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

Start planning your Trip

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

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

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Super Sales

Solo-ish Italy - September 2027

(4 reviews )

No booking fees

Best price guaranteed

Wonderful community feel amongst travelers. A wonderful introduction to Italy, kudos to you guys for putting this together. Planning and logistics on this level is impressive. Would highly recommend, just not when Alive is CEO

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Florence, Venice, Cinque Terre, Lake Como

Duration9 days

From

USD 2,699

USD 2,618

Saving

USD 81

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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

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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 3,099

USD 3,006

Saving

USD 93

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Super Sales

Hike the Tour du Mont Blanc - September 2027

No booking fees

Best price guaranteed

Uncover the Alps in all their glory as you spend eight days hiking the iconic Tour du Mont Blanc. Following a circuit route from Chamonix in France, come face to face with dizzying peaks, glittering lakes and rolling pastures, passing through Switzerland and Italy on the way. Each day ends in charming accommodation, and your luggage will be transported for you to lighten the load. With a highly qualified International Mountain Leader as your guide who will not only ensure your safety, but also show you what makes this part of the world so special, you can focus on the gorgeous natural scenery!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Lodge

Age Range

15-99 yrs

Operated in

english

Destinations

Chamonix, Argentiere, Champex, C

Chamonix, Argentiere, Champex, Courmayeur, Les Chapieux, Les Contamines-Montjoie

Duration8 days

From

USD 4,780

USD 4,637

Saving

USD 143

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All Italy Tours in September 2027

Page 10 of 131 Trips in Italy during September 2027 with 3,544 Reviews

Get a customized trip to Italy in September 2027

See Italy tours by duration

Get a customized trip to Italy in September 2027

Highlights of Italy - September 2027

Solo-ish Italy - September 2027

Journeys: Southern Italy, Naples to Rome - September 2027

Journeys: Northern Italy, Venice to Florence - September 2027

Hike the Tour du Mont Blanc - September 2027

Page 10 of 131 Trips in Italy during September 2027 with 3,544 Reviews

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 2027

Page 10 of 131 Trips in Italy during September 2027 with 3,544 Reviews

Get a customized trip to Italy in September 2027

See Italy tours by duration

Get a customized trip to Italy in September 2027

Highlights of Italy - September 2027

Solo-ish Italy - September 2027

Journeys: Southern Italy, Naples to Rome - September 2027

Journeys: Northern Italy, Venice to Florence - September 2027

Hike the Tour du Mont Blanc - September 2027

Page 10 of 131 Trips in Italy during September 2027 with 3,544 Reviews