What gives Sicily its magnetic pull? Sicily captivates everyone with a unique blend of ancient wonders, sun drenched coastlines, centuries old traditions, and flavors found nowhere else in Italy. Greek temples rise above sea cliffs, Roman villas stand steps away from open- air markets glowing with exotic scents and color, and baroque towns hum with a mix of tradition and modern daily life.

From volcanic landscapes to sparkling sea coves, from historic cathedrals to family-run kitchens, circling the entire island lets us experience Sicily’s past and present in one unforgettable sweep and each day promises to reveal another layer of Sicily’s soulful charm – Sicily is a special kind of Italy.

Days & Experiences

September 25 • Friday • Day 1: Taormina Arrival & Sunset Over the Greek Theater

Land on the mythical island of Sicily and a driver will pick you up and bring you to the town of Taormina, the jewel of the Ionian coast. Our chosen accommodations for the first 4 days is a very centrally located private complex of individual apartments with full kitchens and living areas – your chance to realty settle in and feel like a local. Unpack, shake off the jet lag and wander Taormina’s pedestrian friendly, easy to navigate, boutique lined streets alive with espresso, gelato and the friendly chatter of Italian life. Late this afternoon we’ll gather for a Benvenuti aperitivo. Then, in the good company of our professional guide Elfi, we’ll visit the Greek Amphitheater to hear ancient stories while the day fades to a rosy light. Our welcome dinner overlooks the sparkling sea - raise a glass of Nero D’Avola and toast to our wonderful adventure ahead. (D)

Saturday • Day 2: Charming Castelmola & Isola Bella Boating

It’s easy to rise early when we have so much to do (and we’re probably still on US time!). A very short ride takes us up to Castelmola village with a quick stop along the way for the Madonna in the Rock, a unique cliff side chapel set inside a rocky cave. Hilltop Castelmola is known for almond wine, sweeping views of Taormina, the Mt. Etna volcano and the endless coastline far below. Then we’ll head down to the sea and Mazzaro’ for a waterfront lunch facing the splendid little island of Isola Bella before boarding our private boat. Glide past hidden coves, relax on deck or jump into the turquoise sea - floaties and snorkeling gear provided. After returning to Taormina the rest of the afternoon and evening are yours to relax or explore. Saturday evenings in Taormina sing. (L)

Sunday • Day 3: Siracusa History & Ortygia Island

A drive south brings us to Siracusa to explore its remarkable Greek history at the Archaeological Park, where the Greek theater and the mysterious Ear of Dionysius echo with stories. We’ll stroll over to the enchanting island of Ortigia to admire the Duomo and baroque streets before our group lunch on a sunlit terrace. Enjoy the rest of the afternoon exploring at your own pace before we return to Taormina for a free evening. (L)

Monday • Day 4: Free Day & The Heart of Sicilian Cooking

A day to savor at your own pace. Wander boutiques or take the cable car back down to Isola Bella’s beaches. Later this evening we’ll join Chef Massimo in his home, immerse ourselves in a hands-on cooking class and learn the cultural secrets and significance behind Sicilian flavors – fresh pastas, fragrant sauces, fresh seafood and sweet cannoli. Enjoy the delicious fruits of our labor over a leisurely dinner. (D)

Tuesday • Day 5: Roman Mosaics & Greek Temples

We bid our Taormina “home” arrivederci and begin circling the island. Our first stop is inland, at the town of Piazza Armerina – you can enjoy the park area or come inside to marvel at the 4th century AD, luxurious Villa Romana del Casale – rooms of intricate, lively colorful mosaic that will take your breath away. We continue to Agrigento, to meet our professional guide Michelle who helps us understand the immense importance of the Greek Valley of the Temples. As the sun begins to set, we check in to our elegant Agrigento farmhouse surrounded by olive trees, with temple views in the background. A lovely dinner awaits. (D)

Wednesday • Day 6: Coastal Marsala Salt Basins & hilltop Medieval Erice

A brief stop at the sugar-white cliffs of Scala dei Turchi, where soft limestone steps tumble into the sea, before heading further west. In Marsala, we explore the windmills and ancient, shimmering coastal salt basins with salt cultivation methods created by the Phoenicians still in use today. After a short detour for the tiny museum and lunch on the water we’ll continue to medieval Erice, a hilltop village with a tangle of charming cobblestone streets, sweeping views over the western coastline and one very special sweet pastry shop we never skip! This evening we check into an elegantly rebuilt 16th century cloister with a stunning roof bar terrace overlooking the gulf and the setting over the sea. (B, L)

Thursday • Day 7: Free to follow your heart!

Enjoy a completely free day in quaint Trapani. Step out of our luxury hotel and you’re already in the very heart of the historic center – San Lorenzo Cathedral, the Church of Purgatory, the clock tower and lively open air market. Explore at your own pace, maybe walk down to the piers for the daily fish market action. Tonight we’ll meet up again to share our adventures dine on main street under the stars. (B, D)

Friday • Day 8: Ferry Ride to Paradise, Favignana Island

A day at sea! We ferry over to the island of Favignana, where turquoise waters, fishermen and their sun-drenched harbor town welcomes us. Join me for an easy e-bike ride around the island – quiet streets, hidden beaches and a dip into crystal clear waters. Or explore the small harbor town on your own, visit small shops of capers and tuna, browse boutiques with the late summer linen, or stop by the Cannery Museum on your own. Either way we’ll all meet up in the same tiny sunny piazza, lunching on freshly caught fish letting the relaxed pace of this ancient island’s life wash over us. We’ll return to Trapani for your free evening. (B)

Saturday • Day 9: Monreale Mosaics & Palermo Vibrancy

We leave Trapani and head north to Monreale to stand in utter awe of its cathedral — massive and marvelous — dazzling mosaic images, each a golden story shimmering in morning light. Free time to explore and lunch in town before we continue to Palermo. Check in is at a 4 star Grand Hotel in the very heart of this bustling city, surrounded by intricate historical churches and lively piazzas pulsing with Saturday night energy. After a short professionally led walking tour with sweet Gabriella, to just a few of Palermo’s iconic spots, we settle in for dinner at a rooftop restaurant above the crowds. (B, D)

Sunday • Day 10: Cefalù’s Coastal Charm & Soaking in the last of La Dolce Vita

Our final carefree day is spent relaxing in Cefalu, a sweet beachfront town with a dramatic backdrop. We’ll visit the town’s central Norman cathedral together before you each wander off down winding streets lined with cafes and more artisan shops. If you’re feeling adventurous you can climb up the Rocca Fortress for the most panoramic views of the sparkling Tyrrhenian Sea. Back in Palermo later tonight we’ll gather for our last arrivederci dinner together – always a bit bittersweet! (B, D)

October 5th • Monday • Day 11 - Departure

Pack our bags and check out. We’ll assist with transfers to Palermo airport. Carry home new memories of Sicily’s warmth – the people, its golden sun, fragrant markets and timeless towns. Buon Viaggio! You may head straight home OR join me for a week of relaxation in PERFECT PUGLIA! Our Puglia “Hub & Spoke” week (unpack just once!) begins on the Tuesday, 6 October!