10 Best Italy Multiday Tours in October 2026

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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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Highlights of Matera and Apulia Private Tour - October 2026

(1 review )

Trip customizable

Best price guaranteed

Private Tour around Apulia and Matera beyond our expectations .Very good the Hotel in Matera, Dimora di Metello..but also Tenuta Monacelle near Alberobello. Great local guide and meals. I only think you should had add an extra day in Apulia, 5 days are not enough. Anyway excellent tour and service. Very good value for money

Sightseeing ToursFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

20-99 yrs

Operated in

english

Destinations

Matera, Puglia, Polignano A Mare

Matera, Puglia, Polignano A Mare, Alberobello, Monopoli, Bari

Duration5 days

From

USD 2,306

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6% OFF TODAY

Italian Vistas - October 2026

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Best price guaranteed

From the ancient ruins of Pompeii to the chic charm of the Sorrento Coast, embark on a spectacular Italian getaway. Enjoy multiple-night stays in Rome, the charming coastal town of Sorrento, Florence, Venice, and Stresa in the Lake District. Discover the treasures of Classical Rome, including the Colosseum. Walk in the footsteps of the ancient Romans in Pompeii. Take a boat to the enchanting Isle of Capri. See the gems of the Renaissance in Florence, a veritable open-air museum. Marvel at the Leaning Tower of Pisa and stroll the streets of Verona. Stop at a Tuscan winery and farm for a lunch of regional specialties and wines. Tour Venice and walk the Castello district. Cruise to Isola dei Pescatori, one of the scenic Borromean Islands. Delve deeper into its history and culture as you visit some of the world’s most beautiful locales.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Lombardy & the Lakes, Veni

Rome, Lombardy & the Lakes, Venice, Stresa, Sorrento, Florence

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Duration13 days

From

USD 4,499

USD 4,249

Saving

USD 250

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Walking the Highlights of Western Sicily Walk - October 2026

(1 review )

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Best price guaranteed

This was a wonderful break. You stay at a number of very beautiful places: Scapello, Marettimo and San Vito La Capo. The walking is enjoyable but not too challenging. There are many opportunities to enjoy the food and culture of this part of Sicily; for example the town of Erice and the ancient site of Segasta. We also had a chance to spend an evening in Trapani and i would really recommend this too. I hadnt done self-guided walking before but really enjoyed it. We went in April and the weather was super. Not too hot so perfect for walking and little rain.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Sicily, Marettimo, Punta Libeccio

Duration8 days

From

USD 1,865

USD 1,809

Saving

USD 56

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Italy: Amalfi Coast to Puglia - October 2026

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Stray off the beaten path and explore a new side to the Italy you know and love. Sample wines created from the rich volcanic soil just outside of Pompeii. Soak up the sun with a free afternoon in Positano, home to colorful hillside houses and local posh boutiques. Spend 2 nights in a unique cave dwelling in Matera and your last 2 nights in the Puglia region in a personal converted trullo house. Uncover the Baroque excellence of Lecce, an artisan city of limestone. Make your way through southern Italy and experience the Amalfi Coast and the Puglia region.

Beach

Tour Type

Group Tour

Accommodation

Resort, Villa, Hotel, Hut

Age Range

1-99 yrs

Operated in

english

Destinations

Bari, Naples, Alberobello, Monop

Bari, Naples, Alberobello, Monopoli, Lecce, Minori, Matera

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Duration14 days

From

USD 4,699

USD 4,449

Saving

USD 250

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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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Venice to Florence Cycle - October 2026

(2 reviews )

No booking fees

Best price guaranteed

Good tour, well organised.

Bicycle toursCity sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Hut

Age Range

18-99 yrs

Operated in

english

Destinations

Florence, Venice, Mestre, Chiogg

Florence, Venice, Mestre, Chioggia, Adria, Comacchio, Ravenna, Brisighella

Duration8 days

From

USD 1,990

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Explore Italy - 4 Days - October 2026

(1 review )

Trip customizable

Best price guaranteed

Our trip was absolutely wonderful! I would like to thank our tour guide, for taking great care of everything. We had something planned every day and the group that travelled with us was so friendly. Everything worked out beautifully. We made memories that will last a lifetime!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-90 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Siena, Bologna, Padua, Venice & Veneto

