Call us on 01707 817260
Or, email us at customersupport@rambleworldwide.co.uk
Call us on 01707 817260
Or, email us at customersupport@rambleworldwide.co.uk
Tuscany is walking perfection. Rolling hills crowned with cypress trees, medieval hilltop towns rising from golden landscapes, and vineyard-lined paths that wind through some of the world's most celebrated wine country. This is the Italy of dreams, and there's no better way to experience it than on foot.
Our walking holidays in Tuscany immerse you in the region's extraordinary blend of art, history, and gastronomy. Wander through Florence's Renaissance streets with a local guide, then escape to the peaceful countryside where olive groves and vineyards stretch to the horizon. Learn to cook authentic Tuscan dishes, taste wines in centuries-old cellars, and discover medieval towns that time forgot.
Whether you prefer a guided journey with expert leaders or the freedom to explore independently, our Tuscany walking holidays let you experience la dolce vita at your own pace.
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A taste of Tuscany - food, wine, art, history and scenic landscapes, Tuscany is a delight for all your senses. Enjoy wine and olive oil tasting in Montecatini Alto, and cook your own Tuscan dinner at a local farm!
CloseOur holiday walking grades
We still class this level as leisurely; walks are generally a little longer than level 2, with undulations but over a longer distance. Where sightseeing distances are longer, we take a full day with opportunities to stop, rest and refuel. Generally, itineraries involve easy countryside walking with plenty of breaks.
Search all Leisurely, Grade 3 walking holidays
Average daily walks - Distance: 4 miles; Ascent/Descent 300m; Terrain: generally good paths and tracks; Walking Time: Half Day or Full Day walks.
Please note this is a guide only; you should refer to the specific Holiday Information Sheet for the holiday that you are looking at for detailed day to day itinerary and grading information.
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Nestled away from the Tuscan tourist trail, a secluded valley, guarded by a horse-shoe of mountains, invites exploration. Discover the captivating allure of the Apuan and Apennine ranges, hiking through Italy's diverse landscapes. This harmonious blend of scenic vistas and cultural richness offers an unforgettable journey through picturesque Italian mountain terrain.
Tuscany offers an unrivalled combination of gentle landscapes, world-class culture, and exceptional food and wine that makes it one of Europe's most rewarding walking destinations.
Landscapes that inspire. The Tuscan countryside is iconic for good reason. Rolling hills dotted with cypress trees, golden fields of sunflowers, and medieval towers rising from distant hilltops create a landscape that has inspired artists for centuries. Walking here feels like stepping into a Renaissance painting.
Art and history at every turn. Tuscany is the birthplace of the Renaissance, and its cities overflow with masterpieces. Florence's Uffizi Gallery, Siena's medieval Piazza del Campo, and the tower-studded skyline of San Gimignano are just the beginning. Every hilltop town reveals layers of history waiting to be discovered.
Food and wine worth travelling for. Tuscan cuisine is simple, seasonal, and utterly delicious. Learn to cook traditional dishes at a local farm, taste award-winning Chianti wines in family-run vineyards, and savour olive oil pressed from groves you've walked through that morning.
Walking for all abilities. Tuscany's terrain suits walkers of every level. Gentle paths meander through vineyards and olive groves, while the Apuan Alps and Apennines offer challenging mountain hikes for experienced walkers. The ancient Via Francigena pilgrimage route provides moderate terrain through historic towns. Our holidays range from leisurely cultural explorations to challenging 14-night mountain adventures.
Our Tuscany's Treasures holiday is based in Montecatini Terme, a UNESCO World Heritage Site known for its thermal waters and historic charm. From here, you'll explore the region's most celebrated cities with expert local guides.
In Florence, discover the artistic heart of the Renaissance. Visit the world-famous Uffizi Gallery, admire the magnificent Duomo, and wander through streets where Michelangelo and Leonardo once walked. In Siena, explore the medieval centre with its stunning Piazza del Campo and Gothic cathedral. Visit San Gimignano, where medieval towers still dominate the skyline, and Lucca, the perfectly preserved artistic city at the foot of the Apuan Alps.
