10 Best Italy Multiday Tours in October 2025

Tuscany Highlights, Private Tour - October 2025

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Tuscany Highlights, Private Tour - October 2025

Trip customizable

Best price guaranteed

Drive through some of Italy's most iconic region on this eight-day tour that takes you through Lucca, Siena and Florence. 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 landscape is complemented by towns overflowing with Renaissance art and architecture.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, italian, german

Destinations

Florence, Lucca, Siena

15% OFF TODAY

Duration8 days

From

USD 3,222

USD 2,739

Saving

USD 483

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Sorrento Dream (on Request) - October 2025

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Sorrento Dream (on Request) - October 2025

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

15% OFF TODAY

Duration4 days

From

USD 1,661

USD 1,412

Saving

USD 249

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Italian Roundabout Complete End Rome - October 2025

No booking fees

Best price guaranteed

Italy’s timeless allure awaits seniors on the 20-day Italian Roundabout Complete End Rome tour. Journey in comfort through Genoa, Bari, and Rome, as well as 11 other enchanting destinations, on a city sightseeing trip designed for relaxation and ease. This guided group tour takes you from grand piazzas to historic cathedrals, weaving through the heart of Italy’s culture and culinary heritage. With accommodation, transport, and meals seamlessly arranged, you can simply enjoy each moment—no strenuous walking required. The unique selling point lies in its comprehensive yet leisurely pace, ensuring mature travelers experience Italy’s wonders without rush or fatigue.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Siena, Florence, Genoa, Mi

Rome, Siena, Florence, Genoa, Milan, Verona, Venice, Perugia, Bari, Brindisi, Naples, Salerno, Taormina, Palermo

Duration20 days

From

USD 3,793

USD 3,679

Saving

USD 114

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Sicily and Eolic Islands - October 2025

No booking fees

Best price guaranteed

Sicily and Eolic Islands invites mature travelers to discover the wonders of Palermo, Agrigento, Taormina, and Milazzo over 8 relaxed days. This guided city sightseeing tour provides all the comforts—accommodation, transport, and meals—so you can focus on sampling local delicacies and admiring ancient sites. For those seeking a serene Mediterranean getaway, the tour’s unique appeal lies in its combination of Sicily’s history with the tranquil beauty of the Eolic Islands.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Milazzo, Taormina, Agrigento

Duration8 days

From

USD 1,271

USD 1,233

Saving

USD 38

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Enchanting Waters: Discovering The Lakes Of Italy, Self-drive - October 2025

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Enchanting Waters: Discovering The Lakes Of Italy, Self-drive - October 2025

Trip customizable

Best price guaranteed

Choose this self-drive tour in the Lombardy region and spend 8 memorable days exploring the beautiful landscapes and culture of Italy. Visit mesmerising lakes of Maggiore, Como and Garda, take a boat to Bellagio and admire the beauty and tranquillity of the scenery that surrounds you. Walk through the medieval streets of Bergamo and visit Verona, a city full of history. This trip will fill all your senses and will leave great memories for a lifetime.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Milan, Lake Maggiore, Lake Garda

15% OFF TODAY

Duration8 days

From

USD 1,722

USD 1,463

Saving

USD 258

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Golden Italy and Beautiful Campania - October 2025

4.5

(2 reviews )

No booking fees

Best price guaranteed

Tour Guides were very nice and helpful...they answered any questions that we had and went out of their way to make sure the experience was the best that it could be. Great, Great tour guides.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Perugia, Naples, S

Rome, Venice, Perugia, Naples, Siena, Florence, Genoa, Milan, Verona

Duration14 days

From

USD 2,292

USD 2,223

Saving

USD 69

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In The Footsteps Of Leonardo, Private Tour - October 2025

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In The Footsteps Of Leonardo, Private Tour - October 2025

Trip customizable

Best price guaranteed

Join our seven days tour for a “full immersion” into Leonardo Da Vinci’s life. Visit Accademia Gallery in Venice, Cenacolo and Pinacoteca Ambrosiana in Milan and Uffizi Gallery in Florence. Our expert guides will lead you to the most important sites of these cities to show you the famous masterpieces of this amazing artist and his life.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Florence, Venice, Milan

15% OFF TODAY

Duration7 days

From

USD 1,986

USD 1,688

Saving

USD 298

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The Dolomites And Prosecco, Self-drive - October 2025

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The Dolomites And Prosecco, Self-drive - October 2025

Trip customizable

Best price guaranteed

Embark on an unforgettable journey through the stunning landscapes of Northern Italy with our Dolomites and Prosecco Self-Drive Tour. This unique adventure offers the perfect blend of natural beauty, cultural richness, and culinary delights. Wind your way through the majestic peaks and verdant valleys of the Dolomites, a UNESCO World Heritage site renowned for its breathtaking scenery and outdoor activities. Then, immerse yourself in the world of Prosecco, exploring the lush vineyards and charming villages where this world-famous sparkling wine is produced. With the freedom of a self-drive tour, you can set your own pace, stop to take in the views and savor the region's delights on your terms. Get ready to experience the best of Italy's alpine and wine country, creating memories that will last a lifetime.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Cortina d'Ampezzo, Treviso, Bolz

Cortina d'Ampezzo, Treviso, Bolzano, Venice

15% OFF TODAY

Duration8 days

From

USD 1,481

USD 1,259

Saving

USD 222

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Sorrento Escape, Private Tour - October 2025

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Sorrento Escape, Private Tour - October 2025

(1 review )

Trip customizable

Best price guaranteed

Great tour, private guides and drivers are great.

