10 Best Italy Multiday Tours in September 2027

Get a customized trip to Italy in September 2027

Plan a multi-country or regional adventure across Italy in September 2027, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Enrico Maria MalacarneTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Simon H.Travel Expert in Belgium, France, Italy & Switzerland

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Super Sales

Best of Northern Italy: Florence to Venice - September 2027

(4 reviews )

No booking fees

Best price guaranteed

The overall experience was a lot of fun. We were busy the entire time, and with the great organization managed to see a whole lot of Northern Italy within such a small amount of time. We were very nicely taken care of by our CEO. She was extremely responsive and helpful when any questions came her way, and she absolutely loved when people asked questions about Italy and it's storied history. Great trip!

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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Super Sales

Premium Puglia - September 2027

No booking fees

Best price guaranteed

Dreamy beaches, inspiring architecture and ancient wonders come together on an eight-day Premium adventure through Italy’s Puglia region. Understated and unbelievably beautiful, this lesser-visited corner of Italy delivers in historical, cultural and natural sights. Begin in the coastal town of Bari, admire unusual trulli buildings in Alberobello, stay in a former palace in Nardo, explore ancient sassi homes in Matera and discover the well-preserved ruins of Pompeii. With a local leader by your side and expert guides joining you along the way, you’ll really get a kick out of this adventure.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Bari, Naples, Polignano A Mare

Bari, Naples, Polignano A Mare, Nardò, Matera

Duration8 days

From

USD 4,890

USD 4,743

Saving

USD 147

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Super Sales

Walks & Food of the Italian Riviera - September 2027

No booking fees

Best price guaranteed

The Italian Riviera still has secrets to share… if you know where to go. One of them is seaside Chiavari, ideally placed between Genoa and the Cinque Terre. From this base, we embark on a well-balanced blend of scenic walks, cultural landmarks and exquisite regional cuisine. You’ll sip wine with world-renowned producers, master pasta and pesto with professional chefs, and hike glorious trails. A free day to visit the Cinque Terre will be a must for most, while the pleasure of staying away from the tourists allows you to enjoy the Italian Riviera in peace. One of Our Top Recommend Trips for 2026… Here’s Why Forbes recently said Chiavari is ‘so delightful, authentic and complete as a holiday destination you can’t help but wonder why it hasn’t yet exploded with international travellers.’ I couldn’t agree more. If you want to explore the Riviera with the benefit of staying in Chiavari, 2026 is the time to go! − Hope Johnson, destination expert

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Genoa, Chiavari, Cinque Terre, Palmaria

Duration7 days

From

USD 3,600

USD 3,492

Saving

USD 108

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Super Sales

Premium Walking & Hiking on Italy's Amalfi Coast - September 2027

No booking fees

Best price guaranteed

Lace up your hiking boots and set your sights towards the spectacular Mediterranean horizon. This seven-day Premium walking and hiking trip on the Amalfi Coast features the best of the short hikes in the area, and is a nature-lover’s dream! Walk the crater rim of the Mount Vesuvius volcano, say Buongiorno to local farmers along the Pathway of the Gods, take in sweeping panoramic views from the Path of the Lemons, and catch a ferry to the glamorous island of Capri. Then, visit Pompeii to explore the preserved ruins and learn about the history of the area. Spend two nights in in a clifftop hotel, soak up sunsets, eat your weight in delicious Italian food (carbs, anyone?) and get active in one of the most beautiful parts of Italy, if not the world.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Naples, Capri, Sentiero Degli De

Naples, Capri, Sentiero Degli Dei, Amalfi

Duration7 days

From

USD 5,460

USD 5,296

Saving

USD 164

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Super Sales

Highlights of Italy - September 2027

No booking fees

Best price guaranteed

Check off every bucket list dream on this highlight-packed adventure through the heart of Italy. Stand in awe of Rome’s ancient history as you explore landmarks that have shaped the world, then lose yourself in Florence’s Renaissance art and architecture that redefined creativity. Walk along Venice’s iconic canals, where every turn feels like a scene from a romantic postcard. And just when you think it can’t get better, indulge in Montepulciano’s rich culinary traditions and savor its world-renowned wines. From timeless history to indulgent flavors, this life-changing journey will leave you longing for just one more taste of Italy’s magic.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Venice, Montepulciano, Florence

Duration9 days

From

USD 2,149

USD 2,085

Saving

USD 64

View Tour

Super Sales

Journeys: Northern Italy, Venice to Florence - September 2027

(4 reviews )

No booking fees

Best price guaranteed

Amazing. Tour guide made the trip worth while!

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Duration7 days

From

USD 2,999

USD 2,909

Saving

USD 90

View Tour

Super Sales

Journeys: Southern Italy, Naples to Rome - September 2027

(3 reviews )

No booking fees

Best price guaranteed

The trip was awesome and a once in a lifetime experience. We hope to book future trips like this, but it will be hard to live up to the quality of this trip, especially our CEO Elisabetta and our fellow ducklings.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Naples, Sorrento, Amalfi Coast

Duration8 days

From

USD 3,399

USD 3,297

Saving

USD 102

View Tour

All Italy Tours in September 2027

Page 5 of 63 Trips in Italy during September 2027 with 3,373 Reviews

See Italy tours by duration

Get a customized trip to Italy in September 2027

Best of Northern Italy: Florence to Venice - September 2027

Premium Puglia - September 2027

Walks & Food of the Italian Riviera - September 2027

Premium Walking & Hiking on Italy's Amalfi Coast - September 2027

Highlights of Italy - September 2027

Journeys: Northern Italy, Venice to Florence - September 2027

Journeys: Southern Italy, Naples to Rome - September 2027

Page 5 of 63 Trips in Italy during September 2027 with 3,373 Reviews

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All Italy Tours in September 2027

Page 5 of 63 Trips in Italy during September 2027 with 3,373 Reviews

See Italy tours by duration

Get a customized trip to Italy in September 2027

Best of Northern Italy: Florence to Venice - September 2027

Premium Puglia - September 2027

Walks & Food of the Italian Riviera - September 2027

Premium Walking & Hiking on Italy's Amalfi Coast - September 2027

Highlights of Italy - September 2027

Journeys: Northern Italy, Venice to Florence - September 2027

Journeys: Southern Italy, Naples to Rome - September 2027

Page 5 of 63 Trips in Italy during September 2027 with 3,373 Reviews