Sicily with Jeff Porter

May 11 – 17, 2026 | One Exclusive Departure

An Epicurean Romp

Dive into the history of Italian wine with Jeff Porter

May 11 - 17, 2026 | 7 Days, 6 Nights

“I've been telling so many people about the trip ever since I got back. Looking forward to another one!”
Royce K.

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.

Day by Day

*On rare occasions, this itinerary may change.

Day 1: Sicily

May 11, Mon

Benvenuti a Sicily! After settling in at our hotel, we’ll meet up with our tastemaker and convene for a delightful wine tasting and 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: Jeff will introduce themselves and toast to the magical road ahead

Day 2: Mt. Etna

May 12, Tue

After 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, complete with delectable pistachio pastries, and sit down for lunch on the grounds.

We’ll round out our wine-centric day with dinner at a spot.

Tastemaker Moment: Jeff will interact with the winegrowers and speak to the specifics of the Mt Etna wines

Day 3: Modica

May 13, Wed

This 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
Panoramic view of Isola Bella and the bay of Taormina, Sicily, with clear turquoise waters and dramatic cliffs along the Mediterranean coast.

Day 4: Bagilo Occhipinti

May 14, Thu

We’ll take some time to relax at the hotel this morning, before convening together for a cooking class featuring local ingredients. 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, Jeff will speak to the secrets of wine pairing

Day 5: Valley of the Temples

May 15, Fri

This 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: Jeff will use their expertise to choose wines for our picnic lunch

Day 6: Palermo

May 16, Sat

There’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: Jeff will toast to an incredible week of travel

Day 7: Palermo

May 17, Sun

Arrivederci Sicilia! We’re off this morning after seven immersive days of culinary exploration. After breakfast we’ll say goodbye, knowing the memory of our journey 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.

I loved how the little things were always taken care of.
Greg A.
Such a totally immersive experience. Incredible.
Ray B.
The trip was curated in a way that provided unique experiences we wouldn't have had if we traveled solo.
Katherine R.

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

Castiglione

Nestled 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 Noto

This 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

Palermo

Within 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

Number of Travelers

Payment

Reserve your spot today with a $1,500 per-person deposit plus room supplements (if relevant). Please see our terms and conditions for full payment details.

$10,800

per person based on double occupancy

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

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.

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Questions?

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; 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 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.

  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 $2,500 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.

  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 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.

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