Sicily Cultural Adventure - October 25-31, 2026

SICILY Cultural Adventure

Prepare to fall under Sicily’s spell on this immersive adventure. From golden stone piazzas and seaside markets to volcanic vineyards and ancient ruins, this journey blends sun-drenched culture with unforgettable flavors and local character.

From the historic centers of Siracusa and Taormina, we’ll explore atmospheric avenues, take in sweeping sea views, and browse lively markets and artisan shops filled with handmade ceramics, woven linens, and local delicacies. Whether you’re pausing to admire a breathtaking overlook, sampling street food in a bustling piazza, or gathering treasures to bring home, each moment of our journey together is rich with Sicilian spirit.

THE WONDER of Bella Sicilia

This is a journey as much about how you feel as where you go—relaxed, inspired, and immersed in the warmth and wonder of sun-kissed Sicily. Together we’ll stroll beneath the glowing stone of Ortigia’s Duomo, walk in the footsteps of ancient Greeks at Siracusa’s remarkable archaeological park, and sip volcanic wines on the slopes of Mount Etna, where vineyards thrive in lava-rich soil. Along the way, we savor meals that are both rustic and refined—celebrations of Sicily’s bold, seasonal flavors, from handmade seafood pastas to pistachio gelato served on freshly-baked brioche.

ITINERARY

DAY 1: Arrival Siracusa

  • Highlights: Arrival, welcome at hotel
  • Dinner

From Catania Airport, our private driver will be waiting to whisk our group to the island of Ortigia—the historic center of ancient Siracusa—where stone streets meet the sparkling Ionian Sea. After settling into our boutique hotel, we’ll kick off our adventure with a relaxed aperitivo—think bubbly spritzes, Sicilian olives, and that golden Mediterranean light. Then, we’ll head to a local restaurant for a warm and welcoming Sicilian dinner, where the flavors are as rich as the history. It’s the perfect start to our Sicilian adventure!

DAY 2: Ortigia 

  • Highlights: Walking tour historic center, food tour
  • Breakfast, dinner

This morning, we set out with our local guide to explore the winding lanes and layered history of Ortigia’s historic center. From ancient Greek ruins and medieval piazzas to vibrant daily life, we’ll uncover the island’s rich cultural at a relaxed pace, with plenty of time for questions, photos, and a few surprises along the way. Afterward, enjoy lunch on your own at a rustic trattoria or chic café.

In the late afternoon, we regroup for a lively street food tour, sampling the bold, beloved flavors of Sicily: arancini, fried seafood, cannoli, and more, all served with stories and charm by our passionate local guide.

DAY 3: Ortigia & Noto

  • Highlights: Greek temples, excursion to Noto
  • Breakfast, Dinner

This morning, we set off on foot to visit the Archaeological Park of Neapolis, home to some of the most impressive ancient ruins in Sicily. We’ll explore the awe-inspiring Greek Theatre, the atmospheric Ear of Dionysius, and the Roman Amphitheatre, all nestled in a peaceful citrus grove just outside Ortigia. Afterward, you can enjoy lunch on your own at a trattoria or a perhaps a quick panino from a local bakery.

In the afternoon, we’ll travel by private vehicle to the stunning town of Noto, the undisputed jewel of Sicilian Baroque. Here, we’ll visit the glorious Cathedral of San Nicolò and stroll the golden-hued streets before sitting down to a group dinner at a local restaurant.

DAY 4: Taormina via Mount Etna

  • Highlights: Mount Etna, wine tasting
  • Breakfast, lunch, dinner

This morning, we say goodbye to Ortigia and journey by private transfer toward the dramatic slopes of Mount Etna, Europe’s highest and most active volcano. As we ascend through ancient lava fields and fertile vineyards, you’ll see why locals call her “Mamma Etna”—both fearsome and life-giving. Our destination is a charming Etna winery where the volcanic soil yields bold, elegant wines. After a tasting and light lunch we continue on to Taormina, Sicily’s most glamorous hilltop town, where our boutique hotel welcomes us with style – and a view to remember. Tonight, we gather for a relaxed group dinner at the hotel—good wine, great company, and the lights of the Ionian coast twinkling below. It’s the perfect way to settle into the Taormina magic.

DAY 5: Taormina 

  • Highlights: Cooking class
  • Breakfast, lunch

This morning, after a leisurely breakfast, we dive into the heart of Sicilian cuisine with a fun and flavorful cooking class led by a local chef. Together, we’ll prepare a traditional menu—think hand-rolled pasta, market-fresh vegetables, and maybe even a sweet finale like cannoli. It’s hands-on, full of laughs, and ends with a shared lunch made by our own hands.

