Romantic Sicily Wine Tour

Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily

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.

Countries Visited

Italy

Places Visited

Palermo, Marsala, Cefalù, Erice, Selinunte

Suggested Duration

9 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Breakfast
Day 2

Palermo – Delight in Palermo’s Ambiance and a Private Cooking Class

Day 3

Cefalù – Travel to Seaside Cefalù for Winetasting at a Local Vineyard

Day 4

Cefalù – Revel in the Majesty of Cefalù with a Food and Highlights Tour

Day 5

Castellammare del Golfo – Visit Greek Segesta and Boutique Wineries

Day 6

Castellammare del Golfo – Enjoy an Olive Oil Estate and Historic Cuisine

Day 7

Marsala – Travel to Marsala for Culture, History, and Tastes of Wine

Day 8

Palermo – Discover the Charms around Marsala with a Day at Leisure

Day 9

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.

4.9

Verified Traveler Reviews

Based on 6218 reviews

Maria S.
Italy Trip Review: Ciociaria, 2-Week Trip

Our trip to Italy was absolutely amazing. Zicasso’s travel company provided exceptional service and attention to detail. We had never used a travel company for arrangements prior to this trip and we are so glad we did. It made the trip stress-free and truly over-the-top.

Our favorite time on the trip was at a location recommended by our travel agent in a very small area called Ciociaria. We loved this location and our resort in Ciociaria. The staff was incredible and we felt so relaxed.

I have been telling all my family and friends about the travel company’s services and that I will use them for future trips. I am so thankful to Zicasso for connecting me to an incredible experience with our travel company.

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Andrew A.
Italy Family Vacation Review: Rome, Florence, Mount Vesuvius, Wine Tasting, 10 Days

This was our first time using a travel agency for a trip like this and Zicasso’s travel company completely exceeded our expectations. Traveling internationally with pre-teen children can be stressful, but from the very beginning, this travel company removed every bit of that anxiety. Every detail was thoughtfully planned, clearly communicated, and flawlessly executed.

From airport transfers to hotels, tours, trains, guides, and daily logistics, everything worked seamlessly. We never once felt lost, rushed, or unsure of what was next. Instead of worrying about schedules or navigating a foreign country, we were able to fully focus on our family and enjoy the experience. That peace of mind alone was invaluable.

What really stood out was how well the trip was tailored to our family. The pacing was perfect, the experiences were engaging for adults and kids, and every guide we worked with was knowledgeable, friendly, and professional. It truly felt like a curated, high-quality experience rather than a generic itinerary.

We came home with incredible memories and zero travel stress, something I didn’t think was possible with kids that age. This travel company was phenomenal and we would absolutely use them again, and recommend them without hesitation to anyone considering international travel, especially families.

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Michael E.
Italy Vacation Review: Venice, Florence, Rome, Sorrento, Murano, Burano, Pisa, Vatican, Colosseum, Pompeii, Capri, Private Tours, Cooking Class, 10 Nights

I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.

Trip Planning:

As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.

Transportation and travel between locations:

Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.

One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.

Venice:

Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.

The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.

Florence:

As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.

While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.

Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.

Day trip to Pisa:

The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.

The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.

Rome:

Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.

Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.

The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.

The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.

The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.

The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.

Sorrento:

We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.

During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.

Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.

On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.

Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.

Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.

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Susan F.
Italy Anniversary Trip Review: Rome, Orvieto, Siena, Montepulciano, Chianti, Florence, Bologna, Venice, Wine Tasting, Food Tour, 2 Weeks

Thank you to Zicasso’s travel specialist and her amazing staff. The itinerary was fabulous. It was filled with food, wine, and highlights of the most important tourist places. Her guidance throughout the year-plus planning was the right amount of checking in and waiting. Thank you for the nudges to have reservations for all the holiday days. Things seemed to be pretty open overall, but it was nice not to worry.

All the restaurants set up for us were wonderful. The app was terrific to keep track of what we were doing when. All the drivers were very friendly, professional, and punctual.

Thank you for making our 35th wedding anniversary trip (December 22 2024 to January 6 2025) a most memorable one. We hope to return to Italy to enjoy the southern area and maybe some of the beaches and islands.

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Mary J.
Italy Tour Review: 11 Nights

We had an excellent itinerary and we really liked the accommodations provided, and their locations within walking distance of our must-see sites.

Excellent tour guides, drivers, and transportation were provided!

The Zicasso travel expert's recommended restaurants were also great and the guidelines were helpful!

My husband and I saw and enjoyed what we needed to see and experience!

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Tracy S.
Italy Trip Review: Bike Tour, 5 Nights

It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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