10 Best Italy Multiday Tours in September 2026

Cycle the Full Via Francigena - Aosta to Rome - September 2026

(1 review )

No booking fees

Best price guaranteed

An amazing trip, seeing so many different sides of Italy, the main tourist centres, but the rural villages. Fantastically organised and supported when things went wrong (personal injury). Highly recommend this trip for adventurers.

Bicycle toursExplorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Turin, Piedmont & Valle d’

Rome, Turin, Piedmont & Valle d’Aosta, Aosta Valley, Aosta, Berceto, Aulla, Massa, Lucca, San Miniato Alto, San Gimignano, Siena, San Quirico d'Orcia, Radicofani, Bolsena, Saint Bernardo Pass, Viterbo, Sutri, Formello, Verres, Viverone, Vercelli, Vigevano, Pavia, Piacenza, Parma

Duration24 days

From

USD 6,150

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Fantasia Italiana - September 2026

Trip customizable

Best price guaranteed

Travelling from eternal Rome and up through the hazy hills of Tuscany, you’ll spend five days sampling the best of Assisi, Siena, Florence, Bologna, Venice, and Montepulciano. 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. Experience a taste of Italy with us!

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration5 days

From

USD 1,005

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Tuscan Adventure: Rome To Florence - September 2026

22% OFF TODAY

Super Sales

Tuscan Adventure: Rome to Florence - September 2026

No booking fees

Best price guaranteed

Immerse yourself in the ancient grandeur of Rome and Florence's Renaissance masterpieces on this seven-day Italian adventure. Your CEO (Chief Experience Officer) will lead you through cobblestone streets while you sample local delicacies, sip wine in Montepulciano, and walk in ancient footsteps through the medieval city of Siena. Your heart and your tastebuds will both be equally grateful.

Explorer

Tour Type

Small Group Tour

Accommodation

Villa, Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Florence, Montepulciano

22% OFF TODAY

Duration7 days

From

USD 1,849

USD 1,435

Saving

USD 414

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27% OFF TODAY

Central & Eastern Europe Explorer - September 2026

No booking fees

Best price guaranteed

Experience the very best of Central & Eastern Europe on this 15-day guided group tour! Uncover hidden gems, be captivated by vibrant capital cities, indulge in delicious cuisine and see famous historical sights up close. Natural beauty abounds from the Swiss Alps and the Bavarian countryside to the Italian Lake District. Wander the fairytale streets of Vienna, Budapest and Prague. Cruise along the Venice canals, admire Renaissance art in Florence and discover the many highlights of Munich. Explore Bratislava, Neuschwanstein Castle, Melk Abbey and much more on this unmissable journey!

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Munich, Vienna, Budapest, Prague

Munich, Vienna, Budapest, Prague, Innsbruck, Swiss Alps, Lake Como, Montecatini, Venice

27% OFF TODAY

Duration15 days

From

USD 3,185

USD 2,325

Saving

USD 860

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15% OFF TODAY

Super Sales

Discovering Bologna - September 2026

Trip customizable

Best price guaranteed

Embark on a delightful four-day tour of Bologna, where you'll immerse yourself in the city's rich culinary and cultural heritage. Start your adventure with a cooking class led by a local Cesarina, learning the secrets of traditional Bolognese cuisine. Explore the city's historic and picturesque streets on a guided bike tour, experiencing its vibrant atmosphere and architectural wonders. Discover the excitement of Italy's famous Motor Valley, home to legendary car brands like Ferrari and Lamborghini, with exclusive visits to museums and factories. This tour offers a perfect blend of gastronomic indulgence, cultural exploration, and automotive passion.

Art and architectureExplorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, italian

Destinations

Bologna

15% OFF TODAY

Duration4 days

From

USD 913

USD 776

Saving

USD 137

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Super Sales

Best of Northern Italy: Florence to Venice - September 2026

No booking fees

Best price guaranteed

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Florence, Venice, Cinque Terre, Lake Como

Duration8 days

From

USD 1,999

USD 1,939

Saving

USD 60

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Italy: Pasta & Piazzas - September 2026

4.6

(102 reviews )

No booking fees

Best price guaranteed

Some of the food that was pre paid for was really average and not all that great.

Explorer

Tour Type

Small Group Tour

Accommodation

Hostel, Hotel, Villa

Age Range

18-39 yrs

Operated in

english

Destinations

Rome

Duration14 days

From

USD 2,669

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Sardinian Splendours: A 7-Day Small Group Tour - September 2026

Trip customizable

Best price guaranteed

Discover the heart and soul of Sardinia on this 7-day small group journey, from historic Cagliari to the luxurious Costa Smeralda—featuring vibrant cities, traditional shepherds’ feasts, ancient Nuragic sites, and breathtaking coastal views. Along the way, explore hilltop villages, immerse yourself in Sardinian culture, and savor the island’s rich culinary heritage with local food and wine experiences. With handpicked accommodations, seamless transportation, and expert local guides, this tour offers an unforgettable blend of authenticity, comfort, and discovery

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Cagliari, Olbia, Alghero

Duration7 days

From

USD 2,427

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Secrets of Puglia - September 2026

4.6

(70 reviews )

