10 Best Italy Multiday Tours in September 2026

Best of Sicily (Small Group Tour) - September 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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Iconic Rome and Amalfi - September 2026

Trip customizable

Best price guaranteed

Immense yourself on this captivating self-driven odyssey from Rome to Amalfi, traversing scenic routes, this journey unfolds amidst picturesque landscapes and historic marvels. Departing Rome's vibrant cityscape, the drive leads through charming villages and past ancient ruins, offering glimpses into Italy's rich heritage. As the road winds along the dramatic cliffs of the Amalfi Coast, the azure expanse of the Tyrrhenian Sea provides a breathtaking backdrop. Experience the charm and beauty of Amalfi, a coastal gem with colorful architecture, a storied cathedral and a relaxed atmosphere. Admire the stunning cliffs, azure waters and picturesque villages. Explore Iconic landmarks like Positano and Ravello which epitomize Mediterranean charm. This self-drive experience encapsulates the essence of Italy, blending cultural richness with natural beauty.

City sightseeing

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Amalfi Coast & Campania, Amalfi

Duration6 days

From

USD 734

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Sensational Sicily - September 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 2,072

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Palermo and Sicilian Baroque Self Drive - September 2026

Trip customizable

Best price guaranteed

About This Trip On this unforgettable self-drive tour through the heart of Sicily witness the architectural wonders, ancient temples, charming villages, stunning beaches and create an unparalleled experience. Start in Palermo and admire its historical charm. Admire the Palermo Cathedral and immerse yourself in the vibrant street life. Then visit Monreale to marvel at the intricate mosaics adorning its cathedral. Enjoy the relaxing atmosphere of Mondello Beach. Journey to Marsala Stagnone to witness the captivating salt pans. Continue to Erice, perched atop Monte San Giuliano and admire its medieval allure. Explore the archaeological site of Segesta, where the Doric temple stands as a testament to ancient history. Continue to Agrigento to witness the grandeur of the Valley of the Temples. Discover the Baroque beauty of Ragusa, wandering through its streets adorned with churches and palaces. Continuing to Modica and Noto, each boasting unique architectural marvels. Embark on an adventure to Mount Etna, the active volcano surrounded by diverse landscapes within Etna Park. Stroll through Taormina's charming streets, admiring Palazzo Corvaja and the Greco-Roman theatre. Conclude your journey in Palermo, soaking in its energetic ambiance and Baroque splendor. Perfect for those seeking immersive Italy vacations, this day-to-day self-drive itinerary offers a rich and varied experience, showcasing the historical, cultural, and natural treasures of each destination in Sicily.

Self-drive or vehicle rental

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Palermo, Mondello, Segesta, Ragu

Palermo, Mondello, Segesta, Ragusa, Noto, Taormina

Duration8 days

From

USD 997

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Scenic Sicily Self Drive - September 2026

Trip customizable

Best price guaranteed

Embark on an extraordinary self-drive tour and immerse yourself in the captivating wonders of Sicily. Your journey begins in Catania, where the fiery majesty of Mount Etna beckons. Witness the awe-inspiring spectacle of Europe's most active volcano, a true marvel of nature. Move on to Taormina, where ancient ruins meet breathtaking views of the Azure Ionian Sea. Delight in the charm of the ancient Greco-Roman Theater, a testament to Sicily's grand past. Syracuse awaits, a living museum boasting well-preserved Greek ruins and the quaint allure of Ortigia Island. The Baroque towns of Ragusa, Modica, and Noto will enchant you with their architectural splendor and tantalizing culinary delights. Journey to Agrigento and stand in awe before the legendary Valley of the Temples, a UNESCO World Heritage Site. Then, Palermo unfolds, revealing its architectural marvels and the breathtaking mosaics of Monreale Cathedral. Venture further to uncover the ancient secrets of Segesta's Greek temple and surrender to the serenity of San Vito Lo Capo's sun-kissed beaches and Scopello's coastal charm. Among many popular tours of Italy, Sicily is one of the highlights because its rich history, picturesque landscapes, and warm hospitality create an unparalleled experience, leaving your heart forever entwined with this magical island.

