10 Best Italy Multiday Tours in October 2026

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Italian Concerto - October 2026

4.7

(130 reviews )

No booking fees

Best price guaranteed

Great tour at a great price

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Amalfi Coast & Cam

Rome, Venice, Amalfi Coast & Campania, Capri, Florence

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Duration11 days

From

USD 3,925

USD 3,374

Saving

USD 551

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Italy Family Holiday - October 2026

No booking fees

Best price guaranteed

Fall in love with Italy and rediscover the rewards of family travel on this carefully crafted trip for both you and the kids. Over eight days, you’ll journey from the ruins of Rome to the shadow of mighty Mt Vesuvius. Deep dive into the history of the ancient ruins of Pompeii, then sit back and relax with a glass of Sangiovese (while the kids chase wild rabbits) on the farmlands of an agriturismo. Take a daytrip to the island of Capri and redesign family pizza night after learning the tricks of the trade in a cooking demonstration in Sorrento. With all the logistics and essential experiences taken care of, you can treat yourself to some family time on an Italian adventure that does the job, so you don’t have to.

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, S

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

Duration8 days

From

USD 3,250

USD 3,153

Saving

USD 98

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Self-Guided Culinary Package - La Spezia & Cinque Terre - October 2026

Trip customizable

Best price guaranteed

Join us on this three-day tour and get to enjoy a region of Italy known for its mild climate, charming port towns, breath-taking landscapes, and fresh local cuisine. Liguria is home to the UNESCO World Heritage site "Cinque Terre," a majestic and astonishing national park free of vehicular traffic and perfect for romantic getaways and fine culinary experiences. The regional cuisine of Liguria is based on seafood, fresh vegetables and herbs, such as in the famous pesto alla Genovese. In a span of few days, you will be able to explore this region, its history, culture and culinary highlights always taking your time and doing everything at your own pace.

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

9-79 yrs

Operated in

English

Destinations

Cinque Terre and Liguria, Liguri

Cinque Terre and Liguria, Liguria, Cinque Terre, La Spezia, Lerici

Duration3 days

From

USD 386

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Southern Italy And Sicily - October 2026

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Southern Italy and Sicily - October 2026

4.4

(108 reviews )

No booking fees

Best price guaranteed

All the options were excellent. The local guides walked at a slow pace giving us time to take pictures. Our guide Alfonso and our driver Tito were great. We would take a tour with them anytime

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Sorrento, Palermo

Pompeii, Rome, Sorrento, Palermo, Capri, Taormina, Agrigento

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Duration10 days

From

USD 3,575

USD 3,051

Saving

USD 524

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Italy Bellissimo - October 2026

4.7

(239 reviews )

No booking fees

Best price guaranteed

Amazing variety of experiences, excellent tour guide and local specialists. I also loved that Trafalgar supports local artists and family run farms. A highlight for me was the Make Travel Matter experience with the weavers.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Capri, Assisi, Venice, Montecatini Terme

Duration11 days

From

USD 3,305

USD 3,206

Saving

USD 99

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Jewels of Italy and Milan by Rail - October 2026

(1 review )

Trip customizable

Best price guaranteed

I’ve always loved Italy, but doing it by rail added a special touch. Over eight days, we hit Rome, Florence, Venice, and wrapped up in Milan, all by high-speed train. The pace worked perfectly for me (I’m 58), with fresh city arrivals each morning and comfortable hotels each night The highlights: a hop-on hop-off loop in Rome hit the Colosseum, Pantheon, Trevi Fountain , an optional wine tasting tour that I booked in Florence and Venice’s gondola ride. Everything flowed perfectly well..no dragging suitcases or missed trains. For travelers in our age bracket, this tour blends comfort, culture, and hassle-free travel. If you want Italy’s treasures without the planning headache, this rail tour delivers in a big way.

City sightseeingTrain tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice

Duration8 days

From

USD 1,417

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European Trail - October 2026

(1 review )

No booking fees

Best price guaranteed

This tour was so much fun. Learnt a lot, met a lot of new friends, and had a ton of fun. Would highly recommend this tour, and to travel through Europe in general.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Hostel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, London, Amsterdam, Berlin

Paris, London, Amsterdam, Berlin, Prague, Vienna, Krakow, Budapest, Ljubljana, Venice, Rome, Florence, Swiss Alps

Duration23 days

From

USD 2,795

USD 2,711

Saving

USD 84

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Jewels of Italy by Rail - October 2026

(1 review )

Trip customizable

Best price guaranteed

Three of us girlfriends decided it was time for an Italian cultural recharge, and we picked the rail tour to hit the highlights with ease. We explored Rome and saw the Coloseum as we opted for an optional tour. Florence was also beautiful. Venice was pure magic. Our shared gondola ride under the Bridge of Sighs (with just six in the gondola) felt cozy and unforgettable . We spent afternoons discovering boutique shops and colorful squares. For us, this tour struck the perfect balance. Relaxed evenings with wine and laughter. The train travel was a breeze, everything was well-coordinated.

Train toursSightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration7 days

From

USD 1,154

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The Heart of the Cilento National Park - October 2026

(2 reviews )

Trip customizable

Best price guaranteed

Thank you so much for making this a GREAT vacation.

