5 Reasons to Celebrate Your Next Holiday at a Luxury Villa in Sicily
In January, something peculiar happens to the human brain.
We start to forget the absolute, sheer mayhem that was the holiday season.
As soon as the New Year rolls around, it all feels like a dream. In March, we’re reminiscing about the holidays fondly. In July, we SWEAR we’re going to start figuring out Christmas presents early (we’re not). By October we are downright giddy to go through it all again.
In America, the frenzy hits full throttle in November. It’s when we gear up for our American Thanksgiving – a holiday that involves at least 4 extensive trips to the grocery store in a 48 hour period. Each visit feels like a race against time, with the shopping cart filling up as fast as the floodwaters in Fantasia. Food disappears from the shelves as if an apocalyptic event is about to strike. People get downright territorial over cans of pumpkin purée.
And then there’s Thanksgiving day itself. Yes, a delicious meal with family is (usually) enjoyed, but dishes pile high in the sink, there is chaos amongst the kids running around, and I can promise – if you’re hosting – something will break. Everyone swears that next year they’re going to do things a little bit differently.
Now let me offer you a different perspective. What if I told you that you could experience genuine relaxation with your family by celebrating your Thanksgiving holiday at a luxury villa in Sicily? Picture this: waking up Thanksgiving morning and slowly making your way with your family to your villa’s private spa, dipping into the jacuzzi for a quick swim. After breakfast, it’s time for everyone to leisurely explore a historic town together. When you return in late afternoon, you’ll smell the familiar scents of rosemary and sage, as a private chef crafts a Thanksgiving dinner with an Italian twist. Celebrating a major holiday at a luxury villa in Sicily isn't just about stepping away from the frenzy – it's about redefining celebration to spend quality time with loved ones in a new way.
In this post, I'll divulge the details of our family’s tranquil Thanksgiving escape, highlighting why Sicily is the perfect destination for families seeking a memorable and stress-free getaway – whether that be for Thanksgiving, any other major holiday, or just a regular family vacation. My first step was choosing a home with The Thinking Traveller, a renowned luxury villa company based in the Mediterranean. I’ll provide a close look at the place we called home for a week, as well as suggesting some other villas in their collection that would serve as an excellent choice.
Your journey to an unforgettable family vacation starts right here. Read on for my top 5 reasons to choose a luxury villa in Sicily for your family holiday.
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Where to Stay in Sicily for an Unforgettable Family Holiday
Did you know that Sicily is the largest island in the Mediterranean? Spanning almost 10,000 square miles, the land includes mountains, dramatic rocky coastlines, quaint hilltop towns, miles of beaches, and one of the most active volcanoes in the world! You could spend 2 weeks road tripping through Sicily, and still have plenty of new things to see on a future trip back.
Given the expansiveness of this island, the most pressing planning question becomes: Where’s the best area to stay in Sicily? The answer to that question depends in part on the time of year you plan to go.
Key Takeaway
The peak summer months provide the most flexibility, meaning every town is open for business. Palermo, Cefalu, and Trapani on the North and West coast are known for spectacular beaches, and vibrant city energy. You’ll find fabulous villa options in these regions, but year-round, especially for a fall or winter trip, I’d recommend zeroing in on the East Coast, near Taormina, Catania, or Siracusa. Even during the off season, you’ll still have plenty to do. Many restaurants, shops, and main attractions remain open. I’m not going to say that I was influenced by The White Lotus, but I might have been…
If you base yourself on the East Coast during the off season, you’ll also have the option to explore smaller towns, like Noto, Modica, and Ragusa. These towns have a quiet and more intimate feel at this time of year, offering a nice balance between its sister cities.
Introducing The Thinking Traveller: The World’s Top Luxury Villa Company
Once you choose which region you'd like to base yourself, it's time for the fun part -- it's time to discover The Thinking Traveller.
I’m going to warn you: browsing their website can become quite addicting. There’s a reason they’ve been ranked by Condé Nast as “the World’s Best Villa Rental Company 2023.”
The Thinking Traveller specializes in curating exclusive and extraordinary villa properties across the Mediterranean, with a significant portion of their portfolio located throughout Sicily. (They’re also based in Puglia, Corsica, and various regions in Greece). Out of the hundreds of villas that apply to join their collection, only 1% are selected, ensuring they offer only the very best.
