Travel Trips

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

6 May 2026 No Comments

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.

Chianti Classico wine tour

14 April 2026 No Comments

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.

Italy gravel bike adventures self-guided tours

Self-Guided Hiking & Cycling Tours in Tuscany | Out of the Box Florence

5 April 2026 No Comments

Discover self-guided and guided hiking & gravel cycling tours in Tuscany and Umbria. Via degli Dei, Florence to Rome, Val d’Orcia and more — with GPX tracks, luggage transfers, hotel booking and local experiences. From €19% service fee only.

Guests walking between vineyards on a full-day Chianti Classico wine hiking tour from Florence

Best Hikes Around Florence and Tuscany: A Local Expert Guide for 2026

1 March 2026 No Comments

Discover the best hikes around Florence and Tuscany — from Chianti Classico and Val d’Orcia to Casentino and the Crete Senesi. A local expert guide to walking in Tuscany.

“Ajò” Gravel Sardinia Loop

17 November 2025 No Comments

The Ajò Gravel Sardinia Loop 2025 is a multi-day gravel bike adventure through the wild landscapes of southern Sardinia. This sustainable tour combines quiet gravel tracks, technical sections, inland climbs and coastal views, guided by local expertise. Each day reveals a different side of the island, from rural villages to scenic ridgelines and pine forests. Designed for riders seeking authentic experiences, Ajò blends challenge, culture and nature. Full route details and GPX tracks are available on our Komoot collection.