Snapshot of the Itinerary
Enchanted Sicily
A Lavish Southern Italian Odessey
Breathtaking Panoramas, Culinary Artistry & Aristocratic Charm
Sicily Tour September 20-28, 2027
9 Days - Maximum 14
“To have seen Italy without visiting Sicily is not to have seen Italy at all, for Sicily is the clue to everything.”
~ Goethe~
There’s no other place on earth like Sicily. The island is a unique place full of art, archeology, history, folklore, and breathtaking scenery. For great food and wines, Sicily is almost a nation unto itself. Sicily is Europe, Africa, and Asia all wrapped up on one island!
Day 1 - Welcome to Sicily & Wine Resort
Your journey begins the moment you touch down in historic Palermo, where a private motor coach awaits to sweep you away into the sun-drenched heart of Sicily. You will journey through rolling hills to a hidden boutique wine resort perched gracefully on a ridge along the rugged southern coast. This intimate oasis, your home for the next two nights, blends rustic Italian charm with modern luxury and offers endless panoramic views of emerald vineyards melting into the distant blue sea.
Upon arrival, you can unwind from your travels with a casual, al fresco welcome lunch featuring estate-to-table flavors. You will savor sun-ripened tomatoes, fresh-pressed olive oils, and artisanal cheeses while drinking in the breathtaking landscape. As twilight paints the sky in shades of amber and violet, the day culminates in an exclusive wine dinner. Your personal host sommelier will lead you through a multi-course feast of local specialties, expertly pairing each dish with hand-selected vintages to create a true sensory celebration of Sicily.
Your sanctuary on the hill features beautifully designed rooms that blend historic Sicilian stone with sleek, modern comforts. Beyond your room, the estate invites you to relax deeply with its world-class amenities. You can take a peaceful dip in the pool, which looks out over the endless rows of grapevines. The resort also boasts a boutique wellness spa offering treatments infused with estate-grown olive oil and volcanic minerals. Every corner of the property is crafted to help you slow down, from the quiet library filled with art books to the hidden garden paths perfect for a sunset stroll.
Day 2 - Cooking Class & Ancient Greek Ruins
The next morning, you will step into the resort’s state-of-the-art kitchen for an extraordinary, private culinary masterclass. Your guide is the estate's acclaimed executive chef, a celebrated cookbook author and master of Sicilian gastronomy. Together, you will unlock the secrets of time-honored family recipes, working with fresh herbs plucked from the resort garden and seafood caught just hours prior. Afterward, celebrate your hard work with an intimate, private lunch on a sun-draped veranda. You will dine on the exquisite feast you created, beautifully plated and paired with wines from the surrounding hills.
In the afternoon, your private driver will escort you to Agrigento for a exploration of the legendary Valley of the Temples. Alongside a private historian, you will enjoy skip-the-line access to skip the crowds and wander among the world’s most spectacularly preserved ancient Greek monuments. As golden hour bathes the giant columns in a warm, amber glow, your guide will bring the myths of antiquity to life just for you. To conclude this unforgettable day, you will head to a handpicked, authentic Sicilian restaurant hidden away from the usual tourist paths. Here, you will enjoy a light, candlelit dinner of local delicacies before a relaxing, chauffeured drive back to your hilltop sanctuary.
Day 3 - Olive Oil & the Pearl of the Mediterranean
As the morning sun casts a golden glow over the countryside, you will bid farewell to the resort and journey to an exclusive, family-owned estate famed for its award-winning olive oils. You will walk through ancient groves of gnarled olive trees alongside the estate owners, discovering the meticulous, centuries-old art of cold-pressing liquid gold. Following the tour, indulge in a private, curated tasting of their finest extra virgin oils, followed by an elegant farm-to-table lunch. This feast is prepared entirely from organic ingredients cultivated and harvested right on the farm, perfectly capturing the pure, sun-drenched essence of the Sicilian soil.
In the afternoon, settle back into the comforts of your private vehicle for a scenic three-hour drive northeast toward Taormina, affectionately known as the "Pearl of the Mediterranean." Your route unfolds along a breathtaking coastline where dramatic cliffs plunge into the azure Ionian Sea. Upon arrival, you will discover a romantic hill town celebrated for its beautifully preserved medieval architecture and sweeping panoramic views. The town provides a magnificent, theatrical backdrop where the glittering sea meets the majestic, snow-capped peak of Mount Etna. You will enjoy a two night stay at a historic boutique hotel in Taormina, celebrated for its spectacular views of Naxos Bay and Mount Etna.