From sprawling estates near ancient ruins, to sleek retreats located along some of the most pristine beaches, or even homes located within nature preserves, The Thinking Traveller's wide-ranging portfolio guarantees you’ll find a villa perfectly tailored to your group’s needs. You’re signing up for premium conveniences such as 5 star service, private chefs, daily maid service, and exclusive use of extravagant amenities like infinity pools, saunas, private tennis courts, or movie theaters. Their team will also organize a customized week-long itinerary for your group, selecting curated experiences only available to their clients. You know you made the right choice when weeks after arriving back home, everyone is still reminiscing about every detail.
How Much Does it Cost to Rent a Luxury Villa in Sicily?
When you hear…luxury villa…infinity pools…saunas…private chefs…tennis courts…you may immediately assume, “Cha-ching! This is going to be very expensive.” However, let's take a closer look at why a Thinking Traveller villa provides significantly more value for your money, at a cost often comparable to a luxury hotel.
With a villa you'll enjoy ample space for your entire group to spend time together. Kids have room to run and explore, while adults can relax by the pool, or savor wine in picturesque al fresco dining areas. At the end of the night, after the little ones have settled in, the adults can simply socailize, or play a leisurely game, instead of siloing off into separate hotel rooms.
In addition to having more space for your family, the villa cost includes a dedicated concierge team and exclusive access to the villa's amenities. Of course the basics like daily cleaning and linen change are included. You'll also have the option to add on private chef services, or partake in The Thinking Traveller's thoughtfully curated experiences. These activities provide genuine insights into local life, and are only available to clients of The Thinking Traveller. More on all these perks below.
With real-time pricing available on their website, you can easily compare cost and select the luxury villa that aligns with your vision and budget. With villas that can accommodate between 4-24 people, there are options best suited for small family gatherings, and also ones for larger, grand multigenerational affairs.
Should I Rent a Luxury Villa if I'm Traveling with a Smaller group?
While luxury villas are often associated with larger groups, they can be an excellent choice for smaller gatherings of 4-6 people as well. In fact, it can enhance your overall experience and offer great value for your money. This insight comes from my personal experience, as I've had the opportunity to stay at both a Thinking Traveller villa in Puglia with a larger group of 11, and more recently, with a smaller family of 5 during our Sicily trip.
Even as a smaller group, we found the additional space to be incredibly valuable. We stayed in a thoughtfully designed countryside estate perfect for our group size (more details below). The total cost was comparable to booking 2-3 rooms, but we had the added benefit of access to private amenities and personalized service.
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5 Reasons to Rent a Luxury Villa in Sicily for the Holidays
As we set our sights on a tranquil Thanksgiving retreat in Sicily, our primary goal was to escape the holiday hustle and bustle, and instead focus on relaxation, and the opportunity to spend quality time with extended family.
Since our trip coincided with shoulder season, we opted for a villa along the east coast, where we could easily visit the towns of Noto, Modica, Ragusa and Siracusa. We could also take day trip excursions to Taormina and Catania. The villa we selected was Tenuta Della Cava - an estate set on 106 acres of farmland outside the Baroque city of Rosolini. Stay tuned for a full tour when I cover reason #2!
#1 CUSTOMIZED CONCIERGE SERVICES THAT FACILIATE ALL THE PLANNING LOGISTICS
You’re in for the easiest trip planning experience of your life.
Once you book your villa, The Thinking Traveller expert concierge team will take the reins. A pre-departure concierge will assist with logistics, such as airport transfers and car rental drop-offs. They'll also take care of any necessary restaurant reservations, and curate a list of recommended activities, while handling all the bookings. The concierges have not only stayed in the same villas, but have also personally experienced the same tours and dined in the recommended restaurants. Their firsthand knowledge enables them to make tailored recommendations that perfectly align with each client's preferences. Your only logistical job is to arrange your own flight.
When "the big day" finally arrives, you’ll meet your host, and local concierge upon arrival at your villa. With 24/7 access to a local expert, help is never more than a text message away. Whether you need to modify a restaurant reservation, seek a local beach recommendation, need someone to pick up diapers for your baby, or have questions about tipping practices, simply send a text. They have a wealth of knowledge about your destination. Don’t be shy – they’ve seen and heard it all. For example, the day after visiting Mt. Etna, I realized I forgot half of my drone on the volcano, which was currently erupting lava! Andrea, my concierge, helped coordinate its location, and returned it back to me…truly going above and beyond!
