10 Best Italy Multiday Tours in October 2025

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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Venetian Treasures (port-to-port cruise) - October 2025

(1 review )

No booking fees

Best price guaranteed

This cruise was great. The only complaint is I did receive information on how to book optional excursions in advance.

CruiseCity sightseeing

Tour Type

Cruise Tour

Accommodation

Ship Cabin

Age Range

18-79 yrs

Operated in

english

Destinations

Venice, Chioggia

Duration5 days

From

USD 645

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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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Super Sales

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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Italy Real Food Adventure - October 2025

13% OFF TODAY

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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

13% OFF TODAY

Duration8 days

From

USD 3,570

USD 3,117

Saving

USD 453

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21% OFF TODAY

Super Sales

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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Amazing Italy - October 2025

(3 reviews )

Trip customizable

Best price guaranteed

Absolutely incredible! Italy’s history, food, and charm blew us away. The small group setting was perfect, and everything was tailored for Canadian travelers. Highly recommend!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Sorrento

Rome, Florence, Verona, Sorrento, Venice, Perugia, Naples, Salerno, Siena, Genoa, Milan

Duration15 days

From

USD 2,624

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5% OFF TODAY

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Treasures of Italy - October 2025

4.9

(69 reviews )

No booking fees

Best price guaranteed

It was a fast paced trip. It is a bit difficult staying only one night in a few places, just the logistics of packing up several nights and having everything ready for the next day is challenging. But, that being said I thoroughly enjoyed seeing so many things through out Italy. That inconvenience was minor in comparison to the amount of ground we covered.

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice

5% OFF TODAY

Duration11 days

From

USD 5,350

USD 5,083

Saving

USD 267

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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 2,838

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11% OFF TODAY

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Cycling in Sicily - October 2025

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

From

USD 2,698

USD 2,401

Saving

USD 297

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La Dolce Vita Experience - October 2025

Trip customizable

Best price guaranteed

As you journey from Rome to Sorrento, you’ll pass through a captivating landscape dotted with medieval villages seemingly frozen in time. This tranquil scene contrasts with the haunting allure of the ancient ruins of nearby Pompeii. Sorrento offers a serene coastal retreat with breathtaking views of the Bay of Naples. Be sure to take the opportunity to visit Capri, where the enchanting Blue Grotto, with its crystalline waters, invites you to experience its shimmering beauty

Cultural, religious and historic sites

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Lazio, Sorrento

Duration3 days

From

USD 916

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Splendid Amalfi Coast - Small-Group Tour - October 2025

Trip customizable

Best price guaranteed

Begin by immersing yourself in the ancient ruins of Pompeii, a once-thriving ancient city frozen in time by the catastrophic eruption of Mount Vesuvius. Afterward, retreat to the idyllic town of Sorrento, where your charming hotel promises a comfortable respite. Venture out to the renowned island of Capri, nestled in the Bay of Naples, and be entranced by its natural beauty and cultural allure. Marvel at the picturesque hillside town of Positano, etched into the rugged coastline, before making your way back to the eternal city of Rome, enriched by the memories of this coastal sojourn

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

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

Duration5 days

From

USD 2,000

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18% OFF TODAY

Super Sales

Grand Italian Experience - October 2025

4.8

(64 reviews )

No booking fees

Best price guaranteed

So much to do! Don't muss out on the additional dinners. Some are spectacular.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Dolomites, Lake Maggiore

Rome, Dolomites, Lake Maggiore, Viareggio, Florence, Puglia, Amalfi Coast & Campania, Naples, Assisi, Venice

18% OFF TODAY

Duration17 days

From

USD 5,750

USD 4,723

Saving

USD 1,027

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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

View Tours

Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

All Italy Tours in October 2025

Page 5 of 438 Trips in Italy during October 2025 with 5,451 Reviews

See Italy tours by duration

Page 5 of 438 Trips in Italy during October 2025 with 5,451 Reviews

Discovery of Italy: 8 Days - October 2025

Venetian Treasures (port-to-port cruise) - October 2025

Walking in Puglia - October 2025

St Francis Way: Rieti to Rome - October 2025

Local Living Italy—Tuscany San Gimignano - October 2025

Italy Real Food Adventure - October 2025

Italian Intermezzo - October 2025

Amazing Italy - October 2025

Treasures of Italy - October 2025

Private Gourmet Wine Tour in Tuscany - October 2025

Cycling in Sicily - October 2025

La Dolce Vita Experience - October 2025

Splendid Amalfi Coast - Small-Group Tour - October 2025

Grand Italian Experience - 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 5 of 438 Trips in Italy during October 2025 with 5,451 Reviews

See Italy tours by duration

Page 5 of 438 Trips in Italy during October 2025 with 5,451 Reviews