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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Southern Italy - October 2026

4.8

(40 reviews )

No booking fees

Best price guaranteed

This trip is for you if you're searching for delicious food, helpful guidance, and entertaining company! Excellent use of ten days! As a solo traveler, I really appreciated having my own room because at some other companies, you have to share a room with a stranger. Alessandro was an excellent guide who added much enjoyment to the trip.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish, portuguese

Destinations

Rome, Taormina, Sorrento, Palerm

Rome, Taormina, Sorrento, Palermo, Agrigento, Ragusa

Duration11 days

From

USD 4,450

USD 4,317

Saving

USD 134

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Southern Pearls (on Request) - October 2026

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Southern Pearls (on Request) - October 2026

Trip customizable

Best price guaranteed

Drive through some of Italy's most iconic locations on this five-day tour that takes you through Naples, Pompeii, Sorrento and Capri. Spend the second half of the tour explore the wonderful coastal town of Positano at leisure. Relax at the hotel, discover the breath-taking surroundings, or even plunge into the warm waters of the Mediterranean.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Rome, Sorrento, Positano

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Duration5 days

From

USD 3,515

USD 2,988

Saving

USD 527

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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

14% OFF TODAY

Duration10 days

From

USD 4,450

USD 3,841

Saving

USD 609

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Italian Vistas - October 2026

No booking fees

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

Duration13 days

From

USD 4,499

USD 4,299

Saving

USD 200

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Italy: Amalfi Coast to Puglia - October 2026

No booking fees

Best price guaranteed

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

Duration14 days

From

USD 4,699

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Art Cities Of Italy, Private Tour - October 2026

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Art Cities Of Italy, Private Tour - October 2026

(1 review )

Trip customizable

Best price guaranteed

They did a great job with everything!

Art and architectureHoneymoon

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Rome, Florence, Venice, Milan

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Duration8 days

From

USD 3,359

USD 2,856

Saving

USD 504

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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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Naples Escape & Sorrento (on Request) - October 2026

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Naples Escape & Sorrento (on Request) - October 2026

(1 review )

Trip customizable

Best price guaranteed

We just returned from a wonderful trip to Italy. Grazia helped plan our trip. She provided excellent advice before and during our journey. We will definitely use TUI Italy again!

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Naples, Sorrento, Rome

15% OFF TODAY

Duration5 days

From

USD 1,974

USD 1,678

Saving

USD 296

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Discovering Lecce - October 2026

Trip customizable

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A mesmerizing feast of baroque architecture, Lecce dazzles the eye with its resplendent historical center, which is lined with buildings from the 17th and 18th centuries. You’ll find dozens of striking churches and palazzi, along with a Norman-style castle and a trove of excellent museums. Lecce has been inhabited for over 2000 years, and you can see ancient Roman ruins in a horseshoe-shaped amphitheatre that once held 15,000 spectators.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, italian

Destinations

Lecce

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Duration4 days

From

USD 1,046

USD 889

Saving

USD 157

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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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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 1,861

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Classic Amalfi Coast - 11 Days - October 2026

4.6

(5 reviews )

No booking fees

Best price guaranteed

Very well organised trip. Logistics were excellent, accommodation was comfortable and central to all amenities of the towns. Hike maps and notes were extremely detailed. I would highly recommend them and am considering another trip in the near future.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Amalfi

Amalfi Coast & Campania, Amalfi, Sorrento, Naples, Praiano, Positano

Duration11 days

From

USD 2,290

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Discovering Palermo - October 2026

Trip customizable

Best price guaranteed

Explore Sicily's largest city during this short four-day trip. Enjoy this lively and thriving city with an amazing blend of cultures and glorious food. You'll discover the charm of Palermo, a layered metropolis with centuries of Arab, Norman, Byzantine and Mediterranean influences. With a local expert, learn about the city's history, art, and architecture.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Palermo

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Duration4 days

From

USD 949

USD 806

Saving

USD 142

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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 189 Trips in Italy during October 2026 with 3,040 Reviews

See Italy tours by duration

Grand Italy & Sicily - October 2026

Southern Italy - October 2026

Southern Pearls (on Request) - October 2026

Country Roads of Northern Italy - October 2026

Italian Vistas - October 2026

Italy: Amalfi Coast to Puglia - October 2026

Art Cities Of Italy, Private Tour - October 2026

Venice to Florence Cycle - October 2026

Naples Escape & Sorrento (on Request) - October 2026

Discovering Lecce - October 2026

Backroads to Venice - October 2026

Rome & La Dolce Vita Experience - October 2026

Classic Amalfi Coast - 11 Days - October 2026

Discovering Palermo - October 2026

Combine Italy in October with Nearby Countries for an Unforgettable Trip

Page 6 of 189 Trips in Italy during October 2026 with 3,040 Reviews

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Asia

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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 189 Trips in Italy during October 2026 with 3,040 Reviews

See Italy tours by duration

Page 6 of 189 Trips in Italy during October 2026 with 3,040 Reviews