10 Best Italy Multiday Tours in September 2027

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Highlights of Italy - September 2027

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How long does it take to fall in love? In a country where history spills from world-class museums and tiny osterias serve up life-changing pasta recipes, eight days might just be enough (but if you have more time, why not extend your adventure?). On this trip, you’ll begin winding your way through the canals of Venice, hiking through the scenic Cinque Terre, soaking up beauty and history of Florence and finishing up in the piazzas of Rome. With plenty of free time for independent exploration and the freedom to discover Italy's history and culture at your own pace, there's no better way to see this popular pocket of Europe.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Hostel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Liguria, Cinque Te

Rome, Venice, Liguria, Cinque Terre and Liguria, Florence

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Duration8 days

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Walking the Amalfi Coast - September 2027

4.7

(426 reviews )

No booking fees

Best price guaranteed

Basically a perfect week in a beautiful part of the world, good food, great companions, great walks, excellent guide, great weather and fantastic views and experiences...

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, Amalfi, Pompeii, Naples

Duration8 days

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Italy Experience - September 2027

5

(2 reviews )

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The comfort level trip allows for the traveller to fully experience Italy as a local with their off the beaten track options but with the convenience of travelling comfort, local guidance and added inclusions.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Liguria, Cinque Te

Rome, Venice, Liguria, Cinque Terre and Liguria, Florence, Perugia

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Duration10 days

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Best of Italy - September 2027

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The enduring phrase ‘la dolce vita’ (the good life) truly captures the essence of Italy. On this trip, you’ll spend 14 days discovering the heart of all things Italian on a culturally rich adventure from the piazzas of Rome to the canals of Venice. Discover the Tuscan countryside on a leisurely cycle along Lucca’s Serchio River, peer into Pisa, take to the trails of the Cinque Terre for some stunning coastal views and walk the Portofino Peninsula with its glamourous residents. With time spent wine tasting in rural villages, cruising along Lake Como and relaxing along canals in Venice, you’ll soon understand why Italy remains in the hearts of all who visit.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Asti, Lake Como, F

Rome, Venice, Asti, Lake Como, Florence, Lucca, Liguria

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Duration14 days

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Rome to Amalfi - September 2027

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If you want a short trip packed with diversity, this eight-day adventure through southern Italy is perfect for you. Acquaint yourself with Italy's 'Eternal City' (Rome) and get up close and personal with a still active volcano in Naples before witnessing the aftermath of a volcanic eruption in Pompeii. Soak up the sunshine in the coastal town of Sorrento and explore the beautiful Amalfi Coast. This trip promises a blend of history, trekking and culinary delights — a taste of la dolce vita awaits.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Hut

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, P

Rome, Amalfi Coast & Campania, Pompeii, Sorrento, Amalfi

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Duration8 days

Private Tour of Sicily from Palermo - September 2027

4.8

(4 reviews )

Trip customizable

Best price guaranteed

This is our first private tour and I must say it met all our expectations. Our driver/guide Carlo took very good care of us, told us informative and amusing stories along the way and took us to wonderful restaurants. He made sure all our needs our taken cared of. In Sicily especially I think the private tour is a big advantage as there are many places where only small vehicles can go through. We made the right decision in choosing this tour.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

20-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Sici

Palermo, Catania, Taormina, Sicily, Agrigento, Marsala, Monreale

Duration8 days

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Cycle Cilento & the Amalfi Coast - September 2027

4.7

(99 reviews )

No booking fees

Best price guaranteed

Amalfi coast is one of the most dramatic coastline in the world and this well organised Exodus Trip will guide you on bike along the coastal road all the way to the end (Termini). There are great do-able climbs, long descents, fantastic scenery, great food, great temples and most beautiful gardens - i.e. just about perfect!

