10 Best Italy Multiday Tours in September 2026

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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Cycling in Sicily - September 2026

4.7

(58 reviews )

No booking fees

Best price guaranteed

This was one of my best Exodus Holidays. This was my first cycling one with Exodus and I can highly recommend this trip.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Modica, Marzamemi, Noto

Duration8 days

From

USD 2,700

USD 2,619

Saving

USD 81

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18% OFF TODAY

Italy Explorer - September 2026

4.5

(27 reviews )

No booking fees

Best price guaranteed

Amazing tour. Full credit to Roma on sharing her recommendations and experience with us. An awesome woman who goes out of her way to ensure an enjoyable tour is had by all. So many places to see & new foods to try. Memories for a lifetime

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Hut, Villa

Age Range

10-99 yrs

Operated in

english

Destinations

Rome, Cinque Terre and Liguria

Rome, Cinque Terre and Liguria, Palermo, Alberobello, Taormina, Agrigento, Venice, Tuscany, Amalfi Coast

18% OFF TODAY

Duration16 days

From

USD 3,370

USD 2,755

Saving

USD 615

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Splendid Amalfi Coast - Small-Group Tour - September 2026

Trip customizable

Best price guaranteed

Begin by immersing yourself in the ancient ruins of Pompeii, a once-thriving ancient city frozen in time by the catastrophic eruption of Mount Vesuvius. Afterward, retreat to the idyllic town of Sorrento, where your charming hotel promises a comfortable respite. Venture out to the renowned island of Capri, nestled in the Bay of Naples, and be entranced by its natural beauty and cultural allure. Marvel at the picturesque hillside town of Positano, etched into the rugged coastline, before making your way back to the eternal city of Rome, enriched by the memories of this coastal sojourn

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Campania, Amalfi, Rome

Duration5 days

From

USD 1,989

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Grand Italian Experience - September 2026

16% OFF TODAY

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Grand Italian Experience - September 2026

4.8

(75 reviews )

No booking fees

Best price guaranteed

So much to do! Don't muss out on the additional dinners. Some are spectacular.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Dolomites, Lake Maggiore

Rome, Dolomites, Lake Maggiore, Viareggio, Florence, Puglia, Amalfi Coast & Campania, Naples, Assisi, Venice

16% OFF TODAY

Duration17 days

From

USD 5,750

USD 4,802

Saving

USD 949

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Classical Sicily - September 2026

4.3

(26 reviews )

No booking fees

Best price guaranteed

Everything went well. Excellent guide, good companions, interesting places (If you like churches and temples), well balanced, everyday something new. No "free time for you to relax by pool" excuses for having nothing much to see. Really good.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Syracusa, Trap

Syracuse, Sicily, Syracusa, Trapani, Palermo, Giardini Naxos, Taormina

Duration8 days

From

USD 2,830

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19% OFF TODAY

Highlights of Southern Italy & Sicily - September 2026

4.5

(29 reviews )

No booking fees

Best price guaranteed

Helpful Tour Guide and Bus Driver made the Tour a pleasure

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Hut

Age Range

10-99 yrs

Operated in

english

Destinations

Rome, Naples, Sorrento, Alberobe

Rome, Naples, Sorrento, Alberobello, Taormina, Agrigento, Palermo

19% OFF TODAY

Duration10 days

From

USD 2,070

USD 1,675

Saving

USD 395

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7% OFF TODAY

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Easy Pace Italy - September 2026

4.8

(113 reviews )

No booking fees

Best price guaranteed

Good introductory cross-section in major cities. Good balance of scheduled vs. free time. Would like a little more emphasis on art--especially Uffizi Gallery and Pisan Camposanto--plus entry into St. Mark's/Doge's Palace and Duomo church (rather than some of the shopping stuff). A little too much commercial, too little history/art. (Some of guides under-informed, including one who said Galileo discovered the "two planets" around Jupiter!).

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence

7% OFF TODAY

Duration10 days

From

USD 5,175

USD 4,835

Saving

USD 340

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Walking in the Dolomites - September 2026

4.4

(11 reviews )

No booking fees

Best price guaranteed

The Dolomites were magical and our self guided walking tour was the perfect way for us to see them!

