10 Best Italy Multiday Tours in September 2026

Country Roads Of Southern Italy And Sicily - September 2026

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Country Roads of Southern Italy and Sicily - September 2026

4.6

(74 reviews )

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It’s a wonderful itinerary however going to Rome and not visiting the San Pedro Basilica makes the itinerary less attractive.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Palermo, Catania

13% OFF TODAY

Duration14 days

From

USD 5,145

USD 4,492

Saving

USD 653

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Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - September 2026

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On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Stroll Assisi’s old city, and explore the Umbrian hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees. Visit Florence, the “Cradle of the Renaissance.” In Siena, stand inside one of Tuscany’s most ancient piazzas. Admire the famous towers of San Gimignano and hunt for truffles in the Umbrian countryside. Delight in regional specialties and Italian wine with every dinner. Feel like a local as you discover the marvels of wine, cuisine, culture, and history.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Tuscany, Chianti, Umbria

Rome, Tuscany, Chianti, Umbria, Pienza

Duration11 days

From

USD 3,749

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Lake Como Walking - September 2026

4.9

(24 reviews )

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This was a great holiday. The hotel was in a perfect location at the quieter northern end of Lake Como with beautiful views of the lake and the Alps. Walks were varied. Tour leader Kristians was excellent and the group all got on well.

Active and outdoor

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-79 yrs

Operated in

english

Destinations

Milan, Gravedona, Livo, Sorico

Milan, Gravedona, Livo, Sorico, Bellagio, Como, Dongo

Duration8 days

From

USD 2,490

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Italy: Highlights of Calabria - September 2026

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Embark on a journey through southern Italy, from Naples (the birthplace of pizza) to Sicily’s Catania, exploring the best spots along the way. For those seeking to venture off Italy’s beaten path, Calabria offers clear waters and the stalwart fortifications of Tropea, as well as active volcanoes on the Aeolian Islands. With plenty of opportunities to relax and soak up the Mediterranean sun by the seaside, you’ll also take a boat ride to the coves of Toarmina, indulge in local granita and maybe even take a dip in Sulphur springs. This trip promises a blend of culture, nature, history and cuisine – truly embodying the essence of Italy!

Sightseeing ToursVolcanoes

Tour Type

Small Group Tour

Accommodation

Guest House, Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Catania

Amalfi Coast & Campania, Catania, Minori, Naples, Civita, Tropea, Reggio Calabria

Duration9 days

From

USD 2,455

USD 2,381

Saving

USD 74

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Tuscan Escape - September 2026

(4 reviews )

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Great trip overall. The day trip were great. I wish the hotel was near a town or close to restaurants, but overall very great trip

Chill outLocal culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Lucca

Rome, Tuscany, Florence, Lucca, Montalcino

Duration7 days

From

USD 1,325

USD 1,285

Saving

USD 40

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25% OFF TODAY

Sizzling Sicily - 7 days - September 2026

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COACH TOUR: Spend seven days soaking up the history, flavours and scenery of Sicily on this round-trip tour from Palermo. Explore the UNESCO-listed cathedral of Monreale and wander the ancient streets of Palermo’s Old Town. Discover medieval Erice, taste wines in Marsala, and marvel at the Valley of the Temples in Agrigento. You’ll visit Baroque hill towns like Ragusa and Noto, stroll through historic Syracuse, and take in coastal charm in Taormina. A visit to Mount Etna adds a dramatic finish to this journey through Sicily’s cultural and natural treasures.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-80 yrs

Operated in

english

Destinations

Palermo, Taormina, Agrigento, Ra

Palermo, Taormina, Agrigento, Ragusa, Syracuse

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Duration7 days

From

USD 2,665

USD 1,999

Saving

USD 666

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Cycle Dolomites, Lake Garda and Verona - September 2026

4.8

(9 reviews )

No booking fees

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Another outstanding tour through Explore. Seeing the north of Italy by following the Adige River trail from Merano, and winding up with a full day in Venice, was simply epic. Riding into Verona to the Colosseum was magical. We had an excellent guide (Massimo) who was very skilled, with great sense of humour. We all laughed the entire journey. Most of the group had e-bikes, though the trails were fairly easy aside from a couple of hilly bits.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Hut

Age Range

16-99 yrs

Operated in

english

Destinations

Venice, Mestre, Merano, Bolzano

Venice, Mestre, Merano, Bolzano, Lake Caldaro, Lake Garda, Verona

Duration8 days

From

USD 2,900

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Cycle Puglia - September 2026

4.9

(21 reviews )

No booking fees

Best price guaranteed

Excellent from start to finish. Everything was so well organised, each day flowed seamlessly. Met a great bunch of people who I soon felt at home with and our tour leader, Fabio, went the extra mile to ensure everyone was happy and well catered for. As for the cycling, it's quite hilly in places so don't expect an easy ride (apart from the last day) but with the encouragement of Fabio and the rest of the group, I managed to get up most of them! Well done Explore for providing such a great trip!

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Hut

Age Range

16-99 yrs

Operated in

english

Destinations

Altamura, Monopoli, Matera, Albe

Altamura, Monopoli, Matera, Alberobello, Locorotondo, Savelletri

Duration8 days

From

USD 2,490

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Spotlight on Tuscany - September 2026

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Discover the rolling hills of Tuscany, home to sprawling vineyards, charming medieval hill towns, and enchanting cities. Savor a 7-night stay in Montecatini Terme, the famous resort and spa town. Visit Pisa, Florence, and San Gimignano, nestled in the Italian countryside. Discover the charming town of Lucca, Italy’s best-kept secret. Enjoy free time in Montecatini or see the Gothic Line of WWII and visit the Museum of Liberation. Explore the cultural treasures of Florence. Partake in a Tuscan cooking class. Sample cheese at the farm where it is made. Enjoy fabulous local wines and the region’s famous cuisine. Steeped in history, culture and legend, this is Tuscany as you always imagined it.

