Sicily’s position in the center of the Mediterranean Sea has made the island a nexus of cultural exchange for millennia. This rich heritage is matched by an amazingly diverse and complex range of wines and gastronomy. On this wine tour, you will taste and drink the contributions of the different civilizations who have settled here for millennia.

Blessed with a varied range of terroirs, Sicily boasts some of the most distinctive grapes and wines of all of Italy. Old head-trained bush vines of Nerello Mascalese and Carricante grow at high altitude on the slopes of the impressive Etna volcano. The southeast part of the island, famous for its unique Sicilian Baroque architecture, is the traditional home to Sicily’s flagship variety Nero d’Avola and Frappato. It’s time to discover this enchanting and wild place.

Join us in Sicily for a seven-day tour of historical and culinary delights surrounded by breathtaking vineyards, stunning Mediterranean coastlines, and seemingly endless bottles of wine!

What's Included

  • 6 nights accommodation and breakfast in 4- and 5-star boutique hotels
  • 10 wine tastings
  • 3 dinners
  • 4 lunches
  • Time Around Tuscany Guide
  • DCanter Wine Guide
  • All of the historical tours and activities included in the itinerary
  • Ground transportation on the tours
  • Mineral water on the bus rides

What's Not Included

  • Airfare to and from Catania, Sicily (CTA)
  • Meals on your own
  • Hotel upgrades


Please note that spaces are limited! If you are interested in coming along, please contact us as soon as possible to avoid missing out!

Book Now


The specific activities on this schedule are tentative and subject to minor adjustments due to logistical and other practical considerations.

SUNDAY, MAY 19 – Arrival

We’ll meet at the Catania Airport in the afternoon and depart for the historic city of Ragusa. Known for its 17th century Baroque architecture, Ragusa is one of the eight cities that make up the Val di Noto UNESCO World Heritage site. We’ll spend our first three nights in Ragusa, exploring the region’s history, tasting its wine, and enjoying its culinary delights.

  • Afternoon departure from Catania Airport
  • Transport to Ragusa
  • Casual group dinner at Ragusa Ibla

MONDAY, MAY 20 – Ragusa

On our first full day together, we will take in the historical sites of the ancient city of Ragusa. The city has counted Greeks, Byzantines, Romans, Arabs, and Bourbons as its inhabitants, so there will be lots to explore. Following a casual lunch in the city center, we will depart for the neighboring town of Modica, where we will enjoy a deliciously fun chocolate-making class. We will conclude the evening with an upscale, Michelin-starred dinner.

  • Guided tour of Ragusa’s historic center with a visit to the Cathedral
  • Casual lunch in the city center
  • Afternoon chocolate class in Modica
  • Welcome dinner at the Michelin-starred Locanda Don Serafino

TUESDAY, MAY 21 – Wines of Vittoria

Sicily’s most famous grapes, Frappato and Nero d’Avola, find the perfect marriage in the wines of Cerasuolo di Vittoria, Sicily’s only DOCG. We’ll explore three approaches to producing wine in the Vittoria region, from a modern producer to one using ancient winemaking techniques, and conclude with one of Italy’s most influential natural wine producers.

  • Mid-morning tasting at a classic producer of Cerasuolo di Vittoria, Sicily’s only DOCG
  • Lunch at a historic producer renowned for its traditional use of clay amphoras
  • Afternoon tasting with one of Italy’s most influential natural wine producers
  • Free evening with dinner on your own

WEDNESDAY, MAY 22 – The Southern Slope of Mount Etna & Taormina

We say goodbye to the surroundings of Ragusa and head north to the southern slopes of Mount Etna. We’ll enjoy a late morning tasting at a boutique organic winery followed by lunch at a multigenerational winery with roots dating back over 150 years. We’ll arrive at our waterfront hotel in Taormina where you can relax and enjoy the evening on your own. Taormina is an idyllic town located precisely where Mount Etna dips into the Mediterranean’s vibrant blue waters.