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Resort, Hut

Age Range

18-99 yrs

Operated in

english

Destinations

Cortina d'Ampezzo, Trentino-Sout

Cortina d'Ampezzo, Trentino-South Tyrol, Campitello Di Fassa, San Cassian, Colfosco

Duration8 days

From

USD 2,690

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Ultimate Italy - September 2026

(30 reviews )

No booking fees

Best price guaranteed

It was a great experience with many highlights throughout our tour. We particularly enjoyed the many immersive stops (i.e. wine tasting, weaving, truffle hunting, pasta making, etc.) in addition to our guided tours. Our tour guide, was very well versed, knowledgeable, and helpful and provided good insights and tips throughout our trip. I can't imagine someone else doing a better job than she did! The local experts were also on top of their games.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Capri, Perugia, Sa

Rome, Venice, Capri, Perugia, San Gimignano, Florence, Rapallo

Duration12 days

From

USD 10,850

USD 10,525

Saving

USD 326

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Cycle Puglia - September 2026

4.7

(30 reviews )

No booking fees

Best price guaranteed

Stress-Free tour with excellent accommodation, luggage transfers that was always waiting for us the end of the day. Scenery was unforgettable, people along the way were welcoming and most spoke English although we did try.

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Resort

Age Range

18-99 yrs

Operated in

english

Destinations

Matera, Lecce, Alberobello, Ostu

Matera, Lecce, Alberobello, Ostuni, Gallipoli, Santa Maria Di Leuca, Otranto

Duration8 days

From

USD 1,630

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Journeys: Iconic Italy - September 2026

(4 reviews )

No booking fees

Best price guaranteed

Overall the trip was extremely enjoyable and I will cherish my memories of the incredible towns and sites that we visited.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Venice, Amalfi, Cinque Ter

Rome, Venice, Amalfi, Cinque Terre, Florence, Naples, Sorrento

Duration14 days

From

USD 6,499

USD 6,304

Saving

USD 195

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Ancient Sicily - September 2026

4.7

(18 reviews )

No booking fees

Best price guaranteed

Antonio has been leading tours around Sicily for 30 years and knows his way around. In his hands, we were fast tracked to all the sites, avoiding the long queues that were very apparent at popular destinations. Something I think that we all took for granted. Over the years, he has determined the pace that will best suit. A considerable art. We were never rushed. He was always good humoured and incredibly knowledgeable. The trip gives a very good overview of the entire island. For me, perhaps too much of an emphasis on the Greek and Roman. Free time made it possible to catch up on the Norman and Baroque. Not to mention the Puppets. I had a good time with a very congenial group of like minded travellers. Hotels weren't great but were adequate. Some could have been better located.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Monreale Cathe

Syracuse, Sicily, Monreale Cathedral, Palermo, Giardini Naxos, Catania, Taormina, CORINTH, Piazza Amerina, Villa Romana Del Casale, Agrigento, Marsala, Mozia Island

Duration15 days

From

USD 4,780

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Local Living Italy—Amalfi Coast - September 2026

(4 reviews )

No booking fees

Best price guaranteed

I?d recommend it to our friends interested in the off the grid sort of travel. I?ve recommended any tour les by Raffo . He?s truly exceptional.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Furore

Duration8 days

From

USD 2,399

USD 2,327

Saving

USD 72

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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 4 of 212 Trips in Italy during September 2026 with 5,937 Reviews

See Italy tours by duration

Private Gourmet Wine Tour in Tuscany - September 2026

Cycling in Sicily - September 2026

Italy Explorer - September 2026

Splendid Amalfi Coast - Small-Group Tour - September 2026

Grand Italian Experience - September 2026

Classical Sicily - September 2026

Highlights of Southern Italy & Sicily - September 2026

Easy Pace Italy - September 2026

Walking in the Dolomites - September 2026

Ultimate Italy - September 2026

Cycle Puglia - September 2026

Journeys: Iconic Italy - September 2026

Ancient Sicily - September 2026

Local Living Italy—Amalfi Coast - September 2026

Page 4 of 212 Trips in Italy during September 2026 with 5,937 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 4 of 212 Trips in Italy during September 2026 with 5,937 Reviews

See Italy tours by duration

Page 4 of 212 Trips in Italy during September 2026 with 5,937 Reviews