Art and architecture

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Montecatini Terme, Lucca, Floren

Montecatini Terme, Lucca, Florence, Pisa, Siena, San Gimignano

Duration9 days

From

USD 2,369

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Premium Sicily and Tuscany - September 2026

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Make your way to the Mediterranean to discover all the natural beauty, warm hospitality and cuisine Italy and Sicily have to offer. On this 17-day adventure, you’ll travel from Rome to postcard-perfect Venice. From visiting one of the Seven Wonders of the World – the Colosseum – to driving up the flank of Mount Etna, Europe’s largest active volcano, this trip goes the extra mile to deliver experiences that go beyond the guidebooks. Visit the famous spots like the Spanish Steps and Trevi Fountain, then go off the path to a local’s favourite restaurant. Get ready to tuck into local eats, explore iconic sites and brush up on your ancient history, all with an experienced local by your side.

Sightseeing ToursWalking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Rome, Chianti, San Gimi

Palermo, Rome, Chianti, San Gimignano, Florence, Venice, Marsala, Agrigento, Siracusa, Catania

Duration17 days

From

USD 10,714

USD 10,393

Saving

USD 321

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Barletta historic tour shore excursion - September 2026

Trip customizable

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Discover Barletta starting with a visit to the medieval castle of the eleventh century, founded by the Normans and expanded by the Spanish in the sixteenth century. Among the sculptures preserved in the castle, you can visit the bust of Emperor Frederick II Hohenstaufen of Swabia limestone, dating from the thirteenth century. Next, visit a historic winery, called the "House of Poison", is the building now known as the "Winery of the Challenge". It was here that was launched the challenge to a duel from 13 italian knights vs 13 French knights, fought in the countryside of the neighboring town of Trani. After the winery, you will discover the Cathedral of Santa Maria Maggiore of the twelfth century, the most important church in Barletta. The cathedral is divided into two parts, the front is typically Romanesque architectural style of the twelfth century, while the final part is of Gothic architectural style of the fourteenth century. The tour will end with a visit outside the palace of baroque architecture called "Della Marra" with paintings of the painter Giuseppe De Nittis and the visit of the bronze giant named Heraclius next to the Basilica of the Holy Sepulchre.

Walking tours

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, german, italian

Destinations

Barletta

Duration2 hours

From

USD 129

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Walking The Amalfi Coast - Summer Edition - September 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

The trip was fabulous -beautiful places , lovely hotel and friendly warm staff , excellent food wine and our leader Veriano was so kind engaging fun and made the trip even more enjoyable and our group was fabulous. Would go back tomorrow! Highly recommend it!

Trekking and HikingBeach

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Bomeran

Amalfi Coast & Campania, Bomerano, Atrani, Sorrento, Mount Vesuvius, Conca Dei Marini, Naples, Amalfi

Duration8 days

From

USD 2,175

USD 2,110

Saving

USD 65

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Mini Tour of Campania - Coastal Gems - September 2026

Trip customizable

Best price guaranteed

Begin in Salerno, where a warm welcome awaits. Explore the coastal gems of Positano and Amalfi, savoring the scenic beauty and local charm. Immerse yourself in the rich flavors of Campanian cuisine with a visit to a cheese factory for a delightful tasting. Unearth the historical treasures of Paestum, followed by a royal experience at the majestic Royal Palace of Caserta. Conclude your adventure in the vibrant city of Naples, where the fusion of history and modernity awaits. Each day promises a tapestry of experiences, creating lasting memories in the heart of southern Italy

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Salerno, Paestum

Duration5 days

From

USD 1,718

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Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - September 2026

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Best price guaranteed

Journey through a crossroads of civilizations in Sicily and on to the spectacular coastlines of Southern Italy. Uncover Sicily’s capital Palermo and its Moorish and Norman influences. Explore Agrigento’s ancient Valley of the Temples and the Ancient Roman mosaics of Piazza Armerina. Travel to the historic hilltop town of Taormina. Visit a local winery for a wine tasting and agriturismo dinner. Venture to the ancient cave dwellings of Sassi di Matera. Explore Sorrento and stunning Positano, the pearl of the Amalfi Coast. Walk in the footsteps of ancient Romans in the excavated Pompeii. Allow the unique culture to capture your heart and get a glimpse into an age-old heritage composed of ancient monuments and cultivated lands.

City sightseeing

Tour Type

Group Tour

Accommodation

Villa, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Palermo, Sicily

Rome, Sorrento, Palermo, Sicily, Agrigento, Giardini Naxos, Matera

Duration13 days

From

USD 3,949

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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 12 of 326 Trips in Italy during September 2026 with 6,357 Reviews

See Italy tours by duration

Country Roads of Southern Italy and Sicily - September 2026

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - September 2026

Lake Como Walking - September 2026

Italy: Highlights of Calabria - September 2026

Tuscan Escape - September 2026

Sizzling Sicily - 7 days - September 2026

Cycle Dolomites, Lake Garda and Verona - September 2026

Cycle Puglia - September 2026

Spotlight on Tuscany - September 2026

Premium Sicily and Tuscany - September 2026

Barletta historic tour shore excursion - September 2026

Walking The Amalfi Coast - Summer Edition - September 2026

Mini Tour of Campania - Coastal Gems - September 2026

Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - September 2026

Page 12 of 326 Trips in Italy during September 2026 with 6,357 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 12 of 326 Trips in Italy during September 2026 with 6,357 Reviews

See Italy tours by duration

Page 12 of 326 Trips in Italy during September 2026 with 6,357 Reviews