Sicily Itinerary

October 1 – October 10, 2025


Sicily is a treasure trove of perfect seafood, intensely flavored vegetables, outstanding olive oil and world-class wines.  Its cuisine is different from any other Italian region.  Strongly influenced by its many conquerors—from the Greeks, to the Romans, the Arabs, the French & the Spanish—the island’s food represents a unique crossroads of the Mediterranean.  Expect hints of exotic spices like saffron and cinnamon paired with local ingredients—lemons, blood oranges, almonds, capers & wild oregano. All of this, plus stunning island geography and an exquisite tapestry of art & architecture, including the best-preserved Greek temples in the world.

This tour has been strategically timed for Sicily’s early autumn’s idyllic weather.  Furthermore,  our visit coincides with wine harvest activities.  Prepare yourself for new varietals that only grow in Sicily and new flavors from grapes grown in mineral-rich volcanic soil.  These “volcano” wines are now capturing the interest of international wine-lovers.   

Simply put, Sicily offers exquisite new food & wine experiences for even the most seasoned of travelers.


• Private tours & tastings at la crema de la crema wine producers

• Outings with professional guides to Sicily’s top cultural sites

• Visits to artisanal food purveyors & outdoor markets

• Accommodation in distinctive boutique properties….most of which do not accept groups


Oct 1: Welcome to Pulsating Palermo

Weather & volcanic soil produces veggies & fruits like no others

***The tour officially kicks off today, however, one or two nights early arrival in Palermo is highly recommended to avoid any missed connections with the group, to recover from jet lag, and to spend extra time in Sicily’s exhilarating capital city, Palermo.   (Wine-Knows is happy to arrange for early arrival rooms in the property in which we’ll be stay tonight.) ***

Morning:  There’s no better way to begin our gastronomic trip of Sicily than in the foodie mecca of Palermo.   Today we combine a historical walking tour featuring the majestic cathedral and opera house with the city’s famous outdoor food markets where boisterous vendors battle one another over who can shout the loudest to hawk their fresh produce, fish and meat.  There are also a plethora of stands selling scrumptious treats such as luscious caponata (braised eggplant, tomatoes & onion), arancini (tiny rice balls filled with mushrooms, or cheese, or meat), and decadent cannoli (small tube pastries filled with mascarpone and dried fruits, nuts or chocolate).

Afternoon:   Free

Evening:   It’s not often one can dine with royalty, but tonight will be one of those nights.  Dinner will be hosted by a Duke & Duchess in their palace’s formal dining room (pending their health status and ability to receive guests).

OCT 2: World-Class Wining & Dining

Dine as guests in the private home of Sicilian wine nobility

Late Morning:  Today we head to the island’s southern coast.  In route we’ll make a stop at one of Sicily’s crema de la crema producers whose wines are among the top-scoring wines in Sicily.

Mid-Afternoon:    Next, we arrive at our final destination, a lodge owned by one of Sicily’s mover-and-shaker wine dynasties.   Their upmarket wine resort is a modern and slick “destination hotel” offering sweeping views of the vineyards and Mediterranean.  There will be time to unpack, take a swim, enjoy a walk, or simply chill out in your sumptuous room.

Evening:   Tonight will be a special experience as we’ll be the private guests of the wine family who owns our hotel.  Dinner will be on the family’s beautiful countryside estate.   The property, filled with heirlooms, has been in the family for 17 generations.

OCT 3: World’s Best Preserved Greek City

One of the most important Greek colonies on the Mediterranean

Morning:    We begin our day with a professionally guided visit to the ancient seaside city of Selinunte.   Founded by the Greeks in 628 BC, Selinunte is the only classical Greek city in the world  where the entire metropolis is still preserved.  Today the site is an active archaeological dig with scientists still discovering many facts about how the historical city functioned. 

Afternoon:   Next, we’ll visit the nearby town of Castelvetrano, known internationally for its famous namesake large green olives. 

Evening:    Dinner tonight is on your own.  Dine in our hotel’s gastronomic restaurant on its splendid terrace overlooking the sea, or visit one of the more traditional Sicilian restaurants in town just a few minutes by taxi.

oct 4: Mind-blowing Collection of Temples

Outstanding example of ancient Greek architecture

Morning:  Today we travel east along the Sicily’s southern seaside. In route we’ll stop at the Temples of Agrigento, Sicily’s most enthralling archaeological site.  Get ready to have your socks knocked off with seven mesmerizing temples on this walking tour with an archaeological expert.

