10 Best Sicily Multiday Tours in October 2026

Classical Sicily - October 2026

4.6

(17 reviews )

No booking fees

Best price guaranteed

We were lucky with the weather and countryside. Apparently the green will go very shortly so this was an excellent time to choose. The route up Etna proved easier than expected. Our guide was very knowledgeable and put much time and effort into giving us information about the island.Well organised !

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Syracusa, Trap

Syracuse, Sicily, Syracusa, Trapani, Palermo, Giardini Naxos, Taormina

Duration8 days

From

USD 2,830

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Ancient Sicily - October 2026

4.7

(17 reviews )

No booking fees

Best price guaranteed

You really do need two weeks to cicumnavigate Sicily and see things properly. Any shorter and you'll get just a couple highlights or get very rushed from place to place. This tour had good pace, gave sufficient time in major sites (Syracuse, Agrigento, Palermo, Villa del Casale) and included gems like Morgantina, Mozia Island, and Enna. Antonio is an exceptional wealth of information, its obvious he has a professional background in Sicilian history. The level of historical, cultural and architectural background information was tremendous, helped greatly to put things in context and understand the flow and changes absorbed by this island that resulted in what we were seeing.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Syracusa, Pale

Syracuse, Sicily, Syracusa, Palermo, Giardini Naxos, Mount Etna, Taormina, Piazza Amerina, Villa Romana Del Casale, Agrigento, Marsala, Mozia Island

Duration15 days

From

USD 4,780

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Best of Sicily - October 2026

(1 review )

Trip customizable

Best price guaranteed

Venture on a transformative 10-day odyssey through the enchanting landscapes of Sicily, immersing yourself in the authentic tapestry of Italian life. Indulge your senses in a symphony of flavors, from the finest local olive oils to exquisite wines and succulent fruits harvested from ancient regal estates. Trace the footsteps of proud empires as you wander amidst the haunting ruins that whisper tales of a bygone era. Ascend to hilltop towns, where time seems to stand still, and lose yourself in the surreal beauty of Mount Etna's lunar-like lava fields. This journey promises not just a vacation, but a collection of cherished memories

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Catania

Campania, Sicily, Lazio, Catania, Taormina, Agrigento, Palermo

Duration10 days

From

USD 2,475

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Sicilian Secrets - October 2026

Trip customizable

Best price guaranteed

Immerse yourself in the island's rich tapestry of history, from renowned archaeological sites to hidden gems nestled within picturesque towns. Delve into the heart of Sicilian culture, savoring its world-renowned cuisine, and wander through the labyrinthine streets where tradition meets modernity. Experience the warmth and authenticity of local life, allowing you to truly absorb the essence of this Mediterranean paradise. By the end, you'll carry with you the sensation of having lived a lifetime on this serene island

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Catania

Campania, Sicily, Lazio, Catania, Agrigento, Palermo

Duration6 days

From

USD 1,422

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Splendours of Sicily - October 2026

Trip customizable

Best price guaranteed

Stand in awe of the resplendent baroque architecture and UNESCO-designated marvels, each a testament to Sicily's storied past. Immerse yourself in the vibrant local culture, embracing the genuine warmth and enchanting allure of this tranquil Mediterranean haven. Revel in the island's diverse offerings, from its captivating natural landscapes to its profound historical legacy, its culturally rich tapestry, and its gastronomic delights. Indeed, Sicily is a tapestry woven with threads of natural beauty, ancient marvels, vibrant culture, and exquisite cuisine, promising an unforgettable adventure

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Catania, Campania, Sicily, Agrig

Catania, Campania, Sicily, Agrigento, Palermo

Duration8 days

From

USD 1,607

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Sensational Sicily - October 2026

Trip customizable

Best price guaranteed

Allow your senses to be enraptured by the breathtaking sceneries that unfold before you. From the rugged coastline to the serene countryside, Sicily's beauty knows no bounds. Indulge your palate with an array of traditional delicacies, each bite a tribute to Sicily's distinctive culinary heritage. From mouthwatering street food to sumptuous feasts, every meal will be a culinary adventure in itself. Traverse picturesque hill towns and UNESCO-listed cities, each one a living testament to the diverse ancient works of art and archaeological wonders that have shaped this island's history

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Palermo, Catania, Campania, Sici

Palermo, Catania, Campania, Sicily, Agrigento

Duration10 days

From

USD 2,055

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Sicilian Fantasy: Small Group Tour - October 2026

Trip customizable

Best price guaranteed

Journey across the Mediterranean's largest island to sample local olive oils and citrus fruits from ancient royal towns, stand among the ruins of proud empires, and venture across Mount Etna’s otherworldly lava fields. Experience a land where medieval villages cling to mountainsides and twisting lanes invite you to stroll down unexpected paths. There’s nothing like your first taste of Sicily—just pair a local dessert wine with a fresh coastal breeze, and you’ll understand how life is truly meant to be savoured

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Palermo, Taormina, Agrigento, Sicily

Duration7 days

From

USD 1,778

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Best of Sicily (Small Group Tour) - October 2026

(1 review )

Trip customizable

Best price guaranteed

Everything we expected and more. Everything was perfecto.

Food toursCity sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Syra

Palermo, Catania, Taormina, Syracuse, Sicily, Mt Etna, Noto, Island Of Ortigia, Agrigento

Duration8 days

From

USD 4,690

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Best of Italy - October 2026

(1 review )

Trip customizable

Best price guaranteed

Christina organized a fantastic first class itinerary for a 28 day tour of Italy by my wife and me. She was very personable and generous with her time and very knowledgeable of the areas we visited. The trip included incredible private tours with top notch guides and smooth transfers all the way. Any minor glitches were handled promptly and professionally. It was a wonderful experience and we look forward to working with her again in the future.

Culture shows and excursions

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Palermo

Rome, Florence, Venice, Palermo, Agrigento, Sicily, Taormina, Sorrento

Duration17 days

From

USD 5,051

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All Sicily Tours in October 2026

9 Trips in Sicily during October 2026 with 36 Reviews

Get a customized trip to Sicily in October 2026

Classical Sicily - October 2026

Ancient Sicily - October 2026

Best of Sicily - October 2026

Sicilian Secrets - October 2026

Splendours of Sicily - October 2026

Sensational Sicily - October 2026

Sicilian Fantasy: Small Group Tour - October 2026

Best of Sicily (Small Group Tour) - October 2026

Best of Italy - October 2026

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Sicily Tours in October 2026

9 Trips in Sicily during October 2026 with 36 Reviews

Get a customized trip to Sicily in October 2026