Welcome to your free tour guide to Sicily!
This journey takes you from the sparkling Mediterranean coast with its UNESCO-recognized ancient ruins through charming medieval villages where Greeks, Romans, Arabs, and Normans have created a unique cultural tapestry, to the breathtaking Sicilian landscapes where volcanic majesty meets golden beaches. Sicily doesn’t try to impress, but we can’t help showing it to you!
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At Wingman, we’re your local friend, guiding you to authentic trattorie where Sicilians gather, and to peaceful lookout points perfect for enjoying a glass of local Nero d’Avola as the sun sets over the Tyrrhenian Sea.
We’ll walk with you from the impressive Valley of the Temples with its panoramic views across the countryside to the beautiful historic streets of Taormina, sharing Sicily’s special feeling—part sophisticated Mediterranean paradise, part rugged southern Italian island, and always wonderfully authentic. Let us show you beyond the postcard views.
Get ready! Our free tour guide takes you beyond Sicily’s postcard views.
Discover more than just Mount Etna and ancient ruins – follow us into the heart of the Mediterranean’s most culturally diverse island!
Discover Sicily Like a Local with Wingman.
Navigate the city’s hidden gems with our GPS-guided audio tours, taking you beyond the tourist spots to authentic local experiences.
Carved into a limestone canyon in Sicily’s interior lies one of Europe’s largest prehistoric burial sites, with over 5,000 rock-cut tombs dating back to 1200 BCE. The necropolis sits within a stunning nature reserve where the Anapo River has carved dramatic gorges, creating an atmospheric setting that feels worlds away from Sicily’s coastal attractions.
Local Guide Tip: Bring swimming gear in summer to enjoy the refreshing river pools near the Byzantine ruins of San Micidiario – follow the unmarked path behind the information center that descends to the valley floor, where you’ll find crystal-clear swimming holes surrounded by wildflowers and ancient history with rarely another soul in sight.
Coordinates: 37.1407° N, 15.0153° E
This spectacular canyon system features Sicily’s “Grand Canyon” – a 300-meter-deep limestone gorge with emerald pools connected by natural waterslides. Locals make the steep descent to swim in these pristine waters, while visitors often miss this inland treasure in favor of coastal beaches.
Local Guide Tip: The official path was damaged years ago, but locals still use the trail starting from the Belvedere di Avola Antica viewpoint – wear proper hiking shoes and bring plenty of water for the challenging climb back up, then reward yourself with a picnic of local cheese and fresh peaches from the small farm stand at the parking area.
Coordinates: 36.9778° N, 15.0958° E
This Arab-founded hilltown made headlines when it began selling €1 homes, but most visitors still overlook its authentic charm. With its labyrinth of saracenic streets, ancient underground Jewish quarters, and abandoned palazzos being carefully restored, Sambuca offers a glimpse into Sicily’s multicultural past without the tourist crowds.
Local Guide Tip: Visit Di Giovanna winery just outside town, where the family takes visitors through their high-altitude organic vineyards by jeep before offering tastings paired with local cheeses in their 200-year-old stone farmhouse.
Coordinates: 37.6478° N, 13.1144° E
At Wingman, we’re passionate about transforming your travel experiences from typical to tremendous.
Each city is a new chapter in your adventure book, filled with unique cultures, sights, and sounds for you.Â
Why stop at one? Explore our global network of destinations, from the romantic streets of Paris to the vibrant landscapes of Bangkok.
Dive into diverse cultures with our expertly crafted tours designed to enlighten and entertain.
Valley of the Temples, Agrigento – Visit at sunset when the ancient Greek temples glow golden and crowds thin out, creating the perfect atmosphere for photos without other tourists in your frame.
Mount Etna – Book a sunrise hiking tour to Europe’s most active volcano to witness the morning light casting shadows across the lunar-like landscape before day-trippers arrive.
Taormina’s Greek Theatre – Come for the views but stay for an evening concert or film screening during summer festivals when the ancient amphitheater becomes a spectacular venue under the stars.
Syracuse’s Ortygia Island – Skip the main restaurant streets and wander three blocks inland where locals eat at family-run trattorias like Apollonion, serving authentic Sicilian dishes at half the price.
Palermo’s Street Markets (Ballarò, Vucciria, Capo) – Go hungry and look for stalls where nonne (grandmothers) are cooking behind the scenes, as these serve the most authentic panelle and sfincione in the city.
Villa Romana del Casale – Arrive early (before 9am) to admire the world’s largest collection of Roman mosaics without the tour groups that flood this UNESCO site by midmorning.
Scala dei Turchi (Turkish Steps) – Visit this stunning white marl cliff in May or October when you can still swim in the clear Mediterranean waters without summer’s overwhelming crowds.
Cefalù’s Medieval Old Town – Climb the imposing La Rocca for sunrise views over the red-roofed town and coastline, then reward yourself with the best granita at Duomo’s small bar facing the cathedral.
Erice’s Medieval Village – Stay overnight in this mountain-top town to experience magical fog-wrapped mornings and empty cobblestone streets after day tourists leave on the last cable car down.
The Aeolian Islands – Instead of focusing only on famous Stromboli, take local ferries to quieter Salina where you can rent a scooter to discover secluded beaches and taste the island’s sweet Malvasia wine.
Ever dreamed of crafting your own tour, showcasing your favorite spots or hidden gems? With Wingman, it’s not just a possibility—it’s your next venture! Our platform empowers locals and travel enthusiasts alike to build personalized tours, add unique landmarks, and even earn money with every purchase made.
Turn your local knowledge into a lucrative opportunity. Whether you’re guiding visitors through bustling city streets, serene parks, or to the doorstep of the obscurest eateries, your insights are valuable. Each tour purchase puts money right back in your pocket.
By joining Wingman, you’re not just building tours; you’re joining a community of creative and passionate tour architects from around the world. Share ideas, get inspired, and expand your reach as you bring your unique perspective to travelers eager for authentic experiences.