Sicily Uncorked: Island Wines, Coastal Flavors & Timeless Traditions
Spring 2027
In partnership with Wine Enthusiast
May 9-14, 2027 | 6 days, 5 nights
From $10,990
Introduction
Discover western Sicily through the lens that matters most to wine lovers: place. Led by Wine Enthusiast Editor-at-Large and Sicily specialist Danielle Callegari, this intimate Cork + Compass journey follows a coastline and hinterland shaped by sea winds, ancient trade routes, and intensely varied soils—where vineyards rise from olive-dotted hills, skirt sunlit terraces above the Mediterranean, and edge the salt flats and lagoons of the west. Here, history isn’t background—it’s part of the terroir: On Mozia, founded in the 8th century BCE as a thriving Phoenician colony and commercial hub, vines grow in a protected lagoon landscape long defined by exchange between east and west.
Across the week, taste Sicily’s diversity in the glass, moving from salt-kissed, sun-drenched whites—notably Grillo and Catarratto—to the structured, expressive reds of Nero d’Avola, each shaped by microclimate, exposure, and site. Explore site-driven wines at Planeta from Menfi and the remote Serra Ferdinandea estate; on Mozia, see firsthand how vineyard conditions in the lagoon influence island-grown fruit; and in Marsala, step into historic aging rooms to sample barrel-matured expressions of Sicily’s most storied fortified wine—born of the region’s long maritime connections and sustained by the distinctive coastal environment in which it matures.
Along the way, meet the families and teams behind names such as Planeta, Tasca,
Donnafugata, Intorcia, and Tonnino through private tastings and thoughtfully paired
meals—an experience designed to connect grape, ground, and tradition with clarity and pleasure, one glass at a time.
Complementing the wine are hands-on cooking classes, vibrant market walks, Norman mosaics in Monreale, and a sunset farewell at sea (subject to weather conditions). To complete the experience, guests are welcomed each evening at two of Sicily’s most distinctive properties—immersed in vineyard calm at La Foresteria Planeta and steeped in Palermo’s Belle Époque elegance at the storied Grand Hotel et Des Palmes—where setting, comfort, and sense of place continue the story long after the last glass is poured.
Your Expert
Danielle Callegari is a writer-at-large and reviewer on the Wine Enthusiast Tasting Panel. She reviews wines from Italy, including Sicily, Tuscany, Lazio, Abruzzo, Campania, Basilicata, Molise, Puglia, Calabria, and Sardinia.
Every year, the Wine Enthusiast Tasting Panel blind tastes and rates roughly 25,000 wines and spirits from across the globe. Its reviews are widely recognized in the industry as reputable and from trusted experts.
Dr. Callegari is also an associate professor in the Department of French and Italian at Dartmouth College and Communications Director of the Dante Society of America. Her teaching and research focus on premodern Italian literature and food and beverage studies.
In addition to her many articles and contributions to academic and trade presses, she is author of Dante’s Gluttons: Food and Society from the Convivio to the Comedy (Amsterdam University Press, 2022) and the forthcoming A Bite-Sized History of Italy (New Press, 2026). She is also the co-host of Gola, a podcast on Italian food and beverage culture.
Dr. Callegari splits her time between New York City and Italy, and is fluent in both English and Italian. Wandering through the picturesque towns of Panzano, Valdarno, Arezzo, Il Borro, Montalcino, Siena, and Montepulciano while tasting wine and learning about the region’s rich culture and history from Dr. Callegari will be a first-hand experience that no guidebook can replicate.
Highlights
Insider Wine Access
Enjoy private tastings at some of western Sicily’s most respected
estates, including Planeta, Tasca, Donnafugata, Intorcia, and Tonnino, often hosted by family members and estate experts.
Terroir in Focus
Explore Sicily’s extraordinary diversity of soils and styles, from inland
terroirs of Serra Ferdinandea to salt-influenced island wines on Mozia and barrel-aged Marsala in historic cellars.
Expert-Led Encounters
Travel with Wine Enthusiast Editor-at-Large Danielle Callegari,
whose deep regional knowledge opens doors to meaningful conversations with agronomists, winemakers, and proprietors.