For walkers seeking dramatic mountain scenery away from the usual Tuscan tourist trail, our Apuans & Apennines holiday explores the serene Garfagnana Valley, nestled between two magnificent mountain ranges. This 14-night adventure takes you through breathtaking landscapes that feel wonderfully undiscovered.
Hike to iconic peaks like Monte Sumbra and Pania della Croce, often called the Queen of the Apuans, for sweeping panoramic views. Explore the dramatic Orrido di Botri Gorge, a natural wonder referenced by Dante himself. The holiday also includes the stunning Cinque Terre coastline and the medieval charm of Lucca. This is Tuscany at its most wild and spectacular, where medieval hamlets dot the hillsides and diverse landscapes reward adventurous walkers.
For those seeking a more immersive walking experience, our Via Francigena: From Lucca to Siena self-guided holiday follows the ancient pilgrimage route through the Tuscan countryside. This historic path, once walked by medieval pilgrims travelling from Canterbury to Rome, passes through incomparable scenery and fascinating towns.
Stop to explore Monteriggioni, a perfectly preserved fortified village encircled by medieval walls and towers. Wander through San Gimignano with its famous skyline of medieval towers. The route combines challenging walking with extraordinary cultural discoveries.
Explore our walking holidays in Tuscany
Tuscany's appeal extends far beyond any single itinerary. The region boasts remarkable attractions that reward curious explorers. The Leaning Tower of Pisa draws visitors from around the world, while the Val d'Orcia's UNESCO-listed landscape of rolling hills and isolated farmhouses is perhaps Italy's most photographed countryside.
Medieval towns like Volterra, Cortona, and Arezzo each deserve a visit, while the thermal springs of Saturnia provide a unique way to unwind after a day's walking. The dramatic coastline of Cinque Terre, accessible from our Apuans & Apennines holiday, offers a stunning contrast to the inland hills.
Guided Tuscany Walking Holidays
Our guided Tuscany walking holidays offer the perfect blend of walking, culture, and culinary discovery with expert support throughout. Local guides share insider knowledge of the region's art, history, and gastronomy, while your tour leader handles every detail so you can simply relax and enjoy the experience. With small groups averaging 12-14 people, you'll enjoy a sociable atmosphere and make lasting connections with fellow walking enthusiasts.
Perfect for: First-time visitors to Tuscany, solo travellers seeking company, those who want insider access to local culture and cuisine.
Self-Guided Tuscany Walking Holidays
Prefer to set your own pace? Our self-guided Tuscany holidays give you complete freedom with comprehensive support. We provide detailed route notes, maps via our app, carefully selected accommodation, and luggage transfers between stops. You walk when you want, pause when you want, and linger over that extra glass of Chianti without watching the clock.
Perfect for: Independent travellers, couples seeking a romantic escape, experienced walkers who enjoy navigating their own route.
At Ramble Worldwide, we've been creating memorable walking holidays since 1946. With over 75 years of expertise and more than 300 meticulously planned itineraries worldwide, our Tuscany tours reflect decades of experience in crafting journeys that balance walking, culture, and authentic local experiences.
Expert guides who bring Tuscany to life. Our Tuscany's Treasures holiday includes local guides in Florence, Siena, and other key destinations who share insights you won't find in any guidebook. Our team of 250 carefully selected, highly trained walk leaders ensures every journey is enriching and enjoyable.
Immersive culinary experiences. We don't just show you Tuscany; we help you taste it. Enjoy an olive oil masterclass at a local farm, learn to cook traditional Tuscan dishes, and savour wine tastings at carefully chosen vineyards. These authentic experiences are included in your holiday, not expensive extras.
Small groups, personal attention. With an average group size of 12-14 people, you'll enjoy a sociable atmosphere while still feeling like you're discovering Tuscany for yourself. Around half of our guests travel solo, so you'll always be in good company.
Everything arranged for you. We handle flights, airport transfers, handpicked accommodation, and most meals. You simply arrive ready to explore.
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