10 Best Italy Multiday Tours in October 2025

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Discover Puglia: Italy's Ancient Heel - October 2025

4.6

(48 reviews )

No booking fees

Best price guaranteed

An excellent trip. The pace of the trip is perfect. A week flew by and we felt we had been all over the Puglia region. So much to do and see in such a short space of time and yet we managed to relax and get some free time in too. The food was outstanding, the wine was delightful, the people were a pleasure to be around. Every stage of the trip was enjoyable and slightly different.

Food toursLocal culture

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Matera, Lecce, Salento, Alberobe

Matera, Lecce, Salento, Alberobello, Grotte Di Castellana, Ostuni, Otranto

Duration8 days

From

USD 2,620

USD 2,541

Saving

USD 79

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15% OFF TODAY

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Gems Of Rome & Florence - October 2025

4.3

(4 reviews )

Trip customizable

Best price guaranteed

The tours were set up with the perfect mix of tour/personal time. Stefan, Claudia and our bus driver were top notch navigating us through the narrow streets to make sure we saw all of the local highlights! Recommend to everyone.

Art and architectureFood tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Rome, Florence

15% OFF TODAY

Duration6 days

From

USD 1,554

USD 1,321

Saving

USD 233

Instant book available

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Small Group Tour of Sicily: Highlights - October 2025

4.8

(6 reviews )

Trip customizable

Best price guaranteed

We had a wonderful day together with Alfredo. Alfredo was the best guide ever!! He was excellent and was so fluent in english, he told us many interesting stories. He is an expert in Sicilian history and culture. he was both singing and dancing for us-we enjoyed it a lot. But most of all, he was such a service minded and understanding person. For example we were come minutes late in the morning and then we enjoyed the tour at the winery so much that we caused a delay in Alfredo's schedule but he was so humble and understanding. We highly recommend it to everyone travelling to Sicily.

Food toursWine tasting tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Palermo, Catania, Sicily, Taormi

Palermo, Catania, Sicily, Taormina, Syracuse

Duration8 days

From

USD 2,925

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Tuscany Walks & Chianti Wines - October 2025

20% OFF TODAY

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Tuscany Walks & Chianti Wines - October 2025

4.8

(89 reviews )

No booking fees

Best price guaranteed

The trip had a really good balance of activities, with plently to do while still leaving you time to relax and chill out. Tuscany is so beautiful and Fattoria Voltrona was a great place to stay. I would definitely recommend this trip to my friends.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Tuscany, Chianti, Pancole

Siena, Tuscany, Chianti, Pancole, Florence, San Gimignano

20% OFF TODAY

Duration8 days

From

USD 2,773

USD 2,226

Saving

USD 547

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Small Group Food & Wine Tour of Sicily - October 2025

4.9

(26 reviews )

Trip customizable

Best price guaranteed

Loved this small group tour. It was a perfect balance of organized activities and free time. All the hotels were beautiful and were in great locations for walking to all the busy areas. Our guides were knowledgeable and easy going. Would highly recommend to anyone.

Food toursWine tasting tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

1-89 yrs

Operated in

english

Destinations

Palermo, Catania, Sicily, Taormi

Palermo, Catania, Sicily, Taormina, Syracuse

Duration8 days

From

USD 2,925

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Private Tour of Sicily from Palermo - October 2025

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 3,147

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Amalfi Coast Walking - Agriturismo - October 2025

4.8

(90 reviews )

No booking fees

Best price guaranteed

Explore are always very efficient, from enquiring, booking and organisation on the trip. Leaders are always excellent in my experience of 28 holidays.

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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9% OFF TODAY

Italy's Treasures Art, Food & Wine of Italy - October 2025

(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

9% OFF TODAY

Duration12 days

From

USD 4,349

USD 3,949

Saving

USD 400

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Rome, Florence & Tuscany Family Adventure - October 2025

(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 7,712

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Super Sales

Italy Real Food Adventure - October 2025

No booking fees

Best price guaranteed

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

From

USD 3,495

USD 3,390

Saving

USD 105

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Private Gourmet Wine Tour in Tuscany - October 2025

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

From

USD 2,843

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Campania Region Highlights, Private Tour - October 2025

15% OFF TODAY

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Campania Region Highlights, Private Tour - October 2025

(1 review )

Trip customizable

Best price guaranteed

The Amalfi Coast is stunning and the people of Italy were very welcoming and helpful. A shout out to Dario, my Pompeii guide - excellent!

Art and architectureFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Sorrento, Minori, Naples

15% OFF TODAY

Duration9 days

From

USD 3,067

USD 2,607

Saving

USD 460

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8% OFF TODAY

Super Sales

Italian Escape - October 2025

No booking fees

Best price guaranteed

This all-Italian adventure swings you from this historic beauty of Rome through the home of pizza, Naples (where you can stop off in the perfectly preserved Roman town of Pompeii). Then, it's all about living the good life on the Amalfi coast, sipping limoncello, and stopping off at picture perfect Positano (if you're here in the summer) and Sorrento during those breezy winter months. Back in Rome you'll get a chance to check out the Colosseum, before this unforgettable 6-day trip comes to an end.

Food tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Pisa, Naples, Amalfi Coast

8% OFF TODAY

Duration6 days

From

USD 1,195

USD 1,102

Saving

USD 93

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Ancient Sicily - October 2025

4.7

(18 reviews )

No booking fees

Best price guaranteed

Antonio, our guide, was extremely knowledgeable about Sicily. He also gave special talks on various topics which were very informative. He was very organized, helpful and patient.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Syracusa, Pale

Syracuse, Sicily, Syracusa, Palermo, Giardini Naxos, Mount Etna, Taormina, Piazza Amerina, Villa Romana Del Casale, Agrigento, Marsala, Mozia Island

Duration15 days

From

USD 4,780

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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 2025

41 Trips in Italy during October 2025 with 383 Reviews

See Italy tours by duration

41 Trips in Italy during October 2025 with 383 Reviews

Discover Puglia: Italy's Ancient Heel - October 2025

Gems Of Rome & Florence - October 2025

Small Group Tour of Sicily: Highlights - October 2025

Tuscany Walks & Chianti Wines - October 2025

Small Group Food & Wine Tour of Sicily - October 2025

Private Tour of Sicily from Palermo - October 2025

Amalfi Coast Walking - Agriturismo - October 2025

Italy's Treasures Art, Food & Wine of Italy - October 2025

Rome, Florence & Tuscany Family Adventure - October 2025

Italy Real Food Adventure - October 2025

Private Gourmet Wine Tour in Tuscany - October 2025

Campania Region Highlights, Private Tour - October 2025

Italian Escape - October 2025

Ancient Sicily - October 2025

Combine Italy in October with Nearby Countries for an Unforgettable Trip

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 2025

41 Trips in Italy during October 2025 with 383 Reviews

See Italy tours by duration

41 Trips in Italy during October 2025 with 383 Reviews