10 Best Italy Multiday Tours in October 2025

Local Living Italy—amalfi Coast Winter - October 2025

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Local Living Italy—Amalfi Coast Winter - October 2025

4.7

(3 reviews )

No booking fees

Best price guaranteed

Such a great experience. Our tour guide was a local and had so many great stories to tell. He was fun, friendly and made everyone feel like a family almost instantly. The accommodation was very homely and the food was delicious. The Amalfi Coast was beautiful and I highly recommend a visit in winter. We had some stunning days in the winter sun and avoided the summer traffic and tourists. Overall an amazing tour. My partner and I highly recommend it!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Furore

22% OFF TODAY

Duration7 days

From

USD 2,099

USD 1,629

Saving

USD 470

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Classic Amalfi Coast - 8 Days - October 2025

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 2025

4.7

(26 reviews )

No booking fees

Best price guaranteed

They organised a fabulous experience. The trip was seamless and the information provided was thorough. The accommodation was fabulous and the trip notes and app were informative and I felt well supported. I would highly recommend them.

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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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 7,699

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Italian Scene - October 2025

4.6

(50 reviews )

No booking fees

Best price guaranteed

The scenery was beautiful. Next time I'd slow it down a bit though and enjoy each city for a few days.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Bay Of Naples, Assisi, Ven

Rome, Bay Of Naples, Assisi, Venice, Milan, Florence

5% OFF TODAY

Duration10 days

From

USD 1,950

USD 1,853

Saving

USD 97

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20% OFF TODAY

Classic Europe - October 2025

4.8

(70 reviews )

No booking fees

Best price guaranteed

This tour was an amazing experience and a great way to see A LOT of Europe in a short amount of time. The trip was fast paced but very well planned out with the itinerary and mix of activities that you see and do. Jemma, our tour guide was absolutely amazing! We couldn't have asked for better! She was charismatic, funny, knowledgeable, organized, and guided us in a positive way where we got the very most out of the travel experience learning the local history, foods, culture and best site seeing spots. She went above and beyond to make sure we were getting the most out of our tour experience. Gabriel, our driver was also phenomenal. We always felt very safe and he was always perfectly punctual and helped us load/ unload and kept us very comfortable on the coach.

Active and outdoor

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Paris, Rome, London, Amsterdam

Paris, Rome, London, Amsterdam, Nuremberg, Beaune, Montecatini Terme, Venice

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Duration14 days

From

USD 3,810

USD 3,038

Saving

USD 772

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Via Francigena: Southern Tuscany from Siena - October 2025

4.5

(8 reviews )

No booking fees

Best price guaranteed

An amazing walk through the Tuscan countryside. Exceptional organisation and attention to detail meant we could concentrate on having a great time and not have to worry about accommodation, meals and transfers. Thanks!

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Siena, Lazio, Lucignano D

Rome, Siena, Lazio, Lucignano D Arbia, Tuscany, San Quirico d'Orcia, Castiglione D Orcia, Radicofani

Duration8 days

From

USD 1,260

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Treasures of Naples & the Amalfi Coast - October 2025

Trip customizable

Best price guaranteed

From Rome, travel to Naples and see the treasures of the ancient city. Stop at the legendary site of Pompeii which was completely destroyed 2,000 years ago in the catastrophic eruption of Mount Vesuvius. Discover Positano, one of Italy's crown jewels, with stunning scenery and colourful cliffside villas. Set sail for the idyllic Italian island of Capri on a full-day tour and relax at the charming town of Sorrento on your Amalfi Coast escape with plenty of free time to explore on your own

BeachArt and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Rome, Lazio, Naples, Sorrento, Amalfi

Duration6 days

From

USD 2,144

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Cycling Puglia & Matera - October 2025

4.7

(66 reviews )

No booking fees

Best price guaranteed

Perfect spring cycling, beautiful scenery, wonderful food

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Matera, Salento, Alberobello, Os

Matera, Salento, Alberobello, Ostuni, Avetrana, Gallipoli, Otranto, Lecce

Duration8 days

From

USD 3,000

USD 2,910

Saving

USD 90

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Discovery of Italy: 8 Days - October 2025

4.5

(2 reviews )

Trip customizable

Best price guaranteed

I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, The Vati

Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

Duration8 days

From

USD 2,750

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Walking in Puglia - October 2025

4.6

(14 reviews )

No booking fees

Best price guaranteed

Travelling in a small group with different abilities the trip gave us a great balance between manageable walks, urban experiences and self managed travel. Instructions for the walks were generally clear but some better formatting/design would be helpful. The booked transport was always punctual, well organised with helpful and friendly drivers. The hotels that were selected had a great atmosphere and evocative of the places we were staying. Their location in the heart of the historic towns was perfect making it easy for quick explorative trips. Puglia as a destination didn't disappoint and we would be very happy to return whenever we have the opportunity.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Matera, Lecce, Salento, Ostuni

Matera, Lecce, Salento, Ostuni, Alberobello

Duration8 days

From

USD 1,690

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St Francis Way: Rieti to Rome - October 2025

(1 review )

No booking fees

Best price guaranteed

This was a wonderful walk through the Italian landscape following quiet trails peppered with villages and ancient hilltop towns. The walking provides a sense of achievement with occasional long days and steep rocky trails.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Rieti, Poggio San Lorenzo

Rome, Rieti, Poggio San Lorenzo, Scandriglia, Nerola, Sabina, Monterotondo

Duration8 days

From

USD 1,390

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Local Living Italy—Tuscany San Gimignano - October 2025

(3 reviews )

No booking fees

Best price guaranteed

It was a great way to see and learn about the Tuscany and area. We received great tips for when we ventured out on our own. These were very helpful. The activities were timely but yet gave us the opportunity to be on mood own.

Wildlife

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, San Gimignano, Florence, Siena

Duration7 days

From

USD 1,749

USD 1,697

Saving

USD 52

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21% OFF TODAY

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Italian Intermezzo - October 2025

4.6

(51 reviews )

No booking fees

Best price guaranteed

This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Venice, Florence

21% OFF TODAY

Duration8 days

From

USD 3,395

USD 2,667

Saving

USD 728

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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

Page 3 of 200 Trips in Italy during October 2025 with 4,820 Reviews

See Italy tours by duration

Page 3 of 200 Trips in Italy during October 2025 with 4,820 Reviews

Local Living Italy—Amalfi Coast Winter - October 2025

Classic Amalfi Coast - 8 Days - October 2025

Via Francigena: Best of Tuscany - October 2025

Rome, Florence & Tuscany Family Adventure - October 2025

Italian Scene - October 2025

Classic Europe - October 2025

Via Francigena: Southern Tuscany from Siena - October 2025

Treasures of Naples & the Amalfi Coast - October 2025

Cycling Puglia & Matera - October 2025

Discovery of Italy: 8 Days - October 2025

Walking in Puglia - October 2025

St Francis Way: Rieti to Rome - October 2025

Local Living Italy—Tuscany San Gimignano - October 2025

Italian Intermezzo - 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

Page 3 of 200 Trips in Italy during October 2025 with 4,820 Reviews

See Italy tours by duration

Page 3 of 200 Trips in Italy during October 2025 with 4,820 Reviews