To cap off this spectacular day, you will be escorted to a handpicked, authentic Sicilian restaurant tucked away in Taormina’s charming lamplit lanes. You will dine on exquisite regional delicacies in an intimate, elegant setting, celebrating the rich culinary heritage of the island.
Day 4 - Mount Etna Winery & Tour of Taormina
This morning, you will ascend the dramatic slopes of Mount Etna to an elite, award-winning estate nestled in the volcano's fertile foothills. Here, you will engage in a private conversation with head viticulturists and winemakers to unlock the secrets of extreme, high-altitude farming. You will learn firsthand how the mineral-rich volcanic soil infuses the native grapes with their distinct, globally acclaimed character. Following this fascinating insight, remain on the mountain for a sophisticated, countryside lunch, where a multi-course menu of rustic refinement is paired with the estate's finest signature vintages.
In the afternoon, you will return to Taormina for an exclusive, privately guided exploration of this enchanting coastal jewel. You will stroll through the town's elegant historic center, wander past exotic flora in the lush botanical gardens, and step back in time at the magnificent ancient Greek Theater, where ancient stone frames unforgettable views of the Ionian Sea. The evening is yours to enjoy entirely at your own leisure, giving you the perfect opportunity to browse Taormina's luxury boutiques or relax over an aperitivo in a lively, lamplit piazza.
Day 5 - Siracusa, Ortigia & Noto
Your journey continues as you travel south toward Siracusa, step back in time at the awe-inspiring Neapolis Archaeological Park. Alongside your guide, you will wander through monumental Greek and Roman ruins that vividly illustrate the immense power, wealth, and theatrical history of ancient Siracusa.
Afterward, cross the bridge onto the magical island of Ortigia, the historic peninsula universally considered the cultural jewel of the city. Here, you will dive into the sensory theater of the Old Market of Ortigia for a legendary lunch at a beloved culinary institution famous for its spectacular, custom-made panini and overflowing charcuterie boards.
Following lunch, you will escape the coastal bustle and check into an exclusive, boutique countryside hotel for a peaceful two-night stay. Originally an aristocratic 18th-century farmstead, this charming estate has been beautifully restored into a secluded, luxurious oasis. As the late afternoon light softens, conclude your day in Noto, a breathtaking masterwork of Sicilian Baroque design. You can stroll through its grand, golden-stone lanes and pause at Caffè Sicilia, a world-renowned pastry shop, to savor artisanal granita and authentic cannoli. Your perfect day ends back at your peaceful hotel estate with an intimate dinner featuring fresh, locally grown ingredients
Day 6 - Ragusa Ibla & Marzamemi
Your journey begins with an exploration of Ragusa Ibla, a breathtaking labyrinth of Sicilian Baroque architecture. You will wander past grand, golden-stone palaces and ornate balconies before stepping into the serene expanse of the Giardini Iblei. This historic park offers a quiet refuge of towering palms, manicured pathways, and panoramic valley views. Your morning culminates in an extraordinary culinary experience at a world-class, Michelin-starred restaurant where legendary Sicilian flavors are reimagined into a spectacular, curated lunch.
Afterward, travel south to the sun-bleached coastal village of Marzamemi. This ancient fishing port possesses a beautiful seaside soul, where timeless seafaring charm blends seamlessly with historic stone cottages. You will explore its iconic piazza and the historic tonnara (tuna fishery) rooted in 10th-century Arab rule, feeling the romance of an unchanged Mediterranean haven.
Day 7 - Cefalu` & Palermo
Your journey begins with a drive northwest to Cefalù, a breathtaking medieval jewel cradled between a dramatic mountain cliff and the azure Mediterranean Sea. Here, you will stroll through charming cobblestone pathways to discover exclusive local boutiques, step into the enchanting history of a hidden medieval laundry, and admire the majestic, gold-leaf mosaics within the fortress-like Norman Cathedral. After indulging in a lunch on a private terrace suspended over the crashing waves, you will be chauffeured to Palermo, Sicily’s captivating 2,700-year-old capital. There, you will check into a palatial, historic Art Nouveau luxury hotel that promises royal comfort, before immersing yourself in the city's vibrant culture and concluding your evening with a reservation at a neighborhood trattoria.
