10 Best Tuscany Multiday Tours in September 2026

Discover 30+ Tuscany trips in September 2026 with 1090+ verified reviews. Crafted by vetted tour operators, these Tuscany September 2026 tours showcase the country at its seasonal best.

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Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

Physical Rating

easy
moderate
challenging

Tour Types

Group tours
Private tours
Small group tours

Accommodations

Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Duration

4 days18 days

Day Tour
Multiday Tour

3 Trips in Tuscany during September 2026

Start & End Location

Price

USD 662USD 7,380

Budget Tours
Luxury Tours

Black Week Super Sales

Tuscany Cycle for Families - September 2026

(1 review )

No booking fees

Best price guaranteed

Explore Tuscan gems on a specially crafted cycle trip for all ages. There are no steep Tuscan hills on this beautifully designed self guided cycle taking in some of Tuscany's most famous towns. Pedal effortlessly along the meandering Arno river cycle paths that take you from one classic Tuscan city to the next. From the leaning tower of Pisa to the elegant Piazza Anfiteatro in Lucca and the famous Duomo of Florence, there are no shortage of sites to engage the whole family. Delve further into the countryside to visit lesser known corners such as Calci, where a famous Natural History Museum is housed and Vinci, where Leonardo da Vinci was born. Cycle through a quintessential Tuscan landscape, taste the many local specialties and stay in three comfortable family run hotels generally with swimming pools and gardens, perfect for relaxing after the cycling day is over.

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Pisa, Empoli, San Giuli

Tuscany, Pisa, Empoli, San Giuliano Terme, Lucca, Vinci, Florence

Duration8 days

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Black Week Super Sales

A Taste of Tuscany Cycling - September 2026

No booking fees

Best price guaranteed

This is not just a cycling holiday it is an immersion into local Tuscan life, from wine and oil sampling to hot thermal spa baths and the chance to taste local wines and olive oils. Sample the Vino Nobile of Monepulciano, rich Pecorino cheese in Pienza or take a bath in Roman Bagno Vignoni.

Bicycle toursFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Tuscany, Chianciano Terme, Radic

Tuscany, Chianciano Terme, Radicofani, Cetona, Chianciano Vecchia, Bagno Vignoni

Duration8 days

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Black Week Super Sales

Italy Coast to Coast by Gravel Bike - September 2026

No booking fees

Best price guaranteed

From the Adriatic to the Tyrrhenian Sea, this 9-day traverse across Central Italy offers a challenging yet dreamy gravel bike ride. Experience the undiscovered trails of Marche and Umbria and feel the crunch beneath your wheels on Tuscany's unmissable chalk white country roads, the 'strade bianche'. We discover medieval towns, savor local cuisine paired with world-famous wines, and spend our nights in cozy hotels, agriturismi (farm stays), and a nature lodge. The journey begins in Marche, where we cycle from the coastal town of Sirolo to the ‘City of Paper', Fabriano, in the foothills of the Apennine Mountains. We ride through historic hinterlands, overnight at a wine estate, and climb to the canyon of Gola di Frasassi. Then we transition into Italy’s green heart, Umbria, passing a sea of vineyards, skirting the shores of Lake Trasimeno, and visiting the beautiful Basilica of Saint Francis of Assisi. The tour’s second half takes us along Tuscany's white roads, winding our way through the rustic countryside to reach the picture-perfect medieval towns of Montepulciano and Montalcino. After glamping under the stars in the Maremma hills of southern Tuscany we roll down to the Argentario promontory on the Tyrrhenian coast. The tour ends in Porto Santo Stefano with views over the azure sea. Join us on this trailblazing gravel bike tour all'italiana!

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Lodge

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Ancona, Umbria & Marche

Tuscany, Ancona, Umbria & Marche, Fabriano, Umbria, Montepulciano, Montalcino, Sant'Antimo, Argentario

Duration9 days

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3 Trips in Tuscany during September 2026

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Tuscany Tours in September 2026

Get a customized trip to Tuscany in September 2026

3 Trips in Tuscany during September 2026

Tuscany Cycle for Families - September 2026

A Taste of Tuscany Cycling - September 2026

Italy Coast to Coast by Gravel Bike - September 2026

3 Trips in Tuscany during September 2026