- Scenic trails through vineyards and olive groves
- Cultural gems from Florence to Siena
- Tastes of Tuscany along the way
Welcome to Florence, the birthplace of the Renaissance! This vibrant city is a living museum, with world-class art, iconic architecture, and a unique atmosphere that blends history with modern Italian flair. After checking into your hotel, you’ll have the afternoon free to relax or explore the nearby piazzas, galleries, and charming side streets. We can help arrange a transfer from nearby airports if you're arriving by plane.
After breakfast, your Tuscan walking adventure begins. You’ll leave the bustle of Florence behind and head into the tranquil countryside, walking along peaceful trails that lead through vineyards, olive groves, and gentle hills. The day ends in Impruneta, a small town famous for its terracotta artisanship and peaceful rural surroundings.
Today’s route brings you deeper into the Chianti region, renowned for its world-class wines and postcard-perfect landscapes. You’ll pass through open fields, wooded paths, and quiet hamlets before reaching Tavarnelle Val di Pesa, a lovely hilltop district surrounded by cypress-lined roads and vine-covered hills.
After breakfast, you’ll head towards Certaldo, following a scenic trail past Barberino Tavarnelle and along the historical Via di Tavolese. Certaldo is a well-preserved medieval town, known for its red-brick buildings, panoramic views, and as the birthplace of writer Giovanni Boccaccio. Take some time to wander its cobbled lanes and soak in the atmosphere.
This is one of the highlights of the journey. Today you’ll walk to San Gimignano, often called the “Manhattan of the Middle Ages” for its towering skyline. Explore its narrow streets, artisan shops, and panoramic viewpoints before continuing to Poggibonsi, a lively town with deep historical roots.
Your path leads through peaceful vineyards and ancient byways to Monteriggioni, a fairytale-like village encircled by 13th-century walls and towers. Pause for a glass of wine in the quiet piazza, and imagine the life of pilgrims and knights who once walked the same route.
On your final walking day, the trail winds through golden fields and oak forests as you make your way to Siena. Known for its Gothic cathedral, medieval streets, and the famous Palio horse race, Siena is the perfect finale to your Tuscan journey. Take the evening to explore its dramatic piazzas and savor a well-earned Tuscan dinner.
After a relaxing breakfast in the heart of Siena, it’s time to say goodbye. If needed, we can organize a transfer to nearby airports. Take with you lasting memories of olive-scented trails, Renaissance towns, and the timeless beauty of Tuscany.
INCLUDED IN PRICE
- Carefully planned tour design and personalized organization
- A detailed itinerary
- 7 nights in hotels (3/4 stars) with breakfast
- Customer support (24/7)
- Luggage transfers
- Tourist tax
OPTIONAL EXTRAS
- Airport transfer
- Single supplement
- Extra days
- Luxury holidays
Discover the soul of Tuscany on this unforgettable 8-day hiking holiday, from the art-filled streets of Florence to the medieval charm of Siena. Walk through rolling hills, vineyards, olive groves, and hilltop villages, soaking in the region’s natural beauty and timeless atmosphere.
This self-guided walking tour blends cultural heritage, scenic landscapes, and authentic Tuscan cuisine. Enjoy wine tastings in Chianti, explore cobbled streets, and unwind in charming countryside accommodations, all with luggage transfers and detailed route notes included.
Ideal for those who love to travel at a slower pace, this journey captures everything that makes Tuscany so special, from peaceful landscapes and rich history to unforgettable food and that unmistakable Tuscan charm.
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Things to Know
We offer various hiking tours in Europe, including self-guided and guided walks, coastal hikes, alpine trekking, and cultural walking routes. You can choose from gentle countryside walks to challenging mountain adventures.
Yes. We have many beginner-friendly hiking holidays with moderate distances, well-marked trails, and flexible pacing. We also offer advanced routes for experienced hikers.
You can choose either a self-guided walking holiday or join a small group with a professional guide. Self-guided trips offer more freedom and flexibility, while guided tours provide deeper insights and local knowledge.
Most tours include breakfast daily. Depending on the tour, dinners or packed lunches may also be provided. You’ll also have opportunities to try local cuisine at recommended restaurants or guesthouses.
We offer hikes for all fitness levels. Daily walking distances vary from 8 km to 25 km, and you can choose the route that suits your ability. Some elevation gain may be involved, especially in mountain or hill regions.
Absolutely! We can create a custom hiking itinerary based on your interests, preferred difficulty, travel dates, and desired region. Just let us know what you're looking for.
