10 Best Italy Multiday Tours in October 2026

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A Taste of Tuscany Self-Guided Walking - October 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

This tour was a welcome change from the fast paced touring of the big cities. We became familiar with the topography and vegetation as we hiked daily, also visiting towns known for wines and cheeses. The town of Chianciano provided a magnificent backdrop to our accomodation of Agriturismo La Pietriccia. We were awakened every morning to the rooster crowing. Stefano was an attentive and knowledgeable host. Plenty of food was served at the 4 course suppers. I feel this tour was necessary to complete my knowledge of the culture of Italy!

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Tuscany, Chianciano Terme, Chian

Tuscany, Chianciano Terme, Chianciano Vecchia, Montepulciano, Bagno Vignoni

Duration8 days

From

USD 2,105

USD 2,042

Saving

USD 63

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Super Sales

Walking The Amalfi Coast - Summer Edition - October 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

The trip was fabulous -beautiful places , lovely hotel and friendly warm staff , excellent food wine and our leader Veriano was so kind engaging fun and made the trip even more enjoyable and our group was fabulous. Would go back tomorrow! Highly recommend it!

Trekking and HikingBeach

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Bomeran

Amalfi Coast & Campania, Bomerano, Atrani, Sorrento, Mount Vesuvius, Conca Dei Marini, Naples, Amalfi

Duration8 days

From

USD 2,175

USD 2,110

Saving

USD 65

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Via Francigena: Aosta to Ivrea - October 2026

(1 review )

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Best price guaranteed

Fourth leg of our Camino. As always, very well organised - hotels, transfers, restaurant suggestions were all great. Stunning walking and scenery

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Turin, Ivrea, Aosta Valley, Aost

Turin, Ivrea, Aosta Valley, Aosta, Nus, Saint Vincent, Verres, Pont-Saint-Martin

Duration7 days

From

USD 1,050

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Via Francigena: Ivrea to Pavia - October 2026

(1 review )

No booking fees

Best price guaranteed

Follow old trails through ancient hamlets and past impressive castles on the Francigena Way, the Italian Camino, between Ivrea and Pavia. From Canterbury in England to Rome in Italy, the 1900km "Francigena Way" dates back to the 11th century when pilgrims travelled across Europe on foot to visit the site of Martyrdom of St Peter and St Paul in Rome. With the modernisation of Europe and the shifting of borders the route became obsolete, until a recent revival of the pilgrimage making it one of the most exciting pilgrimage trails in Europe today. This section travels through the plains of Piedmont. From March to May the rice fields are flooded and treat you to a wonderful view of the "chequered sea". At other times of the year you will spot herons and egrets. The trail continues into the Lombardy region before ending in Pavia. Here you can enjoy the artistic wealth of Pavia's old town, while reveling in the vivacity of the student quarters.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Lombardy & the Lakes, Pavia, Ivr

Lombardy & the Lakes, Pavia, Ivrea, Viverone, Santhia, Vercelli, Mortara

Duration8 days

From

USD 1,070

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Super Sales

Walking in the Venetian Hills - October 2026

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Best price guaranteed

This walking holiday is based in the wonderfully unspoilt Euganean Hills, tucked in a quiet corner below the beautiful medieval city of Padua, west across the plain from Venice. Once volcanic islands, these hills have a striking conical appearance; they are cloaked in an astonishing variety of plant life including holm oak, maple, orchids, heather and poppies and have been recognised as a National Park. The lower slopes give way to colourful meadows and immaculately groomed vineyards so it's little wonder the region produces such a fine variety of wines! Starting in the tiny hamlet of Cortela, nestled amongst vines, you head across poppy fields and through forests to Valnogaredo. You discover the jumbled cobbled streets of medieval Arqua Petrarca, where the famous 14th century Italian poet, Petrarch, made his home, before continuing through fertile fruit orchards to Galzignano. A convenient stone's throw from the Italian Baroque gardens of Valsanzibio, there's time to explore its magnificent maze before a series of outstanding views leads you to panoramically perched Teolo.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Venice & Veneto, Cortela

Venice, Venice & Veneto, Cortela, ARQUA PETRARCA, GALZIGNANO, TEOLO

Duration9 days

From

USD 1,835

USD 1,780

Saving

USD 55

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Via Francigena: Pontremoli to Lucca - October 2026