Self-drive or vehicle rental

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Palermo, Catania, Taormina, Syra

Palermo, Catania, Taormina, Syracuse, Noto, Agrigento, Monreale, Sicily

Duration8 days

From

USD 1,207

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15% OFF TODAY

Super Sales

Great Italian Cities - September 2026

4.8

(162 reviews )

No booking fees

Best price guaranteed

It was a beautiful, historic overview of the heart of Italy. Our guide , was fantastic, caring and knowledgeable.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Munich, Venice, Florence

15% OFF TODAY

Duration10 days

From

USD 2,875

USD 2,449

Saving

USD 426

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Rome by golf-cart private tour - September 2026

(4 reviews )

No booking fees

Best price guaranteed

We had a 7 hour private golf cart tour with Eduardo. He took us to see all the sites that we wanted to see. He brought us to unique places we would never of known about. Eduardo was so personable and knowledgeable . I highly recommend this tour!!

Sightseeing Tours

Tour Type

Private Tour

Age Range

1-99 yrs

Operated in

english, german, dutch, italian, spanish

Destinations

Rome

Duration3 hours

From

USD 117

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Best of Sicily - September 2026

(1 review )

Trip customizable

Best price guaranteed

Sicily was absolutely stunning! The food, the history, and the warm hospitality made this one of our favorite trips ever. Taormina and Palermo were just magical!

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Catania, Sicily

Duration8 days

From

USD 944

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22% OFF TODAY

Super Sales

Premium Sicily - September 2026

No booking fees

Best price guaranteed

Explore Sicily and see how much this island in the heart of the Mediterranean has to offer. Join an expert local leader on a fully immersive 10-day Premium journey – with a sprinkling of Arab, Norman, Greek and Roman influence, this region is a hive of history and culture. See intricate mosaics, towering palaces, crumbling ruins and marble-lined laneways. Head out of the main hubs to discover Mount Etna – Europe’s largest active volcano. Taste Genovesi, arancini, local dishes like caponata and cannoli, and take a traditional cooking class to get the most out of Sicily’s celebrated cuisine. With Exclusive Experiences and a gorgeous Feature Stay in the countryside, what are you waiting for?

City sightseeingAdventure

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Catania, Marsala, Agrig

Palermo, Catania, Marsala, Agrigento, Siracusa

22% OFF TODAY

Duration10 days

From

USD 5,975

USD 4,637

Saving

USD 1,338

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Upgraded - Walking Italy: Rome & Umbria - September 2026

(2 reviews )

No booking fees

Best price guaranteed

Discover the historical wonders of Rome and the picturesque landscapes of Umbria on this week-long walking holiday. Explore charming hill towns, stunning basilicas, Orvieto's cathedral and caves, and Rome's ancient landmarks. Montefalco and Assisi - Leisurely and moderate grade walks to charming hill towns with breath-taking Umbrian views Orvieto - Enchanting town with a magnificent cathedral, underground caves, and wine-tasting Rome - Ancient landmarks like the Colosseum and Roman Forum, plus delicious Italian cuisine Upgraded range - Immerse yourself in Umbria's beautiful countryside with our hand-picked Premium accommodations

Walking toursCity sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Rome, Colosseum, Umbria, Montefa

Rome, Colosseum, Umbria, Montefalco, Assisi, Spoleto, Orvieto

Duration8 days

From

USD 4,010

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15% OFF TODAY

Puglia Explorer - 8 days - September 2026

No booking fees

Best price guaranteed

Join us on this 8-day tour of Puglia in southern Italy. Spend seven nights in the beautiful hilltop town of Ostuni, explore the whitewashed streets of Locorotondo and enjoy an included wine tasting. See the UNESCO-listed Trulli of Alberobello, taste Puglia's renowned olive oil in Martina Franca and delve into the baroque elegance of Lecce, often called the "Florence of the South." Visit the vibrant capital of Bari and stroll through Trani, a town rich in Arab, Byzantine, and Norman influences.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Puglia, Ostuni

