Sicily in Depth - Small Group - Insight Tour
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Insight Guided Tour

Sicily in Depth - Small Group

9 Days 15 Departures
From $4,975 per person

Tour Overview

See every slice of Sicily during this 9-day guided tour. Take off to Paradise Quarry in Syracuse with a Local Expert to see the Ear of Dionysius, an ear-shaped limestone grotto where voices may echo up to 16 times. At Casa Nepeta, stroll organic crops before tasting an artisanal bitter infused with Sicilian botanicals. Visit the Palatine Chapel, travel to the salt pans and windmills on the western coast and taste Marsala wine in its hometown. Finally, in Taormina, join a Local Expert at the cliffside Greek theater, with views towards Mount Etna, the island’s active Strato volcano.

Tour Summary

Duration9 Days / 8 Nights
OperatorInsight
Departures15 in 2027
Starting From$4,975 pp

Tour Route

Map of your 9-day journey

Sicily in Depth - Small Group route map

Day-by-Day Itinerary

9 days through your journey

Day 1

Welcome to Palermo

Relax and settle in before meeting your Travel Director and small group for dinner at a local restaurant. It’s the perfect chance to connect with your fellow travelers as you begin your journey through Sicily.
Day 2

Palermo & the Golden Age of the Normans

Trace Palermo’s layered history on a walking tour that leads into the 12th-century Palatine Chapel, explored in the company of a Local Expert. The afternoon opens into unhurried time in and around Palermo Cathedral, where shifting architectural styles reveal the city’s changing story. As evening settles, join your small group for a relaxed Dine-Around, sampling the dishes locals favor and the way they like to enjoy them.
Day 3

Trapani and Marsala

Nestled along its crescent-shaped coastline, Trapani sits close to the Mediterranean Sea. You’ll discover the age-old tradition of salt production on a MAKE TRAVEL MATTER® Experience, visiting the colorful salt pans and an ancient stone windmill where seawater settles into clear salt crystals. Then continue to Marsala and savor an exclusive tasting at a local winery with your group - enjoying the town’s renowned wine in quiet, sunlit surroundings.
Day 4

Explore the Valley of the Temples

Journey along the southern coast of Sicily towards Agrigento, where the Valley of the Temples unfolds across a ridge above the sea. Walk the site with a Local Expert, taking in how this UNESCO-recognized site remains as some of the finest expressions of ancient Greek architecture. Marvel at the Temple of Concordia and the cliff-top Temple of Juno, each carrying centuries of stories in their columns and outlook. Afterwards, gather back at the hotel for dinner with the group, sharing reflections on the day’s unforgettable discoveries.
Day 5

Discover Villa Romana del Casale and Ragusa

Today, you’ll travel inland to the Villa Romana del Casale, a luxurious UNESCO World Heritage Site, known for mosaics that reflect the scale and skill of Roman craftsmanship. Continue to Ragusa and follow a Local Expert through the narrow alleyways of Ragusa Ibla, a town shaped by Bronze Age roots and early Sicel tribe settlements, who gave their name to Sicily. Admire the area’s Sicilian Baroque architecture before a Farm-to-Table dinner that brings the small group together over local flavors.
Day 6

Modica, Noto and Casa Nepeta

Begin your day in Modica, a town rebuilt after the 17th-century earthquake and known for its chocolate-making tradition. At an artisanal workshop, discover techniques rooted in older Mediterranean methods and how local craft shapes daily life. Later, enjoy a short drive to the UNESCO World Heritage city of Noto, where Baroque palaces and honey-colored streets set the scene for time at leisure. Choose a local spot for lunch at your own pace before completing the day with an early aperitivo at Casa Nepeta, a sensory botanical journey among aromatic herbs followed by a tasting of Sicily’s authentic artisanal bitters.
Day 7

Ancient Syracuse

Choose your way to discover Syracuse today. You can opt for sightseeing with your Local Expert at Syracuse’s Paradise Quarry - home to the unique Ear of Dionysius, an ear-shaped grotto with remarkable acoustics - before visiting the Greek theater. Alternatively, you can explore the Old City on the island of Ortigia, a labyrinth of narrow streets lined with palaces. This historic area is where the famed mathematician Archimedes ran through the streets, exclaiming 'Eureka!' Continue your journey along Sicily’s Ionian Riviera to the charming resort of Giardini Naxos or Marina Forza d'Agrò (departure dependent).
Day 8

Taormina and the Dawn Coast of Europe

After breakfast, consider an optional journey through the vineyards towards Mount Etna, the largest active volcano in Europe. Next, you’ll continue to Taormina, perched on Monte Tauro with views of the Ionian Sea and Etna. With a Local Expert, visit the ancient Greek theater, set on a cliff and open to the sky, and even see Etna through its broken arches. Wander along Corso Umberto and take in the outlook from Piazza IX Aprile. Later, gather for dinner at a local restaurant, sharing Sicilian dishes and wines with the group.
Day 9

Depart Catania

Your time in Sicily comes to an end as you transfer to the airport. Take in steady views of Mount Etna - a final glimpse of the volcanic landscape that has shaped the journey.

Departure Dates & Pricing

15 departures available

Departure DateEnd DateStatusPrice Per Person
Apr 18, 2027 Apr 26, 2027 Available $4,975per person Get Quote
May 2, 2027 May 10, 2027 Available $5,025per person Get Quote
May 16, 2027 May 24, 2027 Available $5,025per person Get Quote
May 30, 2027 Jun 7, 2027 Available $5,050per person Get Quote
Jun 13, 2027 Jun 21, 2027 Available $5,095per person Get Quote
Jun 27, 2027 Jul 5, 2027 Available $5,150per person Get Quote
Jul 11, 2027 Jul 19, 2027 Available $5,095per person Get Quote
Jul 25, 2027 Aug 2, 2027 Available $5,095per person Get Quote
Aug 8, 2027 Aug 16, 2027 Available $5,095per person Get Quote
Aug 22, 2027 Aug 30, 2027 Available $5,095per person Get Quote
Sep 5, 2027 Sep 13, 2027 Available $5,075per person Get Quote
Sep 19, 2027 Sep 27, 2027 Available $5,075per person Get Quote
Oct 3, 2027 Oct 11, 2027 Available $5,075per person Get Quote
Oct 17, 2027 Oct 25, 2027 Available $5,075per person Get Quote
Oct 31, 2027 Nov 8, 2027 Available $4,975per person Get Quote

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