10 Best Italy Multiday Tours in October 2026

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Plan a multi-country or regional adventure across Italy in October 2026, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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Page 19 of 218 Trips in Italy during October 2026 with 3,988 Reviews

Showing 1 - 10 of 218 results

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.

Cyber Monday Super Sales

Sorrento Dream (on Request) - October 2026

Trip customizable

Best price guaranteed

Join this four-day tour to discover the essence of the Campania region, including Naples, Capri and Sorrento. A wonderful experience through Italian landscapes, history, and culture. Immerse yourself into an archaeological journey through the ancient city of Pompeii. Discover Sorrento, a city with a colourful historical centre and a beautiful waterfront filled with bobbing fishing boats, as well as the new Marina Grande cruise pier. Sail to the rocky island of Capri, and enjoy the beauty of its unique landscape.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Sorrento, Rome

Duration4 days

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Cyber Monday Super Sales

Naples Express & Sorrento (on Request) - October 2026

Trip customizable

Best price guaranteed

Discover the Sorrento peninsula and the isle of Capri on this four-day tour beginning and ending in Rome. Along the way, stop to absorb the history of Naples and jump back in time by visiting the ghostly excavations of Pompeii. The Sorrento peninsula is easily one of the country's most lavish and beautiful regions, ideal for relaxing and sightseeing alike. From there, Capri and its famed Blue Grotto are only a ferry ride away.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Naples, Sorrento, Rome

Duration4 days

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Cyber Monday Super Sales

Puglia Express: 5 Days of Southern Charm - October 2026

Trip customizable

Best price guaranteed

Begin in Bari and transfer to the Itria Valley for a warm welcome and dinner. Explore the Grotte di Castellana, the trulli houses of Alberobello, and the “white city” of Ostuni. Visit Lecce, the “Florence of the South,” and the historic treasures of Otranto. Experience the unique Sassi neighborhoods of Matera before concluding your adventure in the Bari area. Enjoy a perfect blend of history, culture, and stunning landscapes throughout this unforgettable tour

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Bari, Itria Valley

Duration5 days

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Cyber Monday Super Sales

Discovering Garda Lake - October 2026

Trip customizable

Best price guaranteed

Discover Lake Garda, Italy's largest lake, which offers breathtaking scenery with its crystal-clear waters surrounded by charming towns and rolling hills. The area offers a variety of activities, from boating and swimming to exploring charming villages like Sirmione. Lake Garda offers a perfect blend of natural beauty, historical intrigue and cultural experiences.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Lake Garda, Sirmione

Duration4 days

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Cyber Monday Super Sales

Discovering Florence - October 2026

Trip customizable

Best price guaranteed

Discover Florence, the capital of Italy’s Tuscany region on this short break. A captivating Italy destination that Mark Twain once described as a “city of dreams.” With its abundance of timeless art, rustic Tuscan cuisine, incredible boutique shopping, and mesmerizing views at every turn, the city of Florence is nothing short of spectacular. Visit the Accademia Gallery, the Uffizi Gallery and the iconic Duomo Cathedral. End the trip in the Tuscany countryside and enjoy a glass of wine in this idyllic landscape.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Florence

Duration4 days

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Local Living Italy - Tuscany San Gimignano - October 2026

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Cyber Monday Super Sales

Local Living Italy - Tuscany San Gimignano - October 2026

No booking fees

Best price guaranteed

If Tuscany has ever called your name, this is your chance to answer. For seven days, you’ll settle into a charming farmhouse in San Gimignano — your home for the week and your base for exploring the heart of central Italy. Wake up to vineyard views, stroll medieval streets, and soak up sunsets over rolling hills, all at a pace that feels truly local. With free days to embrace the countryside or head out on day trips to Florence, Siena, and Volterra, this isn’t just a visit — it’s living Tuscany, one unforgettable day at a time.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, San Gimignano