#2 SPACIOUS ACCOMMODATIONS THAT COMFORTABLY FIT EVERYONE FOR A HOLIDAY GATHERING
Whether you're planning an intimate holiday, or envisioning Thanksgiving as a grand multigenerational affair, The Thinking Traveller has you covered. Their villas can comfortably fit between 4 and 24 people, ensuring that everyone has their own space to relax, but can also easily come together for festivities. After carefully assessing our own group's needs—a family of five, including two young children—our pre-departure concierge recommended Tenuta Della Cava: a charming 4-bedroom estate nestled within a secluded 106-acre property. Let's explore this exquisite retreat.
When we arrived at Tenuta Della Cava , the owner, Nino, extended a warm welcome, greeting us along a stone-walled pathway lined by palm and lemon trees. He lovingly gave us a tour, passionately explaining how the home had been meticulously restored to highlight its historical features, while seamlessly incorporating modern elements too. As a skilled metal artisan, Nino had personally crafted many of the design details himself, from intricate metal finishes, to tables adorned with vibrant green maiolica tiles.
Inside, the villa presented historic stone walls, broad arches, and vaulted ceilings, juxtaposed with bursts of vibrant green hues. There was a large welcoming living area, perfect for communal gatherings around an inviting dinner table. You could lounge for hours on the large linen sofas, or enjoy a cup of coffee or tea in the morning. The living room flowed seamlessly into a country kitchen, which was so beautifully designed in shades of Biachi green and bespoke design details, that it almost made me want to cook Thanksgiving dinner myself. For anyone who does enjoy cooking while traveling, this kitchen is simply one of the best!
Adjacent to the kitchen lay the wellness oasis, including a jacuzzi, steam room, sauna, and massage room. Nino had even installed a retractable metal roof over the pool! I’m not talking about a typical skylight feature. I’m talking about a full sized ceiling that seamlessly retracted! It was an architectural wonder. We swam under blue skies by simply pushing a button, allowing us to feel connected to the outdoors even in late November. More about the wellness area to come!
The villa comprised of 4 bedrooms, with two located on the ground floor, and the second two accessed through a beautiful exterior staircase. Each bedroom had an en suite bathroom and contemporary furnishings. The walled estate also featured a small playground and lawn, providing a safe haven for kids to run around and expend their boundless energy. In summer months, guests can enjoy the additional outdoor pool and al fresco dining area shaded by a garden veranda.
In addition to the generous villa space, guests also have the opportunity to explore the extensive property, which boasts remarkable features such as a well-preserved Roman Aqueduct and a rock cave church dating back to 1000 A.D.! Nino kindly offered us a brief tour of the church, granting us the chance to step inside and explore its historical depths further.
# 3 Unforgettable PROPERTIES WITH unique 5 STAR AMENITIES
Every property in The Thinking Traveller’s collection has “that special something” that landed them a spot in the exclusive collection. It may be a stunning infinity pool overlooking the sea, a tennis court surrounded by palm trees, inviting movie theaters for cozy family gatherings, or wellness centers for rejuventation.
At Tenuta Della Cava, the defining feature was its indoor spa, complete with a large jacuzzi, steam room, sauna, and massage area. This amenity is what set the villa apart for our late November visit. The "spa hub" became a gathering point for everyone in our group, regardless of age. The kids thoroughly enjoyed the oversized jacuzzi pool, while the adults developed a nightly ritual of sauna, steam, and relaxation. With a welcoming lounge area, we found it easy to spend hours here, unwinding together.
A swim in the spa organically became part of our daily routine before embarking on each adventure. On Thanksgiving morning, we began by splashing in the warm pool with the kids. After a quick dip, we ventured out to explore Siracusa, indulging in a sandwich from “the best sandwich maker in the world,” and meandering through historic streets. When we returned in late afternoon, everyone beelined straight for the spa pool again. While a private chef was busy preparing our Thanksgiving feast (more on that below), we leisurely relaxed by swimming and relishing the warmth of the hammam.
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#4 HAVE A PRIVATE CHEF HANDLE THE HOLIDAY MEAL
At your villa in Sicily, you'll have access to a full service kitchen, where you can prepare meals yourself, or have a private chef take over.
We chose to leave the Sicilian cooking to the Sicilian chefs.
When you rent a luxury villa in Sicily for the Thanksgiving holiday, you’ll never enter a grocery store, stand in line with two baskets filled with food, nor spend the day chopping, cooking and cleaning. Instead, a private chef will handle all the logistics of your holiday meal. Your only job is to relax, enjoy each other’s company, and savor each satisfying bite. And, no, it’s not as expensive as you might think – I’ll cover the cost further down.