Wine & Table
Pair exceptional wines with hands-on cooking classes, market tastings, and estate lunches that showcase Sicily’s native grapes, olive oils, and culinary heritage.
Culture & Setting
Experience Sicily beyond the glass, from Monreale’s Norman mosaics and Palermo’s vibrant markets to a sunset farewell cruise along the coast, perfectly matched with local wines.
“
Contessa Entellina is where Donnafugata’s story began, among the rolling hills of western Sicily, where vineyards, Mediterranean light, art, and literature come together. Together with Danielle Callegari, Cork & Compass travelers will discover our wines, vineyards, Gabriella’s garden, and the biodiversity of a family estate that welcomes guests with the authentic warmth of Sicily.
Chiara Laudicina
International PR Lead and Project Manager
Donnafugata
Itinerary
Day 1
SICILY
Arrival and Planeta
Arrive in Sicily this afternoon and transfer from Palermo to the vineyards of Menfi, in the heart of Planeta’s storied wine estate. Settle into La Foresteria, the Planeta family’s elegant country retreat set amid rolling vines and olive groves, where contemporary comfort meets the rhythms of rural Sicily. Enjoy a relaxed aperitivo by the pool with local almonds and olives, overlooking the estate’s sunlit landscape. The evening culminates with a welcome dinner, perfectly paired with Planeta’s wines, as sunset settles over the Sicilian countryside.
Included Meal: Dinner
Accommodations: La Foresteria Planeta, Menfi
Day 2
SICILY
Planeta Legacy & Sicilian Terroir
Begin the day with a hands-on cooking class using seasonal Sicilian ingredients at La Foresteria, before setting out on a wine-focused journey led by Cork+Compass wine expert and Wine Enthusiast Editor-at-Large Danielle Callegari. Travel to Planeta’s historic Ulmo winery, where the family welcomes you, before venturing by Jeep to visit the Palmento di Risinata, a beautifully preserved 19th-century stone grape-crushing facility that reveals how Sicilian wines were once created by gravity, foot, and time. Sample a glass of Serra Ferdinandea Rose. Return to Ulmo to taste four site-driven wines at the estate house. Return to La Foresteria for a relaxed evening at leisure.
Included Meals: Breakfast, Lunch
Accommodations: La Foresteria Planeta, Menfi
Wineries: Cantine Planeta Ulmo (Sambuca di Sicilia), Serra Ferdinandea
Day 3
SICILY
Salt, Sea & Fortified Legends
Today’s wine exploration moves west to the lagoon of Mozia, where ancient history and Mediterranean terroir intersect. Accompanied by a Tasca agronomist-enologist, cross by ferry to this evocative island to explore its archaeological sites, the Giuseppe Whitaker Museum, and wind-swept vineyards rooted in saline soils. A leisurely Sicilian lunch follows in a rose garden, featuring local specialties such as couscous alla trapanese with fresh fish and caponata of eggplant, olives, and capers, paired with coastal wines that echo the sea. In the afternoon, delve into one of Sicily’s most storied styles with a private tasting at Cantine Intorcia, sampling barrel-aged Marsala wines in the cellar itself. Return to the hotel by early evening, then enjoy an independent dinner in Sciacca.
Included Meals: Breakfast, Lunch
Accommodations: La Foresteria Planeta, Menfi
Wineries: Tasca, Cantine Intorcia
Day 4
SICILY
Noble Estates, Native Grapes & Golden Mosaics
The day begins in the rolling countryside of Contessa Entellina at Donnafugata, where a walk through cinematic vineyards—featured in Il Gattopardo (The Leopard), Luchino Visconti’s classic film adaptation of Giuseppe Tomasi di Lampedusa’s novel about Sicily’s 19th-century aristocracy—leads into the cellar and a refined tasting of the estate’s elegant, terroir-driven wines inside the family villa. Continue to the Tonnino family’s historic Baglio Ceuso for a hands-on cooking class and guided tasting of native Sicilian varieties, including the iconic Ceuso paired with seasonal dishes and the estate’s organic olive oil. From vineyard to masterpiece, end the afternoon in Monreale, home to Sicily’s most extraordinary Norman cathedral, famed for its dazzling gold mosaics that narrate biblical stories in shimmering detail. Arrive in Palermo for a stylish evening at leisure and dinner nearby.
