10 Best Italy Multiday Tours in September 2026

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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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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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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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A Taste of Italy: 11 Days - Classic - September 2026

Trip customizable

Best price guaranteed

Traveling from eternal Rome and up through the hazy hills of Tuscany, you’ll spend eleven days sampling the best of Assisi, Siena, Florence, Bologna, Venice, the Tuscan wine region, and Capri! Catch the spirit of la vita bella as you explore elegant Florentine piazzas, rummage through handcrafted artisanal treasures, sip world-class wines, and float down intimate Venetian canals. You will then discover the treasures along Italy’s Amalfi Coast, to sun-bleached Capri before returning to Rome!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Lazio, Sorrento

Duration11 days

From

USD 2,348

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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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8% OFF TODAY

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Simply Italy - September 2026

No booking fees

Best price guaranteed

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

8% OFF TODAY

Duration15 days

From

USD 2,755

USD 2,538

Saving

USD 217

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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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8% OFF TODAY

Super Sales

Italian Espresso - September 2026

No booking fees

Best price guaranteed

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

8% OFF TODAY

Duration10 days

From

USD 2,035

USD 1,875

Saving

USD 160

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Sicily Grand Tour - September 2026

4.4

(12 reviews )

No booking fees

Best price guaranteed

The 15 day tour of Sicily was absolutely fantastic. The best tour guide ever, her name is Milena. A wonderful driver Alessandro. I felt that it was a pretty comprehensive tour of Sicily seeing all the highlights plus more. Fabulous food in restaurants where we ere taken by Milena. Verdict EXCELLENT.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Catania, Taormina, Palermo, Cefa

Catania, Taormina, Palermo, Cefalu, Mount Etna, Syracuse, Sicily, Modica, Piazza Armerina, Trapani

Duration15 days

From

USD 4,800

USD 4,656

Saving

USD 144

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15% OFF TODAY

Rome, Florence & Venice - 8 days - September 2026

(1 review )

No booking fees

Best price guaranteed

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

15% OFF TODAY

Duration8 days

From

USD 2,235

USD 1,900

Saving

USD 335

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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 287 Trips in Italy during September 2026 with 6,301 Reviews

See Italy tours by duration

Cycling in Sicily - September 2026

Italy Explorer - September 2026

La Dolce Vita Experience - September 2026

Splendid Amalfi Coast - Small-Group Tour - September 2026

Grand Italian Experience - September 2026

Classical Sicily - September 2026

A Taste of Italy: 11 Days - Classic - September 2026

Highlights of Southern Italy & Sicily - September 2026

Easy Pace Italy - September 2026

Simply Italy - September 2026

Ultimate Italy - September 2026

Italian Espresso - September 2026

Sicily Grand Tour - September 2026

Rome, Florence & Venice - 8 days - September 2026

Page 4 of 287 Trips in Italy during September 2026 with 6,301 Reviews

Combine Italy in September with Nearby Countries for an Unforgettable Trip

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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 287 Trips in Italy during September 2026 with 6,301 Reviews

See Italy tours by duration

Page 4 of 287 Trips in Italy during September 2026 with 6,301 Reviews