Day 8 -Palermo’s Markets, Street Food & Farewell Dinner
As the morning sun warms the city, you will plunge into the mysterious heart of Palermo on an exclusive walking tour with street food tastings designed to awaken your senses. You will navigate a labyrinth of ancient open-air markets, where the air is thick with the scent of wild oregano and citrus, and meet legendary local merchants who guard centuries of culinary secrets. Each corner reveals a new, bold Sicilian street food to taste, leading you to a door into one of the city's oldest, atmospheric taverna for a tasting of rare local beverages and historic snacks. Along the way, your guide will decode the enigmatic symbols etched into the city's soaring architecture, revealing the dramatic triumphs and secrets of Palermo's 2,700-year history.
Finally, as twilight falls, the journey culminates in an intimate farewell group dinner, a grand final celebration to raise a glass, share stories, and look back on an unforgettable week of shared adventures.
Day 9 - Arrivederci & Keep in Touch!
As your unforgettable Sicilian journey comes to a close, transfers to the Palermo airport will be provided based on your individual flight schedule. Enjoy a smooth and relaxing 30-to-45-minute drive to the airport, giving you one last look at the stunning landscape as you head home with a lifetime of beautiful memories.
ALL INCLUSIVE PRICING
Everything you need for an unforgettable 9 days in Sicily
✓What's Included
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8 nights in four locations throughout Sicily at 4 and 5 star luxury boutique hotels (wine resort, historical boutique villa hotel, countryside boutique estate & historic Art Nouveau hotel)
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Explore UNESCO World Heritage sites across the island. Discover ancient civilizations such as Agrigento’s Valley of the Temples, Taormina’s cliffside Greek Theater, Siracusa’s Neapolis Archaeological Park, the baroque towns of Ragusa and Noto, and wander the medieval streets of seaside Cefalù. Conclude with a visit to the grand Palermo Cathedral and a guided culinary tasting through Palermo's bustling historic food markets.
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Daily breakfast
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8 Lunches (a few light lunches or street food tastings), as per itinerary
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6 Dinners with wines picked by our very own wine expert, as per the itinerary
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Tastings and tour of a family-run and owned olive oil farm with country-style lunch
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Cooking class led by the resort chef
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Local winery tour allows you to discover the art of winemaking from vine to glass. Explore the estate grounds and cellars before savoring a premium tasting and lunch.
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A wine expert at your disposal for the week
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Visit to many of Sicily’s UNESCO World Heritage sites
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glish-speaking local tour guides, as per the itinerary
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Private motorcoach transportation throughout the tour
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Round-trip transfers between Palermo Airport (PMO) and our hotels are included on the official start and end dates of your tour. If you arrive a day or two early, your arrival transfer will automatically shift to a direct pickup from your pre-tour hotel in Palermo on the day that the tour officially starts
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Lunch at a two star Michelin restaurant
✗Not Included
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Flights
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Meals not mentioned in the itinerary
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Alcoholic beverages outside of included tastings and meals
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Additional accommodations before or after the trip dates
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Travel Insurance
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Gratuities are optional (can be offered for exceptional service to our tour guides and the bus driver)
Tour Cost
$ 9,500 before December 31 2026
$ 9,900 after December 31 2026
Per person, double occupancy
CREDIT CARDS ACCEPTED
Secure your spot with a 50% deposit
before December 31, 2026
How do I book my spot? Please click the “Reserve Your Spot” button, which will take you to the Tour Forms page. Shortly after, you will receive an email from us with further instructions on how to make your deposit and book your spot. Reservations will be available on a first-come, first-served basis. Credit cards are accepted with no additional fees.
When should I arrive for this trip? As you plan your travel, please be sure to arrive by 11:00 AM in Palermo, Italy on September 20th. We’ll have one scheduled group transfer to our hotel in Sicily. If you arrive after this time, you’ll need to make your own way to the hotel which is about one and half hours away. We can’t wait to welcome you!
Who would enjoy this tour? This tour is an intimate, small-group tour and will not have more than 14 travelers. The tour is perfect for wine lovers, food enthusiasts, and curious travelers who want a deeper taste of Sicily, culturally and literally. You don’t need to be a foodie or wine geek, just someone who enjoys good company and beautiful places. Past travelers range from couples and friends connecting over shared interests. If you appreciate quality over quantity and authentic experiences over tourist traps, you will love this tour.
What is the price of this tour? The Early Bird price is $9,500.00 per person double occupancy. After December 31, 2026 the price is $9,900.00 per person double occupancy.
