Sicily Tours in September 2027
Planning for a trip to Sicily during September? We offer 10+ tour packages to Sicily departing in September 2027 that have 190+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Sicily on your September holiday.
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Discover Sicily, the scenic Italian island forged over centuries by Phoenician, Greek, Roman, Arab, Norman and Spanish rulers. On this comprehensive adventure, we explore the very best bits, starting on the volcanic slopes of Mount Etna, before continuing to the towns of Syracuse, Agrigento, and Selinunte – all World Heritage sites. A day in Zingaro National Reserve offers magnificent views over the coast, while there’s also plenty of opportunities to discover the history and heritage of the biggest island in the Mediterranean.
9 days
From cannoli to arancini, Sicilian food is known across the planet, but this tour shows how varied and diverse the cuisine here really is. The various civilisations that have occupied the island over millennia have not only left an unparalleled cultural heritage, but also a culinary history that sets Sicily apart from mainland Italy. Sample the street food of Palermo in vibrant markets, practise hands-on cooking with local chefs in Erice, sip wines in Marsala and Etna, and indulge in gelatos while relaxing in baroque piazzas. Let food lead the way in this captivating journey through culinary and cultural highlights.
8 days
Sicily’s dazzling heritage takes center stage on the 15-day Sicily Grand Tour, crafted especially for seniors who appreciate culture-rich journeys at a comfortable pace. From Catania to Taormina, traverse a tapestry of destinations—Syracuse, Piazza Armerina, Trapani, and more—each brimming with history left by Phoenicians, Greeks, Romans, Byzantines, and beyond. Explore UNESCO sites, grand archaeological treasures, charming villages, and the island’s breathtaking landscapes, with time to delve into the famous mosaics of Piazza Armerina. The USP of this tour package is its comprehensive yet unhurried itinerary, ensuring seniors can fully absorb Sicily’s rich legacy and scenic beauty without feeling rushed.
15 days
Sicily comes alive on this spirited 8-day adventure, created especially for young adults hungry for authentic experiences. Start in Catania and journey to the hillside allure of Taormina, where you’ll join a cooking class and descend Mt. Etna’s volcanic slopes. Explore UNESCO sites, relax on pristine beaches, and wander Palermo’s vibrant streets, sampling some of Italy’s best food along the way. With all the logistics sorted—accommodation, meals, and transport—you’re free to savor every sight and flavor. The USP: a tour package that unlocks the real Sicily, blending hands-on activities with ancient heritage and culinary delights.
8 days
Sip wine on Mount Etna, stroll chic Taormina streets, and indulge in Modican chocolate—the Colours of Sicily tour brings the island’s vibrant palette to life over nine days. Designed for experienced travelers, this easy-paced mountains tour winds from Palermo to Catania, weaving through Marsala, colorful villages, and sunlit vineyards.
Every day blends natural beauty with rich local culture, from meeting friendly Sicilians to sampling regional treats. The standout feature of this tour package is its immersive approach, offering a true taste—both literal and metaphorical—of Sicily’s charm.
9 days
Sicily’s tapestry of history, cuisine, and natural beauty unfolds on this 8-day cultural tour, ideal for travelers who savor both ancient wonders and modern delights. Explore the remarkable Doric temples of Agrigento, the medieval streets of Erice, and the intricate mosaics at Villa Romana del Casale. Venture to the slopes of Etna, Europe’s largest active volcano, and lose yourself in the allure of Taormina, Sicily’s coastal jewel.
With a moderate activity rating, the trip blends guided walks with ample free time for gelato, arancini, and seaside relaxation. Extend your journey by combining with Malta and Gozo for a two-week island adventure.
The unique selling point is Sicily’s rich layering of Greek, Roman, and Byzantine history—few tours offer such a comprehensive immersion into the island’s diverse heritage, paired with its delectable food culture.