Art and architectureFood tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Naples, Sorrento, Capri

15% OFF TODAY

Duration7 days

From

USD 2,948

USD 2,506

Saving

USD 442

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Private Mini-cruise Around Gulf Of Naples, 4 Days (klase 50) (on Request) - October 2025

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Private Mini-cruise Around Gulf Of Naples, 4 Days (klase 50) (on Request) - October 2025

Trip customizable

Best price guaranteed

Stunning scenery and dramatic landscape during the day and the twinkling lights of the coastal villages by night. Give yourself over experiencing the thrill of a short cruise with all the luxury of an expert private crew ready to take care of all your needs. Get on board the Klase 50 HT, a prestigious yacht featuring a comfortable and sporty layout, equipped with a dual Caterpillar engine, which allows it to reach the maximum speed of 32 knots, the Klase 50 will satisfy the most demanding guests with its spacious and reﬁned interior and exterior. Treat yourself to our four-day mini cruise for memories that will last a lifetime. Explore from Sorrento to Capri and The Amalfi Coast by the sea in complete comfort and total safety.

BeachCruise

Tour Type

Private Tour

Accommodation

Ship Cabin

Age Range

6-99 yrs

Operated in

english

Destinations

Sorrento, Capri, Positano

15% OFF TODAY

Duration4 days

From

USD 14,634

USD 12,439

Saving

USD 2,195

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Discovering Bari - October 2025

Trip customizable

Best price guaranteed

Bari is an elegant white town on the Adriatic Sea, it combines both the sophisticated atmosphere of South Italy and the simplicity of a small provincial area. Explore the beautiful white town of Bari, visit the Basilica Pontificia di San Nicola, Museo Nicolaiano, and other areas while learning about the history and culture of the city.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, italian

Destinations

Bari

15% OFF TODAY

Duration4 days

From

USD 730

USD 620

Saving

USD 109

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Mini Tour Of Sicily, Self-drive - October 2025

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Mini Tour Of Sicily, Self-drive - October 2025

Trip customizable

Best price guaranteed

Discover the beauties of Sicily during this five days self-drive tour. Drive through several UNESCO Heritage Sites and unique towns, and admire splendid views and art masterpieces.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Palermo, Catania

15% OFF TODAY

Duration5 days

From

USD 628

USD 534

Saving

USD 94

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15% OFF TODAY

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Discovering Matera - October 2025

Trip customizable

Best price guaranteed

Matera is a small jewel carved out of the mountains. Time seems to have stood still in the city of Basilicata, where the surrounding landscape is not unlike a painting. Matera, which in past years has captivated photographers and filmmakers, including Henri Cartier-Bresson, Pier Paolo Pasolini and Mel Gibson, has a unique charm. A complex beauty that can only be understood when walking around the narrow alleys of the historic center and the houses carved out of the tuff. The layers of history and the delicate relationship with the surrounding nature make it an amazing open-air museum.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, italian

Destinations

Matera

15% OFF TODAY

Duration4 days

From

USD 894

USD 760

Saving

USD 134

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Tuscany Escape, Self-drive - October 2025

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Tuscany Escape, Self-drive - 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.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Florence, Chianti

15% OFF TODAY

Duration7 days

From

USD 1,056

USD 898

Saving

USD 158

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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 7 of 142 Trips in Italy during October 2025 with 1,983 Reviews

See Italy tours by duration

Tuscany Highlights, Private Tour - October 2025

Sorrento Dream (on Request) - October 2025

Italian Roundabout Complete End Rome - October 2025

Sicily and Eolic Islands - October 2025

Enchanting Waters: Discovering The Lakes Of Italy, Self-drive - October 2025

Golden Italy and Beautiful Campania - October 2025

In The Footsteps Of Leonardo, Private Tour - October 2025

The Dolomites And Prosecco, Self-drive - October 2025

Sorrento Escape, Private Tour - October 2025

Private Mini-cruise Around Gulf Of Naples, 4 Days (klase 50) (on Request) - October 2025

Discovering Bari - October 2025

Mini Tour Of Sicily, Self-drive - October 2025

Discovering Matera - October 2025

Tuscany Escape, Self-drive - October 2025

Page 7 of 142 Trips in Italy during October 2025 with 1,983 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 7 of 142 Trips in Italy during October 2025 with 1,983 Reviews

See Italy tours by duration

Page 7 of 142 Trips in Italy during October 2025 with 1,983 Reviews