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Sicily with Jeff Porter
May 11 – 17, 2026 | One Exclusive Departure
An Epicurean Romp
Dive into the history of Italian wine with Jeff Porter
“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
$10,800
per person based on double occupancy
World-Class Sommelier & Italian Wine Authority, Jeff Porter
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
- Try street foods at Palermo’s market

3 Reasons to Travel with Jeff Porter
Jeff Porter is a renowned sommelier, educator, and host of the travel and wine series Sip Trip. A former Beverage Operations Director for the Bastianich Hospitality Group, he shaped wine programs for acclaimed restaurants like Del Posto and Babbo. Now based between NYC and Torino, Jeff brings decades of experience—from Napa to Sicily—leading tastings, curating wine lists, and demystifying wine with warmth and depth. His deep connection to Italy’s vineyards, including Sicily’s volcanic terroir, informs his storytelling approach and passion for sharing the cultural richness behind every bottle.
Sicily Is Love
Jeff first stepped foot in Sicily in 2009 and has returned again and again for the same reasons: soulful wine, unforgettable food, and the kind of laughter that carries late into the night. For a lifelong devotee of Italian wine, Sicily isn’t just a destination—it’s the heart of his passion.
No Pretense
With a Texas-born warmth and a deep well of wine knowledge, Jeff makes even the most complex concepts feel approachable. His laid-back, storytelling style is part Southern charm, part oenological expertise—an ideal match for Sicily’s bold, generous spirit and one-of-a-kind wines.
Fruit of the Earth
In Sicily, grapes grow in volcanic ash, limestone, and seaside clay—stubborn, sun-drenched, and wildly expressive. These ancient varieties thrive under extreme conditions and reward those who listen closely. Jeff delights in sharing these stories, guiding guests through wines as distinctive and compelling as the land they come from.
I loved how the little things were always taken care of.
Such a totally immersive experience. Incredible.
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 Jeff Porter
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 $2,500 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?
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. See our full terms and conditions for details.