No booking fees

Best price guaranteed

We wouldn’t hesitate to recommend Back Roads for a small group interesting tour. Our guide Sylvia was excellent looking after our needs and provided wonderful communication. Our driver was skilful and safe. The accomodation was always interesting and comfortable. The towns were a highlight and staying two nights in several places was a real bonus. You need to be quite fit and able to manage steps and stairs comfortably.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Naples, Polignano A Mare, Lecce

Naples, Polignano A Mare, Lecce, Itria Valley, Matera

Duration9 days

From

USD 3,609

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Rome Revealed: A Classic City Break - September 2026

Trip customizable

Best price guaranteed

Discover the timeless charm of Rome with this 3-night city break, featuring 4-star accommodation and daily breakfast. Enjoy seamless private transfers to and from the airport or train station, and immerse yourself in the city’s rich history with guided tours of the Vatican Museums and the Sistine Chapel, as well as the Roman Forum, Palatine Hill, and Colosseum. With entrance tickets, professional guides, and headsets included, this package offers an unforgettable journey through the Eternal City

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome

Duration4 days

From

USD 804

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Flavours of Tuscany & Cinque Terre - September 2026

Trip customizable

Best price guaranteed

Experience the best of Italy with this 8-day tour, staying in Rome, Florence, and the charming Monterosso al Mare. Explore Rome’s rich history with a 24-hour Hop-On Hop-Off ticket. Enjoy a scenic half-day tour from Florence to the Chianti region, complete with wine and olive oil tastings. Discover the stunning beauty of Cinque Terre with a 48-hour Train Card. Your journey includes a private airport transfer in Rome and high-speed train travel between cities, offering the perfect balance of guided tours and independent exploration

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, Montero

Rome, Florence, Tuscany, Monterosso, Cinque Terre

Duration8 days

From

USD 1,364

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Essence of Italy: Rome, Sorrento, and Venice - September 2026

Trip customizable

Best price guaranteed

Begin your journey with a private transfer from Rome's airport to your hotel, followed by a half-day guided small group tour of the Colosseum and Roman Forum. Travel by high-speed train to Naples, where you'll enjoy a private transfer to Sorrento with a 2-hour stop to explore Pompeii. In Sorrento, take an excursion to the enchanting Capri Island, including a visit to the Blue Grotto. Continue to Florence via high-speed train, and immerse yourself in the city's rich history. Conclude your Italian adventure in Venice, with a gondola ride through its picturesque canals

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Sorrento

Rome, Florence, Venice, Sorrento, Capri

Duration9 days

From

USD 2,578

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A Taste of Italy: 8 Days - Classic - September 2026

Trip customizable

Best price guaranteed

Like a creamy gelato or hot espresso, one taste of Italy can linger for a lifetime. Travelling from the Eternal City of Rome and up through the hazy hills of Tuscany, you’ll spend eight days sampling the best of Assisi, Siena, Florence, Bologna, Venice, and Montepulciano. 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

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration8 days

From

USD 1,529

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Rome Florence Venice and Milan by Rail - September 2026

Trip customizable

Best price guaranteed

This tour will take you on a memorable train ride across the major touristic cities of Italy. You’ll begin by exploring Rome, with stunning feats of civilization, modern and age-old alike. Colosseum, Navona Square, Pantheon, Spain Square, and Trevi Fountain are a few places that you can visit. The next place where you’ll take a train would be Florence. History, art, countryside, and delicious food are the gist of what this capital city of Tuscany has in store for you. Accademia and Uffizi Galleries are a must-visit. After Florence, The City of Water, Venice, awaits your arrival. Though the journey to Venice via rail is gorgeous, the city itself has its charm. Riding into a gondola through the Grand Canal and being mesmerized by the city’s beauty should be on your list. In addition, take a walking tour covering St Mark’s Square, Doge's Palace, Bell Tower, etc. Finally, we are at the last city of this train tour—Milan. An epitome of great fashion and design, Milan is a heart stealer. Apart from the latest cultural trends, you can even get a slice of history by visiting the Milan Cathedral. Also, ensure not to miss Leonardo Da Vinci’s stupefying Cenacolo, the Last Supper, which is one of the most famous artworks in the world. This train journey is one of the most popular Italy travel packages, offering a comprehensive tour of Italy's iconic cities.

Explorer

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Milan, Rome, Florence, Venice

Duration9 days

From

USD 1,102

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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

95 Trips in Italy during September 2026 with 715 Reviews

See Italy tours by duration

95 Trips in Italy during September 2026 with 715 Reviews

Cycle the Full Via Francigena - Aosta to Rome - September 2026

Fantasia Italiana - September 2026

Tuscan Adventure: Rome to Florence - September 2026

Central & Eastern Europe Explorer - September 2026

Discovering Bologna - September 2026

Best of Northern Italy: Florence to Venice - September 2026

Italy: Pasta & Piazzas - September 2026

Sardinian Splendours: A 7-Day Small Group Tour - September 2026

Secrets of Puglia - September 2026

Rome Revealed: A Classic City Break - September 2026

Flavours of Tuscany & Cinque Terre - September 2026

Essence of Italy: Rome, Sorrento, and Venice - September 2026

A Taste of Italy: 8 Days - Classic - September 2026

Rome Florence Venice and Milan by Rail - September 2026

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

95 Trips in Italy during September 2026 with 715 Reviews

See Italy tours by duration

95 Trips in Italy during September 2026 with 715 Reviews