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Sicily with Matthiasson Wines
Oct 26 – Nov 1, 2025 | One Exclusive Departure
An Epicurean Romp
Dive into the history of Italian wine with Matthiasson Wines
October 26 - November 1, 2025 | 7 Days, 6 Nights
“I've been telling so many people about the trip ever since I got back. Looking forward to another one!”
Questions? Text or call us
+1 (855) 219-8018
$9,900
per person based on double occupancy
California Wine Pioneers, Matthiasson Wines
Thousands of feet above the world, you breathe in the salty Mediterranean air, mesmerized by the churning surf below. You’re in Sicily, an island kingdom where the culture and cuisine mingle with legacies of Roman, Byzantine, Arab, English and French rule over three millennia. In recent days, you wandered through ancient amphitheaters and markets, fragrant with orange blossoms and bergamot, sampled golden arancini from street vendors and rolled fresh pasta for lunch. On the slopes of Mt Etna, you discerned volcanic minerals in glasses of fine Carricante and Nerello Mascalese, as the winemaker shared the delicate alchemy of her craft. Yesterday, you made fresh ricotta with a local shepherd, and tomorrow, you’ll sail the sparkling over the Ionian Sea, pausing for lunch and to explore Greek temples in a quiet fishing village. This is the Sicily of legends — where tradition rises daily with the morning sun, lending comfort and beauty to all it touches.
Trip Highlights
- Cook with local ingredients
- Jeep ride up Mt. Etna
- Have lunch inside a volcanic cave
- Learn about the art of low-intervention wines
- Savor unique Sicilian wines
- Picnic at the Valley of the Temples
- Visit Marsala’s scenic salt flats
- Try street foods at Palermo’s market
Travel with Matthiasson Wines
Steve and Jill Matthiasson are farmers and winemakers behind Napa’s Matthiasson Wines. Often dubbed “pioneers of new California winemaking," the Matthiassons produce balanced, food-friendly wines using old-world traditions and organic farming methods. They’re unapologetic environmentalists who believe that growing grapes and making wine can be a positive force in the battle against climate change, and they champion the well-being of their employees as a crucial element of their business.
Wine is Farming
Steve and Jill are excited to share in Sicily’s many millennia of winemaking this fall. They’re ready to lend their expertise to a deep dive on Sicilian wine’s richness of history and the challenge of farming on the side of a volcano. With them as our guides, we’ll focus on sustainability and how that results in lower yields of concentrated, high-quality grapes that create beautiful, expressive wines.
Ripe for the Picking
Most oenophiles are familiar with the grapes and wines of Tuscany, Piedmont or Veneto, but as a wine region, Sicily remained under the radar until fairly recently. In the past decade or so, the island has gained traction as drinkers started exploring wines crafted with regional varietals and are eager to learn from Sicilian winemakers who’ve been quietly tending their vineyards for generations.
They’re Naturals
Matthiasson Wines have been at the cutting edge of organic farming for over 20 years. Their low-intervention wines are inspired by Old World traditions and their wine offerings include lesser known grape varieties as well as more familiar varieties. Steve and Jill are respected, influential, and critical to the forward movement of this style of winemaking.
Day by Day
*On rare occasions, this itinerary may change.
Day 1: Sicily
October 26, SunBenvenuti a Sicily! After settling in at our hotel, we’ll meet up with our tastemaker and convene for a delightful welcome dinner. The meal—designed to introduce us to the core flavors of Sicily—is the perfect beginning of a journey filled with culinary delights, cultural discoveries, and moments of pure joy.
Tastemaker Moment: Steve and Jill will introduce themselves and toast to the magical road ahead
Day 2: Mt. Etna
October 27, MonAfter breakfast we’ll head out to visit majestic Mount Etna, an active volcano that towers almost 11,000 feet over the island — and occasionally glows red with lava! We’ll head for a beautiful local winery 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.
While there, we’ll indulge in a few tastings at renowned local wineries and sit down for lunch in a cave on Mt. Etna, built from black lava stone with its wine cellar inside a cave left by the volcano lava flows.
We’ll round out our wine-centric day with dinner and a tasting at an 18th century aristocratic villa in a 25-hectare estate.
Tastemaker Moment: Steve and Jill will interact with the winegrowers and speak to the specifics of the Mt Etna wines
Day 3: Taormina
October 28, TueThis morning, we will depart for Siracusa and its ancient heart, the island of Ortigia.
Once there, we’ll savor traditional fare in the Ortigia food market and take in the sights, shouts, and smells that will transport you to an atmosphere far away from today’s modern world. While there, we’ll collect ingredients for a cooking class tomorrow.
