How to Spend One Magical Week in Tuscany by Car
August 3, 2025
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How to Spend One Magical Week in Tuscany by Car Why a Road Trip is the Best Way to See Tuscany Two Itinerary Options Without
5 Best Wineries to Visit in Chianti, Tuscany (2025 Guide)
July 27, 2025
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Exploring Chianti through its wineries is one of the most rewarding ways to experience Tuscany. In this guide, we share five of our best wineries to visit in Chianti—each offering a unique blend of tradition, wine making, and breathtaking scenery.
You’ll find practical travel tips, detailed introductions, and honest pros and cons for each winery, along with advice on where to stay and the best times to visit.
5 Best Wineries in Val d’Orcia
July 24, 2025
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Few places on Earth capture the timeless romance of Tuscany quite like Val d’Orcia. A UNESCO World Heritage Site, this sweeping valley of golden hills, cypress-lined lanes, and storybook villages is also home to some of Italy’s most celebrated wineries.
Framed by medieval towns such as Montalcino, Pienza, and San Quirico d’Orcia, the region’s unique terroir and centuries-old winemaking traditions have produced wines that are not only rich in character but deeply connected to the landscape.
Newsletter in July
July 23, 2025
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Welcome to Timeless Wanderers – Our Travel Story Begins Here Hello fellow wanderer, We’re Gary and Sally—two Aussies who traded routine for the road,
5 Best Wineries in Tuscany to Visit in 2025
July 18, 2025
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Tuscany is known the world over for its rolling hills, cypress-lined roads, and historic towns—but it’s the wine that often leaves the most lasting impression.
From bold reds aged in ancient cellars to crisp whites enjoyed on sun-drenched terraces, Tuscany offers a wine experience like no other.
Discover Tuscany’s 5 Top Medieval Towns
July 15, 2025
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On our travels through the region, we found ourselves drawn again and again to these ancient towns. Some like Siena, with its proud palazzos and famous piazza. Others, like Monteriggioni or Volterra, feel almost untouched, their cobbled streets winding through centuries of history and local life. What they all share is that unmistakable sense of the past—alive, tangible, and beautifully worn.
VISIT TUSCANY’S 8 BEST TOWNS (2025 GUIDE)
July 3, 2025
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8 STUNNING TOWNS TO VISIT IN TUSCANY (2025 GUIDE) Tuscany Beyond the Postcards While many travelers rush through its cities, it’s the smaller towns that
WHERE TO STAY IN FLORENCE
June 26, 2025
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Best Places to Stay in Florence: Hotels & Neighborhoods You’ll Love “Where to Stay in Florence: A Neighborhood Guide for Food, History, and Local Charm”
10 FANTASTIC DAY TOURS FROM FLORENCE
June 24, 2025
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10 FANTASTIC DAY TRIPS FROM FLORENCE Florence as Your Gateway to Tuscany Florence is a city of grand museums, soaring domes, and cobbled lanes that
TUSCANY’S 5 BEST HILLTOP TOWNS
June 17, 2025
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Discover the 5 Best Hilltop Towns in Tuscany Step back in time in Tuscany’s five most beautiful hilltop towns. Tuscany’s landscape is dotted with enchanting
A PERFECT DAY TRIP FROM FLORENCE TO PISA AND LUCCA
June 12, 2025
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Best Florence Day Trip: Explore Pisa and Lucca in One Day A day trip to Pisa and Lucca is the perfect way to see two
TUSCANY’S ULTIMATE WINE LOVER’S GUIDE
June 2, 2025
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Florence is the perfect base for discovering the best of Tuscany’s world-renowned wine regions. With its central location, the city gives easy access to everything from the rolling vineyards of Chianti Classico to the coastal estates of Bolgheri. Wine lovers will find an incredible range of tasting experiences just a short drive away, with each region offering its own distinctive grape varietals, traditions, and scenery.