10 Best Italy Multiday Tours in September 2026

Alpine Elegance: Small Group Tour to the Dolomites - September 2026

Trip customizable

Best price guaranteed

Experience the magic of Northern Italy and the scenic Alps on this 9-day small group tour that combines elegant cities and breathtaking Alpine landscapes. Begin in Milan with a guided city tour and ride the world-renowned Bernina Express through dramatic mountain passes. Discover the lakeside charm of Peschiera del Garda, explore medieval towns like Bolzano, Merano, and Vipiteno, and savor the natural wonders of the Dolomites, including Lake Braies and Tre Cime di Lavaredo. With curated local experiences, this journey is perfect for travelers seeking culture, nature, and unforgettable views

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Bolzano, Merano, Cortina

Milan, Bolzano, Merano, Cortina, Dolomites

Duration9 days

From

USD 3,501

View Tour

Northern Lakes & the Dolomites with Bernina Expres - September 2026

Trip customizable

Best price guaranteed

Begin in Venice with its timeless charm, then explore historic Verona, the vineyards of Franciacorta, and the scenic beauty of Lake Garda and Lake Como. Ride the famous Bernina Express through the Swiss Alps, uncover Milan’s cultural gems, and journey through the elegant towns of Bolzano, Merano, and Cortina d’Ampezzo. With guided tours, wine tastings, scenic boat rides, and unforgettable landscapes, this immersive itinerary blends Italy’s refined heritage with natural beauty at every turn

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Venice, Cortina, Dolomite

Milan, Venice, Cortina, Dolomites, Bergamo, Bolzano, Merano

Duration13 days

From

USD 4,653

View Tour

Italy’s Lakes & Bernina Express: Small Group Tour - September 2026

Trip customizable

Best price guaranteed

Experience the best of Northern Italy and the Swiss Alps on this unforgettable 8-day small group tour. Explore the romantic canals of Venice, sip wine in Franciacorta, cruise across Lakes Garda and Como, and ride the iconic Bernina Express through breathtaking alpine landscapes. With guided city tours, scenic boat rides, and wine tastings, this journey blends culture, charm, and natural beauty—perfect for travelers seeking a relaxed yet enriching Italian escape

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Venice, Bergamo

Duration8 days

From

USD 2,648

View Tour

Classic Italy & the Dolomites - September 2026

Trip customizable

Best price guaranteed

From the historic wonders of Rome, Florence, and Venice to the chic elegance of Milan, discover Italy’s rich culture, art, and cuisine. Travel by train and coach through Bologna, Verona, and Lake Garda, then board the scenic Bernina Express into the Swiss Alps. Explore the enchanting Dolomites, picturesque lakes, and hidden gems like Bolzano, Cortina, and Bassano del Grappa. With guided tours, local tastings, and unforgettable scenery, this immersive itinerary offers the perfect blend of Italy’s classics and natural treasures

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Dolomites

Milan, Rome, Florence, Dolomites, Venice, Bolzano, Merano

Duration13 days

From

USD 4,940

View Tour

Italy’s Grand Tour - September 2026

Trip customizable

Best price guaranteed

Discover world-famous landmarks, medieval towns, and stunning natural landscapes while indulging in Italy’s rich culinary traditions. Explore ancient ruins in Rome, the masterpieces in Florence, and romantic canals in Venice. Journey through the lakes of Como and Garda, ride the scenic Bernina Express through the Swiss Alps, and wander the cultural treasures of Milan, Bolzano, and Cortina d’Ampezzo. With guided tours, regional delicacies, and unforgettable scenic drives, this grand tour offers the very best of Italy—perfectly crafted for travelers seeking a once-in-a-lifetime Italian experience

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome, Bolzano, Merano, Do

Milan, Rome, Bolzano, Merano, Dolomites, Florence, Venice, Bergamo

Duration17 days

From

USD 6,014

View Tour

Rome & Puglia Discovery: Small Group Experience - September 2026

Trip customizable

Best price guaranteed

Explore Rome at your own pace before heading south by high-speed train to discover charming whitewashed villages, UNESCO-listed wonders like Alberobello and Matera, dramatic coastal towns, and rich Baroque architecture. With guided tours, authentic regional cuisine, local wine tastings, and stays in handpicked accommodations, this itinerary offers a perfect blend of culture, history, and culinary delights—all wrapped in warm southern hospitality