The Thinking Traveller chefs are experts at crafting diverse meals tailored to your palate or food restrictions. They utilize fresh ingredients sourced from Sicilian markets, or simply ones from the villa’s backyard! Each culinary team is intimately familiar with these homes, and the cooks have undergone the same rigorous selection process as the properties themselves. By the end of our stay at Tenuta Della Cava, Giuseppe felt like family. We even ate at his personal restaurant one night, La Donna Patrizia, because his food was simply exceptional. He opened his restaurant doors, just for us, and cooked a 6 course meal including a delectable fish that he’d roasted for 10 hours in preparation for our visit.
Our Thanksgiving meal was just as unforgettable. For the holiday, Giuseppe concocted a meal that reflected traditional Thanksgiving flavors, but with a savory Sicilian twist. He even made sure the side dishes – pillars of an American Thanksgiving – were just as delicious as the main course. These included homemade arancini (fried rice balls), filled with mozzarella cheese and hints of sage. An eggplant caponata with fall vegetable compliments like carrots and squash. For the main course, Giuseppe substituted swordfish for poultry (food restriction in our family), and melded Thanksgiving flavors by creating a delicate stuffing, filled with sage and rosemary from the garden, served over warm green beans. And, a true Italian meal wouldn’t be complete without pasta. Ours was a perfectly cooked pumpkin filled ravioli, followed by the “dolci” course, where we tried Giupseppe’s homemade pistachio cannoli.
Common questions about hiring a private chef
How much does it cost? Total cost of a 5-course home cooked Italian meal for 5 people: 172 Euro, including cost of ingredients, grocery shopping, cooking, and clean up. That’s about $190. Raise your hand if you spent more than that at Whole Foods this past holiday season!
Can The Thinking Traveller accommodate dietary restrictions? Yes! We provided dietary information for our group in the weeks leading up to our visit. They showed us a wide range of menu options we could choose from, even customizing them a bit further based on allergies. In essence, their team is there to make this an unforgettable vacation for you, so if you’re envisioning a particular (Italian) meal, just let them know ahead of time.
Do we need to plan chef services ahead of time? I’d recommend scheduling in-villa meals ahead of time for one or two dinners. Besides our Thanksgiving dinner, I also requested dinner on our arrival day, making it easier to unpack and “troubleshoot” jet lag. The kids could freely run around, while us adults could leisurely eat a home cooked meal. However, The Thinking Traveller can usually also arrange “impromptu” meals with 24-48 hours notice, if you prefer a more spontaneous approach. Additionally, I had also requested breakfast each morning.
Can the chefs cook for large groups? Absolutely! Some of the villas in Sicily accommodate up to 24 people! The larger properties typically also have a larger staff. For comparison, this past summer, we visited this Thinking Traveller property in Puglia with 11 people. They organized breakfast every morning, as well as 3 dinners, and 1 lunch, with a kitchen staff of 2-3 people to make it all happen.
#5 CURATED EXPERIENCES CUSTOMIZED FOR YOUR GROUP
Just as The Thinking Traveller has meticulously selected their villas, they have conducted the same level of thorough research to unearth the most remarkable adventures – many of which are difficult to replicate without their vast network of relationships. Before your trip, your pre-booking concierge will take the time to understand your group – considering everyone's ages, interests, and any "must-see" places on your wish-list. Based on this, they will recommend a tailored itinerary with a range of activities that everyone in the group may enjoy. Here's what we did in late November over Thanksgiving.
Chocolate Making In Modica:
This activity was voted as “favorite activity in Sicily,” by our 5 year old daughter. Hmm...I wonder why?
Of course devouring the delicious delicacy was a highlight; however, it wasn’t just the sweet treat that made this tour truly fantastic.
While some chocolate tours in Modica are held in factories, The Thinking Traveller took a different approach, sending us to a local woman's residence to delve into the city's rich chocolate-making tradition.
We met Elisa outside her family apartment in Modica — a picturesque Sicilan town tucked into the hilltops of southeast Sicily. With warm hospitality, she welcomed us in, sharing that she had spent her childhood in these very rooms. Our class took place in the same kitchen where her grandmother taught her the secrets to chocolate making.