18% OFF TODAY

Duration7 days

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Cyber Monday Super Sales

Discovering Amalfi Coast - October 2026

Trip customizable

Best price guaranteed

An exciting tour to discover the Amalfi Coast through its history and flavors. Immerse yourself into an archaeological journey through the ancient cities of Pompeii and Ercolano. Sail to the rocky island of Capri, and wander around its tiny pedestrian alleys.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Amalfi

Duration4 days

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Cyber Monday Super Sales

Puglia Panorama - October 2026

Trip customizable

Best price guaranteed

The tour is designed for those seeking a delightful mix of cultural exploration, culinary delights, and breathtaking landscapes. Embark on a captivating journey through the enchanting landscapes of southern Italy with this unforgettable tour that takes you from the bustling city of Bari to the spiritual haven of San Giovanni Rotondo, the coastal charm of Vieste, and the natural wonders of the Gargano Peninsula. Each day unfolds a new chapter in the rich tapestry of southern Italy's cultural and natural treasures

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

7-99 yrs

Operated in

english

Destinations

Bari, Monte Sant'Angelo

Duration5 days

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Cyber Monday Super Sales

Tutta Italia To Sicily by Plane And Aeolian Islands - October 2026

No booking fees

Best price guaranteed

Travel from Rome to Palermo on the Tutta Italia To Sicily by Plane And Aeolian Islands trip, an 18-day sightseeing adventure tailored for seniors. This easy-paced group tour explores Taormina, Verona, and several other Italian treasures, blending city strolls, cultural sites, and scenic landscapes. With all logistics—including comfortable accommodations, transfers, and meals—handled for you, the journey prioritizes relaxation and discovery. The tour’s standout feature is its inclusion of the enchanting Aeolian Islands, offering a tranquil Mediterranean escape alongside Italy’s classic cities.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Venice, Milazzo

Rome, Palermo, Venice, Milazzo, Taormina, Agrigento, Siena, Florence, Genoa, Milan, Verona

Duration18 days

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Cyber Monday Super Sales

Tutta Italia and Sicily with Aeolian Islands - October 2026

No booking fees

Best price guaranteed

Let the charm of Italy sweep you away on the 16-day Tutta Italia and Sicily with Aeolian Islands tour, crafted for those who appreciate a relaxed, insightful journey. Starting in Rome and ending in Palermo, this group tour weaves through Siena, Florence, and seven other captivating destinations. Senior travelers will appreciate the easy pace, comfortable accommodations, and seamless transport. The highlight is the opportunity to explore the picturesque Aeolian Islands—providing an idyllic contrast to Italy’s bustling cities and rich history.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Venice, Milazzo

Rome, Palermo, Venice, Milazzo, Taormina, Siena, Florence, Genoa, Milan, Verona

Duration16 days

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Hi there

Italy Tours in October 2026

See Italy tours by duration

Get a customized trip to Italy in October 2026

Page 19 of 218 Trips in Italy during October 2026 with 3,988 Reviews

Combine Italy in October with Nearby Countries for an Unforgettable Trip

Sorrento Dream (on Request) - October 2026

Naples Express & Sorrento (on Request) - October 2026

Puglia Express: 5 Days of Southern Charm - October 2026

Discovering Garda Lake - October 2026

Discovering Florence - October 2026

Local Living Italy - Tuscany San Gimignano - October 2026

Page 19 of 218 Trips in Italy during October 2026 with 3,988 Reviews

Discovering Amalfi Coast - October 2026

Puglia Panorama - October 2026

Tutta Italia To Sicily by Plane And Aeolian Islands - October 2026

Tutta Italia and Sicily with Aeolian Islands - October 2026

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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

Hi there

Italy Tours in October 2026

See Italy tours by duration

Get a customized trip to Italy in October 2026

Page 19 of 218 Trips in Italy during October 2026 with 3,988 Reviews

Page 19 of 218 Trips in Italy during October 2026 with 3,988 Reviews