10 Best Italy Multiday Tours in September 2026

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Grand Italy & Sicily - September 2026

4.7

(77 reviews )

No booking fees

Best price guaranteed

It covers so many areas in Italy We got exposed to so much history and culture

Wine tasting tours

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Palermo, Sorrento, Capri

Rome, Palermo, Sorrento, Capri, Alberobello, Giardini Naxos, Santa Margherita, Portofino, Lake Maggiore, Venice, Florence

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Duration17 days

From

USD 8,250

USD 6,993

Saving

USD 1,257

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Southern Pearls (on Request) - September 2026

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Southern Pearls (on Request) - September 2026

Trip customizable

Best price guaranteed

Drive through some of Italy's most iconic locations on this five-day tour that takes you through Naples, Pompeii, Sorrento and Capri. Spend the second half of the tour explore the wonderful coastal town of Positano at leisure. Relax at the hotel, discover the breath-taking surroundings, or even plunge into the warm waters of the Mediterranean.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Rome, Sorrento, Positano

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Duration5 days

From

USD 3,352

USD 2,849

Saving

USD 503

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Art Cities Of Italy, Private Tour - September 2026

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Art Cities Of Italy, Private Tour - September 2026

(1 review )

Trip customizable

Best price guaranteed

They did a great job with everything!

Art and architectureHoneymoon

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Rome, Florence, Venice, Milan

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Duration8 days

From

USD 3,364

USD 2,859

Saving

USD 505

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Explore Italy - 4 Days - September 2026

(1 review )

Trip customizable

Best price guaranteed

Our trip was absolutely wonderful! I would like to thank our tour guide, for taking great care of everything. We had something planned every day and the group that travelled with us was so friendly. Everything worked out beautifully. We made memories that will last a lifetime!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-90 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Siena, Bologna, Padua, Venice & Veneto

Duration4 days

From

USD 1,630

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Naples Escape & Sorrento (on Request) - September 2026

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Naples Escape & Sorrento (on Request) - September 2026

(1 review )

Trip customizable

Best price guaranteed

We just returned from a wonderful trip to Italy. Grazia helped plan our trip. She provided excellent advice before and during our journey. We will definitely use TUI Italy again!

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Naples, Sorrento, Rome

15% OFF TODAY

Duration5 days

From

USD 1,976

USD 1,680

Saving

USD 296

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Discovering Lecce - September 2026

Trip customizable

Best price guaranteed

A mesmerizing feast of baroque architecture, Lecce dazzles the eye with its resplendent historical center, which is lined with buildings from the 17th and 18th centuries. You’ll find dozens of striking churches and palazzi, along with a Norman-style castle and a trove of excellent museums. Lecce has been inhabited for over 2000 years, and you can see ancient Roman ruins in a horseshoe-shaped amphitheatre that once held 15,000 spectators.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, italian

Destinations

Lecce

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Duration4 days

From

USD 1,048

USD 890

Saving

USD 157

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Rome & La Dolce Vita Experience - September 2026

Trip customizable

Best price guaranteed

Experience a delectable journey through Rome's Trastevere district, guided by a culinary expert. Savor authentic Roman cuisine amidst historic surroundings. Explore the Vatican's treasures with a knowledgeable guide, enjoying VIP access to the Vatican Museums. Journey from Rome to Pompeii, encountering charming medieval villages along the route. Unearth the haunting ruins of Pompeii, frozen in time by Mt. Vesuvius's eruption. Conclude with a revitalizing coastal escape in Sorrento and Capri, immersing in the rejuvenating sea breeze and captivating vistas

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Lazio, Sorrento

Duration6 days

From

USD 1,864

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Rome And Tuscan Highlights - September 2026

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Rome and Tuscan Highlights - September 2026

4.7

(51 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

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Duration9 days

From

USD 2,750

USD 2,357

Saving

USD 393

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Discovering Palermo - September 2026