Included Meals: Breakfast, Lunch, Dinner
Accommodations: Grand Hotel et Des Palmes, Palermo
Wineries: Donnafugata Contessa Entellina and Tenute Tonnino Baglio Ceuso
Day 5
SICILY
Markets, Sea Air & a Toast to Sicily
Your final full day immerses you in the flavors and rhythms of Palermo. Explore the historic center and its legendary markets—Ballarò and Vucciria—sampling classic street foods shaped by centuries of cultural exchange, from panelle (crispy chickpea fritters) and crocchette to golden arancine (fried rice balls) and sfincione, Palermo’s beloved thick-crust pizza, topped with slow-cooked onion, tomato, anchovy, oregano, and breadcrumbs. The afternoon is free for relaxation or shopping before a memorable farewell: a sunset boat cruise along the coast with Sicilian wines on board and a celebratory buffet dinner, raising a final glass to an extraordinary journey.
Included Meals: Breakfast, Lunch, Dinner
Accommodations: Grand Hotel et des Palmes
Day 6
SICILY
Ciao Sicilia!
Independent departures from Palermo Airport.
“
At Tenuta Regaleali, in the heart of Sicily, guests will discover an unexpected landscape of rolling green hills, historic vineyards, and extraordinary biodiversity. Together with Danielle Callegari and Cork & Compass Travel, guests will experience the authentic soul of Sicily through great wines, seasonal cuisine, and the timeless beauty of the “blessed hills” of Regaleali.
Ivo Basile
Director of Communications
Tasca d’Almerita
“
At Tonnino, wine is the starting point for telling the story of authentic Sicily. Through visits to our production winery, the historic Baglio Ceuso dating back to 1860, and our wine tourism experiences, guests discover the deep connection between land, history, people, and tradition. Welcoming Cork & Compass guests alongside Danielle Callegari means sharing not only our wines, but also a way of life, a culture, and a spirit of hospitality that make every visit truly memorable.
Antonio Tonnino
Founder & CEO
Tenute Tonnino Baglio Ceuso
Accommodations
La Foresteria Planeta
MENFI
Set amid the rolling vineyards and olive groves of Menfi, La Foresteria Planeta is the flagship wine resort of one of Sicily’s most celebrated wine families. This intimate, four-star retreat blends contemporary comfort with rural elegance, offering serene views across the estate to the sea beyond. Thoughtful design, a tranquil pool, and a culinary program deeply rooted in local ingredients make it an ideal base for immersive wine-focused travel in western Sicily.
Grand Hotel et Des Palmes
Palermo
Hotel et Des Palmes is one of Palermo’s grand historic hotels, set along the elegant Via Roma and long associated with the city’s cultural and social life. Restored with Belle Époque flair, its interiors feature high ceilings, period details, and refined salons balanced by modern comforts.The hotel’s central location makes it an ideal base for exploring Palermo’s historic center, theaters, cafés, and markets, while offering a graceful retreat at the end of each day’s discoveries.
Get the Brochure
All details about the Sicily trip are available in the PDF version of our brochure.
Frequently Asked Questions
Trip Details
How do I reserve my spot?
A deposit of $1,000.00 (unless otherwise specified) is due to secure your space on the tour. Deposits are refundable up to 50% until 120 days prior to departure (unless otherwise specified).
When do I need to pay for my trip?
Your deposit is due upon reservation. Your final balance is due upon receipt of your invoice, 90 days prior to departure. If you are making a reservation within 90 days of the trip’s departure, full payment will be required upon confirmation.
How big will the group be?
Our trips have a maximum group size of 25 people. They are large enough to meet new people with diverse backgrounds, but small enough to be on a first-name basis with everyone.
Are solo travelers welcome?
Of course! There is always a good number of solo travelers on our trips, and they are welcomed with open arms. Group meals generally take place at medium to large tables, and our Travel Directors ensure that everyone is included in conversation. Because our trips are priced for doubles sharing a room, there is a supplemental cost for those who choose not to share.
