10 Best Italy Multiday Tours in September 2026

Sicily - Magna Via Francigena - September 2026

4.6

(16 reviews )

No booking fees

Best price guaranteed

Walking the Magna Via Francigena was challenging - many steep hills, mud and rain. They organised everything else so that all we had to do was walk, making the walk much easier. The scenery was stunning.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Palermo, Sicily, Corleone, Prizz

Palermo, Sicily, Corleone, Prizzi, Cammarata, Sutera, Racalmuto, Agrigento

Duration8 days

From

USD 1,250

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Private Tour of Sicily from Palermo - September 2026

4.8

(4 reviews )

Trip customizable

Best price guaranteed

This is our first private tour and I must say it met all our expectations. Our driver/guide Carlo took very good care of us, told us informative and amusing stories along the way and took us to wonderful restaurants. He made sure all our needs our taken cared of. In Sicily especially I think the private tour is a big advantage as there are many places where only small vehicles can go through. We made the right decision in choosing this tour.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

20-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Sici

Palermo, Catania, Taormina, Sicily, Agrigento, Marsala, Monreale

Duration8 days

From

USD 3,151

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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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Explore Malta 5 Days, Self-drive - September 2026

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Explore Malta 5 Days, Self-drive - September 2026

Trip customizable

Best price guaranteed

Discover the best of Malta during this short self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

15% OFF TODAY

Duration5 days

From

USD 423

USD 359

Saving

USD 63

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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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Explore Malta 7 Days, Self-drive - September 2026

15% OFF TODAY

Super Sales

Explore Malta 7 Days, Self-drive - September 2026

Trip customizable

Best price guaranteed

Discover the best of Malta during this seven-day self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

15% OFF TODAY

Duration7 days

From

USD 612

USD 520

Saving

USD 92

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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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Rome, Florence & Tuscany Family Adventure - September 2026

(3 reviews )

Trip customizable

Best price guaranteed

Hi Stefania! Sorry to take so long to write back. It has been crazy trying to get back into the swing of things at work after that trip. Italy was amazing!! We absolutely loved it! As for feedback on the trip, we really don't have anything that was negative. We loved everything that was planned! We especially loved how you planned the sites that we went and how the pattern flowed (not sure if you did it on purpose but we think so). Also, thank you for being very accessible to us during the whole planning of the trip. You helped put us at ease and it was very reassuring that we chose the right company. That is all that I can given you that might be considered constructive. The rest I could say would just be compliments on everything else. If I can think of anything else that I think is useful I will definitely email you. Hope all is well, Jane P.S. - Does your company only provide trips for Italy or other countries as well, just wondering for the future :)

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, San Gim

Rome, Florence, Tuscany, San Gimignano, Chianti, The Vatican

Duration8 days

From

USD 7,721

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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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Walking in Puglia - September 2026

4.6

(14 reviews )

No booking fees

Best price guaranteed

Travelling in a small group with different abilities the trip gave us a great balance between manageable walks, urban experiences and self managed travel. Instructions for the walks were generally clear but some better formatting/design would be helpful. The booked transport was always punctual, well organised with helpful and friendly drivers. The hotels that were selected had a great atmosphere and evocative of the places we were staying. Their location in the heart of the historic towns was perfect making it easy for quick explorative trips. Puglia as a destination didn't disappoint and we would be very happy to return whenever we have the opportunity.

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

From

USD 1,690

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St Francis Way: Rieti to Rome - September 2026

(1 review )

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

From

USD 1,390

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Private Gourmet Wine Tour in Tuscany - September 2026

4.5

(2 reviews )

Trip customizable

Best price guaranteed

What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

From

USD 2,846

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La Dolce Vita Experience - September 2026

Trip customizable

Best price guaranteed

As you journey from Rome to Sorrento, you’ll pass through a captivating landscape dotted with medieval villages seemingly frozen in time. This tranquil scene contrasts with the haunting allure of the ancient ruins of nearby Pompeii. Sorrento offers a serene coastal retreat with breathtaking views of the Bay of Naples. Be sure to take the opportunity to visit Capri, where the enchanting Blue Grotto, with its crystalline waters, invites you to experience its shimmering beauty

Cultural, religious and historic sites

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Lazio, Sorrento

Duration3 days

From

USD 911

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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.

All Italy Tours in September 2026

126 Trips in Italy during September 2026 with 274 Reviews

See Italy tours by duration

126 Trips in Italy during September 2026 with 274 Reviews

Sicily - Magna Via Francigena - September 2026

Private Tour of Sicily from Palermo - September 2026

Puglia Coastal Walk - September 2026

Explore Malta 5 Days, Self-drive - September 2026

Via Francigena: Orvieto to Rome - September 2026

Explore Malta 7 Days, Self-drive - September 2026

Classic Amalfi Coast - 8 Days - September 2026

Via Francigena: Best of Tuscany - September 2026

Rome, Florence & Tuscany Family Adventure - September 2026

Via Francigena: Southern Tuscany from Siena - September 2026

Walking in Puglia - September 2026

St Francis Way: Rieti to Rome - September 2026

Private Gourmet Wine Tour in Tuscany - September 2026

La Dolce Vita Experience - 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

126 Trips in Italy during September 2026 with 274 Reviews

See Italy tours by duration

126 Trips in Italy during September 2026 with 274 Reviews