SOLD OUT

November 1-8, 2025

7 Nights
Cost: $4,700

Per person based on double occupancy.

Experience a different side of Sicly. As the extreme summer heat gives way to ideal fall temps, we take this opportunity to experience south eastern Sicily’s magical food, wine and architecture. Visit an artesian cheese farm and watch how the product happens from farm to table. Visit the vineyards and wine making facilities just after harvest and learn about the beginning stages of the wine making process. Depending on the season, olive for olive oil will be in full harvest and we may have the option to participate in the harvest. Take advantage of the ideal temps to fully explore many baroque cities and their stunning architecture and 3000+ years of history form the greeks, romans, bourbons and present.

What is included:

  • All meals – breakfast, lunch and dinner each day 
  •  All deluxe villa / hotel accommodations 
  •  Arrival and departure airport transfer and designated times 
  •  All private tours, transfers, wine tastings, guides, private boats etc. 

 What is NOT included: 

  •  International flights and transportation to Sicily 
  •  Alcoholic beverages outside of those lunches and dinners which include wine, additional meals, tips or gratuities!

Late Spring in Eastern Sicily

May 16 -May 23, 2026

7 Nights
Cost: $5,150

Early booking discount available.
Per person based on double occupancy.

The showers of winter begin to fade away and the quintessential Sicilian sun returns in full force. Temperatures are generally ideal not too hot but often warm enough for an early season ocean swim for the daring. During this experience we will stick to eastern Sicily and as always search to see the real sicily by meeting local people, tasting wines in the vineyards they are grown, exploring the hidden corners of many ancient cities and devouring delicious Sicilian cuisine.

What is included:

  • All meals – breakfast, lunch and dinner each day 
  •  All deluxe villa / hotel accommodations 
  •  Arrival and departure airport transfer and designated times 
  •  All private tours, transfers, wine tastings, guides, private boats etc. 

 What is NOT included: 

  •  International flights and transportation to Sicily 
  •  Alcoholic beverages outside of those lunches and dinners which include wine, additional meals, tips or gratuities!

Sicily from West To East

June 3-13, 2026

11 Nights

Cost: $6,800

Early booking discount available
Per person based on double occupancy.

We will kick of summer Italian style. This is a more comprehensive trip where we traverse the island from the west to the east. Sicily is the largest island in the mediterranean and landscape and culture vary from one side to the other. See beautiful and wild places like Sicily’s first nature reserve on the western coast, Zingaro. Take to the sea and explore island chains just off the coast of Sicily like the Egadi islands. As always meet the local people, farmers, restauranteurs and winegrowers who give Sicily its pulse and enjoy all the fruits of their labor - local cheese, wine , produce and culinary masterpieces. Don’t miss this opportunity to see all Sicily has to offer.

What is included:

  • All meals – breakfast, lunch and dinner each day 
  •  All deluxe villa / hotel accommodations 
  •  Arrival and departure airport transfer and designated times 
  •  All private tours, transfers, wine tastings, guides, private boats etc. 

 What is NOT included: 

  •  International flights and transportation to Sicily 
  •  Alcoholic beverages outside of those lunches and dinners which include wine, additional meals, tips or gratuities!

Sicilian Summer Send Off

August 29 to September 5, 2026

7 Nights

Cost: $5,200

Early booking discount available
Per person based on double occupancy.

In many ways early September is the optimal moment to visit Sicily. The summer crowds have begun to subside along with a slight dip in temperatures, however the weather is still quite warm and the sea is at it absolute warmest. Experience a real Sicilian summer, meeting local people, tasting wines in the vineyards they are grown, exploring the hidden corners of many ancient cities and devouring delicious Sicilian cuisine.

What is included:

  • All meals – breakfast, lunch and dinner each day 
  •  All deluxe villa / hotel accommodations 
  •  Arrival and departure airport transfer and designated times 
  •  All private tours, transfers, wine tastings, guides, private boats etc. 

 What is NOT included: 

  •  International flights and transportation to Sicily 
  •  Alcoholic beverages outside of those lunches and dinners which include wine, additional meals, tips or gratuities!

Fall in the Val di Noto

October 31 – November 7, 2026

7 Nights
Cost: $4,900

Per person based on double occupancy.

Experience a different side of Sicly. As the extreme summer heat gives way to ideal fall temps, we take this opportunity to experience south eastern Sicily’s magical food, wine and architecture. Visit an artesian cheese farm and watch how the product happens from farm to table. Visit the vineyards and wine making facilities just after harvest and learn about the beginning stages of the wine making process. Depending on the season, olive for olive oil will be in full harvest and we may have the option to participate in the harvest. Take advantage of the ideal temps to fully explore many baroque cities and their stunning architecture and 3000+ years of history form the greeks, romans, bourbons and present.

What is included:

  • All meals – breakfast, lunch and dinner each day 
  •  All deluxe villa / hotel accommodations 
  •  Arrival and departure airport transfer and designated times 
  •  All private tours, transfers, wine tastings, guides, private boats etc. 

 What is NOT included: 

  •  International flights and transportation to Sicily 
  •  Alcoholic beverages outside of those lunches and dinners which include wine, additional meals, tips or gratuities!

Sicily Your Way

Dates - ON REQUEST

None of our above trips fit your schedule? Looking to special and focus on a different aspect of travel? Minimum group size for a custom trip is only 6 so if you have a specific request just reach out!