10 Best Italy Multiday Tours in September 2026

Get a customized trip to Italy in September 2026

Plan a multi-country or regional adventure across Italy in September 2026, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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Page 2 of 502 Trips in Italy during September 2026 with 6,840 Reviews

Showing 1 - 10 of 42 results

Combine Italy in September with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

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Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

32% OFF TODAY

European Trail - September 2026

(2 reviews )

No booking fees

Best price guaranteed

Goated trip manager

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Hostel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, London, Amsterdam, Berlin

Paris, London, Amsterdam, Berlin, Prague, Vienna, Krakow, Budapest, Ljubljana, Venice, Rome, Florence, Swiss Alps

32% OFF TODAY

Duration23 days

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Jewels of Italy by Rail - September 2026

(1 review )

Trip customizable

Best price guaranteed

Three of us girlfriends decided it was time for an Italian cultural recharge, and we picked the rail tour to hit the highlights with ease. We explored Rome and saw the Coloseum as we opted for an optional tour. Florence was also beautiful. Venice was pure magic. Our shared gondola ride under the Bridge of Sighs (with just six in the gondola) felt cozy and unforgettable . We spent afternoons discovering boutique shops and colorful squares. For us, this tour struck the perfect balance. Relaxed evenings with wine and laughter. The train travel was a breeze, everything was well-coordinated.

Train toursSightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration7 days

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32% OFF TODAY

Italian Expresso - 5 days - September 2026

No booking fees

Best price guaranteed

COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Bologna

Rome, Tuscany, Florence, Bologna, Venice

32% OFF TODAY

Duration5 days

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Highlights of Matera and Apulia Private Tour - September 2026

(1 review )

Trip customizable

Best price guaranteed

Private Tour around Apulia and Matera beyond our expectations .Very good the Hotel in Matera, Dimora di Metello..but also Tenuta Monacelle near Alberobello. Great local guide and meals. I only think you should had add an extra day in Apulia, 5 days are not enough. Anyway excellent tour and service. Very good value for money

Sightseeing ToursFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

20-99 yrs

Operated in

english

Destinations

Matera, Puglia, Polignano A Mare

Matera, Puglia, Polignano A Mare, Alberobello, Monopoli, Bari

Duration5 days

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Unesco Puglia & Matera wonder holiday package - September 2026

Trip customizable

Best price guaranteed

In 6 amazing days, visit the 3 most beautiful UNESCO sites in southern Italy! Explore Matera, Alberobello and Castel del Monte in addition to the cities of Bari, Ostuni, and Lecce, all in a single organized tour that includes tour guides, hotels, and transfers. Learn more about the culture, history, and region, and recharge your batteries in the open air, while hunting for authentic wonders. This tour is perfect for couples, solo travelers, and for those who prefer a great quality, comprehensive, organized trip. If you would like an unforgettable holiday but without the worry of doing all the organizing, or if you simply don’t want the stress of driving, this holiday is for you! Make it easy on yourself and worry-free. This tour departs from Bari every Saturday and finishes in Lecce.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-79 yrs

Operated in

english, italian

Destinations

Matera, Puglia, Bari, Trani, Alb

Matera, Puglia, Bari, Trani, Alberobello, Ostuni, Lecce

Duration6 days

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Tuscany To Cinque Terre: Wines, Villages & Unforgettable Walks - September 2026

18% OFF TODAY

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Tuscany to Cinque Terre: Wines, Villages & Unforgettable Walks - September 2026

(7 reviews )

No booking fees

Best price guaranteed

I don't like planning trips and couldn't find a time that worked to travel with a friend, so decided to go on a group tour, and this trip was a great choice! I was really impressed with the organization of the trip, I loved the mix of planned activities and downtime, and I'm really glad I went.

Sightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Cinque Terre, Chianti

18% OFF TODAY

Duration7 days

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Naples Escape & Sorrento - Small-Group Tour - September 2026

Trip customizable

Best price guaranteed

Embark from Rome to Naples, uncovering the ancient city's treasures. Visit the legendary site of Pompeii, frozen in time by the cataclysmic eruption of Mount Vesuvius over 2,000 years ago. Continue your journey with a full-day tour to the idyllic Italian island of Capri, and later, unwind in the enchanting town of Sorrento on your Amalfi Coast getaway, with ample free time for independent exploration

Sightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Lazio, Naples, Sorrento, Rome

Duration5 days

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Via Degli Dei: Bologna to Florence - September 2026

4.8

(6 reviews )

No booking fees

Best price guaranteed

The Via Degli Dei is a fantastic walk - 2 great Italian cities and stunning landscapes every day which made the tough climbs worthwhile. They dealt with everything once we arrived, the accommodation was good and varied which added to the appeal of the trip. It's helpful to have some basic Italian as a couple of places did not speak English but everyone was so friendly. Will use them again - we are already planning next year's trip!

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Florence, Bologna, Sasso Marconi

Florence, Bologna, Sasso Marconi, Monzuno, Bruscoli, San Piero A Sieve, Olmo, Fiesole

Duration8 days

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Discovering Amalfi Coast - September 2026

22% OFF TODAY

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Discovering Amalfi Coast - September 2026

Trip customizable

Best price guaranteed

An exciting tour to discover the Amalfi Coast through its history and flavors. Immerse yourself into an archaeological journey through the ancient cities of Pompeii and Ercolano. Sail to the rocky island of Capri, and wander around its tiny pedestrian alleys.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Amalfi

22% OFF TODAY

Duration4 days

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22% OFF TODAY

Super Sales

Discovering Verona - September 2026

Trip customizable

Best price guaranteed

The home of Shakespeare’s Romeo and Juliet, Verona is an incredible city located in the North of Italy, and it has a lot to offer visitors interested in history through the Middle Ages and all the way back to Ancient Rome. During this short break you will also visit the beautiful Sirmione peninsula and sail along the Lake Garda.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Verona

22% OFF TODAY

Duration4 days

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Italy Tours in September 2026

Get a customized trip to Italy in September 2026

See Italy tours by duration

Get a customized trip to Italy in September 2026

Page 2 of 502 Trips in Italy during September 2026 with 6,840 Reviews

Page 2 of 502 Trips in Italy during September 2026 with 6,840 Reviews

Combine Italy in September with Nearby Countries for an Unforgettable Trip

European Trail - September 2026

Jewels of Italy by Rail - September 2026

Italian Expresso - 5 days - September 2026

Highlights of Matera and Apulia Private Tour - September 2026

Unesco Puglia & Matera wonder holiday package - September 2026

Tuscany to Cinque Terre: Wines, Villages & Unforgettable Walks - September 2026

Naples Escape & Sorrento - Small-Group Tour - September 2026

Via Degli Dei: Bologna to Florence - September 2026

Discovering Amalfi Coast - September 2026

Discovering Verona - September 2026

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Africa

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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

Italy Tours in September 2026

Get a customized trip to Italy in September 2026

See Italy tours by duration

Get a customized trip to Italy in September 2026

Page 2 of 502 Trips in Italy during September 2026 with 6,840 Reviews

Page 2 of 502 Trips in Italy during September 2026 with 6,840 Reviews