Elisa had made careful preparations to ensure the tour would captivate the kids. When we arrived, our workstations were neatly arranged, complete with a small assortment of coloring supplies for the little ones in case they needed a distraction or break. She kept the historical lesson concise, but informative. We learned that in the 1500s, Spanish conquistadors introduced chocolate to this region upon their return from the Americas. The people of Modica became connoisseurs in the art of chocolate-making, crafting a delicacy with a unique texture and flavor distinct from the Belgian and Swiss varieties. Even today, families uphold the traditions, making the chocolate together using custom molds, passed down through generations. In fact, we were using the very molds passed down to Elisa by her own grandmother!
After our short history lesson, it was time to embark on the chocolate making adventure! The kids donned their aprons at their designated chocolate workstations, as Elisa guided us through the process of melting the chocolate to achieve the characteristic grainy texture synonymous with Modica chocolate. There was not a second where the kids, ages 5 and 2, were not completely absorbed in the chocolate making process. We all added our chosen spices, poured the chocolate into molds, and then placed them in the freezer to set. We took a well timed break on Elisa's balcony, gazing at the city views, before it was time to taste test the final result. The chocolate bars came out delicious! We devoured some of the rich dessert right there on the spot, and also packaged some to take home.
Treasure Hunt in Ragusa
A walking historical tour, combined with little kids, may not initially strike you as an ideal activity, but that perception changes swiftly when you set out on a treasure hunt through the enchanting streets of Ragusa.
Ragusa is a hilltop town in Sicily, which was heavily destroyed in the 1600s by an earthquake. The buildings today resemble a picturesque jigsaw puzzle, interconnected by Medieval staircases, and an intricate labyrinth of lanes that only locals seem to navigate with ease.
The town's fairy-tale appearance provided the perfect stage for our guide, Sabine, to lead us on a mythical treasure hunt through its historic streets. While our 2-year-old was preoccupied with his own quest to spot imaginary dragons, our 5-year-old daughter listened with rapt attention, as if she were engrossed in the most enthralling bedtime story. Sabine came well-prepared with activity booklets, treasure maps, and even fairy-tale props for role-playing. As we traversed the narrow alleyways, winding staircases, and quaint streets, our trusty activity booklets became our guiding companions, challenging us to solve puzzles and decipher codes to unveil the next clue.
Our adventure culminated in the serene and picturesque Giardino Ibleo, a breathtaking garden perched above the valley that also had a fantastic playground. Although the official tour had concluded, we continued to wander through Ragusa's charming streets as day transformed into night. The town exuded a peaceful energy, with only the locals in sight. We, of course, couldn't resist indulging in a scoop of gelato from Gelati Divini., which turned out to be my favorite gelateria of the entire trip.
Jeep Tour of Mt. Etna
If your family craves adventure and the great outdoors, then this tour is tailor-made for you!
Mt. Etna is Europe’s most active volcano, and the 4th most active volcano in the world! While this may sound daunting, rest assured your visit won't resemble a Pompeii-like catastrophe. In fact, the high level of activity on Mt. Etna mostly involves slow, mesmerizing lava flows, making it a fantastic place to learn about volcanoes in a safe and enjoyable way.
Our journey commenced at the base of the mountain, where we met our guide, Roberto, and hopped in his sturdy 4x4 jeep for an exhilarating ride. Soon, we found ourselves navigating past hardened lava fields. It was a surreal sight—black lava expanses strewn across what used to be lush terrain. Fresh trees and vegetation tried stubbornly to make a comeback, pushing through the Earth’s soil boasting their resilience.
Since our jeep tour was a private, customizable experience, we could request stops along the way, and linger a little longer in some spots. When we stopped for a brief hike to the summit of a former lava crater, there was a fresh layer of snow all around us. The kids of course wanted to immediately make snow angels and have an epic snowball fight. Upon reaching the summit, we were rewarded with breathtaking panoramic vistas that seemed to span different seasons and colors. In the distance, the vibrant blues of the Ionian Sea and the coastal towns of Taormina and Castlemola unfolded before our eyes, hinting at residual summer days. However, right in front of us lay the rugged, snow-dusted remnants of black volcanic pebbly terrain, creating a mesmerizing contrast.
Following our invigorating hike, we drove further up the winding roads, where the landscape underwent another dramatic transformation. The slender Aspen and Birch trees gave way to towering Pines reminiscent of a Bavarian forest, with a thick layer of pristine snow at our feet. Claire gazed around in wonder, and asked me if we had wandered into the world of "Frozen." As we hopped out of the jeep, we ventured into a cozy chalet, where we refueled with a quick snack and hot chocolate. Somehow the day flew by, and it was time to start our descent back down to our meeting point.
