10 Best Italy Multiday Tours in September 2026

Puglia Coastal Walk - September 2026

4.6

(8 reviews )

No booking fees

Best price guaranteed

Communication when booking and questions afterwards was good. The trip itself was fantastic

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Otranto, Lecce, Salento, Porto B

Otranto, Lecce, Salento, Porto Badisco, Santa Cesarea Terme, Marittima, Marina Serra

Duration8 days

From

USD 1,160

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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

Duration11 days

From

USD 5,695

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Via Francigena: Orvieto to Rome - September 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

A truly memorable holiday which enabled us not only to see parts of the wonderful Lazio countryside that we wouldn’t normally see by car, but also to soak up the atmosphere of the various villages and towns where we stayed.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Orvieto, Bolsena, Montefia

Rome, Orvieto, Bolsena, Montefiascone, Viterbo, Vetralla, Sutri, Campagnano Di Roma, Isola Farnese, Piazza San Pietro

Duration10 days

From

USD 1,453

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Super Sales

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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Amalfi Coast Walking - Agriturismo - September 2026

4.8

(93 reviews )

No booking fees

Best price guaranteed

The trip had a varied itinerary. Gennaro the guide was excellent. He had a wealth of knowledge, took great care to include everyone in the group. This meant that everyone enjoyed their trip. Throughly enjoyed myself .

Walking toursFood tours

Tour Type

Small Group Tour

Accommodation

Resort, Villa, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Naples, San Lazzaro, Amalfi, Capri

Duration8 days

From

USD 2,070

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Super Sales

Cycle Cilento & the Amalfi Coast - September 2026

4.7

(99 reviews )

No booking fees

Best price guaranteed

Amalfi coast is one of the most dramatic coastline in the world and this well organised Exodus Trip will guide you on bike along the coastal road all the way to the end (Termini). There are great do-able climbs, long descents, fantastic scenery, great food, great temples and most beautiful gardens - i.e. just about perfect!

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Minori

Amalfi Coast & Campania, Minori, Palinuro, Casalvelino, Paestum

Duration8 days

From

USD 3,300

USD 3,201

Saving

USD 99

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Tuscany Walking and Wine - September 2026

4.9

(9 reviews )

No booking fees

Best price guaranteed

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of years old? A wine and food buff? Then this is for you. I had a great time on this trip. Had a full day in Sienna and a nice orientation tour of Florence (I spent a few extra days) Plus to get to visit lesser known towns that the big companies overlook. My favorite was Pienza. A nice little town that also had my favorite hotel and great places to eat. And yes, we tasted wonderful Italian wines, as well as the best cold cuts and cheeses I’ve ever tasted. And did I also mention hiking to wineries and hill towns? Wonderful sights, with spectacular views. One hike it rained towards the end, but that didn’t dampen our spirits.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

From

USD 2,830

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Classic Amalfi Coast - 8 Days - September 2026

4.8

(9 reviews )

No booking fees

Best price guaranteed

It was very well organised. Everything worked smoothly, we had a great holiday.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Positan

Amalfi Coast & Campania, Positano, Amalfi, Maestra Dei Villaggi, Praiano, Naples

Duration8 days

From

USD 1,790

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Via Francigena: Best of Tuscany - September 2026

4.6

(25 reviews )

No booking fees

Best price guaranteed

They organised a fabulous experience. The trip was seamless and the information provided was thorough. The accommodation was fabulous and the trip notes and app were informative and I felt well supported. I would highly recommend them.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Buonconvento, San Minia

Tuscany, Buonconvento, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena, Lucignano D Arbia

Duration9 days

From

USD 1,290

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Super Sales

Walk The Prosecco Hills & Hidden Venice - September 2026

4.8

(77 reviews )

No booking fees

Best price guaranteed

Walking on this holiday is varied and well within most people's grasp. Aside from the rolling hills of Prosecco vineyards it includes forest walking and following along side a river. The hotel is most comfortable with large airy bedrooms and updated bathrooms which do not detract from the historic building. It sits within its own grounds including a large swimming pool and a bookable spa. The village of Soligo is small with 3 cafe's and a small shop which stocks a wide range of biscuits, soft drinks and bottled water. There is one sure thing about this holiday and this is you will not go hungry. Lunches are freshly made by the local shop and will keep you going during the walks. The hotel food is second to none and the other resturants we eat at also supplied delicous food. The highlight of this trip is Prosecco in all its forms. I learnt a lot about how the wine was made and how to tell one bottle from another.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Treviso, Pieve Di Cadore

Venice, Treviso, Pieve Di Cadore, Cison Di Valmarino, Asolo, Conegliano, Pieve Di Soligo

Duration8 days

From

USD 2,820

USD 2,735

Saving

USD 85

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Super Sales

Italian Scene - September 2026

4.6

(57 reviews )

No booking fees

Best price guaranteed

The scenery was beautiful. Next time I'd slow it down a bit though and enjoy each city for a few days.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Bay Of Naples, Assisi, Ven

Rome, Bay Of Naples, Assisi, Venice, Milan, Florence

Duration10 days

From

USD 1,795

USD 1,741

Saving

USD 54

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Via Francigena: Southern Tuscany from Siena - September 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

An amazing walk through the Tuscan countryside. Exceptional organisation and attention to detail meant we could concentrate on having a great time and not have to worry about accommodation, meals and transfers. Thanks!

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

From

USD 1,260

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Super Sales

Cycling Puglia & Matera - September 2026

4.7

(66 reviews )

No booking fees

Best price guaranteed

Perfect spring cycling, beautiful scenery, wonderful food

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Matera, Salento, Alberobello, Os

Matera, Salento, Alberobello, Ostuni, Avetrana, Gallipoli, Otranto, Lecce

Duration8 days

From

USD 3,000

USD 2,910

Saving

USD 90

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Discovery of Italy: 8 Days - September 2026

4.5

(2 reviews )

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

Duration8 days

From

USD 2,750

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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

View Tours

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

All Italy Tours in September 2026

Page 2 of 171 Trips in Italy during September 2026 with 4,805 Reviews

See Italy tours by duration

Puglia Coastal Walk - September 2026

Grand Journey of Italy - 11 Days - September 2026

Via Francigena: Orvieto to Rome - September 2026

Sicily Food & Wine - September 2026

Amalfi Coast Walking - Agriturismo - September 2026

Cycle Cilento & the Amalfi Coast - September 2026

Tuscany Walking and Wine - September 2026

Classic Amalfi Coast - 8 Days - September 2026

Via Francigena: Best of Tuscany - September 2026

Walk The Prosecco Hills & Hidden Venice - September 2026

Italian Scene - September 2026

Via Francigena: Southern Tuscany from Siena - September 2026

Cycling Puglia & Matera - September 2026

Discovery of Italy: 8 Days - September 2026

Page 2 of 171 Trips in Italy during September 2026 with 4,805 Reviews

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 2 of 171 Trips in Italy during September 2026 with 4,805 Reviews

See Italy tours by duration

Page 2 of 171 Trips in Italy during September 2026 with 4,805 Reviews