirement is a valid US passport. We recommend that your passport is valid for six calendar months beyond your planned departure date from Italy.

  10. Where can I find the complete terms of my booking?

    See our Terms & Conditions for complete details about our policies regarding your MO/AD Private Departure booking.