Italy Tours in September 2026

Discover 500+ Italy trips in September 2026 with 6830+ verified reviews. Crafted by vetted tour operators, these Italy September 2026 tours showcase the country at its seasonal best.

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Page 4 of 502 Trips in Italy during September 2026 with 6,840 Reviews

Via Francigena: Southern Tuscany from Siena - September 2026

4.4

(10 reviews )

No booking fees

Best price guaranteed

Having worked with them on a trip in Northern Italy last year, I was confident they would deliver a great experience. They did. From the quality of the hotels, included meals, the navigation app used down to the distances covered each day, everything was well thought out and first rate. Along the way I met other walkers who’d used other companies. Every single one had a complaint about the company they used. I had no complaints and recommended them repeatedly along the route. I’m already making arrangements for an Italian walk next year with this company.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Siena, Lazio, Lucignano D

Rome, Siena, Lazio, Lucignano D Arbia, Tuscany, San Quirico d'Orcia, Castiglione D Orcia, Radicofani

Duration8 days

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37% OFF TODAY

Discovery of Italy: 8 Days - September 2026

(1 review )

Trip customizable

Best price guaranteed

I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, The Vati

Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

37% OFF TODAY

Duration8 days

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Walking in Puglia - September 2026

4.6

(19 reviews )

No booking fees

Best price guaranteed

Well organised with punctual pick ups. Fabulous accommodation and amazing walks. Loved the whole experience.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Matera, Lecce, Salento, Ostuni

Matera, Lecce, Salento, Ostuni, Alberobello

Duration8 days

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37% OFF TODAY

Grand Journey of Italy - 11 Days - September 2026

(2 reviews )

Trip customizable

Best price guaranteed

Awesome tour, Many fantastic sights throughout the tour, great experience I'll never forget. Well organised and good value for money. Thanks for all you do. We really appreciated it.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Florence, Venice

Pompeii, Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Naples, Sorrento, Tuscany, Bologna, Padua

37% OFF TODAY

Duration11 days

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St Francis Way: Rieti to Rome - September 2026

(2 reviews )

No booking fees

Best price guaranteed

This was a wonderful walk through the Italian landscape following quiet trails peppered with villages and ancient hilltop towns. The walking provides a sense of achievement with occasional long days and steep rocky trails.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Rieti, Poggio San Lorenzo

Rome, Rieti, Poggio San Lorenzo, Scandriglia, Nerola, Sabina, Monterotondo

Duration8 days

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Italy Real Food Adventure - September 2026

18% OFF TODAY

Super Sales

Italy Real Food Adventure - September 2026

No booking fees

Best price guaranteed

Italians are the masters of creating simple dishes that burst with flavour. Inspired by nonnas’ kitchens all over the country, this food is regional, seasonal and fresh, and on this eight-day trip through everybody’s favourite culinary hub, you’ll discover that pizza and pasta are only the tip of the iceberg. Uncover the diverse array of unforgettable street eats, meals and cicchetti (small bites) from the postcard-perfect Venice to Rome, where medieval meets modern. Delight in local wine, fresh produce, homemade dinners and seasonal favourites in San Gimignano, Tuscany and Bologna – all with a local by your side – and take your tastebuds on an unforgettable adventure.

Food tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Bologna, San Gimignano

18% OFF TODAY

Duration8 days

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23% OFF TODAY

Italian Intermezzo - September 2026

4.6

(68 reviews )

No booking fees

Best price guaranteed

This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Venice, Florence

23% OFF TODAY

Duration8 days

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Amazing Italy - September 2026

(3 reviews )

Trip customizable

Best price guaranteed

Absolutely incredible! Italy’s history, food, and charm blew us away. The small group setting was perfect, and everything was tailored for Canadian travelers. Highly recommend!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Sorrento

Rome, Florence, Verona, Sorrento, Venice, Perugia, Naples, Salerno, Siena, Genoa, Milan

Duration15 days

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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.

14% OFF TODAY

Treasures of Italy - September 2026

4.8

(95 reviews )

No booking fees

Best price guaranteed

It was a fast paced trip. It is a bit difficult staying only one night in a few places, just the logistics of packing up several nights and having everything ready for the next day is challenging. But, that being said I thoroughly enjoyed seeing so many things through out Italy. That inconvenience was minor in comparison to the amount of ground we covered.

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Capri, Florence, S

Rome, Venice, Capri, Florence, Santa Margherita, Lake Maggiore

14% OFF TODAY

Duration11 days

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Super Sales

Walking in Sardinia - September 2026

4.6

(57 reviews )

No booking fees

Best price guaranteed

For anyone with coeliac disease, this trip is perfection. You get wonderful food, and lots of it. I managed to put on weight in spite of the energy expenditure, which was considerable!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Hut

Age Range

16-99 yrs

Operated in

english

Destinations

Sardinia, Dorgali, Gulf Of Orose

Sardinia, Dorgali, Gulf Of Orosei, Gorropu Gorge, Serra Orrios, Bue Marino Grotto, Tiscali

Duration8 days

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Showing 1 - 10 of 235 results

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Italy Tours in September 2026

Page 4 of 502 Trips in Italy during September 2026 with 6,840 Reviews

Get a customized trip to Italy in September 2026

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Page 4 of 502 Trips in Italy during September 2026 with 6,840 Reviews