The afternoon is yours to relax, shop, or explore more of Taormina’s charming corners. Then, as the sun begins to dip, we regroup for a casual aperitivo in town, raising a glass to this enchanting hilltop town.

DAY 6: Taormina

  • Highlights: Guided walking tour, Greco-Romano theater, farewell dinner
  • Breakfast, lunch, dinner

On our final full day in Sicily, we dive into Taormina’s rich history and timeless beauty with a guided walking tour led by a local expert. We’ll explore the elegant historic center, visit the medieval Palazzo Corvaja, and stand in awe inside the legendary Greek–Roman Theatre, where ancient drama once unfolded against a backdrop of sea and volcano.

After the tour, enjoy lunch on your own, and then take the afternoon at your leisure to browse the chic boutiques, art galleries, and ceramic shops that line Taormina’s picturesque streets. In the evening, we gather one last time for an elegant farewell dinner at a favorite local restaurant as we toast our unforgettable journey together.

DAY 7: Departure

Early morning departure for Catania Airport

The Unexpected is Part of the Journey: Note that the itinerary will be subject to change. Should that happen, just know that we will include something that is equally as wonderful and interesting. The quality of your experience is never at risk. ☺️

ACCOMMODATIONS

Boutique Hotels in Ortigia & Taormina

We enjoy our first three nights at Hotel Gran Bretagna, an elegant boutique hotel set in a restored 19th-century palazzo at the edge of Ortigia’s historic seafront. With its charming rooms, classic Sicilian décor, and ideal location just steps from Piazza Duomo and the island’s vibrant streets, the hotel offers a perfect base for exploring Siracusa’s cultural treasures.

Our next three nights are spent at the Splendid Hotel Taormina, nestled on a quiet hillside with panoramic views of the Bay of Naxos and Mount Etna. This refined and peaceful hotel features light-filled rooms, a garden-framed pool, and easy access to Taormina’s historic center, including its ancient Greek Theatre, charming shops, and inviting cafés.

INCLUSIONS

  • 6 nights: 3 nights Siracusa (Ortigia), 3 nights Taormina
  • Group transport from Catania Airport to Ortigia on arrival day
  • Group transport from Taormina to Catania Airport on departure day
  • Private driving service on all excursions and transfers
  • All breakfasts
  • 2 Lunches
  • 5 Dinners
  • Guided tour Ortigia historic center
  • Street food tour
  • Archeological site Siracusa
  • Wine tasting on Mount Etna
  • Cooking lesson
  • Guided tour Taormina historic center
  • Entrances to all museums/sites included in the trip itinerary
  • Daily accompaniment with Pamela Haack
  • Daily opportunities for exploring, shopping and sightseeing on your own

Not included: Airfare, transportation and meals outside of that which is specifically listed in the trip package, gratuities for hotel staff and drivers.

WALKING & ACTIVITY LEVEL …What to Expect

‼️➡️ Is this trip right for you? 

The itinerary for this trip involves a significant amount of walking, often over uneven terrain, cobblestone streets, steep slopes, and stairs. You must be able to walk independently without assistance, cover significant distances over the course of the day, remain on your feet for extended periods during tours and site visits, and keep up with the rest of the group.

If you question your physical condition or mobility level, this trip is likely not the right fit.

DATES & DETAILS

  • Dates: October 25-31, 2026
  • Trip Price:
    • $3,895 USD per person, double occupancy
    • $4,495 USD per person, single occupancy
  • Room Description: All rooms include wifi, air conditioning, hair dryer and safe. In Ortigia, rooms include a mini-fridge. In Taormina, rooms include a balcony. Note that we will be staying in boutique hotels that do not have an elevator. Please expect to handle your own luggage when/if needed.
  • Luggage: We suggest traveling with no more than one medium-size checked bag and one carry-on bag. No oversized baggage. Please also be prepared to handle your own luggage, if/when necessary. We suggest packing light.
  • Walking:  The itinerary for this trip involves a significant amount of walking, often over uneven terrain, cobblestone streets, steep slopes, and stairs. You must be able to walk independently without assistance, cover significant distances over the course of the day, remain on your feet for extended periods during tours and site visits, and keep up with the rest of the group.
  • $700 deposit is required to book your space on this tour
  • Terms and Conditions

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