Trip customizable

Best price guaranteed

Explore Sicily's largest city during this short four-day trip. Enjoy this lively and thriving city with an amazing blend of cultures and glorious food. You'll discover the charm of Palermo, a layered metropolis with centuries of Arab, Norman, Byzantine and Mediterranean influences. With a local expert, learn about the city's history, art, and architecture.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Palermo

15% OFF TODAY

Duration4 days

From

USD 950

USD 807

Saving

USD 142

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Northern Italy Including Cinque Terre - September 2026

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Northern Italy Including Cinque Terre - September 2026

4.5

(98 reviews )

No booking fees

Best price guaranteed

Very enjoyable, with a variety of interesting locations.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Italian Riviera

Milan, Baveno, Italian Riviera, Cinque Terre, Lake Maggiore

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Duration8 days

From

USD 2,395

USD 2,021

Saving

USD 374

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Discovering Taormina - September 2026

Trip customizable

Best price guaranteed

Taormina is a synonym of sea and sun, ancient history, and atavistic cultures. It's one of the most evocative cities of Sicily, with its gaze turned to the Ionian Sea and its soul enraptured by Isola Bella. Climb the magnificent Mt Etna volcano and cruise along the Sicilian coast during this short four-day tour.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, italian

Destinations

Taormina

15% OFF TODAY

Duration4 days

From

USD 758

USD 645

Saving

USD 114

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Charming Costiera (on Request) - September 2026

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Charming Costiera (on Request) - September 2026

Trip customizable

Best price guaranteed

Discover the Sorrento peninsula and the isle of Capri on this six-day tour beginning and ending in Rome. Along the way, stop to absorb the history of Naples and jump back in time by visiting the ghostly excavations of Pompeii. The Sorrento peninsula is easily one of the country's most lavish and beautiful regions, ideal for relaxing and sightseeing alike.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Naples, Sorrento, Amalfi, Rome

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Duration6 days

From

USD 2,486

USD 2,113

Saving

USD 373

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Best Of Italy And Sicily - September 2026

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Best of Italy and Sicily - September 2026

4.7

(55 reviews )

No booking fees

Best price guaranteed

The Hotel were ok but did not cater to the tourist. The rooms did not have the use of the fans and found the air stagnant. A little air moving would helped. The Hotel in Sicily in Jiardini Naxos, Caeser palace, found the hotel desk determinitly unhelpful.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Palermo, Assisi, L

Rome, Venice, Palermo, Assisi, La Spezia, Florence, Monreale, Agrigento, Taormina, Sorrento, Capri, Vatican City

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Duration15 days

From

USD 5,225

USD 4,422

Saving

USD 803

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Discovering Syracuse - September 2026

Trip customizable

Best price guaranteed

A tour of Siracusa, located on the southeastern coast of Sicily, offers a rich blend of ancient history, stunning architecture, and vibrant local culture. Climb the magnificent Mt Etna volcano, taste some local culinary delights and discover the historic center of Syracuse and Taormina during this short four-day tour.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Syracuse

15% OFF TODAY

Duration4 days

From

USD 822

USD 698

Saving

USD 123

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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 5 of 129 Trips in Italy during September 2026 with 2,222 Reviews

See Italy tours by duration

Page 5 of 129 Trips in Italy during September 2026 with 2,222 Reviews

Grand Italy & Sicily - September 2026

Southern Pearls (on Request) - September 2026

Art Cities Of Italy, Private Tour - September 2026

Explore Italy - 4 Days - September 2026

Naples Escape & Sorrento (on Request) - September 2026

Discovering Lecce - September 2026

Rome & La Dolce Vita Experience - September 2026

Rome and Tuscan Highlights - September 2026

Discovering Palermo - September 2026

Northern Italy Including Cinque Terre - September 2026

Discovering Taormina - September 2026

Charming Costiera (on Request) - September 2026

Best of Italy and Sicily - September 2026

Discovering Syracuse - September 2026

Combine Italy in September with Nearby Countries for an Unforgettable Trip

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North America

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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 5 of 129 Trips in Italy during September 2026 with 2,222 Reviews

See Italy tours by duration

Page 5 of 129 Trips in Italy during September 2026 with 2,222 Reviews