Afternoon:   Next stop will be Sicily’s most famous olive estate.  With a portfolio of international awards, their olive oil is used by many of Italy’s Michelin star chefs and gourmands in-the-know.  This family owned & run property will be our home for the next two nights.

Evening:  Dinner will be at the estate and feature a meal of classical Sicilian home-style cooking.

oct 5: The Making of Olive Oil

Watch every step of the process

Morning:  After a breakfast featuring home-made delicacies rarely seen outside of Sicilian homes, we’ll follow the making of oil from picking of olives to the actual bottling.  We’ll finish with a tasting of these extraordinary oils guided by the owner of the estate.

Afternoon:   Free at the estate.  There’s a pretty pool, as well as hiking trails.  For those who simply want to chill, there’s plenty of comfy areas to relax both inside and outside.

Evening:  Dinner at the olive estate on the terrace among the olive groves.

oct 6: Stay in a Setting Right Out of Hollywood

James Bond would have loved this estate

Morning:  We continue our journey east along the island’s southern coast to one of the most highly regarded wineries in Sicily.   At this super-star producer we’ll taste Nero D’Avola & Frappato, both native varieties of the island, along with a lunch of Sicilian tapas.

Afternoon:  Onward to our home for the next two nights, a drop-dead gorgeous wine-estate in a setting straight out of the movies.    A former 18th century hilltop manor, this exquisite hotel is encircled by a 150 acre sea of grape vines.

Dinner:  We’ll begin the evening with a wine tasting led by the winemaker.  Then, we’ll dine at the estate’s gastronomic restaurant that is working hard to achieve a Michelin star.  

oct 7: Private Lunch in a Royal Castle

World’s richest collection of mosaics

Morning:  We’re off to view one of the most spectacular sight-seeing venues on all of Sicily, a 4th century Roman villa containing the largest and most complex collection of mosaics on the planet.  The former hunting lodge of Roman Emperors, it was abandoned in the 12th century when a landslide caused by a Mt. Etna eruption covered it with 20 feet of mud.  Excavations, begun in the early 20th century, are still underway.

Afternoon:  Lunch today will be at the castle that once belonged to Sicily’s Prince.  Today, the once royal property is a winery that is owned by a famous Italian wine family from the mainland.  Using all local grapes, the winemaker has created an award-winning portfolio of wine.

Evening:  Dinner tonight is free.  

oct 8: Mt. Etna’s Volcano Wines

Stay on an island joined to the mainland by a small bridge

Morning:  Breakfast will be a feast that includes fresh-squeezed juice from local blood oranges, homemade cakes and jams, along with local meats and freshly laid eggs.  Eat up because we have a few hours drive across the base of Mt Etna to its wine-making region on the east coast.

Mid-day:   We’ve perhaps saved the best to last.   The most famous wine producer on Mt Etna will welcome us with a portfolio of their wines which have a cult-like following.

Late afternoon:   Out last stop is Ortigia Island which is part of the city of Syracuse.   Ortigia,  the spot of the original Greek colony in Sicily nearly 3,000 years ago, will be our home for the last two nights.

Evening: Tonight will be pizza at one of the island’s culinary shrines featuring this specialty.  Pizza is an art form in Sicily.

oct 9: Market Reflects Arab, Greek & North African Roots

Sicily’s cuisine is a mélange of its past conquerors

Morning:  We’re off to Ortigia’s farmer’s market.  Watch fishmongers cut up gigantic swordfish, marvel at their uniquely round-shaped eggplants, smell the fragrant lemons in all sizes and shapes, taste the glorious pistachios and almonds, and don’t miss the spice vendors selling a cornucopia of exotic treasures. We’ll learn the difference between capers and caper berries, as well as capers preserved in a brine versus salt.  Last, we’ll taste sun-dried tomatoes preserved in olive-oil that are sure to knock your socks off. 

Afternoon:   Free.

Evening:   Our farewell dinner will be at a ristorante that is sure to please the most discerning traveler with its gracious service, fabulous food, and a killer wine list.

oct 10: Arrivederci, Sicilia!

Enjoy your last cannoli for breakfast

Morning:  Say ciao to your new Wine-Knows friends as the trip ends after breakfast.  Wine-Knows will be happy to arrange transport to the airport, or up the coast to the do-not-miss resort of Taromina.


