Back to All Events

The Best of Sicily: Food, Wine, Culture & Coastlines


View images of past trips by clicking or tapping the arrows.


Discover the soul of Sicily on this immersive 10-night journey through one of Italy’s most captivating destinations. From the vibrant markets of Palermo and the seaside charm of Cefalù to the vineyard-covered hills of Menfi, the ancient ruins of Agrigento, the baroque beauty of Ragusa and Syracuse, and the dramatic landscapes of Mount Etna and Taormina, this tour blends history, culture, food, wine, and authentic local experiences. Enjoy exclusive winery visits, a hands-on Sicilian cooking class, guided explorations of UNESCO World Heritage sites, breathtaking coastal scenery, and ample free time to soak up Sicily’s relaxed Mediterranean lifestyle.Visit Europe’s most active volcano, Mount Etna, and taste impressive wines produced from grapes grown in its volcanic soil.

  • 10 nights in carefully selected accommodations throughout Sicily

  • Explore Palermo and Monreale, including its magnificent Norman cathedral and golden mosaics

  • Experience Palermo's famous outdoor markets and sample authentic Sicilian street food

  • Stay in the beautiful seaside town of Cefalù

  • Visit the ancient Greek temple of Segesta, one of the best-preserved temples in the world

  • Enjoy a wine tasting and estate dinner at La Foresteria by Planeta in Menfi

  • Participate in a hands-on Sicilian cooking class with a local chef

  • Discover the UNESCO-listed Valley of the Temples in Agrigento

  • Visit Villa Romana del Casale and its world-renowned Roman mosaics

  • Explore the baroque towns of Ragusa and Ragusa Ibla or the historic city of Syracuse and Ortigia

  • Experience Mount Etna, Europe's most active volcano

  • Taste exceptional wines grown in the volcanic soils of Etna

  • Cruise along Sicily's stunning Ionian Coast and visit the Grotta Azzurra

  • Enjoy free time in beautiful Taormina for shopping, sightseeing, and relaxation

  • Savor authentic Sicilian cuisine, regional wines, and special group dinners throughout the journey

  • Travel with experienced local guides while enjoying a balance of planned activities and independent exploration


What’s Included:

  • Accommodations: 4-star boutique hotels, wine resorts, restored castles and villas.

  • Private guided tours.

  • Special insider activities that could include food and wine experiences, truffle hunting, visits to wine and food producers, and more.

  • All entrance fees to museums and other sites.

  • All ground transportation between destinations. (Does not include transportation, such as taxis, to and from airports and not described in the itinerary.)

  • Meals included as noted in itinerary.

  • Guide and driver tips.

What’s Not Included:

  • Airfare

  • Travel Insurance

  • Personal Expenses

Previous
Previous
September 10

Best of Italy: Rome, Umbria, Tuscany & the Cinque Terre Fall 2027

Next
Next
October 11

Discover Piedmont: Truffles, Barolo, Lake Views & Hidden Villages