Next, we head to Tenuta Cavasecca for a visit to its olive groves and the ancient temple that now houses vats of freshly pressed oil. Finally, we will taste this liquid gold and feast on a homemade lunch with fresh ingredients straight from the farm’s garden.
Our road trip will continue meandering through the countryside taking us to our new home for the next couple of nights where we’ll enjoy dinner after we check in.
Tastemaker Moment: Steve and Jill will help choose the wine pairing for tonight's dinner
Day 4: Vittoria
October 29, WedWe’ll take some time to relax at the hotel this morning, before convening together for a cooking class featuring the ingredients we collected at yesterday’s market. Afterwards,
We’ll head to a local vineyard where grapes, olives, and other produce grow from the sandy, red topsoils of decomposed volcanic sediments, and taste the unique and historical blends they have to offer.
Dinner this evening is on your own to enjoy.
Tastemaker Moment: During our wine tastings, Steve and Jill will speak to the secrets of wine pairing
Day 5: Valley of the Temples
October 30, ThuThis morning we’re off to 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 a picnic lunch.
We will then depart for Palermo for a few hours of driving through Italy before arriving in time to enjoy the beautiful grounds of our hotel and a group dinner.
Tastemaker Moment: Steve and Jill will use their expertise to choose wines for our picnic lunch
Day 6: Palermo
October 31, FriThere’s no better introduction to freewheeling Palermo than the colorful Capo market; as we wander the stalls, listening to the singsong calls of vendors and inhaling an intoxicating swirl of aromas, we’ll be tantalized by 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.
Next, we’ll be treated to a historical tour as we take in Palermo’s stunning seafront, its terraces and courtyards a tapestry of hanging gardens perfumed with subtropical essence. After a a few hours of independent exploration, we’ll meet up again for a truly magical farewell dinner. Alongside our tastemaker and our new friends, we’ll toast to an incredible Sicilian experience!
Tastemaker Moment: Steve and Jill will toast to an incredible week of travel
Day 7: Palermo
November 1, SatArrivederci Sicilia! We’re off this morning after seven immersive days of adventure and culinary adventure. After breakfast we’ll say goodbye, 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.
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I loved how the little things were always taken care of.
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Such a totally immersive experience. Incredible.
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The trip was curated in a way that provided unique experiences we wouldn't have had if we traveled solo.
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 island's story.
*On rare occasions, our hotels will change. Our standards for luxury and authenticity will not.
Dimora Cottanera
CastiglioneNestled on the slopes of Mt. Etna, our historic hotel blends rustic charm with unique architectural flair. Originally owned by engineer Priolo and later acquired by Francesco Cambria, the property features a restored villa, a mill, and lush hazelnut groves. Enjoy a serene retreat with a touch of Sicilian nobility and contemporary comfort.
Baglio Occhipinti
Val di NotoThis hotel is a serene retreat where twelve thoughtfully restored rooms honor the region’s heritage and architecture, offering guests an immersive experience of relaxation and renewal on a fully organic farm.
Grand Hotel et Des Palme
PalermoWithin the hallowed halls of this palatial hotel, we walk among centuries of tradition and artistry. The high-frescoed ceilings and Art Nouveau stained glass make our stay in Palermo more of an immediate immersion into both the past and present of the urban heart of Sicily.
Book Sicily with Matthiasson Wines
Make It Private
We understand that certain dates can work better than others, or sometimes a more private experience is more appealing. We’d be happy to modify this departure so it fits the needs of you and your group.
Start HereQuestions?
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.
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What does the price include?
Six nights at unique four- and five-star accommodations; 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.
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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.
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Where does this trip start and end?
Our adventure begins in Sicily at the Dimora Cottanera 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 Palermo’s Falcone-Borsellino (PMO) airport. Your flight should be scheduled to depart at 12pm or later from PMO airport.
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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.
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Do I need to pay a solo traveler supplement?
For solo travelers, there is a $3,000 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.
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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.
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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.
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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.
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What is the cancellation policy?
For group departures booked on or after January 1, 2025, you may cancel 120 days or more before departure and receive a full refund minus a $1500 per person service fee ($500 of which may be retained as a future travel credit, valid for one year after cancellation). If you cancel on or after 119 days in advance, there is a 50% cancellation fee. On or after 59 days in advance, there is a 100% cancellation fee.
For group departures booked before January 1, 2025, you may cancel more than 90 days before departure and receive a full refund minus a $500 per person service fee. If you cancel on or after 90 days in advance, there is a 50% cancellation fee. On or after 45 days in advance, there is a 100% cancellation fee. See our full terms and conditions for details.