15% OFF TODAY

Duration8 days

From

USD 2,385

USD 2,027

Saving

USD 358

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Super Sales

Simply Italy Reunion 35 to 45 - September 2026

No booking fees

Best price guaranteed

Welcome to 15 days of pure Italian travel immersion with your squad of awesome 35-45 year old travellers. Covering Rome, Florence, Milan, Venice and beyond, this one brings you the blissful best of this soul-stirring country. Explore Rome's historical highlights, travel through the streets of Michelangelo's Florence, indulge in some authentic pasta on the Amalfi Coast. Stop by to see the stooping slopes of Sorrento in the breezy winter or the picture perfect Positano for your summery soul. And that's just an aperitivo. Beauty, romance and all the pasta you can fit in; the good life just got even better. That's amore!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Naples, Amalfi Coast, Flor

Rome, Naples, Amalfi Coast, Florence, Cinque Terre, Milan, Venice

Duration15 days

From

USD 3,035

USD 2,944

Saving

USD 91

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25% OFF TODAY

Best of Sardinia - 7 days - September 2026

No booking fees

Best price guaranteed

SMALL GROUP TOUR: Discover the picturesque coastline, historic cities and mouth-watering food of the Mediterranean island of Sardinia on this 7-day escorted group tour. Enjoy three included gastronomic experiences to sample some of the island's delicious flavours and discover Cagliari and Alghero with included guided touring. See the historic cathedral of Oristano, explore the archaeological site of Palmavera and Tharros, relax with free time in Palau and stroll along the windswept trails of Capo Caccia Natural Reserve.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Hut

Age Range

18-80 yrs

Operated in

english

Destinations

Sardinia, Cagliari, Bosa, Algher

Sardinia, Cagliari, Bosa, Alghero, Palau

25% OFF TODAY

Duration7 days

From

USD 3,355

USD 2,516

Saving

USD 839

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27% OFF TODAY

Super Sales

European Escapade - September 2026

4.9

(27 reviews )

No booking fees

Best price guaranteed

Loved the whole experience- visited all the best countries in Europe, tasted wines, spirits and other European alcohol In cheapest prices. It’s not suitable for asians with dark skin and if you’re over 34 yrs old unless you have a thick skin to not give any reaction to the comments some people make as a joke- only because they are white and still young. Not sure what they are so proud about in those moments. Other than that I enjoyed my time with rest of them. The price was on discount- I had to add on some extra adventures which worth it. Honestly 24 days is finished so quickly. Recommend to all the people who like explore Europe more in less time in cheaper price. Great work contiki, I am on my second one now- in Thailand, this group of approx 30 people is much better than European escapades (just my personal experience).

City sightseeing

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort, Guest House

Age Range

18-35 yrs

Operated in

english

Destinations

London, Paris, Lucerne, Lyon, Ba

London, Paris, Lucerne, Lyon, Barcelona, French Riviera, Florence, Rome, Venice, Vienna, Munich, Prague, Berlin, Amsterdam, Beaujolais

27% OFF TODAY

Duration24 days

From

USD 4,232

USD 3,079

Saving

USD 1,153

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All Italy Tours in September 2026

Page 6 of 90 Trips in Italy during September 2026 with 2,369 Reviews

See Italy tours by duration

Page 6 of 90 Trips in Italy during September 2026 with 2,369 Reviews

Best of Sicily (Small Group Tour) - September 2026

Iconic Rome and Amalfi - September 2026

Sensational Sicily - September 2026

Palermo and Sicilian Baroque Self Drive - September 2026

Scenic Sicily Self Drive - September 2026

Great Italian Cities - September 2026

Rome by golf-cart private tour - September 2026

Best of Sicily - September 2026

Premium Sicily - September 2026

Upgraded - Walking Italy: Rome & Umbria - September 2026

Puglia Explorer - 8 days - September 2026

Simply Italy Reunion 35 to 45 - September 2026

Best of Sardinia - 7 days - September 2026

European Escapade - September 2026

Combine Italy in September with Nearby Countries for an Unforgettable Trip

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 Italy Tours in September 2026

Page 6 of 90 Trips in Italy during September 2026 with 2,369 Reviews

See Italy tours by duration

Page 6 of 90 Trips in Italy during September 2026 with 2,369 Reviews