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

Rome, Puglia, Bari, Alberobello

Rome, Puglia, Bari, Alberobello, Matera, Lecce

Duration11 days

From

USD 3,916

View Tour

Timeless Southern Italy: Rome, Sorrento & Puglia - September 2026

Trip customizable

Best price guaranteed

From the Eternal City of Rome to the sun-kissed shores of Sorrento and the enchanting island of Capri, the adventure continues across Puglia’s most iconic treasures—Alberobello’s Trulli, Matera’s ancient cave dwellings, Lecce’s baroque elegance, and the coastal charm of Otranto and Monopoli. With a mix of guided sightseeing, cultural experiences, and culinary delights, this 12-day tour offers the perfect balance of discovery and leisure through Italy’s most captivating southern landscapes

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

Bari, Rome, Lecce, Sorrento, Cap

Bari, Rome, Lecce, Sorrento, Capri, Alberobello, Matera

Duration12 days

From

USD 4,281

View Tour

Rome & Live Like a Local in a Tuscan Villa - September 2026

Trip customizable

Best price guaranteed

Experience Italy like never before with a stay at the historic Villa Casagrande, where rolling vineyards, timeless villages, and authentic Italian living await. This immersive journey blends comfort and culture—enjoy guided tours of Florence and San Gimignano, hands-on cooking classes, wine tastings, and free time to unwind in the villa’s gardens or by the pool. More than a tour, it’s your chance to live like a local in the heart of Tuscany from Rome

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Tuscany, Lucca, San Gimignano

Duration9 days

From

USD 2,341

View Tour

Best of Puglia: Small Group Tour - September 2026

Trip customizable

Best price guaranteed

Discover the heart of Puglia on a perfectly paced tour that blends history, charm, and culture. From the lively streets of Bari to the fairytale Trulli of Alberobello, the cave city of Matera, the elegant baroque towns of Lecce and Martina Franca, and the coastal gems of Otranto and Monopoli — this immersive experience showcases the best of Italy’s hidden south. With UNESCO sites, whitewashed hilltowns, and panoramic Adriatic views, this is Southern Italy at its finest

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

Bari, Alberobello, Lecce

Duration8 days

From

USD 2,985

View Tour

Super Sales

Simply Italy Reunion 35 to 45 - September 2026

No booking fees

Best price guaranteed

Welcome to 15 days of pure Italian travel immersion with your squad of awesome 35-45 year old travellers. Covering Rome, Florence, Milan, 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 or the picture perfect Positano for your summery soul. 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!

City sightseeing

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

Duration15 days

From

USD 3,035

USD 2,944

Saving

USD 91

View Tour

Puglia Express: 5 Days of Southern Charm - September 2026

Trip customizable

Best price guaranteed

Begin in Bari and transfer to the Itria Valley for a warm welcome and dinner. Explore the Grotte di Castellana, the trulli houses of Alberobello, and the “white city” of Ostuni. Visit Lecce, the “Florence of the South,” and the historic treasures of Otranto. Experience the unique Sassi neighborhoods of Matera before concluding your adventure in the Bari area. Enjoy a perfect blend of history, culture, and stunning landscapes throughout this unforgettable tour

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Bari, Itria Valley

Duration5 days

From

USD 1,360

View Tour

Sicily Art, Food & Wine Tour - September 2026

15% OFF TODAY

Super Sales

Sicily Art, Food & Wine Tour - September 2026

Trip customizable

Best price guaranteed

This 8-day tour of Sicily starts in the vibrant city of Catania and takes you on a journey through the island’s most stunning destinations. Begin by exploring the charming town of Tindari and the picturesque coastal village of Cefalu before heading to Palermo and Erice where you’ll enjoy a visit to a traditional winery for a delightful wine tasting. Continue your adventure with a visit to the ancient archaeological site of Selinunte, followed by a stop in Agrigento to marvel at the Valley of the Temples. The tour also includes stops in the baroque city of Noto, the historical treasures of Siracusa and Ortigia, and ends with a visit to Taormina, where you’ll indulge in a tasting experience while soaking in the scenic beauty of this iconic hilltop town.

