10 Best Sicily Multiday Tours in October 2025

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Highlights of Sicily - October 2025

4.6

(78 reviews )

No booking fees

Best price guaranteed

This was a fabulous trip, with a well thought-out itinerary enhanced by a wonderful guide, a great group of people, delicious Italian food and beautiful weather.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Catania, Taormina, Sicily, Viagr

Catania, Taormina, Sicily, Viagrande, Noto, Agrigento, Trapani, Palermo

13% OFF TODAY

Duration9 days

From

USD 2,998

USD 2,619

Saving

USD 379

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Small Group Tour of Sicily: Highlights - October 2025

4.8

(6 reviews )

Trip customizable

Best price guaranteed

We had a wonderful day together with Alfredo. Alfredo was the best guide ever!! He was excellent and was so fluent in english, he told us many interesting stories. He is an expert in Sicilian history and culture. he was both singing and dancing for us-we enjoyed it a lot. But most of all, he was such a service minded and understanding person. For example we were come minutes late in the morning and then we enjoyed the tour at the winery so much that we caused a delay in Alfredo's schedule but he was so humble and understanding. We highly recommend it to everyone travelling to Sicily.

Food toursWine tasting tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Palermo, Catania, Sicily, Taormi

Palermo, Catania, Sicily, Taormina, Syracuse

Duration8 days

From

USD 2,936

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Small Group Food & Wine Tour of Sicily - October 2025

4.9

(26 reviews )

Trip customizable

Best price guaranteed

Loved this small group tour. It was a perfect balance of organized activities and free time. All the hotels were beautiful and were in great locations for walking to all the busy areas. Our guides were knowledgeable and easy going. Would highly recommend to anyone.

Food toursWine tasting tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

1-89 yrs

Operated in

english

Destinations

Palermo, Catania, Sicily, Taormi

Palermo, Catania, Sicily, Taormina, Syracuse

Duration8 days

From

USD 2,936

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Sicily - Magna Via Francigena - October 2025

4.6

(18 reviews )

No booking fees

Best price guaranteed

Walking the Magna Via Francigena was challenging - many steep hills, mud and rain. They organised everything else so that all we had to do was walk, making the walk much easier. The scenery was stunning.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Palermo, Sicily, Corleone, Prizz

Palermo, Sicily, Corleone, Prizzi, Cammarata, Sutera, Racalmuto, Agrigento

Duration8 days

From

USD 1,250

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Sicily Grand Tour - October 2025

4.4

(12 reviews )

No booking fees

Best price guaranteed

The 15 day tour of Sicily was absolutely fantastic. The best tour guide ever, her name is Milena. A wonderful driver Alessandro. I felt that it was a pretty comprehensive tour of Sicily seeing all the highlights plus more. Fabulous food in restaurants where we ere taken by Milena. Verdict EXCELLENT.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Catania, Taormina, Palermo, Cefa

Catania, Taormina, Palermo, Cefalu, Mount Etna, Syracuse, Sicily, Modica, Piazza Armerina, Trapani

Duration15 days

From

USD 4,800

USD 4,656

Saving

USD 144

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Sicily & Amalfi Coast Escape - October 2025

Trip customizable

Best price guaranteed

A trip from Sorrento to Sicily promises a journey filled with scenic beauty, rich history, and vibrant culture. Explore the wonders of the Amalfi Coast, and Sicily on an Italian adventure from Rome! Walk the ruins of Pompeii, soak up the atmosphere along the Sorrentine Coast, and sun-bleached Capri. Discover the Mediterranean island of Sicily through its unique architecture, charming villages, and traditional cuisine. Stroll through endless stretches of stunning beaches and explore the majestic ancient ruins of past empires!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Palermo, Rome, Taormina, Agrigento, Sicily

Duration11 days

From

USD 3,101

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Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - October 2025

No booking fees

Best price guaranteed

Journey through a crossroads of civilizations in Sicily and on to the spectacular coastlines of Southern Italy. Uncover Sicily’s capital Palermo and its Moorish and Norman influences. Explore Agrigento’s ancient Valley of the Temples and the Ancient Roman mosaics of Piazza Armerina. Travel to the historic hilltop town of Taormina. Visit a local winery for a wine tasting and agriturismo dinner. Venture to the ancient cave dwellings of Sassi di Matera. Explore Sorrento and stunning Positano, the pearl of the Amalfi Coast. Walk in the footsteps of ancient Romans in the excavated Pompeii. Allow the unique culture to capture your heart and get a glimpse into an age-old heritage composed of ancient monuments and cultivated lands.

City sightseeing

Tour Type

Group Tour

Accommodation

Villa, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Palermo, Sicily

Rome, Sorrento, Palermo, Sicily, Agrigento, Giardini Naxos, Matera

6% OFF TODAY

Duration13 days

From

USD 3,949

USD 3,699

Saving

USD 250

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Sicilian Fantasy: Small Group Tour - October 2025

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 1,660

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Best of Italy - October 2025

(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 4,638

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All Sicily Tours in October 2025

9 Trips in Sicily during October 2025 with 141 Reviews

9 Trips in Sicily during October 2025 with 141 Reviews

Highlights of Sicily - October 2025

Small Group Tour of Sicily: Highlights - October 2025

Small Group Food & Wine Tour of Sicily - October 2025

Sicily - Magna Via Francigena - October 2025

Sicily Grand Tour - October 2025

Sicily & Amalfi Coast Escape - October 2025

Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - October 2025

Sicilian Fantasy: Small Group Tour - October 2025

Best of Italy - October 2025

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 2025

9 Trips in Sicily during October 2025 with 141 Reviews

9 Trips in Sicily during October 2025 with 141 Reviews