8:00 am Get to know Castellammare (the town where my mother was born and I spent most of my summers), from the ground up! Meet early in the morning at the marina for the catch of the day as local fisherman set up shop, the fish does not get fresher than this. Next we’ll walk through town as we food shop for fresh vegetables, bread and dessert of course!

11:00 am We’ll meet in terrazza at my mothers home where chef will prepare a traditional plate of pasta and local fish.  

Enjoy an afternoon walk, grab some gelato, enjoy a dip in the pool and rest up for a truly unforgettable week ahead experience!

7:00 pm

As the sun begins to set, we’ll meet for a traditional Sicilian aperitivo — think crisp local wines, refreshing spritzes, and small bites bursting with flavor — all enjoyed al fresco with sweeping views of the sea. From there, we’ll take a slow stroll along the marina promenade, where the charm of Castellammare truly comes alive. Lined with fishing boats, glowing lanterns, and the scent of salt in the air, this walk sets the perfect tone for our first evening together.

We’ll end the night with a delicious welcome dinner at one of my favorite local spots — a place known for its fresh fish and warm hospitality. Expect a relaxed yet refined meal full of traditional Sicilian flavors!

Day 2

Immerse yourself in the heart of Sicilian tradition with a unique day at a Baglio in the Sicilian countryside , where you can enjoy an exquisite olive oil tasting and an immersive pasta-making class.This charming estate, rich with history and surrounded by stunning landscapes, offers the perfect setting for a day of culinary delight and cultural immersion.

10:00 am - Head to a rustic "Baglio" nestled in the town of Balestrate. Embark on this journey of Sicilian tradition as the owner takes you through her families ulivetto(olive grove) lined with lush, hundred year old olive trees. Learn about the meticulous process of cultivating and harvesting olives, a tradition that has been perfected over generations and savor the Essence of Sicily as you taste the “liquid gold”. Following the olive oil tasting, dive into a hands-on pasta-making class with Daniella. Sicilian cuisine is renowned for its simplicity and flavor, and this class offers you the chance to learn the secrets behind creating perfect pasta from scratch as she shares her families traditions in her families “baglio”.

5 pm - We will head to the quaint town of Borgo Parini known for its charming architecture, and colorful architecture.

6:30 pm We will head to terrasini for one of the most breathtaking sunsets complete with aperitivo and dinner to follow

Day 3

10:00 am- Embark on a captivating day tour to Segesta, where ancient history and breathtaking landscapes await. Discover the majestic Doric temple and the grand amphitheater, marvels of classical architecture set against the stunning backdrop of rolling hills and serene countryside. Let the echoes of ancient civilizations guide you through this archaeological treasure, offering a profound connection to Sicily’s storied past.

12:30 PM – A Walk Through Silence at Il Cretto di Burri

After exploring the grandeur of Segesta, we’ll journey into a different kind of history — one that is quiet, powerful, and deeply moving. At Il Cretto di Burri, experience contemporary art fused with memory and loss. This monumental white labyrinth, created by artist Alberto Burri, blankets the ruins of Gibellina — a town destroyed by the 1968 earthquake — preserving its streets in a striking and symbolic way. As we walk through its silent corridors, we honor the resilience of the Sicilian people and witness how beauty can rise from devastation.

2:00 PM – Our path then leads us to Partanna, a charming town nestled in the Belice Valley, where we’ll enjoy a slow lunch featuring regional specialties and local wines. Expect bold flavors rooted in the land — from handmade pastas to seasonal vegetables and robust olive oil pressed just miles away. Here, in a setting untouched by time, we’ll dine like locals and savor the authenticity that defines the Sicilian table.

8:00 pm Join me for dinner at another of my favorite restaurants perched amid olive groves and ancient stone walls, La Tavernetta offers a magical dining experience as evening falls over the Zingaro cliffs in Scopello.

Day 4

9:00 am - Meet at the marina and get ready to set sail along the stunning coast of Sicily and explore the pristine beauty of Riserva dello Zingaro, where crystal-clear waters, hidden coves, and breathtaking landscapes await!

1:30 - Lunch at a local landmark right at the marina

Rest up 

5:00 - Head to the town of Marsala to savor the magic of a Sicilian sunset with an aperitivo by Marsala's picturesque salt flats, where the beauty of the landscape and the flavors of the region come together for a truly enchanting experience. Dinner to follow in the historic center city known for Marsala Wine

10:00 AM – Today we head to Sicily’s vibrant capital—Palermo, a city where centuries of culture, architecture, and flavor collide in the most captivating way.

Our journey begins in the Centro Storico, Palermo’s historic heart, where every corner tells a story. Stroll down Via Maqueda, a lively pedestrian street lined with elegant buildings, artisan shops, and the unmistakable buzz of city life.

Pause at Quattro Canti, the theatrical crossroads of Palermo. This stunning Baroque square marks the meeting point of the city’s four ancient quarters and is one of the most photographed spots in all of Sicily.

Next, we’ll dive into the sensory overload of Mercato di Ballarò—one of the oldest and most energetic markets in Palermo. Here, among the vibrant stalls and echoing voices of vendors, you’ll sample traditional Sicilian street food: think panelle, arancine, sfincione, and fresh seasonal delights.

Our walk continues to La Chiesa di Santa Caterina, a stunning Baroque church tucked behind the market chaos. But here’s the hidden gem, nestled inside the cloister..you';; have to wait and see!

1:30 PM – Sicilian Street Food Lunch

We’ll keep things authentic and casual with lunch at one of Palermo’s top street food spots or trattorias, depending on the vibe of the day. Expect bold flavors, no frills, and a true taste of Sicilian daily life.

4:00 PM – Rooftop Aperitivo & City Views

We’ll end our Palermo adventure on a high note—literally—with an aperitivo overlooking Teatro Politeama. Sip a cool glass of wine or a Sicilian spritz as you take in panoramic views of the city’s rooftops, domes, and distant sea. It’s the perfect moment to unwind and reflect on the layers of history and flavor you’ve just experienced.

6:30 PM – Return to Castellammare for Pizza Under the Stars

As the city begins to glow in the golden hour, we’ll head back to Castellammare. The day concludes with a cozy traditional pizza dinner, where the dough is light, the toppings are local, and the company is perfetta.

Day 7

It’s not goodbye, it’s Ciao for now! - Hope to see everyone back on the island for an east coast tour in 2026!

Not quite ready to leave?

I'd be happy to help curate the remainder of your trip!