10 Best Italy Multiday Tours in October 2026

Private Tour of Sicily from Palermo - October 2026

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

From

USD 3,153

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Puglia Coastal Walk - October 2026

4.6

(7 reviews )

No booking fees

Best price guaranteed

Communication when booking and questions afterwards was good. The trip itself was fantastic

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Otranto, Lecce, Salento, Porto B

Otranto, Lecce, Salento, Porto Badisco, Santa Cesarea Terme, Marittima, Marina Serra

Duration8 days

From

USD 1,160

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Super Sales

Amalfi Coast Family Adventure - October 2026

4.9

(42 reviews )

No booking fees

Best price guaranteed

If you are thinking about booking this holiday just do it - you won't regret it.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

9-99 yrs

Operated in

english

Destinations

Pompeii, Amalfi Coast & Campania

Pompeii, Amalfi Coast & Campania, Naples, Positano, Vesuvius, Capri

Duration8 days

From

USD 2,400

USD 2,328

Saving

USD 72

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Via Francigena: Orvieto to Rome - October 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

A truly memorable holiday which enabled us not only to see parts of the wonderful Lazio countryside that we wouldn’t normally see by car, but also to soak up the atmosphere of the various villages and towns where we stayed.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Orvieto, Bolsena, Montefia

Rome, Orvieto, Bolsena, Montefiascone, Viterbo, Vetralla, Sutri, Campagnano Di Roma, Isola Farnese, Piazza San Pietro

Duration10 days

From

USD 1,480

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Amalfi Coast Walking - Agriturismo - October 2026

4.8

(93 reviews )

No booking fees

Best price guaranteed

Great itinerary with plenty of free time to explore! Friendly group and field leader who went above and beyond. Still in contact with other travelers 😎

Walking toursFood tours

Tour Type

Small Group Tour

Accommodation

Resort, Villa, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Naples, San Lazzaro, Amalfi, Capri

Duration8 days

From

USD 2,070

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Super Sales

Explore Southern Sicily - October 2026

(8 reviews )

No booking fees

Best price guaranteed

Sicily is an extraordinary place and this trip really made me feel I got the most out of it in the time I had.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Palermo, Catania, Syracuse, Agri

Palermo, Catania, Syracuse, Agrigento, Trapani

Duration8 days

From

USD 2,049

USD 1,988

Saving

USD 61

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Best of Italy - October 2026

No booking fees

Best price guaranteed

Be whisked away into the beauty and history of Italy when you journey to Venice, Florence, and Rome. Journey to the wine-producing Romagna countryside for a relaxing two-night stay in a wine resort, and visit the Republic of San Marino, an enclave state of Italy. See how gondola oars are crafted before cruising the canals of Venice on one yourself. Witness a performance of Vivaldi’s famous Four Seasons in the city he lived in. Explore Orvieto, an ancient Etruscan hilltop city. Try your hand at making Italian culinary classics before sitting down to dinner. Discover Rome’s artistic masterpieces. Come along with us and embrace the history, culture, art and romance of this incredible country.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Venice, Romagna, Florence

Duration12 days

From

USD 3,899

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Super Sales

Cycle Cilento & the Amalfi Coast - October 2026

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

From

USD 3,300

USD 3,201

Saving

USD 99

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10% OFF TODAY

Italy's Treasures Art, Food & Wine of Italy - October 2026

(1 review )

No booking fees

Best price guaranteed

The tour was great from beginning to the end. The tour guide was awesome , very professional and courteous.The itinerary was filled with great experiences which were memorable. I would highly recommend this tour.

Food toursWine tasting tours

Tour Type

Group Tour

Accommodation

Villa, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Venice, Lombardy & the Lakes, St

Venice, Lombardy & the Lakes, Stresa, Italian Riviera, Tuscany

10% OFF TODAY

Duration12 days

From

USD 5,149

USD 4,649

Saving

USD 500

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Tuscany Walking and Wine - October 2026

4.9

(10 reviews )

No booking fees

Best price guaranteed

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of years old? A wine and food buff? Then this is for you. I had a great time on this trip. Had a full day in Sienna and a nice orientation tour of Florence (I spent a few extra days) Plus to get to visit lesser known towns that the big companies overlook. My favorite was Pienza. A nice little town that also had my favorite hotel and great places to eat. And yes, we tasted wonderful Italian wines, as well as the best cold cuts and cheeses I’ve ever tasted. And did I also mention hiking to wineries and hill towns? Wonderful sights, with spectacular views. One hike it rained towards the end, but that didn’t dampen our spirits.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

From

USD 2,830

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Classic Amalfi Coast - 8 Days - October 2026

4.8

(9 reviews )

No booking fees

Best price guaranteed

It was very well organised. Everything worked smoothly, we had a great holiday.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Positan

Amalfi Coast & Campania, Positano, Amalfi, Maestra Dei Villaggi, Praiano, Naples

Duration8 days

From

USD 1,790

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Via Francigena: Best of Tuscany - October 2026

4.6

(26 reviews )

No booking fees

Best price guaranteed

We walked the Via from San Miniato to Buonconvento, a major life experience. The Tuscan countryside unfolds and offers picture-perfect vistas every day. The track is very quiet, some days we would only see one or two other walking groups, so plenty of time for reflection. The days were longer than we expected, we certainly weren't fast walkers, so obviously that plays in, but we did find that some of the stretches were uncomfortably hot, in full sun. Often there was long stretches between water, and not many places to stop. You need to factor this in to your thinking and expectations. We had thought about this in advance and carried sun umbrellas that clipped onto our belts and backpacks so that we could walk with our own shade with hands free to use poles... strongly recommend investment. Some of the accommodations were fantastic, others quirky and fun, and a couple disappointing. Highlights in Gambassi Terme and our last night before Buonconvento.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Buonconvento, San Minia

Tuscany, Buonconvento, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena, Lucignano D Arbia

Duration9 days

From

USD 1,290

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Super Sales

Walk The Prosecco Hills & Hidden Venice - October 2026

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

From

USD 2,820

USD 2,735

Saving

USD 85

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Rome, Florence & Tuscany Family Adventure - October 2026

(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

From

USD 7,725

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Combine Italy in October 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 October 2026

Page 2 of 197 Trips in Italy during October 2026 with 5,546 Reviews

See Italy tours by duration

Private Tour of Sicily from Palermo - October 2026

Puglia Coastal Walk - October 2026

Amalfi Coast Family Adventure - October 2026

Via Francigena: Orvieto to Rome - October 2026

Amalfi Coast Walking - Agriturismo - October 2026

Explore Southern Sicily - October 2026

Best of Italy - October 2026

Cycle Cilento & the Amalfi Coast - October 2026

Italy's Treasures Art, Food & Wine of Italy - October 2026

Tuscany Walking and Wine - October 2026

Classic Amalfi Coast - 8 Days - October 2026

Via Francigena: Best of Tuscany - October 2026

Walk The Prosecco Hills & Hidden Venice - October 2026

Rome, Florence & Tuscany Family Adventure - October 2026

Combine Italy in October with Nearby Countries for an Unforgettable Trip

Page 2 of 197 Trips in Italy during October 2026 with 5,546 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 October 2026

Page 2 of 197 Trips in Italy during October 2026 with 5,546 Reviews

See Italy tours by duration

Page 2 of 197 Trips in Italy during October 2026 with 5,546 Reviews