10 Best Sicily Multiday Tours in September 2026

Private Tour of Sicily from Palermo - September 2026

4.8

(4 reviews )

Trip customizable

Best price guaranteed

This is our first private tour and I must say it met all our expectations. Our driver/guide Carlo took very good care of us, told us informative and amusing stories along the way and took us to wonderful restaurants. He made sure all our needs our taken cared of. In Sicily especially I think the private tour is a big advantage as there are many places where only small vehicles can go through. We made the right decision in choosing this tour.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

20-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Sici

Palermo, Catania, Taormina, Sicily, Agrigento, Marsala, Monreale

Duration8 days

From

USD 3,095

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Walking the Highlights of Western Sicily Walk - September 2026

(1 review )

No booking fees

Best price guaranteed

This was a wonderful break. You stay at a number of very beautiful places: Scapello, Marettimo and San Vito La Capo. The walking is enjoyable but not too challenging. There are many opportunities to enjoy the food and culture of this part of Sicily; for example the town of Erice and the ancient site of Segasta. We also had a chance to spend an evening in Trapani and i would really recommend this too. I hadnt done self-guided walking before but really enjoyed it. We went in April and the weather was super. Not too hot so perfect for walking and little rain.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Sicily, Marettimo, Punta Libeccio

Duration8 days

From

USD 1,940

USD 1,882

Saving

USD 58

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Sicily - Magna Via Francigena - September 2026

4.7

(12 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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Self-Guided Cycling through Baroque Sicily - September 2026

No booking fees

Best price guaranteed

Your journey takes you along a mix of inland and coastal routes, starting amidst the Baroque splendour of Ragusa and Modica and ending in stunning Siracusa on the east coast. You'll cycle through lush valleys filled with olive trees, almond groves, vineyards and citrus orchards and patchwork puzzles of dry-stone-wall farms, as you cycle between UNESCO World Heritage Sites rebuilt in the typical late Baroque style after the famous 1693 earthquake. You'll take in plenty of Inspector Montalbano country - a treat for fans of the fictional detective series - including Scicli with its atmospheric streets and hilltop mausoleum as well as the charming fishing villages of Punta Secca and Sampieri. Following the scenic Mediterranean Route cycleway you'll head towards the sea, taking in sublime coastline, punctuated by golden sandy beaches and picturesque fishing villages such as Portopalo di Capo Passero and pretty Marzamemi with its Arab history. After passing through Nero D'Avola wine country your holiday finishes in beautiful Siracusa, an ancient Greek city whose 'historical heart' is the island of Ortigia, accessed by a bridge from the mainland. Ortigia's grand squares, narrow medieval streets and romantic palaces and castles are a delight to behold.

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Villa, Resort

Age Range

13-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Modica, Marina

Syracuse, Sicily, Modica, Marina Di Modica, Portopalo Di Capo Passero, Noto

Duration9 days

From

USD 2,735

USD 2,653

Saving

USD 82

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All Sicily Tours in September 2026

4 Trips in Sicily during September 2026 with 17 Reviews

Get a customized trip to Sicily in September 2026

4 Trips in Sicily during September 2026 with 17 Reviews

Private Tour of Sicily from Palermo - September 2026

Walking the Highlights of Western Sicily Walk - September 2026

Sicily - Magna Via Francigena - September 2026

Self-Guided Cycling through Baroque Sicily - September 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 September 2026

4 Trips in Sicily during September 2026 with 17 Reviews

Get a customized trip to Sicily in September 2026

4 Trips in Sicily during September 2026 with 17 Reviews

Private Tour of Sicily from Palermo - September 2026

Walking the Highlights of Western Sicily Walk - September 2026

Sicily - Magna Via Francigena - September 2026

Self-Guided Cycling through Baroque Sicily - September 2026