Sicily & Naples with Jason Dady

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Italy Uncovered

Immerse yourself in the food, art and culture of Sicily & Naples with Chef Jason Dady

May 22 - 28, 2023

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7 Days, 6 Nights

Best of Sicily, Siracusa, Mt Etna, Taormina, Naples

Price from


per person based on double occupancy, including internal flight from Sicily to Naples

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+1 (855) 219-8018

Join our waitlist, and we will contact you if and as space becomes available.

You roll out the dough, pinch the ends with your fingers and toss it up in the air as a master pizzaiolo looks on and smiles. You’re in the beating heart of Naples, beside a wood-fired oven in the literal birthplace of pizza. Just hours from now, after you’ve perfected the Neapolitan pie, you’ll be dining at one of the city’s finest restaurant and toasting a week’s worth of joy and exhilaration. You’ll tell stories of Sicilian cheesemakers, recall the sharp mercurial wines from the slopes of Mount Etna, wax nostalgic about your adventures on the Ionian sea. This is southern Italy like you’ve always dreamed of, an experience made richer by the kindred spirits at the table and the company of a humble chef at the pinnacle of his craft.

With us on this trip is the award-winning chef Jason Dady. He’s the culinary star and entrepreneurial force behind his namesake restaurant group in San Antonio, where you can find five of his iconic restaurants serving up everything from authentic Italian food at Tre Trattoria at the San Antonio Museum of Art to his latest concept, Jardin, in the San Antonio Botanical Garden. His thirst for heritage recipes and delightful Aperol spritzes are just the beginning of why we can’t wait to experience Sicily and Naples through his eyes.

If you want to venture into iconic Italy, but do it like a local, this is the trip for you. Uncover the delicious backstory of southern Italy’s great dishes. Meet vintners, cheesemakers and pizzaiolo chefs, as we go deep in the story behind what makes southern Italy so deliciously unforgettable.


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

Go Deeper

Connect with local winemakers, artists and chefs, with Chef Jason Dady


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


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

3 Reasons to Travel with Jason Dady

For nearly two decades, Jason Dady and his family-run restaurants have been pushing culinary boundaries in San Antonio. He’s known for reinvigorating the city’s food scene, thanks in part to his flagship Tre Trattoria, where family recipes wow the regulars as much as the uninitiated.

Big in Texas

Jason Dady is a James Beard Award semifinalist who has appeared on the likes of the Food Network's Iron Chef Gauntlet and Beat Bobby Flay. His accolades in Texas as just as impressive: a “40 under 40 Rising Star” and “Best Chef in San Antonio”.

Market as the Menu

Jason is ready to “eat like the Italians,” which he translates to strolling through open-air markets not knowing what you are going to make until you get there, in addition to getting to the source of San Marzano tomatoes, or the 00 flour used for pizza dough in Naples for a pie like you’ve never tasted before in your life!

Innovation is Key

In addition to slinging some of the best Italian and barbecue in the Lone State, Jason is also known around San Antonio for encouraging chefs and entrepreneurs to explore their wild ideas in the name of innovation and fresh dining experiences.

Your Experience

“I love how time passes in Italy, just rolls from one thing into another…it allows you to spend time with people without interruption.”
Jason Dady

Sicily, Siracusa, Mt Etna, Naples

“It doesn't matter where you travel in the world—the dinner table is kind of the meeting ground of community and family.”
Jason Dady

Day by Day

Day 1

Benvenuto a Sicily! We meet up with Jason and our fellow adventurers in historic Catania, then dive right into the epic market scene. We’ll sample some of Sicily’s finest street foods as fishmongers hawk fresh swordfish and octopus hauled in overnight. Afterwards, we head to nearby Siracusa, a seaside wonder basking in 2,700 years of history with deep Greek, Roman, Byzantine, North African and Norman influences.

Here, we’ll embark on a walking tour of the island of Ortigia, the bustling city center of Siracusa that still lives like a village—watch out for uneven cobblestones! Later we’ll join the locals on a passeggiata, or evening walk, on the promenade for an unforgettable first sunset together over the Mediterranean en route to an elegant and locally-sourced welcome dinner.

Day 1 Highlights

  • Catania market tour
  • Transfer to Siracusa
  • Walking Tour of Ortigia
  • Stay at Ortea Palace in Siracusa

Day 2

After a grand breakfast, we’ll be treated to a full-on exposé of traditional Sicilian cheeses at the CoRFiLaC Laboratory, where we find out how to taste cheese like pros and see all stages of the best Sicilian cheesemaking.

Next, we’ll move onto the next Sicilian ingredient: tomatoes. We’ll meet one of Italy’s most respected tomato growers, Casa Morana, where we’ll learn how they make epic tomato sauce and sit down to a picnic lunch on the farm.

Heading back to the hotel, we will stop at Noto, a breezy, walkable town, famed for its limestone Baroque buildings. Our afternoon pick-me-up? A fresh slice of hazelnut sponge cake and a cappuccino ghiacciato (iced coffee with almond milk granita) at a beloved family-run bakery.

Tonight, the dream-like lanes of Siracusa are yours to explore on your own.