(1 review )

No booking fees

Best price guaranteed

Journey by foot through the little-known region of Tuscany between Pontremoli and the walled town of Lucca along the Via Francigena, the Italian Camino. The Via Francigena has experienced a recent revival and is now one of the most exciting pilgrimage trails in Europe. This section of the trail takes you through a little-known region of Tuscany. Starting in Pontremoli, in the heart of the Lunigiana region where the green hills are dotted with fine castles, you will descend to the sea in Versilia. Enjoy the coastal scenery as you walk along the sandy beaches and during the warmer months you can happily stop for a swim en route. Leaving the coast behind, you will head back toward the Tuscan hills. You can visit the fascinating artists' workshops in Pietrasanta, known as the Italian Athens, which rests at the foot of the Apuan Alps. The highlights continue as you reach the walled town of Lucca, one of the most captivating old town centres of Tuscany.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Lucca, Pontremoli, File

Tuscany, Lucca, Pontremoli, Filetto, Aulla, Sarzana, Massa, Camaiore

Duration8 days

From

USD 1,190

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Super Sales

Highlights of Calabria & Sicily - October 2026

No booking fees

Best price guaranteed

See a lesser-known part of Italy on this 16-day adventure, all with a handy local leader by your side. From the fresh waters and fortifications of Tropea, all the way to the volcanoes of the Aeolian Islands, you’ll stray off Italy’s beaten path. Discover this less-visited part of the country before delving into the spectacular sights of bustling Sicily, the volcanic valleys of Mt. Etna, timeworn streets of Syracuse, the Baroque wonders of Ragusa and the rich anti-Mafia history of Palermo. Starring dramatic cliffside villages, clear waters and delicious seafood, this is a chance to experience the highlights of this European gem.

National parks

Tour Type

Small Group Tour

Accommodation

Guest House, Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Palermo

Amalfi Coast & Campania, Palermo, Minori, Amalfi, Catania, Syracuse, Agrigento, Marsala, Civita, Tropea, Reggio Calabria, Naples

Duration16 days

From

USD 5,595

USD 5,427

Saving

USD 168

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Super Sales

Premium Walking & Hiking on Italy's Amalfi Coast - October 2026

No booking fees

Best price guaranteed

Lace up your hiking boots and set your sights towards the spectacular Mediterranean horizon. This seven-day Premium walking and hiking trip on the Amalfi Coast features the best of the short hikes in the area, and is a nature-lover’s dream! Walk the crater rim of the Mount Vesuvius volcano, say Buongiorno to local farmers along the Pathway of the Gods, take in sweeping panoramic views from the Path of the Lemons, and catch a ferry to the glamorous island of Capri. Then, visit Pompeii to explore the preserved ruins and learn about the history of the area. Spend two nights in in a clifftop hotel, soak up sunsets, eat your weight in delicious Italian food (carbs, anyone?) and get active in one of the most beautiful parts of Italy, if not the world.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Naples, Capri, Sentiero Degli De

Naples, Capri, Sentiero Degli Dei, Amalfi

Duration7 days

From

USD 5,460

USD 5,296

Saving

USD 164

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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 4 of 50 Trips in Italy during October 2026 with 1,208 Reviews

See Italy tours by duration

Page 4 of 50 Trips in Italy during October 2026 with 1,208 Reviews

A Taste of Tuscany Self-Guided Walking - October 2026

Walking The Amalfi Coast - Summer Edition - October 2026

Via Francigena: Aosta to Ivrea - October 2026

Via Francigena: Ivrea to Pavia - October 2026

Walking in the Venetian Hills - October 2026

Via Francigena: Pontremoli to Lucca - October 2026

Highlights of Calabria & Sicily - October 2026

Premium Walking & Hiking on Italy's Amalfi Coast - October 2026

Combine Italy in October with Nearby Countries for an Unforgettable Trip

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All Italy Tours in October 2026

Page 4 of 50 Trips in Italy during October 2026 with 1,208 Reviews

See Italy tours by duration

Page 4 of 50 Trips in Italy during October 2026 with 1,208 Reviews