While it's no secret that jeep tours of Mt. Etna are a popular activity for tourists in Sicily, allowing The Thinking Traveller to organize it through their extensive network of contacts, truly elevated our experience. This customization allowed us to cater the tour to accommodate our children's young ages, all while exploring a significant portion of the mountain in just a few hours. For fellow adventure enthusiasts, this is an absolute must-do!
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Best Luxury Villas in Sicily
In this article, I've shared our experience at Tenuta Della Cava, an exquisite luxury villa located in the southeastern region of Sicily. It was the perfect choice for an intimate family gathering for the holiday. However, if you’re traveling to Sicily with a larger group, whether that be for Thanksgiving or any other time of the year, The Thinking Traveller has a number of additional luxury villas that are equally unforgettable. Here are just a few of the favorites:
Don Venerando
Nestled between Taormina and Catania, you'll find Don Venerando, affectionately known as "the house of 10,000 trees." Situated amidst expansive garden grounds, this villa not only affords unobstructed vistas of Mount Etna, but also panoramic views of the Ionian Sea.
Accommodating up to 10 people, guests can enjoy the private heated pool, numerous al fresco dining areas, and even a cozy fireplace for those seeking a visit during the cooler off-season months. From Don Venerando’s location, it’s easy to embark on day trips to Taormina, an exceptionally picturesque seaside city. Taormina is celebrated for its vibrant ambiance, lively city energy, and unforgettable views of both the Ionian Sea, and Mt. Etna. Don't miss the opportunity to visit the ancient Greek Theater at sunset for an unforgettable experience. Guests are also conveniently located near Catania, where it’s easy to spend a day immersed in the bustling streets, lively markets, and rich culinary scene.
Baia dei Turchi
Baia dei Turchi is the ideal retreat for those in search of a family-friendly villa that also elevates the experience of a seaside getaway. With accommodations for up to 13 guests, it’s an ideal home for a larger family getaway. The villa includes an infinity pool and a seafront sauna that provides breathtaking views of the water. There’s also an indoor hammam and a fitness center. For those traveling here with younger kids, it’s just steps away from the nearest beach, making it convenient to head off property to explore. Positioned conveniently between Catania and Siracusa, guests can embark on day trips to either city. Catania, renowned as a culinary mecca, is a perfect destination for foodie-focused travelers. Alternatively, Siracusa, a UNESCO World Heritage-listed city, invites you to step back in time with its ancient Greek ruins. Make sure to also check out the marina of Ortigia in Siracusa– with its lively atmosphere, charming shops, and stunning sea views, it’s the perfect city for an easy day trip destination.
Villa Tenuta Baroniblei
Villa Tenuta Baroniblei is a stunningly modern and expansive villa designed to accommodate up to 16 guests. Its vibrant and colorful interiors create an atmosphere that’s simply put…just pure fun! The real charm of this villa, however, lies in its beautifully landscaped gardens, adorned with fragrant flowers, and expansive views of the sea. During the warmer months, you can easily relax all day long by the saltwater pool. For those seeking nature and adventure, a short drive will take you to the serene Vendicari Nature Preserve. Here, you can hike the scenic trails, swim in some of Sicily's most pristine beaches (if visiting in the summer), and even try your luck at spotting flamingos. If you’re itching to visit some towns, you are in close proximity to both Noto and Marzamemi. In the summer, both towns come alive with an array of restaurants and shops, and they offer a more peaceful ambiance during the shoulder season.
Ready to Roam?
As a travel advisor, I can help you get this dream villa vacation booked!
Is November a Good Month to Travel to Sicily?
Traveling to Sicily in the fall offers a truly magical experience. Even if you’ve visited Sicily during peak summer months, trust me when I say that it’s refreshingly different when you wander its streets and scenic landscapes after the crowds have dissipated. Here’s a few reasons to consider November for your Sicily travels:
- Mild Weather: While early November can see temperatures lingering near 80°F, by mid-month, temperatures moderate to a mild 60-70°F during the day, and in the low 50s°F at night. You can enjoy the scenery without the scorching summer heat!
