10 Best Italy Multiday Tours in September 2026

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Classic Dolomites Hikes - Premium Adventure - September 2026

4.9

(24 reviews )

No booking fees

Best price guaranteed

What a wonderful trip ! An exciting walking adventure with a wonderful guide, magnificent scenery , a great group of likeminded hikers and an awesome hotel

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Hut

Age Range

16-99 yrs

Operated in

english

Destinations

Niederdorf, Dolomites, Lago Di B

Niederdorf, Dolomites, Lago Di Braies, Alpe Nemes, Strudelkopf, Brunico, Tre Cime Di Lavaredo, Monte Piano

Duration8 days

From

USD 3,420

USD 3,317

Saving

USD 103

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Splendid Tour (on Request) - September 2026

15% OFF TODAY

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Splendid Tour (on Request) - September 2026

(1 review )

Trip customizable

Best price guaranteed

Discover some of the most essential parts of Italy on this five-day cultural trip, beginning with an exploration of the ruins of ancient Pompeii and continuing to the magnificent views of Positano and its surrounding fishing villages.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Rome, Sorrento, Amalfi

15% OFF TODAY

Duration5 days

From

USD 2,312

USD 1,965

Saving

USD 347

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19% OFF TODAY

Europe Explorer - September 2026

4.8

(42 reviews )

No booking fees

Best price guaranteed

This was my first trip to Europe and I could not imagine experiencing it any better than on the 18 day EX tour. Although we only scratched the surface of many places it gave a wonderful perspective for places I want to come back to for further exploration. We covered a lot of ground in 18 days and made unforgettable memories. I was expecting to see beautiful things and have great experience but the relationships that formed within our group were an unexpected, and delightful, surprise. I'm so thankful I choose to do this tour and have recommended to all of my friends. I will definitely do another Expat tour when I'm able. Disclaimer; This is not a trip for those who want to kick back and relax. It was very active with many early mornings, late night and non-stop adventure days.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Paris, Amsterdam, Rome, Venice

Paris, Amsterdam, Rome, Venice, Lauterbrunnen, Black Forest, Toulouse, Barcelona, Avignon, Nice, Tuscany

19% OFF TODAY

Duration18 days

From

USD 4,100

USD 3,315

Saving

USD 785

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Portofino and the Cinque Terre - September 2026

(1 review )

No booking fees

Best price guaranteed

The Portofino Cinque Terre self-guided walking holiday was perfectly organized.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Cinque Terre and Liguria, Liguri

Cinque Terre and Liguria, Liguria, Bonassola, Genoa

Duration8 days

From

USD 1,160

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The Tuscan Dream Self-Drive - September 2026

(2 reviews )

Trip customizable

Best price guaranteed

GO!!! Our first time in Italy and this package was absolutely amazing. The price, sights, hotels and people couldn’t be beat. Really, just go!

City sightseeing

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Siena, Tuscany, Chianti, Pistoia

Duration7 days

From

USD 629

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Dolomites Hut to Hut Guided Hike - September 2026

4.6

(24 reviews )

No booking fees

Best price guaranteed

Trip was very energetic, extremely well led and organized and covered stunning scenery.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hut

Age Range

18-99 yrs

Operated in

english

Destinations

Cortina d'Ampezzo, Refuge Guissa

Cortina d'Ampezzo, Refuge Guissani, Fanes Hütte, Lago Di Braies, Dürrenstein Hütte, Drei Zinnen, Rifugio Lavarredo

Duration7 days

From

USD 2,090

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16% OFF TODAY

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Country Roads of Italy - September 2026

4.6

(65 reviews )

No booking fees

Best price guaranteed

This tour was a wonderful experience. A nice size at 28 happy people, luxurious coach, amazing driver & guide extraordinaire . Accommodations were very good & often pleasantly out of the ordinary. The optional activities are worth the extra expense. Highly recommend this tour.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Monteriggioni, Luc

Rome, Venice, Monteriggioni, Lucca, Sorrento, Todi

16% OFF TODAY

Duration16 days

From

USD 7,895

USD 6,665

Saving

USD 1,230

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Hilltop Towns of Italy - September 2026

4.8

(4 reviews )

No booking fees

Best price guaranteed

We had a spectacular trip. We did a self-guided trip in Piemonte and Tuscany/Umbria. The hotels were much nicer than we expected. Very comfortable and the owners/proprietors were so helpful. The transfer of luggage each day was seamless! The routes were generally well marked and the app was very good. We didn't need anything more than the app. Only got lost twice which I'd say is pretty good. The routes were a bit more challenging than we expected. We choose two hikes which were marked as 'Introductory - Moderate' which were tougher than we expected. So just pay attention to this. At home, we would consider ourselves quite capable of moderate+ trails, but the classification in Italy is a bit more demanding. Glad we wore hiking pants as we went through a lot of grasses so never had a concern about tics. Also were very happy we had hiking sticks with us. Invaluable on many of the trails. I would definitely recommend them to anyone considering a hiking trip. And absolutely no problem doing the self-guided version. Thank you!! Griffy and Marg

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Orvieto, Sorano, Bolsena, Pitigliano

Duration8 days

From

USD 1,570

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15% OFF TODAY

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Italian Glory - September 2026

4.8

(55 reviews )

No booking fees

Best price guaranteed

Great itinerary and tour director. Suggest: a slightly slower pace - limiting yourself to 1 optional experience/ day to avoid too/ long days -exhaustion, provide more suggestions for authentic food / restaurants on ‘free’ days.

