Romantic Sicily Wine Tour

What to expect on this itinerary
Capture the romance of Italy during your custom-tailored Sicily wine tour for couples. Revel in the perfect mixture of seductive history and enchanting flavors with private tours that offer exclusive access to boutique vineyards from Palermo to Marsala. The art and artistry of tradition bring a deep well of heritage that spans the millennia and shapes the captivating ambiance in which you will find Byzantine mosaics, ancient Greek architecture, delicate olive oil, and complex wines. Relax in the beauty of seaside towns, indulge in the splendor of golden architecture, and embrace the immersive panoramas seen during your luxurious wine tour of Sicily.
Customizable Itinerary
Palermo – Arrive in Palermo with a Charming Walking Tour
Palermo is Sicily’s largest city, and it has a charm and intrigue that rises from a rich history thanks to a unique culture at the crossroads of the Mediterranean Sea. Your private transfer will greet you at Falcon Borsellino Airport and escort you to your gorgeous hotel in the heart of the bustling city. You will have time to freshen up and settle into the comforts of your luxury accommodations before meeting your guide in the lobby to begin your private walking tour. Palermo is a city of romance that is accentuated by the flamboyant architecture that combines Norman, Arab, and Baroque designs with Gothic palaces that are framed by soaring palm trees. Stucco decorations adorn the chapels and the vintage stores that are scattered around the distinct neighborhoods with antiques that highlight the faded aristocracies from around the island.
Your guide will lead you deep into the welcoming culture of the city that embraces the refreshing aromas of orange citrus, freshly brewed espresso, and delicious arancini. You will discover the grandeur of the cathedral and the marvels of the Normal Palace before reaching the sensational Cappella Palatina. The Normal chapel was consecrated in the 12th century and features a collection of remarkable mosaics with a harmonious ambiance that combines a Latinate floorplan with a Byzantine dome and Arabic stalactite ceiling. You will find the alluring ambiance of the interior filled with mystical darkness pierced by sporadic glints of decorative gold catching the light.
What's Included:
Palermo – Delight in Palermo’s Ambiance and a Private Cooking Class
Cefalù – Travel to Seaside Cefalù for Winetasting at a Local Vineyard
Cefalù – Revel in the Majesty of Cefalù with a Food and Highlights Tour
Castellammare del Golfo – Visit Greek Segesta and Boutique Wineries
Castellammare del Golfo – Enjoy an Olive Oil Estate and Historic Cuisine
Marsala – Travel to Marsala for Culture, History, and Tastes of Wine
Palermo – Discover the Charms around Marsala with a Day at Leisure
Palermo – Depart for Home
Trip Highlights
- Enjoy the romantic ambiance of the seaside city of Cefalù with a guided tour of the narrow lanes and golden coastline
- Indulge in the unique flavors of Marsala wine at a selection of vineyards that produce elevated wines that are modeled on local cultivation
- Revel in the classic passion of Sicilian cuisine with a multi-course cooking class with each dish paired with an exceptional wine
- Learn the delicate art of sampling olive oil during a special tasting on a family-owned estate
- Discover the enchanting history of Palermo as captured in the gilded mosaics that encompass the walls, ceilings, apses, and archways of Cappella Palatina
- Explore the ancient Greek world of Sicily with a private guided tour of Segesta to view the fascinating preserved temple and theater
- Delight in the unique amorous ambiance of Selinunte that combines enchanting ancient ruins with the elegant views of the Mediterranean Sea
- Feel the quintessential passion in the continued custom of farming salt at an ancient saline with picturesque windmills and levees across the shoreline
Detailed Description
The history of the vine runs deep in Italy, and your 9-day wine tour of Sicily will celebrate the marvels of both new and historical vineyards on the island that are steeped in the romance of a couple’s getaway. Whether you are oenological enthusiasts or looking for a new interest to share, your wine tour will place romance at the forefront by accentuating the seductive charms of the cities, towns, scenery, and flavors of Sicily that promise endless moments that will immerse you in ancient Greek life and contemporary culinary techniques.Your fascinating couple’s wine tour of Sicily will begin with your arrival in Palermo. You will have three nights in the fascinating city with private guided tours leading you through the exceptional architectural, cultural, and culinary history of Sicily’s capital. You will visit grand displays of devotion in the form of the Palatine Chapel and the interior of the Monreale Cathedral, and then discover the splendor of Norman design, the embellishments of Arab engineering, and the continuation of traditional flavors in recipes passed down through the generations.
