Siena October 2026 Tours and Trip packages

Amazing Italy - October 2026

(3 reviews )

Trip customizable

Best price guaranteed

Absolutely incredible! Italy’s history, food, and charm blew us away. The small group setting was perfect, and everything was tailored for Canadian travelers. Highly recommend!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Sorrento

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

Duration15 days

View Tour

The Essential of Italy end Milan - October 2026

4.8

(12 reviews )

No booking fees

Best price guaranteed

Hi, I really enjoyed this trip. I would suggest to put just two stops/visits for each day and not more: otherwise this could easly cause daley during the tour.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Milan, Rome, Siena, Florence, Genoa

Duration9 days

View Tour

Golden Italy and Beautiful Campania - October 2026

4.5

(4 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

View Tour

Barcelona to Rome - October 2026

No booking fees

Best price guaranteed

Dreaming of the perfect European getaway? The "Barcelona to Rome" tour package blends iconic city sightseeing with leisurely discovery, guiding you through the vibrant cultures and landscapes of Spain, France, and Italy over 15 days. Start your journey in the bustling streets of Barcelona, where art, architecture, and tapas set the tone for an unforgettable adventure. Venture into the picturesque Spanish Pyrenees, then treat your senses to the flavors of Provençal cuisine and renowned wines along the sun-drenched French Riviera—famous for its glamorous atmosphere and Mediterranean charm. This small group trip continues with a visit to the dramatic, cliff-hugging villages of the Cinque Terre, offering panoramic coastal views and a taste of authentic Ligurian life. In Florence, immerse yourself in Renaissance masterpieces, then capture the must-have photo at the iconic Leaning Tower of Pisa. Wander through medieval Siena’s enchanting streets before culminating your travels in the ancient city of Rome, where layers of history await at every turn. Designed for travelers who appreciate a relaxed pace and easy physical activity, this tour includes comfortable hotel accommodations, seamless transport, select meals, and the guidance of experienced local leaders. Whether you’re a first-time visitor or a seasoned explorer, the itinerary ensures you enjoy ample free time to soak in local culture, cuisine, and stunning scenery at your own speed. The unique selling point of this tour is its seamless blend of legendary sights and hidden gems—allowing you to experience three diverse countries and their highlights in one thoughtfully curated journey. With logistics handled and expert guidance at every step, you’re free to simply savor the magic of Europe’s most captivating regions.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Barcelona, Cinque Terre an

Rome, Barcelona, Cinque Terre and Liguria, Florence, Siena, Ribes De Freser, Toulouse, Provence, Nice

Duration15 days

View Tour

Discover Tuscany: Culture, Food & Wine - October 2026

(1 review )

No booking fees

Best price guaranteed

This tour was an amazing way to experience the heart of Tuscany. The itinerary was perfectly balanced with cultural visits, delicious food and wine experiences, and plenty of free time to explore or relax. Some highlights for me were the guided tour of Siena, where we tasted incredible pastries made from unique local recipes, the pasta-making class in Chianti with a warm and welcoming family, and the wine tastings at beautiful family-run estates where we learned so much about what we were enjoying. Our day in Florence was equally wonderful. The hotel in Pancole was cozy and inviting and all the family and staff were so welcoming, and our tour leader made everything smooth and enjoyable. A fantastic trip filled with unforgettable memories!

Active and outdoor

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Siena

Duration8 days

View Tour

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

View Tour

Rome, Tuscany, Côte d Azur, Provence and Barcelona - October 2026

No booking fees

Best price guaranteed

The 'Rome, Tuscany, Côte d’Azur, Provence and Barcelona' tour invites you to experience the best of Italy, France, and Spain over 11 gentle days. Perfect for those who prefer relaxed sightseeing, this guided group trip covers Rome’s historic marvels, the scenic beauty of Tuscany and Provence, and the lively atmosphere of Barcelona. With all accommodations, meals, and transportation included, the trip’s unique appeal lies in its wide-ranging yet comfortably paced itinerary, making it an exceptional choice for seniors eager to explore three iconic destinations in one go.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Barcelona, Siena, Florence

Rome, Barcelona, Siena, Florence, Cote D'Azur, Marseille

Duration11 days

View Tour

Tutta Italia With Beautiful Campania and Sicily - October 2026

No booking fees

Best price guaranteed

Experience an enchanting blend of Italy’s celebrated cities and southern gems on the Tutta Italia With Beautiful Campania and Sicily tour. Over 17 leisurely days, seniors will traverse from Rome to Palermo, visiting Venice, Siena, and Palermo plus nine other scenic stops. This easy-paced city sightseeing tour includes all the essentials—accommodation, transport, and meals—so you can focus on enjoying Italy’s art, cuisine, and culture. The unique selling point is its inclusion of both Campania’s coastal beauty and Sicily’s distinct heritage, creating a truly well-rounded Italian adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Venice, Perugia

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

Duration17 days

View Tour

Italian Roundabout Complete End Venice - October 2026

No booking fees

Best price guaranteed

For seniors seeking a comfortable yet immersive Italian experience, the 18-day Italian Roundabout Complete End Venice tour is an excellent choice. Starting in Rome and concluding in the romantic city of Venice, this easy-paced sightseeing trip covers Genoa, Siena, Taormina, and ten other must-see locations. With all accommodations, transport, and meals expertly organized, you can relax as you soak up Italy’s art, history, and cuisine. The USP of this tour is its thoughtfully balanced itinerary, allowing guests to savor the country’s highlights at a gentle, enjoyable rhythm.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Siena, Florence, G

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

Duration19 days

View Tour

Tours and Trip Packages to Siena in October 2026

Get a customized trip to Siena in October 2026

Page 2 of 21 Trips in Siena during October 2026 with 399 Reviews

Amazing Italy - October 2026

The Essential of Italy end Milan - October 2026

Roman Holiday - October 2026

Golden Italy and Beautiful Campania - October 2026

Barcelona to Rome - October 2026

Discover Tuscany: Culture, Food & Wine - October 2026

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

Rome, Tuscany, Côte d Azur, Provence and Barcelona - October 2026

Tutta Italia With Beautiful Campania and Sicily - October 2026

Italian Roundabout Complete End Venice - October 2026

Page 2 of 21 Trips in Siena during October 2026 with 399 Reviews

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

Hi there

Tours and Trip Packages to Siena in October 2026

Get a customized trip to Siena in October 2026

Page 2 of 21 Trips in Siena during October 2026 with 399 Reviews

Page 2 of 21 Trips in Siena during October 2026 with 399 Reviews