What is included in the price? ● 8 nights in four locations throughout Sicily at 4 and 5 star luxury boutique hotels (wine resort, historical boutique villa hotel, countryside boutique estate & historic Art Nouveau hotel). ● Explore enchanting historic villages and celebrated UNESCO World Heritage sites across the island. Discover ancient civilizations at Agrigento’s Valley of the Temples, Taormina’s cliffside Greek Theater, and Siracusa’s Neapolis Archaeological Park. Take in the architectural brilliance of the Baroque towns of Ragusa and Noto, and wander the medieval streets of seaside Cefalù to its Norman Cathedral. Conclude with a visit to the grand Palermo Cathedral and a guided culinary tasting through Palermo's bustling historic food markets. ● Daily breakfast ● 8 Lunches (a few light lunches or street food tastings), as per itinerary ● 6 Dinners with wines picked by our very own wine expert, as per the itinerary ● Tastings and tour of a family-run and owned olive oil farm with country-style lunch ● Cooking class led by the resort chef ● Local winery tour allows you to discover the art of winemaking from vine to glass. Explore the estate grounds and cellars before savoring a premium tasting and lunch. ● A wine expert at your disposal for the week ● Visit to many of Sicily’s UNESCO World Heritage sites. ● English-speaking local tour guides, as per the itinerary ● Private motorcoach transportation throughout the tour ● Round-trip transfers between Palermo Airport (PMO) and our hotels are included on the official start and end dates of your tour. If you arrive a day or two early, your arrival transfer will automatically shift to a direct pickup from your pre-tour hotel in Palermo on the day that the tour officially starts. ● Lunch at a two star Michelin restaurant
What is not Included? ● Flights ● Meals not mentioned in the itinerary ● Alcoholic beverages outside of included tastings and meals ● Additional accommodations before or after the trip dates ● Travel Insurance ● Gratuities are optional (can be offered for exceptional service to our tour guides and the bus driver)
What’s the pace of the trip? Expect a relaxed but full itinerary. Moderate walking is involved, especially in historic hill towns and some towns where the streets are slick from worn pavement. There’s plenty of wining, dining, and touring, but also time to explore, rest, or sip your favorite beverage in a sunny piazza.
What will the weather be like in Sicily in September? At the end of September, Sicily transitions beautifully from intense summer heat to an exceptionally pleasant, comfortable late-summer climate, featuring average coastal daytime highs between 78°F and 82°F and refreshing evening drops to around 68°F. The sea remains thoroughly warmed from the summer months at a highly swimmable 77°F.
What should I pack? ● We hope for beautiful, sunny days, but please be sure to prepare for rain, just in case Mother Nature decides not to cooperate. It’s a good idea to bring a lightweight rain jacket, a sweater or light fleece, a packable umbrella and comfortable walking shoes with good gripping rubber soles. We will be walking on cobblestone streets and uneven pavement, and visiting a countryside vineyard and farm. We suggest you dress in layers for warm days and cooler evenings. Pack a swimsuit, should you want to take a dip in one of the hotel pools. ● Your passport!! Please check the expiration date; it must be valid for six months beyond your travel dates. We will need a copy of your passport information page for the hotels. ● Sun protection (hat, sunscreen, sunglasses) ● Bring your appetite for wine and delicious food!
How do I get to Palermo,Sicily where the tour begins? Fly into Palermo Falcone-Borsellino Airport (PMO). The most convenient connections are usually through Rome (FCO) on ITA Airways, but there are connections through other cities. As you plan your travel, please be sure to arrive by 11:00 AM in Palermo, Sicily on September 20th , 2027. We’ll have one scheduled group transfer to our wine resort on the southern coast. If you arrive after this time, you’ll need to make your own way to the resort which is about one and half hours away.
What's the payment plan? A 50% deposit per person of the total price is due upon booking, based on double occupancy. The balance is due by June 1, 2027. Credit cards are accepted with no additional fees.
What's the cancellation policy? A cancellation must be received in writing and confirmed by Sips Sites & Bites. Deposits are refundable up until 120 days prior to the departure date of September 20, 2027, an administrative fee of $200 will be charged per person. If canceled between 119 days to 90 days prior to departure date the penalty will be 50% of the total tour price. If canceled 89 days or less the penalty is 100% (nonrefundable).
What if I have dietary restrictions or food allergies? We can accommodate most dietary restrictions. Please let us know at the time of booking on your tour form.
Can I extend my stay in Sicily before or after the trip? Absolutely! Many travelers choose to arrive in Europe early or stay longer to explore other parts of Sicily or Italy independently.
What's your health policy? We follow current Italian travel requirements and health guidelines. We recommend all travelers have comprehensive travel insurance that includes medical coverage. If you feel unwell during the trip, let us know immediately—your health and the group's safety are our priority.