- Fewer tourists: There are drastically fewer tourists from October-March. You can stroll the streets of the major cities in a more peaceful way, or join kids playing soccer in the local town squares. You’ll almost never require a restaurant reservation. And, you can enjoy the magnificent beauty of the Greek Theater and Mt. Etna without vying for the view.
- Grab the best deals: Visiting in shoulder season means more favorable pricing for accommodations, flights, and activities. You can rent a luxury villa in Sicily with The Thinking Traveller at significantly lower rates than peak summer season.
- Seasonal scenic beauty: You can experience variations of all 4 seasons in November. On one occasion, we awoke to spring-like temperatures, spent the morning walking the beach next to palm trees, and then hopped in a jeep to climb Mt Etna. Along the way, we passed trees shedding their autumnal colors of orange and yellow, and the afternoon wrapped up with a snowball fight at the summit of an erupting volcano!
- Christmas decor: Taormina had the Christmas lights already hung in November, creating a magical holiday feel. There were even a few Christmas themed shops, which allowed us to get a jump start on some holiday shopping.
What is the easiest way to get from the USA to Sicily?
To fly from the U.S. to Sicily, you’ll need to connect through a major European city. There are numerous flights everyday to the island, especially if connecting through Rome (as we did). In Sicily, there are 3 major airports: Palermo Airport (PMO) in the west, Catania Fontanarossa Airport (CTA) in the east, or Trapani Airport (TPS) in the west. Given the size of Sicily, be sure to choose the airport closest to your accommodation.
Travel Tips:
- Layovers: Allow for plenty of time in your connecting city. As a rule of thumb, when traveling with kids, I usually budget at least 2-3 hours in my connecting city. This allows us to clear customs, stretch our legs, grab something to eat, and walk to our next gate, without feeling rushed.
- Great opportunity to use points: At times, when you need to travel from point A to point B, you might be limited to a single route, making it difficult to utilize credit card or airline points for your ticket. Fortunately, that's not the situation here. On the contrary, since there are several connecting cities you can choose from to reach Sicily, there are also numerous opportunities to secure a value-packed ticket using your points. Keep this in mind while searching for flights!
- Sleep aids: For kids under 2, I highly recommend the Flyaway Bed. It’s an easy way to transform an airplane seat into a bed, making overnight flights much easier. Use code “compassroam” for 5% off your purchase!
- Thanksgiving travel: Contrary to what you might expect when envisioning Thanksgiving travel, journeying from the U.S. to Sicily involves a surprisingly hassle free experience. While the domestic terminals in many major airports at this time of year are filled with people, the international terminals are less chaotic.
Things to Do in Sicily with Your Family
If you're traveling to Sicily during the shoulder season, you may be wondering what you can see and do with your family for a week. From top to bottom here’s a brief overview of of my must-do activities. If you're interested in accessing my comprehensive 9-day Sicily itinerary, packed with specific activity details, and all our restaurant recommendations, be sure to subscribe to the newsletter.
- Explored Noto, a beautiful city filled with Baroque style architecture.
- Roamed the streets in the historic port cities of Siracusa + Ortigia, while grabbing lunch from "the world's best sandwich maker."
- Embarked on a treasure hunt tour through the hilltop town of Ragusa, and explored Giardino Ibleo.
- Learned how to make chocolate in Modica, and explored this Medieval town by train.
- Full day Mt. Etna guided Jeep tour.
- Explored the cliffside city of Taormina and the Greek Theater of Taormina.
- Strolled through the coastal beach town of Marzamemi.
- Ventured on nature hikes through the family friendly Vendicari Nature Preserve.
And just think… that was only one part of the island!
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That's a Wrap
If you're yearning for a Thanksgiving – or any holiday – that retains all the cherished elements of the day itself without the usual chaos, I wholeheartedly recommend breaking away from tradition and celebrating it in Sicily. While our Thanksgiving festivities at home will always hold a special place in our hearts, what truly set this experience apart was the opportunity to fully embrace the essence of gratitude by spending quality time together. From the villa's serene amenities, to the unforgettable Thanksgiving feast, to the warm hospitality of the owners, and the meticulous care provided by The Thinking Traveller, this particular Thanksgiving will undoubtedly be etched in our family's memories for years to come.
I hope this article has inspired your own family getaway to a Thinking Traveller villa in Sicily. If you have any questions, or your own travel tips, please leave them in the comments below. Also, don't forget to sign up for the monthly newsletter, packed with travel tips, upcoming news, and access to FREE destination itineraries.
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