10 Best Italy Multiday Tours in October 2025

Via Francigena: Lucca to Siena - October 2025

4.7

(17 reviews )

No booking fees

Best price guaranteed

Varied hotels en route, all good standard. Smooth delivery of luggage daily. Helpful app.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Lucca, San Miniato Alto

Siena, Lucca, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni

Duration8 days

From

USD 1,190

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In the heart of Italy - October 2025

3.8

(4 reviews )

No booking fees

Best price guaranteed

For those drawn to Italy’s storied past and vibrant present, the 'In the Heart of Italy' tour is a nine-day city sightseeing journey based around Rome. This group tour provides comfortable hotel stays, transportation, and meals, all with an easy activity level suited to seniors. Explore Rome’s ancient wonders and modern life with expert guidance, ensuring both comfort and enrichment. The standout feature is the tour’s focus on the capital’s historic heart, offering a thorough yet relaxed exploration of Italy’s cultural capital.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Perugia

Duration9 days

From

USD 1,220

USD 1,183

Saving

USD 37

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Tuscany Escape, Semi-private Tour - October 2025

15% OFF TODAY

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Tuscany Escape, Semi-private Tour - October 2025

Trip customizable

Best price guaranteed

Tuscany is brimming with secluded valleys, magnificent rolling hills and majestic medieval villages boasting bustling restaurants, piazzas and ancient narrow cobble-stoned streets. Its rich landascape is complemented by towns overflowing with Reinassance art and architecture. Proud of its olive oil, there’s acclaimed gastronomy and, perhaps the best-know wine area, Chianti, is stunningly beautiful with gentle hills clocked by olive groves and vineyards and ancient castles and grand palazzi which have been magnificently restored as impressive hotels.

Art and architectureFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Florence, Gaiole In Chianti

15% OFF TODAY

Duration7 days

From

USD 1,847

USD 1,570

Saving

USD 277

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The Marco Polo - October 2025

Trip customizable

Best price guaranteed

Travel from energetic Rome to Florence, Bologna, and soothingly romantic Venice on this four-day experience. You’ll marvel at Michelangelo’s gift for turning marble into skin as you gaze up at the perfection of the David in Florence, and dare to feed the pigeons in Venice’s St. Mark’s Square. With ample cobblestone alleys to roam, breathtaking monuments and churches to discover, narrow canals to float along, and tiny shops to dip into, you’ll experience the eternal beauty of each city on this unforgettable tour!

Art and architectureChill out

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Lazio

Duration4 days

From

USD 932

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5% OFF TODAY

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Best of Italy - October 2025

4.8

(149 reviews )

No booking fees

Best price guaranteed

Our guide was very professional and knowledgeable which helped a great deal. It got us to places we never would have gone to by ourselves .

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Sorrento

5% OFF TODAY

Duration11 days

From

USD 5,795

USD 5,514

Saving

USD 281

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Journey through Puglia to Matera - October 2025

(1 review )

No booking fees

Best price guaranteed

I took the "Reverse Puglia" trip June 18 to 25, 2024. It was a great trip and overview of Puglia. We stayed in trulias in Alberobello and a cave room in Matera. Everything about the grip was perfect, the pace, the places we visited, the food and local guides. However the best part of the trip was Gabriele the tour guide. He took care of everyone and was funny, intelligent, gracious and a pure delight. He is what made the trip so special and memorable, a philosopher that showed us Puglia.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Bari, Monopoli, Locorotondo, Alb

Bari, Monopoli, Locorotondo, Alberobello, Matera

Duration8 days

From

USD 1,925

USD 1,867

Saving

USD 58

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Splendid Tour (on Request) - October 2025

15% OFF TODAY

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Splendid Tour (on Request) - October 2025

(1 review )

Trip customizable

Best price guaranteed

Discover some of the most essential parts of Italy on this five-day cultural trip, beginning with an exploration of the ruins of ancient Pompeii and continuing to the magnificent views of Positano and its surrounding fishing villages.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Rome, Sorrento, Amalfi

15% OFF TODAY

Duration5 days

From

USD 2,314

USD 1,967

Saving

USD 347

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Portofino and the Cinque Terre - October 2025

(1 review )

No booking fees

Best price guaranteed

The Portofino Cinque Terre self-guided walking holiday was perfectly organized.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Cinque Terre and Liguria, Liguri

