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Casentino e Poppi

Best Day Trips from Florence: The Complete Local Guide (2026)

Planning the best day trips from Florence? This guide was written by Stefano, a certified wine sommelier and licensed tour guide with over 20 years of experience leading private tours through Florence and Tuscany. It covers every major destination within reach of Florence — Chianti Classico, Siena, San Gimignano, Val d’Orcia, Brunello di Montalcino, Pisa, Lucca, Cinque Terre, Volterra, and the hidden valleys of the Casentino and Mugello — with verified distances, honest travel advice, and practical information on how to reach each place by train, car, or private guided tour.
Each destination includes what to see, what to eat, the best season to visit, and a clear-eyed assessment of whether it is worth your time. You will also find a full comparison of private tours versus public transport, a seasonal guide to Tuscany, answers to the most frequently asked questions about day trips from Florence, and direct links to bookable private experiences for groups of 2 to 7 people.
Whether you are visiting Florence for three days or three weeks, this is the only day trip guide you need — written by a local, based on firsthand knowledge, and updated for 2026.

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Chianti Classico wine tour

Discover all 11 Chianti Classico UGA micro-areas and plan the perfect wine tour from Florence. Panzano, Radda, Gaiole and more — fully customised by Out of the Box Florence.

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Tuscany Wine Regions Guide – Ep.5

NEW 2025 Tuscany wine regions ultimate guide for wine lovers and wine travellers! Episode 5: Carmignano DOCG!

The hidden treasure of Tuscany!

Travel following your favourite wine regions!

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Tuscan Food Experiences: Truffle, Olive Oil, Cheese and Cooking

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Autumn Foliage in Tuscany: A Local’s Guide (2026)

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3 Days in Tuscany from Florence: A Day-by-Day Itinerary That Works

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Mushroom Foraging in Tuscany: Porcini Season Guide 2026

Mushroom foraging in Tuscany runs on rain and rumor, not a calendar Here is where...

How many days do you need in Tuscany?

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Chianti Harvest (Vendemmia) in September: What Actually Happens in the Cellar

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Grape Harvest in Tuscany: A Local’s Vendemmia Guide (2026)

The grape harvest in Tuscany, la vendemmia, runs through September and October...

La Leonessa Gravel: Tuscany’s Coolest Summer Ride (2026)

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Alta Via del Sale by Gravel Bike: Our Full Guide

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Microbreweries in Tuscany: A Local’s Craft Beer Guide

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Boat Tour Florence: See the Arno Like a Local

Ponte Vecchio is packed with tour groups by noon Discover the boat tour Florence...

Chianti Wine Tour from Florence: A Local’s Honest Guide

Not every Chianti wine tour from Florence is built the same way Learn the real...

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