Duration4 days

From

USD 1,630

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Absolute Italy by Rail - October 2026

Trip customizable

Best price guaranteed

Visit Italy’s major highlights as you travel by rail on one of our exclusive Italy tours and packages. Your tour starts in Italy’s capital: Rome where you will get to see the incredible monumental heritage of the city and its ancient Roman architecture. Embrace the remarkable topography of the country while on a high-speed rail. In Florence you will get to see intact medieval walls at Monteriggioni and famous medieval towers at walled town San Gimignano. In Cinque Terre, you will have the opportunity to discover the area freely, as you will have a pass that give you access all over the village of Cinque Terre. Next stop would be Milan the city of Fashion and Arts, where you will discover the Last Supper of Leonardo Da Vinci, the famous Gothic Cathedral, La Scala Opera House or the other hidden treasures of Milan. From here you will be visiting Venice which would be your last stop on this wonderful trip. You will get to see Piazza San Marco with the Basilica and the Clock Tower, the Rialto Bridge, Campo Santa Maria Formosa and the Grand Canal or escape to the more tranquil side streets and small canals that criss–cross the city.

Train tours

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Florence, Venice, La Spezi

Rome, Florence, Venice, La Spezia, Milan

Duration12 days

From

USD 2,467

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Backroads to Venice - October 2026

4.6

(7 reviews )

No booking fees

Best price guaranteed

Wonderful, spectacular scenery, comfortable mountain gites, good food, great guide highly recommend.

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Trentino-South Tyrol, Do

Venice, Trentino-South Tyrol, Dolomites, Bolzano, Trento, Peschiera, Verona, Vicenza, Padova, Mestre

Duration8 days

From

USD 1,460

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Exploring The Amalfi Coast - October 2026

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Exploring the Amalfi Coast - October 2026

(8 reviews )

No booking fees

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All in all this was a great week for us. We liked the itinerary and especially the fact it was two nights at each place. We did struggle with some of the other people in our group, but not so much that it impacted too much on our holiday. We just found them very loud and quite self centred which can be difficult in a group environment. We simply spent more time alone when we could. We would have liked some more detailed information about what to do in our free time as most of the group wanted to go shopping but that’s not our thing.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Naples, Sorrento, Amalfi

27% OFF TODAY

Duration7 days

From

USD 1,849

USD 1,344

Saving

USD 505

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Rome & La Dolce Vita Experience - October 2026

Trip customizable

Best price guaranteed

Experience a delectable journey through Rome's Trastevere district, guided by a culinary expert. Savor authentic Roman cuisine amidst historic surroundings. Explore the Vatican's treasures with a knowledgeable guide, enjoying VIP access to the Vatican Museums. Journey from Rome to Pompeii, encountering charming medieval villages along the route. Unearth the haunting ruins of Pompeii, frozen in time by Mt. Vesuvius's eruption. Conclude with a revitalizing coastal escape in Sorrento and Capri, immersing in the rejuvenating sea breeze and captivating vistas

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Lazio, Sorrento

Duration6 days

From

USD 1,864

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Rome And Tuscan Highlights - October 2026

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Rome and Tuscan Highlights - October 2026

4.7

(51 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

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Duration9 days

From

USD 2,750

USD 2,357

Saving

USD 393

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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 7 of 198 Trips in Italy during October 2026 with 5,567 Reviews

See Italy tours by duration

Grand Italy & Sicily - October 2026

Country Roads of Northern Italy - October 2026

Highlights of Matera and Apulia Private Tour - October 2026

Italian Vistas - October 2026

Walking the Highlights of Western Sicily Walk - October 2026

Italy: Amalfi Coast to Puglia - October 2026

Jewels of Italy and Cinque Terre by Rail - October 2026

Venice to Florence Cycle - October 2026

Explore Italy - 4 Days - October 2026

Absolute Italy by Rail - October 2026

Backroads to Venice - October 2026

Exploring the Amalfi Coast - October 2026

Rome & La Dolce Vita Experience - October 2026

Rome and Tuscan Highlights - October 2026

Page 7 of 198 Trips in Italy during October 2026 with 5,567 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 7 of 198 Trips in Italy during October 2026 with 5,567 Reviews

See Italy tours by duration

Page 7 of 198 Trips in Italy during October 2026 with 5,567 Reviews