  • Check-out of our hotel in Ragusa
  • Late-morning tasting at a boutique organic winery on the southeastern slope of Mount Etna
  • Lunch and wine tasting at a traditional Mount Etna winery
  • Check-in to our hotel in Taormina
  • Free evening with dinner on your own in Taormina

THURSDAY, MAY 23 – The Northern Slope of Mount Etna

The northern slope of Mount Etna has some of the most sought after terroir in all of Italy. We will visit three wineries, each taking a unique approach to vine cultivation and winemaking in the region.

  • Late-morning tasting at a boutique natural winery on the southeastern slope of Mount Etna that’s a leader in distinguishing the unique terroirs of the volcano’s slopes
  • Lunch and wine tasting at a traditional Mount Etna winery
  • Late afternoon tasting at a modern, experimental winery
  • Free evening with dinner on your own in Taormina

FRIDAY, MAY 24 – The Northern Slope of Mount Etna

Our journey will conclude on some of the most picturesque terraced vineyards of Mount Etna. We will begin the morning with a deep dive into the Nerello Mascalese grape and its uncanny ability to reflect terroir specificity. We will enjoy lunch at a winery that produces wine throughout Sicily and enjoy flavors from beyond the island’s eastern edge. Our evening will conclude with a Michelin-starred dinner featuring locally sourced ingredients.

  • Mid-morning tasting
  • Winery tasting and lunch
  • Free afternoon in Taormina
  • Farewell dinner at a Michelin-starred restaurant in Taormina

SATURDAY, MAY 25 – Farewell

Depart or extend your trip on your own

  • Check-out of the hotel in Taormina
  • Early morning departure to Catania Airport


DATES: Sunday, May 19 – Saturday, May 25, 2024

COST: $4,995 per person (double occupancy) // $550 single occupancy supplement


Enjoy superior 4- and 5-star accommodations during your stay in Sicily.

Your 5-star hotel in Ragusa will be a remarkable boutique hotel located in the old town center within an 18th Century building. The 16 beautiful rooms are fitted with all the most modern facilities that, combined with the exclusive and elegant atmosphere of the rooms, make for a comfortable and memorable stay.

Your 4-start waterfront hotel in Taormina includes a private beach, wellness center, and saltwater swimming pool. The hotel is ideally situated for exploring the unspoilt commune of Taormina and its surrounding area.

To Reserve Your Spot

Reserve your spot by contacting us at [email protected]. Please note that spaces are limited to 15 people!

Book Now

Meet Your Guides



If you have visited DCanter, then you have probably attended one of Michael’s many wine classes or received a personal wine recommendation. Michael Warner is a Co-founder and Chief Operating Officer of DCanter, where he is the wine buyer. He holds a Certified Specialist of Wine designation from the Society of Wine Educators, consults frequently with specialty wine importers, and has been featured in publications, such as the Washington Post, Fast Company, France2 News, and Meininger's Wine Business International. A frequent traveler, he has visited wine regions throughout France, Germany, Spain, Italy, the Balkans, and – of course – the United States. Michelle is a Co-founder and Chief Executive Officer of DCanter, where she also manages its innovative Concierge by DCanter personal wine shopping service. In her role, Michelle developed wine curation decision support tools and customer resource management software to help DCanter's Concierge clients receive the right wine every time. She is a Certified Sommelier by the Court of Master of Sommeliers. A great lover of learning and education, Michelle has appeared on several wine industry speaking panels, and she has been featured in publications, such as the Washington Post and Wine Enthusiast magazine.



Claudia’s career started in the international hospitality industry and event organizing at the St. Regis Grand Hotel in Rome and then at Vinopolis in London. She then worked in India for the famous Italian wine company Marchesi Antinori, training the staff about wine at prestigious hotels. Claudia is also a member of the Italian Sommelier Association and an experienced guide specializing in Italy.

I’m Interested in traveling with DCANTER

Sips of fun for your inbox

Sign up to get the latest info about upcoming tasting events and wine classes, new products, and fun wine tips and stories delivered straight to your inbox!

No Thanks