Trekking and Hiking

Tour Type

Private Tour

Age Range

18-99 yrs

Operated in

English

Destinations

Amalfi Coast & Campania, Paestum

Amalfi Coast & Campania, Paestum, Valle Dell'Angelo, Roscigno, Sant'Angelo A Fasanella

Duration9 days

From

USD 808

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Via Degli Dei: Bologna to Florence - October 2026

4.9

(7 reviews )

No booking fees

Best price guaranteed

The Via Degli Dei is a fantastic walk - 2 great Italian cities and stunning landscapes every day which made the tough climbs worthwhile. They dealt with everything once we arrived, the accommodation was good and varied which added to the appeal of the trip. It's helpful to have some basic Italian as a couple of places did not speak English but everyone was so friendly. Will use them again - we are already planning next year's trip!

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Florence, Bologna, Sasso Marconi

Florence, Bologna, Sasso Marconi, Monzuno, Bruscoli, San Piero A Sieve, Olmo, Fiesole

Duration8 days

From

USD 1,190

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Piedmont: Land of Barolo and Barbera - October 2026

4.9

(10 reviews )

No booking fees

Best price guaranteed

We loved our walking trip the land of Barolo and Barbera. We learnt an enormous amount about the Piedmont and experienced firsthand the vineyards and wineries of the area. The scenery was amazing. The walk was easy to intermediate but we had some extremely hot weather which was unexpected, making the walk more challenging, but without the heat it would’ve been a very pleasant and manageable walk. Accommodation along the way was terrific. The transfers and other administrative aspects of the walk went incredibly smoothly. The last hotel was amazing with Carlo the owner of the restaurant and hotel being an amazing chef and host. But many others were wonderful as well. The accomodation and restaurant in Cissone was also worthy of special comment. The trip notes said it may be possible to buy lunch along the way but it is generally best to be prepared with your own food. Sometimes there is nothing available or open. We would highly recommend the trip. We went back over the route by car two weeks later which expanded our knowledge and understanding and love of the area.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Piedmont & Valle d’Aosta, Cortem

Piedmont & Valle d’Aosta, Cortemilia, Alba, Roddi, Monforte D'Alba, Cissone, Cravanzana

Duration8 days

From

USD 1,120

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Grand Italy & Sicily - October 2026

4.7

(77 reviews )

No booking fees

Best price guaranteed

It covers so many areas in Italy We got exposed to so much history and culture

Wine tasting tours

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Palermo, Sorrento, Capri

Rome, Palermo, Sorrento, Capri, Alberobello, Giardini Naxos, Santa Margherita, Portofino, Lake Maggiore, Venice, Florence

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Duration17 days

From

USD 8,250

USD 6,993

Saving

USD 1,257

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Country Roads Of Northern Italy - October 2026

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Country Roads of Northern Italy - October 2026

4.5

(48 reviews )

No booking fees

Best price guaranteed

Keep the flexibility of the add on activities.

AdventureCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Trento, Lake Maggiore

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Duration10 days

From

USD 4,450

USD 3,841

Saving

USD 609

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Jewels of Italy and Cinque Terre by Rail - October 2026

Trip customizable

Best price guaranteed

This incredible trip offers you the opportunity to discover three major cities in Italy by rail. Your tour starts in Italy’s capital: Rome. You will get to see the incredible monumental heritage of the city and its ancient Roman architecture. You will have a walking city tour in Rome and Florence. Embrace the remarkable topography of the country while on a high-speed train. In Cinque Terre, you will have the opportunity to discover the area freely, as you will have a pass that gives you access to all the villages of Cinque Terre. You will come across numerous photo stops on this trip—Italy has beautiful scenic landscapes and architectural masterpieces. This is one of the most popular Italy tours and packages, offering a perfect balance of iconic landmarks and flexible exploration. Besides, there are many optional tours available to choose from to make this trip even more exciting!

Train toursCity sightseeing

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Cinque Terre and Liguria

Rome, Cinque Terre and Liguria, Florence, Monterosso

Duration8 days

From

USD 1,207

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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 6 of 176 Trips in Italy during October 2026 with 4,487 Reviews

See Italy tours by duration

Italian Concerto - October 2026

Italy Family Holiday - October 2026

Self-Guided Culinary Package - La Spezia & Cinque Terre - October 2026

Southern Italy and Sicily - October 2026

Italy Bellissimo - October 2026

Jewels of Italy and Milan by Rail - October 2026

European Trail - October 2026

Jewels of Italy by Rail - October 2026

The Heart of the Cilento National Park - October 2026

Via Degli Dei: Bologna to Florence - October 2026

Piedmont: Land of Barolo and Barbera - October 2026

Grand Italy & Sicily - October 2026

Country Roads of Northern Italy - October 2026

Jewels of Italy and Cinque Terre by Rail - October 2026

Page 6 of 176 Trips in Italy during October 2026 with 4,487 Reviews

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 2026

Page 6 of 176 Trips in Italy during October 2026 with 4,487 Reviews

See Italy tours by duration

Page 6 of 176 Trips in Italy during October 2026 with 4,487 Reviews