Chill outSightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Lake Como, Como, Ve

Milan, Rome, Lake Como, Como, Venice, Florence, Amalfi Coast & Campania

15% OFF TODAY

Duration13 days

From

USD 4,575

USD 3,880

Saving

USD 695

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St Francis Way: Assisi to Spoleto - September 2026

4.8

(9 reviews )

No booking fees

Best price guaranteed

The information provided was excellent and the navigation app worked well. The accommodation was extremely good. Overall I found the walk more difficult than I expected, but in the end very rewarding.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Assisi, Spoleto, Spello, Vegnole

Assisi, Spoleto, Spello, Vegnole, Bovara Di Trevi, PORETA

Duration7 days

From

USD 1,050

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14% OFF TODAY

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Italian Concerto - September 2026

4.6

(122 reviews )

No booking fees

Best price guaranteed

Great tour at a great price

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Amalfi Coast & Cam

Rome, Venice, Amalfi Coast & Campania, Capri, Florence

14% OFF TODAY

Duration11 days

From

USD 3,925

USD 3,374

Saving

USD 551

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Super Sales

Italy Family Holiday - September 2026

No booking fees

Best price guaranteed

Fall in love with Italy and rediscover the rewards of family travel on this carefully crafted trip for both you and the kids. Over eight days, you’ll journey from the ruins of Rome to the shadow of mighty Mt Vesuvius. Deep dive into the history of the ancient ruins of Pompeii, then sit back and relax with a glass of Sangiovese (while the kids chase wild rabbits) on the farmlands of an agriturismo. Take a daytrip to the island of Capri and redesign family pizza night after learning the tricks of the trade in a cooking demonstration in Sorrento. With all the logistics and essential experiences taken care of, you can treat yourself to some family time on an Italian adventure that does the job, so you don’t have to.

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, S

Rome, Amalfi Coast & Campania, Sorrento, Pompeii, Minori

Duration8 days

From

USD 3,250

USD 3,153

Saving

USD 98

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Self-Guided Culinary Package - La Spezia & Cinque Terre - September 2026

Trip customizable

Best price guaranteed

Join us on this three-day tour and get to enjoy a region of Italy known for its mild climate, charming port towns, breath-taking landscapes, and fresh local cuisine. Liguria is home to the UNESCO World Heritage site "Cinque Terre," a majestic and astonishing national park free of vehicular traffic and perfect for romantic getaways and fine culinary experiences. The regional cuisine of Liguria is based on seafood, fresh vegetables and herbs, such as in the famous pesto alla Genovese. In a span of few days, you will be able to explore this region, its history, culture and culinary highlights always taking your time and doing everything at your own pace.

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

9-79 yrs

Operated in

English

Destinations

Cinque Terre and Liguria, Liguri

Cinque Terre and Liguria, Liguria, Cinque Terre, La Spezia, Lerici

Duration3 days

From

USD 387

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Southern Italy And Sicily - September 2026

15% OFF TODAY

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Southern Italy and Sicily - September 2026

4.4

(108 reviews )

No booking fees

Best price guaranteed

All the options were excellent. The local guides walked at a slow pace giving us time to take pictures. Our guide Alfonso and our driver Tito were great. We would take a tour with them anytime

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Sorrento, Palermo

Pompeii, Rome, Sorrento, Palermo, Capri, Taormina, Agrigento

15% OFF TODAY

Duration10 days

From

USD 3,575

USD 3,051

Saving

USD 524

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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

Page 9 of 465 Trips in Italy during September 2026 with 6,591 Reviews

See Italy tours by duration

Classic Dolomites Hikes - Premium Adventure - September 2026

Splendid Tour (on Request) - September 2026

Europe Explorer - September 2026

Portofino and the Cinque Terre - September 2026

The Tuscan Dream Self-Drive - September 2026

Dolomites Hut to Hut Guided Hike - September 2026

Country Roads of Italy - September 2026

Hilltop Towns of Italy - September 2026

Italian Glory - September 2026

St Francis Way: Assisi to Spoleto - September 2026

Italian Concerto - September 2026

Italy Family Holiday - September 2026

Self-Guided Culinary Package - La Spezia & Cinque Terre - September 2026

Southern Italy and Sicily - September 2026

Combine Italy in September with Nearby Countries for an Unforgettable Trip

Page 9 of 465 Trips in Italy during September 2026 with 6,591 Reviews

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 9 of 465 Trips in Italy during September 2026 with 6,591 Reviews

See Italy tours by duration

Page 9 of 465 Trips in Italy during September 2026 with 6,591 Reviews