You will transfer to the gorgeous seaside city of Cefalù for two nights where you can relax in the casual ambiance of the narrow lanes and charismatic promenade, as well as sample select wines from wineries that texture the Mediterranean landscape with lush vines. Once in Castellammare del Golfo, you will experience the splendor of boutique vineyards and the popular purveyors of wine in Sicily with multi-course meals accompanied by wine pairings.
Move next to discover the medieval streets and grand views of Erice located at the top of Mount Eryx, and then be immersed in the ancient wonders of Sicily with a guided tour of the ruins at Segesta. You will sample delightful olive oil on a private estate, and then learn pleasures of salt when visiting a historical salt farm. Spend one night in Marsala to uncover the beauty of the western landscape and the complex flavors of the wineries that are shaping the new and celebrated reputation of local wines. Consider learning more about our travelers’ best Italy travel experiences by reading their Italy travel reviews.
Starting Price
$4,100 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 3343 reviews
First time to the Olympics and an add-on to Switzerland! Zicasso’s travel specialist was great at listening to our needs and putting together an itinerary.
Our trip to Livigno was fantastic! The location to the two Olympic venues was ideal.
All of the details were covered and when we had a change in one of our day tours due to potential avalanches, the team at the travel company was extremely responsive and was able to adjust.
All of our transportation was well organized and on time. We also had to pivot when our flights home to the US were changed due to weather and the team quickly helped with adjustments to our schedule.
We loved the train from Italy to Switzerland.
We highly recommend this travel specialist and the travel company!
See more
Our experience with Zicasso’s travel company was simply outstanding! Our travel specialists provided top-notch service, from the initial planning to the entirety of the trip.
They were able to secure housing for us in Livigno during the Olympics when no one else was able to do so. Responsiveness to our inquiries during the planning process was always prompt and thorough. Communication regarding the next day's agenda throughout the trip was excellent, including the contact information for our drivers and tour guides, tickets for events, and links to Google Maps, with directions, when needed. If we could give them more than five stars, we would!
See more
We had a fabulous trip to Italy, including to Sorrento, Taormina, and Rome. Zicasso’s travel specialist made sure every detail was taken care of, including stays in beautiful, well-located hotels and excursions that were interesting and fun for our family.
For example, she arranged for an airport host to assist us with our arrival to and departure from the Rome airport, and she was simply amazing, whisking us through the airport and eliminating stress for our family.
See more
In all respects, a well-planned and well-executed trip to London and Rome. The guides were exceptional in knowledge, kindness, and sense of humor. The best restaurant recommendation was the one in London.
See more
Our recent trip to Rome, Florence, and Venice, planned by Zicasso’s travel specialist and her team, was nothing short of exceptional. Every detail was handled with care, precision, and an obvious commitment to excellence. The hotels were truly top rate, perfectly located, and impeccably chosen to enhance the experience of each city. The tour guides were extremely knowledgeable, engaging, and clearly passionate, adding depth and context that made each destination come alive.
What truly set this trip apart was the level of service. From seamless transfers to on-the-ground assistance, everything felt effortless. The recommendations and tips provided along the way were incredibly useful and allowed us to experience each city with confidence and ease. The assistants who helped guide us through logistics and navigation were attentive, professional, and reassuring, making the entire journey feel like true white-glove service from start to finish.
The travel specialist and her team exceeded every expectation. Their planning, responsiveness, and attention to detail transformed an already incredible itinerary into an unforgettable experience. I would recommend them without hesitation to anyone looking for a flawlessly executed, high-end travel experience.
See more
Zicasso’s travel company was amazing to work with! They really took care of every detail for a worry-free experience! They were very responsive during planning and the trip. All of the locations and accommodations were exactly what I wanted. I cannot recommend them enough!
See more





