10 Best Sicily Multiday Tours in September 2026

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Highlights of Sicily - September 2026

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

Duration9 days

From

USD 3,300

USD 3,201

Saving

USD 99

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Classical Sicily - September 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 - September 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 - September 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 2,482

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A Taste of Sicily - September 2026

Trip customizable

Best price guaranteed

Immerse your taste buds in a symphony of Sicilian treats, each bite a testament to the region's culinary prowess. Wander through coastal towns adorned with medieval castles, and let the ancient Greek ruins whisper their stories to you. Witness the sunsets that paint picture-perfect seaside villages in hues of gold and pink. Marvel at the commanding presence of towering volcanoes, and discover even more hidden gems along the way. This five-day escapade promises an unforgettable immersion into the heart of Sicily's unparalleled beauty and cultural richness

Food tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Palermo

Campania, Sicily, Lazio, Palermo, Catania

Duration5 days

From

USD 1,070

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Sicily Food & Wine - September 2026

4.7

(40 reviews )

No booking fees

Best price guaranteed

Sicily is a fascinating treasure trove of history and beauty. This trip allows you to experience the Sicilian way of life using food as a lure to explore its villages, towns and landscape as you move from one side of the island to the other.

Food tours

Tour Type

Small Group Tour

Accommodation

Lodge, Villa, Bungalow, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Palermo, Taormina, Marsala, Agri

Palermo, Taormina, Marsala, Agrigento, Sicily, Syracuse, Catania

Duration8 days

From

USD 3,525

USD 3,419

Saving

USD 106

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Sicilian Secrets - September 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 1,426

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Sicily & Aeolian Islands Discovery - September 2026

Trip customizable

Best price guaranteed

Embark on a journey that takes you from the mainland of Sicily to the enchanting Aeolian Islands. Set sail from Milazzo and let the beauty of this Mediterranean paradise unfold before your eyes. Immerse yourself in the rich history and breathtaking landscapes as you explore the captivating beaches and archaeological treasures from Palermo to Catania including the enchanting islands of Lipari, Panarea, and Stromboli. Indulge your senses with Sicily's culinary delights, and create memories that will last a lifetime in this remarkable corner of the world

Chill out

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Palermo

Campania, Sicily, Lazio, Palermo, Catania, Lipari, Taormina

Duration9 days

From

USD 2,425

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Super Sales

Sicily Grand Tour - September 2026

4.5

(13 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 6,150

USD 5,966

Saving

USD 185

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Sicily & Amalfi Coast Escape - September 2026

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 3,538

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13% OFF TODAY

Colours of Sicily - September 2026

4.7

(99 reviews )

No booking fees

Best price guaranteed

Your tour involves an intimate weaving of the Sicilian people and their lives and customs. We saw church celebrations ate special foods, saw volcanic activity, toured organic farms and gardens and much more!

MountainsLocal culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Palermo, Catania, Marsala, Sicil

Palermo, Catania, Marsala, Sicily, Ragusa, Syracuse, Taormina

13% OFF TODAY

Duration9 days

From

USD 2,275

USD 1,985

Saving

USD 291

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Splendours of Sicily - September 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 1,612

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Malta and Gozo Discovery + Classical Sicily - September 2026

4.8

(5 reviews )

No booking fees

Best price guaranteed

Althea was an exceptionally good tour leader in Malta. Placido in Sicily was fine. A thoroughly good introduction to both countries.

Active and outdoorFood tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Valletta, Sicily, Giardini Naxos

Valletta, Sicily, Giardini Naxos, Syracusa, Palermo, Taormina, Xaghra, Xwejni Bay Beach, Mdina

Duration16 days

From

USD 4,980

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Old World Sicily & Malta - September 2026

4.6

(28 reviews )

No booking fees

Best price guaranteed

I cannot think of one thing the whole trip was fantastic or tour guide Michela , was so fantastic. You truly felt that you were family. She explained everything told us what we expect ahead of time took care of everyone’s needs and still made it so much fun a bunch of us were in our 70s and upper 70s and did not feel that we couldn’t keep up with the tour because it was done so well I think one of the best vacations that we ever took

Walking tours

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Sliema, Taormina, Sicily, Ragusa

Duration12 days

From

USD 3,949

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25 Trips in Sicily during September 2026 with 391 Reviews

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All Sicily Tours in September 2026

25 Trips in Sicily during September 2026 with 391 Reviews

25 Trips in Sicily during September 2026 with 391 Reviews

Get a customized trip to Sicily in September 2026