8 days
Step off the beaten path and discover Sicily’s wild western reaches with the "Walking the Highlights of Western Sicily Walk". This self-guided, 8-day trekking tour starts in the atmospheric village of Scopello and leads you through tranquil national parks, rugged coastlines, and the enigmatic islands of Marettimo and Sicily itself.
Tailored for experienced travelers who appreciate independence and discovery, the itinerary blends peaceful walks with cultural exploration: uncover ancient ruins, wander medieval churches, and delve into prehistoric caves. With accommodations, transport, and meals included, you’re free to immerse yourself in the region’s serenity and secrets.
The unique selling point of this tour is its access to some of Sicily’s most remote and untouched landscapes—ideal for those seeking both natural beauty and quiet cultural treasures on their walking holiday.
8 days
Unlock the mysteries of Sicily’s ancient past on the "Ancient Sicily" tour, a 15-day cultural and historic journey from Syracuse to Giardini Naxos. Guided by local expert Antonio Marretta, you’ll delve into iconic archaeological sites like the Valley of the Temples in Agrigento, the Roman mosaics of Villa Romana del Casale, and the atmospheric ruins of Syracusa. Alongside spectacular history, enjoy local cuisine, wine, and coastal relaxation. The unique advantage? An in-depth, expertly led exploration that combines UNESCO World Heritage sites, classic Sicilian fare, and the island’s stunning scenery for a truly comprehensive experience.
15 days
Uncover the treasures of Sicily with a private guided tour that’s perfect for experienced travelers seeking both culture and comfort. Your English-speaking driver-guide will lead you through iconic sites such as Taormina and Siracusa, revealing the island’s captivating blend of art and architecture.
Evenings are spent in hand-picked hotels that exude Sicilian charm and elegance, ensuring restful nights between explorations. Along the way, indulge in curated wine and food experiences—sampling local specialties and witnessing the craftsmanship behind Sicily’s renowned culinary scene.
The unique selling point of this tour package is its seamless combination of personalized guidance, cultural immersion, and epicurean delights, making it an exceptional journey for those who appreciate the finer things in travel.
8 days
Experience the best of Italy’s mainland and Sicily on this 13-day adventure crafted for young adults. Starting in Rome, you’ll journey to Naples—birthplace of pizza and gateway to Pompeii—then glide along the Amalfi Coast to the sun-drenched islands of Capri and Positano. The second half of the trip unveils Sicily’s legendary beaches, ancient ruins, and vibrant food scene, with Palermo providing a grand finale. With all accommodations, meals, and transport arranged, you can fully immerse in Italian culture and landscapes. The USP: a tour package that fuses Italy’s iconic cities, coastlines, and island treasures into a single, seamless journey.
13 days
See all Sicily September 2027 Tours
Discover Sicily, the scenic Italian island forged over centuries by Phoenician, Greek, Roman, Arab, Norman and Spanish rulers. On this comprehensive adventure, we explore the very best bits, starting on the volcanic slopes of Mount Etna, before continuing to the towns of Syracuse, Agrigento, and Selinunte – all World Heritage sites. A day in Zingaro National Reserve offers magnificent views over the coast, while there’s also plenty of opportunities to discover the history and heritage of the biggest island in the Mediterranean.
9 days
From cannoli to arancini, Sicilian food is known across the planet, but this tour shows how varied and diverse the cuisine here really is. The various civilisations that have occupied the island over millennia have not only left an unparalleled cultural heritage, but also a culinary history that sets Sicily apart from mainland Italy. Sample the street food of Palermo in vibrant markets, practise hands-on cooking with local chefs in Erice, sip wines in Marsala and Etna, and indulge in gelatos while relaxing in baroque piazzas. Let food lead the way in this captivating journey through culinary and cultural highlights.
