10 Best Italy Multiday Tours in September 2026

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Simply Italy - September 2026

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Welcome to 15 days of pure Italian travel immersion. Covering Rome, Florence, Venice and beyond, this one brings you the blissful best of this soul-stirring country. Explore Rome's historical highlights, travel through the streets of Michelangelo's Florence, indulge in some authentic pasta on the Amalfi Coast. Stop by to see the stooping slopes of Sorrento in the breezy winter. And that's just an aperitivo. Beauty, romance and all the pasta you can fit in; the good life just got even better. That's amore!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Naples, Amalfi Coast, Flor

Rome, Naples, Amalfi Coast, Florence, Cinque Terre, Milan, Venice

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Duration15 days

From

USD 2,755

USD 2,538

Saving

USD 217

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Ultimate Italy - September 2026

(30 reviews )

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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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Italian Espresso - September 2026

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10 days of la dolce vita, pronto. This one is pure Italian travel, covering all the big bucket-list destinations of Venice, Florence & Rome, plus the smaller charms of Pisa, Verona, and Siena. We'll ooh and aah over antipasto & chianti, dine on regional specialities in local trattorias, boat through the canals and islands of Venice, and explore the architecturally magnificent city of Florence. Expect plenty of world-famous espresso & pizza on the way.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Cinque T

Rome, Venice, Florence, Cinque Terre, Milan

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Duration10 days

From

USD 2,035

USD 1,875

Saving

USD 160

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Rome, Florence & Venice - 8 days - September 2026

(1 review )

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COACH TOUR: Take in the best of central Italy on this 8-day group tour which starts and ends in Rome. Explore the capital, visit medieval Siena, and relax in the Tuscan town of Montepulciano. Marvel at the stunning Renaissance architecture of Florence, enjoy a stroll around Bologna and visit Padua. Discover the highlights of Venice on a walking tour and skip the line at the Vatican City to see St Peter's Basilica and the impressive Sistine Chapel.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Florence, Venice

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Duration8 days

From

USD 2,235

USD 1,900

Saving

USD 335

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Italian Escape - September 2026

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This all-Italian adventure kicks off in the historic heart of Rome, then heads to Naples—the birthplace of pizza. You'll explore the perfectly preserved ruins of Pompeii before soaking up the sun and sipping limoncello along the stunning Amalfi Coast (with a stop in postcard-perfect Sorrento, of course). By the end of this unforgettable 6-day Italian escape, you'll have a belly full of pizza, a camera full of memories, and a serious craving to come back for more.

Food tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Pisa

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Duration6 days

From

USD 1,331

USD 1,227

Saving

USD 104

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Ancient Sicily - September 2026

4.7

(18 reviews )

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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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Wonders of Italy - September 2026

4.7

(95 reviews )

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Very laid back and easy with two days in most places and a good quantity of free time. Fantastic tour director who kept her flock in control. Driver was phenomenal and a pleasure to talk to. As always there is too much to see and remember so picture taking is essential.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Lucca, Florence, Venice, Assisi

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Duration11 days

From

USD 3,075

USD 2,606

Saving

USD 469

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Italian Escapade - September 2026

4.8

(76 reviews )

No booking fees

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It was a very busy itinerary but in knew it would be in order to see so many wonderful sites in Italy! Fantastic trip!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Capri, Florence

Rome, Sorrento, Capri, Florence, Lake Maggiore, Venice, Assisi

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Duration13 days

From

USD 6,795

USD 6,407

Saving

USD 388

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Best of Italy - September 2026

(1 review )

Trip customizable

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Christina organized a fantastic first class itinerary for a 28 day tour of Italy by my wife and me. She was very personable and generous with her time and very knowledgeable of the areas we visited. The trip included incredible private tours with top notch guides and smooth transfers all the way. Any minor glitches were handled promptly and professionally. It was a wonderful experience and we look forward to working with her again in the future.