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Minori

Amalfi Coast & Campania, Minori, Palinuro, Casalvelino, Paestum

Duration8 days

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Walk The Prosecco Hills & Hidden Venice - September 2027

4.8

(77 reviews )

No booking fees

Best price guaranteed

Walking on this holiday is varied and well within most people's grasp. Aside from the rolling hills of Prosecco vineyards it includes forest walking and following along side a river. The hotel is most comfortable with large airy bedrooms and updated bathrooms which do not detract from the historic building. It sits within its own grounds including a large swimming pool and a bookable spa. The village of Soligo is small with 3 cafe's and a small shop which stocks a wide range of biscuits, soft drinks and bottled water. There is one sure thing about this holiday and this is you will not go hungry. Lunches are freshly made by the local shop and will keep you going during the walks. The hotel food is second to none and the other resturants we eat at also supplied delicous food. The highlight of this trip is Prosecco in all its forms. I learnt a lot about how the wine was made and how to tell one bottle from another.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Treviso, Pieve Di Cadore

Venice, Treviso, Pieve Di Cadore, Cison Di Valmarino, Asolo, Conegliano, Pieve Di Soligo

Duration8 days

Rome, Florence & Tuscany Family Adventure - September 2027

5

(3 reviews )

Trip customizable

Best price guaranteed

Hi Stefania! Sorry to take so long to write back. It has been crazy trying to get back into the swing of things at work after that trip. Italy was amazing!! We absolutely loved it! As for feedback on the trip, we really don't have anything that was negative. We loved everything that was planned! We especially loved how you planned the sites that we went and how the pattern flowed (not sure if you did it on purpose but we think so). Also, thank you for being very accessible to us during the whole planning of the trip. You helped put us at ease and it was very reassuring that we chose the right company. That is all that I can given you that might be considered constructive. The rest I could say would just be compliments on everything else. If I can think of anything else that I think is useful I will definitely email you. Hope all is well, Jane P.S. - Does your company only provide trips for Italy or other countries as well, just wondering for the future :)

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, San Gim

Rome, Florence, Tuscany, San Gimignano, Chianti, The Vatican

Duration8 days

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Explore Southern Italy - September 2027

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Take off on an unforgettable journey down Italy’s rarely visited heel, getting to know another side of this beautiful country. See the beauty of Amalfi, unwind in style among the sophisticates of Trani and tour the Roman ruins, baroque churches and whitewashed alleyways of Lecce. Wander among the peculiarly shaped houses of Alberobello, wander the hillside dwellings of Matera and discover the Old Town’s life surrounding Bari's Basilica di San Nicola. Head down and say ciao to Italy’s southernmost slice of the Adriatic.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Bari, Amalfi Coast & Campania, A

Bari, Amalfi Coast & Campania, Amalfi, Trani, Lecce, Alberobello, Matera

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Duration10 days

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Italy Real Food Adventure - September 2027

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Italians are the masters of creating simple dishes that burst with flavour. Inspired by nonnas’ kitchens all over the country, this food is regional, seasonal and fresh, and on this eight-day trip through everybody’s favourite culinary hub, you’ll discover that pizza and pasta are only the tip of the iceberg. Uncover the diverse array of unforgettable street eats, meals and cicchetti (small bites) from the postcard-perfect Venice to Rome, where medieval meets modern. Delight in local wine, fresh produce, homemade dinners and seasonal favourites in San Gimignano, Tuscany and Bologna – all with a local by your side – and take your tastebuds on an unforgettable adventure.

Food tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Bologna, San Gimignano

Duration8 days

Private Gourmet Wine Tour in Tuscany - September 2027

4.5

(2 reviews )

Trip customizable

Best price guaranteed

What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

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Cycling in Sicily - September 2027

4.6

(54 reviews )

No booking fees

Best price guaranteed

This was one of my best Exodus Holidays. This was my first cycling one with Exodus and I can highly recommend this trip.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Modica, Marzamemi, Noto

11% OFF TODAY

Duration8 days

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Cinque Terre: Hike, Bike & Kayak - September 2027

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Explore a surreal region of Italy that looks straight out of a postcard (only better) with this eight-day multi-active trip. The houses are painted in multi-coloured shades, the sea is brighter than the sky, and the sun beams down brightly – welcome to the Cinque Terre. This jewel of Europe changes with the light of the day and is best explored on foot, on a bike or on a kayak. On this trip, you’ll witness natural beauty on all three! Cycle past olive groves, hike to medieval monuments, kayak to sandy beaches and refuel your energy every afternoon with cocktails and carbs. This is living!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Cinque Terre and Liguria, Levant

Cinque Terre and Liguria, Levanto, Santa Margherita