8 days
Sicily’s dazzling heritage takes center stage on the 15-day Sicily Grand Tour, crafted especially for seniors who appreciate culture-rich journeys at a comfortable pace. From Catania to Taormina, traverse a tapestry of destinations—Syracuse, Piazza Armerina, Trapani, and more—each brimming with history left by Phoenicians, Greeks, Romans, Byzantines, and beyond. Explore UNESCO sites, grand archaeological treasures, charming villages, and the island’s breathtaking landscapes, with time to delve into the famous mosaics of Piazza Armerina. The USP of this tour package is its comprehensive yet unhurried itinerary, ensuring seniors can fully absorb Sicily’s rich legacy and scenic beauty without feeling rushed.
15 days
Sicily comes alive on this spirited 8-day adventure, created especially for young adults hungry for authentic experiences. Start in Catania and journey to the hillside allure of Taormina, where you’ll join a cooking class and descend Mt. Etna’s volcanic slopes. Explore UNESCO sites, relax on pristine beaches, and wander Palermo’s vibrant streets, sampling some of Italy’s best food along the way. With all the logistics sorted—accommodation, meals, and transport—you’re free to savor every sight and flavor. The USP: a tour package that unlocks the real Sicily, blending hands-on activities with ancient heritage and culinary delights.
8 days
Sip wine on Mount Etna, stroll chic Taormina streets, and indulge in Modican chocolate—the Colours of Sicily tour brings the island’s vibrant palette to life over nine days. Designed for experienced travelers, this easy-paced mountains tour winds from Palermo to Catania, weaving through Marsala, colorful villages, and sunlit vineyards.
Every day blends natural beauty with rich local culture, from meeting friendly Sicilians to sampling regional treats. The standout feature of this tour package is its immersive approach, offering a true taste—both literal and metaphorical—of Sicily’s charm.
9 days
Experience the best of Italy’s mainland and Sicily on this 13-day adventure crafted for young adults. Starting in Rome, you’ll journey to Naples—birthplace of pizza and gateway to Pompeii—then glide along the Amalfi Coast to the sun-drenched islands of Capri and Positano. The second half of the trip unveils Sicily’s legendary beaches, ancient ruins, and vibrant food scene, with Palermo providing a grand finale. With all accommodations, meals, and transport arranged, you can fully immerse in Italian culture and landscapes. The USP: a tour package that fuses Italy’s iconic cities, coastlines, and island treasures into a single, seamless journey.
13 days
See all Sicily September 2027 travel deals
Anne | Traveled in September
Fascinating tour with great variety of archaeological sites and Baroque architecture. Our guide, Antonio, was very informative and looked after us extremely well. The planning was excellent and the accommodation very comfortable and well sited.
Jason | Traveled in September
An in depth journey through Sicily's layered history and stunning terrain. From Phonecians to Greeks, Romans, Byzantines and Arabs, towns rose and fell leaving spectacular ruins. The tour picks up on the islands Norman heritage and later development of baroque architecture.
Isobel L. | Traveled in September
Sicily is an absolutely stunning destination - definitely recommend this trip for someone who has already seen the main cities in Italy and wants an easy way to get around the island. was an amazing tour manager who I wish I could have every trip and our driver was a legend too. The only two criticisms would be the night in Catania - it wasn’t really worth staying and it felt unsafe at times. An extra night in Taormina would be better. The second being that the hotel in Palermo was quite disgusting and dirty.
Anthea Magarey | Traveled in September
This was a wonderful discovery of the treasures of Sicily. Amazing ancient monuments dating back 300 to 2500 years, beautiful villages and seascapes, the barren landscape of Mt Etna, and great food everywhere.
Pat Natale | Traveled in September
Trip was excellent from beginning to end. Excellent itinerary and accommodations. Guides were very friendly and knowledgeable. Massimo and Graziana are extraordinary with their communication and availability. A pleasure to deal with persons like these! Highly recommend!
Sara Miller | Traveled in September
Well organized tour with plenty of down time to stroll and explore the towns. Graziana was wonderful in letting us know the scheduled events/times. The guides were very knowledgeable and enjoyable. Highly recommend this company. Loved Sicily!