Culture shows and excursions

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Palermo

Rome, Florence, Venice, Palermo, Agrigento, Sicily, Taormina, Sorrento

Duration17 days

From

USD 4,596

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Mamma Mia! Best Of Italy - September 2026

4.7

(19 reviews )

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My husband and I brought our entire family on this vacation to celebrate our 50th wedding anniversary. Great trip, the best way to see much of Italy in a short time - 8 days. The country, food and people are wonderful in Italy. Our tour guide was great! I highly recommend.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english

Destinations

Rome, Venice, Sorrento, Florence

10% OFF TODAY

Duration10 days

From

USD 3,400

USD 3,060

Saving

USD 340

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Discovering Rome - September 2026

Trip customizable

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Rome is a fabulous mix of history, archaeology, art, religion, and delicious food; and it certainly is the most popular place to visit in Italy. Truth is, Rome is a city that hardly leaves you indifferent. It's the kind of place you either love or hate – and most inevitably love it.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Rome

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Duration4 days

From

USD 1,350

USD 1,147

Saving

USD 202

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Ultimate Italy - September 2026

(1 review )

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Best price guaranteed

I met some amazing people and saw so many incredible sights in Italy! This trip exceeded my expectations!

Chill outAdventure

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Naples, Amalfi, Ca

Rome, Venice, Naples, Amalfi, Catania, Taormina, Syracuse, Cefalu, Florence, Palermo, Cinque Terre, Milan

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Duration22 days

From

USD 4,485

USD 4,140

Saving

USD 345

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Tuscany Escape, Semi-private Tour - September 2026

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Tuscany Escape, Semi-private Tour - September 2026

Trip customizable

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Tuscany is brimming with secluded valleys, magnificent rolling hills and majestic medieval villages boasting bustling restaurants, piazzas and ancient narrow cobble-stoned streets. Its rich landascape is complemented by towns overflowing with Reinassance art and architecture. Proud of its olive oil, there’s acclaimed gastronomy and, perhaps the best-know wine area, Chianti, is stunningly beautiful with gentle hills clocked by olive groves and vineyards and ancient castles and grand palazzi which have been magnificently restored as impressive hotels.

Art and architectureFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Florence, Gaiole In Chianti

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Duration7 days

From

USD 1,846

USD 1,569

Saving

USD 277

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Best of Sicily - September 2026

(1 review )

Trip customizable

Best price guaranteed

Venture on a transformative 10-day odyssey through the enchanting landscapes of Sicily, immersing yourself in the authentic tapestry of Italian life. Indulge your senses in a symphony of flavors, from the finest local olive oils to exquisite wines and succulent fruits harvested from ancient regal estates. Trace the footsteps of proud empires as you wander amidst the haunting ruins that whisper tales of a bygone era. Ascend to hilltop towns, where time seems to stand still, and lose yourself in the surreal beauty of Mount Etna's lunar-like lava fields. This journey promises not just a vacation, but a collection of cherished memories

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Catania

Campania, Sicily, Lazio, Catania, Taormina, Agrigento, Palermo

Duration10 days

From

USD 2,499

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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 3 of 120 Trips in Italy during September 2026 with 2,207 Reviews

See Italy tours by duration

Simply Italy - September 2026

Ultimate Italy - September 2026

Italian Espresso - September 2026

Rome, Florence & Venice - 8 days - September 2026

Italian Escape - September 2026

Ancient Sicily - September 2026

Wonders of Italy - September 2026

Italian Escapade - September 2026

Best of Italy - September 2026

Mamma Mia! Best Of Italy - September 2026

Discovering Rome - September 2026

Ultimate Italy - September 2026

Tuscany Escape, Semi-private Tour - September 2026

Best of Sicily - September 2026

Page 3 of 120 Trips in Italy during September 2026 with 2,207 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 3 of 120 Trips in Italy during September 2026 with 2,207 Reviews

See Italy tours by duration

Page 3 of 120 Trips in Italy during September 2026 with 2,207 Reviews