Cinque Terre and Liguria, Liguria, Bonassola, Genoa

Duration8 days

From

USD 1,160

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16% OFF TODAY

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Country Roads of Italy - October 2025

4.6

(59 reviews )

No booking fees

Best price guaranteed

This tour was a wonderful experience. A nice size at 28 happy people, luxurious coach, amazing driver & guide extraordinaire . Accommodations were very good & often pleasantly out of the ordinary. The optional activities are worth the extra expense. Highly recommend this tour.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Monteriggioni, Luc

Rome, Venice, Monteriggioni, Lucca, Sorrento, Todi

16% OFF TODAY

Duration16 days

From

USD 7,895

USD 6,665

Saving

USD 1,230

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Hilltop Towns of Italy - October 2025

4.8

(4 reviews )

No booking fees

Best price guaranteed

We had a spectacular trip. We did a self-guided trip in Piemonte and Tuscany/Umbria. The hotels were much nicer than we expected. Very comfortable and the owners/proprietors were so helpful. The transfer of luggage each day was seamless! The routes were generally well marked and the app was very good. We didn't need anything more than the app. Only got lost twice which I'd say is pretty good. The routes were a bit more challenging than we expected. We choose two hikes which were marked as 'Introductory - Moderate' which were tougher than we expected. So just pay attention to this. At home, we would consider ourselves quite capable of moderate+ trails, but the classification in Italy is a bit more demanding. Glad we wore hiking pants as we went through a lot of grasses so never had a concern about tics. Also were very happy we had hiking sticks with us. Invaluable on many of the trails. I would definitely recommend them to anyone considering a hiking trip. And absolutely no problem doing the self-guided version. Thank you!! Griffy and Marg

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Orvieto, Sorano, Bolsena, Pitigliano

Duration8 days

From

USD 1,570

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St Francis Way: Assisi to Spoleto - October 2025

4.8

(9 reviews )

No booking fees

Best price guaranteed

The information provided was excellent and the navigation app worked well. The accommodation was extremely good. Overall I found the walk more difficult than I expected, but in the end very rewarding.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Assisi, Spoleto, Spello, Vegnole

Assisi, Spoleto, Spello, Vegnole, Bovara Di Trevi, PORETA

Duration7 days

From

USD 1,050

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A Saunter in Sardinia - October 2025

(2 reviews )

No booking fees

Best price guaranteed

This was a great walk, with very varied topography in an underappreciated part of Sardinia

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Sardinia, Cabras, Santu Lussurgi

Sardinia, Cabras, Santu Lussurgiu, Santa Caterina Di Pittinuri, Putzu Idu, San Salvatore Di Sinis, San Giovanni Di Sinis

Duration8 days

From

USD 1,450

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Local Living Italy—sorrento - October 2025

22% OFF TODAY

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Local Living Italy—Sorrento - October 2025

(4 reviews )

No booking fees

Best price guaranteed

This was a bucket list trip for me and I highly recommend this tour. It exceeded my expectations. Looking forward to more G Adventures!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Sorrento

22% OFF TODAY

Duration7 days

From

USD 2,199

USD 1,706

Saving

USD 493

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Via Degli Dei: Bologna to Florence - October 2025

4.8

(8 reviews )

No booking fees

Best price guaranteed

Beautiful, varied walk through Emilia Romagna and Tuscany.

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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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 2025

Page 5 of 218 Trips in Italy during October 2025 with 2,641 Reviews

See Italy tours by duration

Via Francigena: Lucca to Siena - October 2025

In the heart of Italy - October 2025

Tuscany Escape, Semi-private Tour - October 2025

The Marco Polo - October 2025

Best of Italy - October 2025

Journey through Puglia to Matera - October 2025

Splendid Tour (on Request) - October 2025

Portofino and the Cinque Terre - October 2025

Country Roads of Italy - October 2025

Hilltop Towns of Italy - October 2025

St Francis Way: Assisi to Spoleto - October 2025

A Saunter in Sardinia - October 2025

Local Living Italy—Sorrento - October 2025

Via Degli Dei: Bologna to Florence - October 2025

Page 5 of 218 Trips in Italy during October 2025 with 2,641 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 2025

Page 5 of 218 Trips in Italy during October 2025 with 2,641 Reviews

See Italy tours by duration

Page 5 of 218 Trips in Italy during October 2025 with 2,641 Reviews