The tour begins on the morning of October 1, 2025 at approximately 9am in downtown Palermo.   It is strongly advised that participants arrive in Palermo at least one day before (preferably two days early) to avoid any possibility of missed connections with the group, recoup from jet-lag & see more of Sicily’s vibrant capital city, Palermo.  Wine-Knows will be happy to offer suggestions for early arrival hotels.

Group airfare has purposefully not been included to allow maximum flexibility in arrival & departure options. You may go early & stay over after the trip concludes.   Wine-Knows Travel Inc. provides land only arrangements and does not provide airfare.

Our groups are composed of people from diverse occupations, singles & couples, men & women, a mix of young & old, well-seasoned international travelers as well as novices.  All have a common interest in food & wine.  The majority of participants on our tours are repeat clients or their referrals.  In addition, each tour participant is a non-smoker.

One of the hallmarks of our brand is seeking out those oh-so-special spots to stay.  We look for historical properties that ooze Old World charm, but offer the latest in 21st century creature comforts (upmarket linens, WIFI, air-conditioning, ensuite bathrooms), as well as excellent service.  Below are some of the unique accommodations that are currently planned for use on this Sicilian trip:

Waterfront 17th century palace lovingly restored by an antique dealer/art collector, this unique hotel offers a rare slice of Sicilian history.  Each room is completely different but all are decorated in antiques & an impressive array of original art pieces.  Perfectly situated overlooking the sea, the property offers several terraces from which to eat breakfast or watch the sun set over the Mediterranean.

A dramatic country estate right out of a James Bond movie, this lovingly restored property from the 1700’s offers glamour, intrigue, and a slice of history that few get to experience.   Perched on a hill, the property is owned by one of the most important wineries in Sicily.  Wine-Knows has taken over this entire magnificent estate featuring 10 bedrooms that were carved out from the ancient winery.

Working Olive Oil property which exudes rustic elegance–you’ll be thrust into the heart of Sicilian family life here where the emphasis will be on conviviality & food.  Rooms have been cleverly crafted out of different out-buildings: one an old railway station, another a centuries-old olive mill.  There are many great spaces for relaxing in and outdoors including a beautiful pool.

Hip & modern with a touch of Old-World charm, this new wine lodge is owned by one of the most powerful wine families in all of Sicily. Offering panoramic views of the vineyards and Mediterranean, this cutting edge accommodation packs in all of the bells & whistles in its 14 rooms. There’s a glorious pool with a view of forever, and massage services can be arranged.

Dining experiences have been mindfully selected and many will be insider opportunities most of which are not available to the general public.   Meals planned will range from dining in the private palace of a Sicilian Count & Countess to informal affairs at a pizzeria, or dinner with the owners of Sicily’s top olive oil producer at their estate.   

Participants must in good physical health and be able to keep up with the pace of the group.  The tour often requires climbing two or more flights of stairs in wineries, walking distances of up to 3/4 mile (1200 meters) at a moderate gait, and negotiating cobble-stone streets and other irregular surfaces including dirt, gravel and/or wet surfaces. 

The tour will be business casual during the day. Men need to bring a sport coat (tie optional) for the more formal dining experiences, & women should plan a similar level of attire (cocktail dress or fancy pantsuit) for these evenings.  Do bring non-skid shoes for visits to wineries…they will be finishing harvest operations & floors will be wet & filled with a variety of equipment which can cause safety hazards. Also, pack a swim suit as two of the properties have a swimming pool.

Late September/early October in Sicily averages in the 70’s during the day.  As Sicily is an island, evenings can be cool due to the cooling effects of the nearby Mediterranean so plan accordingly for evening clothing.

The price is based upon double occupancy.  Should you wish to share a room, every attempt will be made to find you a roommate (most of the time we have been quite successful in doing so), however if we are unable to find you a roommate, you will need to pay the single supplement.

We have provided free time as detailed in the itinerary.  Furthermore, it is not mandatory that you attend all of the planned experiences, although most of our clients do!  This is your trip—if you would rather sleep in, shop, or simply chill out at a sidewalk café, then do it!

Yes.  We accept payment through PayPal (  Since PayPal charges us a fee, this fee must added to the cost of the trip. 


*based upon a minimum of 12 participants

Tour Dates*

Book Before Feb 1, 2024:

Book After Feb 1, 2024:

Oct 1 – Oct 10 2025





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