Art and architectureFood tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Catania, Palermo, Agrigento, Cal

Catania, Palermo, Agrigento, Caltagirone, Taormina

15% OFF TODAY

Duration8 days

From

USD 3,288

USD 2,795

Saving

USD 493

View Tour

Food And Walking On The Amalfi Coast, Small Group Tour - September 2026

15% OFF TODAY

Super Sales

Food And Walking On The Amalfi Coast, Small Group Tour - September 2026

Trip customizable

Best price guaranteed

Embark on an unforgettable journey along the Amalfi Coast, where tradition, adventure, and technology converge in a single tour. Experience the flavours of Southern Italy as you dine on traditional Neapolitan pizza, enjoy creamy limoncello gelato, and feast on the freshest seafood from the Tyrrhenian Sea. Explore local markets, discover the art of pasta making, and indulge in wine tastings at scenic vineyards. Lace up your hiking boots for breathtaking adventures along rugged coastal paths, guided by experts through lemon groves, wildflower meadows, and nature reserves. Capture stunning vistas of the Gulf of Naples, Mount Vesuvius, and the Amalfi Coast, ensuring unforgettable memories. This tour offers a fusion of culinary delights and outdoor exploration, providing a well-rounded and captivating experience on the breathtaking Sorrento Coast. Join our eight-day small group tour of up to 16 people for an unforgettable experience.

Active and outdoorAdventure

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

20-99 yrs

Operated in

english

Destinations

Naples, Agerola, Positano, Pompe

Naples, Agerola, Positano, Pompeii, Sorrento, Capri

15% OFF TODAY

Duration8 days

From

USD 2,096

USD 1,782

Saving

USD 314

View Tour

27% OFF TODAY

Super Sales

European Escapade - September 2026

4.9

(27 reviews )

No booking fees

Best price guaranteed

Loved the whole experience- visited all the best countries in Europe, tasted wines, spirits and other European alcohol In cheapest prices. It’s not suitable for asians with dark skin and if you’re over 34 yrs old unless you have a thick skin to not give any reaction to the comments some people make as a joke- only because they are white and still young. Not sure what they are so proud about in those moments. Other than that I enjoyed my time with rest of them. The price was on discount- I had to add on some extra adventures which worth it. Honestly 24 days is finished so quickly. Recommend to all the people who like explore Europe more in less time in cheaper price. Great work contiki, I am on my second one now- in Thailand, this group of approx 30 people is much better than European escapades (just my personal experience).

City sightseeing

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort, Guest House

Age Range

18-35 yrs

Operated in

english

Destinations

London, Paris, Lucerne, Lyon, Ba

London, Paris, Lucerne, Lyon, Barcelona, French Riviera, Florence, Rome, Venice, Vienna, Munich, Prague, Berlin, Amsterdam, Beaujolais

27% OFF TODAY

Duration24 days

From

USD 4,232

USD 3,079

Saving

USD 1,153

View Tour

Combine Italy in September with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

View Tours

Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

All Italy Tours in September 2026

Page 10 of 152 Trips in Italy during September 2026 with 2,573 Reviews

See Italy tours by duration

Alpine Elegance: Small Group Tour to the Dolomites - September 2026

Northern Lakes & the Dolomites with Bernina Expres - September 2026

Italy’s Lakes & Bernina Express: Small Group Tour - September 2026

Classic Italy & the Dolomites - September 2026

Italy’s Grand Tour - September 2026

Rome & Puglia Discovery: Small Group Experience - September 2026

Timeless Southern Italy: Rome, Sorrento & Puglia - September 2026

Rome & Live Like a Local in a Tuscan Villa - September 2026

Best of Puglia: Small Group Tour - September 2026

Simply Italy Reunion 35 to 45 - September 2026

Puglia Express: 5 Days of Southern Charm - September 2026

Sicily Art, Food & Wine Tour - September 2026

Food And Walking On The Amalfi Coast, Small Group Tour - September 2026

European Escapade - September 2026

Page 10 of 152 Trips in Italy during September 2026 with 2,573 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 10 of 152 Trips in Italy during September 2026 with 2,573 Reviews

See Italy tours by duration

Page 10 of 152 Trips in Italy during September 2026 with 2,573 Reviews