Day 2 Highlights

  • Cheese tasting at CoRFiLaC Laboratory
  • Meet tomato growers at Casa Morana and farm lunch
  • Visit to Noto
  • Stay at Ortea Palace in Siracusa

Day 3

After breakfast, we pack our things and move our Sicilian adventure to an active volcano over twice the size of Mt Vesuvius. At nearly 11,000 feet, Mt Etna is a towering green mountain that sometimes glows red. We’ll hike its craggy fissures with a local volcanologist who shares the ins and outs of Etna’s fascinating history.

Appetites worked up, we’ll move on to one of the area’s top-notch vineyards set atop the volcano’s slopes with panoramic views. At Tenuta San Michele, we’ll 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. For the night, we’re sticking around Etna’s shadow. We set up in an intimate boutique hotel in a village at the volcano’s foot, where we can toast our day under a starlit sky.

Day 3 Highlights

  • Transfer to Mt Etna
  • Hike around Mt Etna with volcanologist
  • Tour, tasting and lunch at Tenuta San Michele vineyards
  • Stay at Relais San Giuliano in Viagrande

Day 4

Don’t sleep in today! Rise early for breakfast as the morning mist hangs over the volcano. Then pack up a sun hat, as we begin the day with a private boat ride along the breathtaking rocky shorelines and beaches of the Ionian Sea. It’s surreal scenery, as we see inside Grotta Azzurra, a sea cave with crystalline waters that glow blue. We 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 with a full coastline panorama below.

We’ll have an afternoon full of Taormina’s endless appeal. Sit with an espresso in vibrant piazzas, browse shops in the alleys bursting with life, pop into a Gothic cathedral, and take some gelato to cliff-hugging terraces overlooking the sea. We’ll return to our hotel by the volcano for another star-lit night under Mt Etna’s gaze.

Day 4 Highlights

  • Private boat ride in Ionian Sea
  • Special lunch prepared at sea
  • Explore coastal town of Taormina
  • Stay at Relais San Giuliano in Viagrande

Day 5

Our adventure of southern Italy moves on today, as we fly to a buzzing Mediterranean capital under the watch of Mt Vesuvius. We’ll jump right into Naples’ oldest spot for street food, Pignasecca Market. We’ll wander this outdoor mercato tasting fresh fruits and pastries, and dig into an Italian favorite, cuoppo Napoletano—because how else would you eat the best fried seafood than in a cone? We’ll then work off our treats on a walking tour of Piazza del Plebiscito in the city center, admiring Naples’ Royal Palace, Castle Nuovo and the immense Galleria Umberto. 

Naples is a blast after dark, and the evening is yours to explore its hipster bars with DJs spinning vinyl, and cozy intimate restaurants with wine lists as long as the night. Enjoy!

Day 5 Highlights

  • Fly to Naples
  • Naples market food tour
  • Explore Naples after dark
  • Stay at Grand Hotel Parker's in Naples

Day 6

After breakfast we’ll find more of Naples’ storied appeal outside our door, and learn why Neapolitan pizza is not just to-go street food—it’s an art form, with a rich history dating back to the 1700s. The ‘modern’ pizza was invented here in 1889, when King Umberto I and Queen Margherita of Savoy visited Naples. The story goes that a local baker crafted a pizza in honor of the queen, with colors inspired by the Italian flag: red (tomatoes), white (mozzarella), and green (basil leaves)… and so the classic Neapolitan pizza was born! We’ll sit for an immersive, hands-on pizza making course with a wood-fired oven to craft different types of Neapolitan pizza, alongside Jason and a local pizzaiolo (pizza maker). Have your appetite ready.

But don’t get too full because our farewell dinner is a meal for the ages. After some rest and independent exploration, we’ll make our way to a restored cloister that has been transformed into a contemporary art gallery with cuisine run by Sabrina Russo, leader of the Food for Soul project. We’ll settle in for unforgettable courses and plenty of wine to toast our journey together. The night ends whenever it ends!

Day 6 Highlights

  • Hands-on pizza course
  • Farewell dinner
  • Stay at Grand Hotel Parker's in Naples

Day 7

This morning, we’ll breakfast together and then say goodbye to Jason, pack up all we’ve collected, along with new memories, and head to the airport. Ciao!

Day 7 Highlights

  • Transfer to Naples 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 Naples

Ortea Palace


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—and Siracusa’s iconic monuments, shops and restaurants are just footsteps away.

Relais San Giuliano


Set at the foot of Mt Etna, this intimate, 13-room hotel is made from a luxurious mansion dating from the early 1700s that makes any guest feel like a Sicilian noble returning home. 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.

Grand Hotel Parker's


Grand Hotel Parker’s — the city’s original luxury hotel — exudes 19th-century craftsmanship with period antiques, bronze sculptures and elaborate chandeliers decorating the palatial lobby. It's the perfect mix of Impeccable hospitality and modern comfort and design sensibility.

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 Sicily & Naples with Jason Dady

Number of Travelers


Reserve your spot today with a $1,000 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, including internal flight from Sicily to Naples

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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?

    Six nights at unique four- and five-star accommodations; internal flight from Sicily to Naples; 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 Catania, Italy, at the Il Principe Hotel. The closest airport is Catania’s Fontanarossa Airport (CTA). We recommend arriving one day early to ensure you’re at our starting point on time. On our last day, the closest airport is Naples International Airport (NAP) in Naples, Italy. Your flight home should be scheduled to depart at 12pm or later from NAP 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 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 January 22, 2023 and receive a full refund minus a $500 per-person service fee. If you cancel on or after January 23, 2023 there is a 50% cancellation fee. On or after March 23, 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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