How much free time should I expect to have?
Our trips are designed to give our travelers special insight and understanding of the places we visit. The talks and commentary by our hosts and local guides, in addition to time set aside for writing and reflection, are what make our itineraries special, and this kind of curated experience cannot be obtained on one’s own. For this reason, our trips generally do not incorporate long periods of free time during the day, although evenings and some meals will be at leisure.
Can I arrive early, or stay on after the tour ends?
Yes, absolutely! If you wish to arrive early at the first hotel on the itinerary or stay on at the last hotel, our Guest Services Advisors will be happy to advise you on the best way to make arrangements.
What do I need to bring on my trip?
We’ll send you a detailed clothing and equipment list well before departure so you know what you’ll need to pack. We provide the rest: comfortable accommodations, an engaging daily itinerary, expert trip management, and access to people and places that will thrill and delight you.
Once I reserve my trip, what happens next?
After you reserve your trip and pay your deposit, you will be sent a confirmation email with our Terms and Conditions, insurance information, and a Traveler Information Form from our Travel Management Company, Academic Travel Abroad. Your Guest Services Advisor will reach out when it’s time to book airfare after a minimum of 10 travelers have enrolled on your departure. Final trip details will be sent roughly 2-3 weeks before departure.
Rates and Cancellation Information
Are tips included?
Yes! Tips to local guides, restaurant staff, bell staff, and drivers are all included in the trip price. Your Trip Leader and Travel Director are taken care of and will not accept tips. The only time tips are not included is during free time and meals on your own, as well as for any personal services.
Are drinks included?
In addition to the tastings included in the itinerary, a couple glasses of wine are included for all group dinners. Any additional alcoholic beverages are not included in the program price. Non-alcoholic beverages are included in all meals.
Is airfare included?
Airfare to and from the starting and ending point of the program is not included in the price in order to give you maximum flexibility in choosing your preferences for air travel. This way you can use frequent flier upgrades, depart from your airport of choice, or add pre- and post- trip extensions with no constraints. Please refrain from booking your airfare until your Guest Services Advisor reaches out to confirm your departure.
What is your cancellation policy?
Deposits will be 50% refundable 120 days prior to departure. Cancellation between 119-91 days before departure: 100% of deposit is forfeited. Cancellation between 90-61 days, 50% of the Trip price is forfeited. Cancellation within 60 days of departure: no refund. You always have the option to transfer your deposit to a future Post and Courier Travel departure up until 90 days prior to departure with no penalty.
Health & Safety
Are you able to accommodate dietary restrictions and allergies?
Every effort will be made to try to accommodate any special dietary requests you may have (e.g., low salt, vegetarian or vegan). Please discuss your requests with us when signing up for a trip.
What are the physical requirements of this trip?
Travelers should be in good health and able to walk up to 3 miles (with stops) over uneven terrain and be able to navigate stairs unassisted. In city centers, we do try to walk from place to place due to traffic restrictions and also in keeping with our commitment to environmental sustainability.
Do I need trip insurance?
We strongly suggest purchasing travel insurance to help protect your investment and provide you with financial recourse in the event of trip cancellation or interruption due to sickness or quarantine. When purchasing a policy, please consult with a trip insurance agent to review what contingencies are covered. While we will do our best to recover any unused portion of your trip due to sickness, it is often the case that payments cannot be refunded. We recommend using our partner insurance provider, Travel Insurance Services, which offers three different policies for you to choose from.
What happens if I get sick on tour?
Our top priority is to keep our travelers, staff, and the communities we visit as healthy and safe as possible. Not only do we care about your well-being, but illness on tour alters the group dynamic, diverts staff attention, and interrupts the smooth functioning of the trip. For this reason, we recommend that all travelers to stay up to date with recommended vaccinations. Additionally, we encourage traveling with a mask and notifying your Tour Director immediately should you feel any symptoms of illness.
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Wine Enthusiast’s Cork+Compass Travel is the magazine’s gateway to exceptional wine travel and tourism. Our philosophy is rooted in the mission of our parent company, Wine Enthusiast—to enhance the wine experience for all.