Uncover the historic charm and world-class wines of Siena and Castellina in Chianti. A perfect combination of cultural exploration and vineyard tastings awaits in this iconic Tuscan landscape.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
6–8 hours
Fitness Level
Good physical shape recommended considering walking and occasional uphill sections
Wildlife
History
The Chianti region has been cultivating grapes since Etruscan times, shaping Italy’s renowned wine culture.
Conservation
Many local vineyards practice sustainable farming, preserving Tuscany’s landscape for future generations.
Tuscany like a Local
Uncover the historic charm and world-class wines of Siena and Castellina in Chianti. A perfect combination of cultural exploration and vineyard tastings awaits in this iconic Tuscan landscape.
Tuscany like a Local is a Firenze-based tour operator offering guided experiences across Florence, Lucca, Siena, Pisa and the Chianti wine region. The company provides a mix of private and shared formats to suit different traveler preferences, with a program that focuses on bike tours, food and wine tastings, cultural walking tours and evening aperitivo experiences.
Tours include scenic bike routes and panoramic viewpoints in Florence, culinary walking tours and tastings in Lucca, sightseeing and local snacks in Pisa, and historic market squares and Palio heritage in Siena. Several itineraries combine sightseeing with local flavors and artisan visits, and at least one itinerary includes a winery visit in Castellina in Chianti.
All experiences depart from Firenze, Toscana, and are designed to pair local knowledge with accessible pacing — options range from gentle bike rides to relaxed food tours and winery visits. The operator offers both private bookings for customized itineraries and shared tours for small groups.
Tuscany like a Local emphasizes authentic local flavors and neighborhood discoveries, connecting travelers with artisans, neighborhood eateries, wine bars and regional specialties such as pecorino, gelato and traditional Tuscan pastries. Clear tour descriptions and distinct private/shared formats help travelers choose the right experience for their interests and schedule.
Base Location
Firenze, Toscana
Operating from Florence hub
Tour Formats
Private & Shared
Small-group or private options
Tours Offered
15
Across Florence, Lucca, Siena, Pisa, Chianti
Themes
Food, Bike, Wine
Culinary, cycling and winery experiences
Reserve a private or shared tour from Florence to discover local food, bike routes and Chianti wineries — available year-round from Firenze, Toscana.
Strap in for hilly terrain
Wear sturdy shoes suitable for uneven cobblestone paths and vineyard slopes.
Stay hydrated
Bring water bottles to keep hydrated while wandering through vineyards and town centers.
Book winery tours in advance
Secure your spot ahead of time for popular tastings and vineyard visits.
Time your visit for sunset views
Visit Castellina in the late afternoon for stunning vistas over vineyards at sunset.
Comfortable walking shoes
Necessary for walking on cobblestone streets and uneven vineyard terrain.
Sun protection gear
Hat, sunglasses, and sunscreen to protect against the Tuscan sun.
summer
Camera or smartphone
Capture breathtaking vineyard views and historic cityscapes.
Small backpack
Carry essentials like water, snacks, and personal items comfortably.