Embarking on a vacation to Tuscany promises an unforgettable journey filled with scenic landscapes, flavorful cuisine, rich history, and vibrant local culture. Whether you're seeking a peaceful retreat, an active adventure, or a lively social scene, Tuscany offers diverse holiday accommodations to suit every traveler’s style. From charming holiday rentals nestled in lush countryside to lively short term rentals in historic towns, your ideal holiday stay in Tuscany awaits. To make the most of your trip, explore these 10 hidden gems in Tuscany, inspiring destinations that promise authentic experiences, memorable activities, and places to stay in the heart of Italy’s cultural treasure trove.
1. Pitigliano: The Little City of Volcanoes
Known as “Little Jerusalem,” Pitigliano is a captivating hilltop town with enchanting narrow streets, ancient Etruscan roots, and a mesmerizing atmosphere. This destination is perfect for travelers seeking unique holiday accommodation in Tuscany that combines history and natural beauty. You can choose to rent a cozy holiday rental in the historic center, offering stunning views of the surrounding valley, or find a countryside villa that immerses you in Tuscany’s rustic charm. When staying here, indulge in local activities such as wine tasting tours in nearby vineyards, exploring underground caves, or enjoying authentic tuscan cuisine. Discover the mystique of Pitigliano and enjoy exploring local experiences like visiting the Jewish historical sites and hiking through scenic trails.
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2. Sovana: A Medieval Dreamland
Just a short drive from Pitigliano lies Sovana, a small yet enchanting medieval village packed with history and character. This hidden gem boasts ancient ruins, charming piazzas, and well-preserved medieval architecture. For your vacation rentals in Tuscany, Sovana offers quaint cottages and traditional farmhouses, ideal for experience-focused travelers eager to immerse themselves in history. During your stay, you can participate in local activities such as exploring the ancient Etruscan tombs, hiking along scenic trails, or discovering artisan workshops producing traditional Tuscan crafts. Visiting Sovana is like stepping back in time, making it a perfect destination for those seeking authentic experiences and quiet places to stay in Tuscany.
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3. Montefioralle: The Village Above Greve in Chianti
Perched above the charming town of Greve in Chianti, Montefioralle is a tiny medieval hamlet that offers an intimate and energetic experience. This destination is perfect for travelers wanting to rent a holiday house with panoramic views and easy access to Chianti’s renowned wine regions. When you stay in Montefioralle, you have the chance to indulge in wine tasting tours, join local cooking classes to learn traditional Tuscan recipes, or explore the rolling vineyards by bike. The narrow streets and historic architecture create a perfect setting for social travelers looking for a lively, authentic town to explore. Whether you want to rent a short-term holiday apartment or a rustic villa, Montefioralle provides engaging experiences and a vibrant local scene.
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4. San Gimignano: The Town of Beautiful Towers
San Gimignano is world-famous for its medieval towers that create a stunning skyline. This UNESCO World Heritage site offers an excellent combination of historic charm and lively local activities. Experience must-do things like climbing Torre Grossa for breathtaking views, exploring artisan shops, or enjoying local festivals and markets. When it comes to holiday rentals, local agriturismo farms and historic apartments offer authentic places to stay in Tuscany. Active travelers can join cooking classes, bicycle through the countryside, or take part in olive oil tasting experiences. The energetic vibe of San Gimignano makes it a perfect hub to explore other hidden gems around Tuscany.
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5. Bagni San Filippo: Natural Hot Springs and Scenic Trails
For those seeking invigorating activities and a unique stay, Bagni San Filippo is a natural wonder. This lesser-known destination in Tuscany offers sulfuric hot springs amid picturesque landscapes perfect for relaxation and adventure. Imagine staying in a cozy holiday rental in the woods or a charming bed and breakfast near the thermal pools. Activities here include soaking in thermal waters, hiking through scenic trails, and exploring waterfalls and natural caves. It’s an ideal destination for adventurous travelers who want to combine health and wellness with outdoor fun and authentic local experiences.
Discover your perfect short-term rental or holiday accommodation at Search and Stay and enjoy a relaxing Tuscany holiday in nature’s own spa.
6. Castiglione della Pescaia: Coastal Charm and Marine Activities
If your ideal holiday involves sun, sea, and sand, Castiglione della Pescaia is the place to rent your vacation home in Tuscany. This seaside town offers relaxing beaches, lively harborfront promenades, and vibrant local markets. Staying in a holiday rental by the sea allows you to enjoy local activities such as boat trips, paddleboarding, or exploring the nearby Maremma natural park. It’s perfect for travelers who want a vibrant, social atmosphere combined with opportunities for water activities and local dining experiences. Choose from seaside apartments, historic villas, or short term rentals in the town center for a dynamic holiday stay in Tuscany.
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7. Colle di Val d’Elsa: The Crystal City
This charming town is renowned for its sparkling glass craftsmanship and picturesque streets. For experience-focused travelers, Colle di Val d’Elsa offers a fascinating insight into traditional Tuscan art, with local workshops and galleries to explore. You can rent a holiday apartment or a boutique stay close to the historic center, perfect for engaging in local experiences like glassblowing workshops, exploring historic churches, or enjoying scenic walks along the Elsa River. Add days of wine tasting in nearby Chianti or leisurely strolls through the vibrant markets, and you'll have a memorable vacation filled with culture and authentic Tuscan life.
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8. Lucca: The Fortress and Romantic Gardens
Lucca is a lively yet relaxed destination, featuring well-preserved Renaissance walls that you can walk or cycle around. Known for its charming squares, historic churches, and beautiful gardens, Lucca is perfect for social travelers who want to combine historical exploration with local activities. Rent a holiday apartment within the city walls and enjoy the vibrant life—picnic in the gardens, attend local festivals, or rent bikes for a city tour. Lucca's lively street cafes and cultural events make it an ideal place to indulge in local experiences and things to do during your Tuscany stay.
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9. Volterra: The Etruscan Legacy
Deep in the heart of Tuscany lies Volterra, a hilltop town with centuries of history, from Etruscan origins to medieval splendor. It offers an excellent backdrop for those seeking a culturally rich holiday with activities like exploring ancient ruins, visiting local alabaster workshops, or enjoying panoramic vistas from medieval city walls. Holiday rentals in Volterra range from quaint historic homes to modern apartments, offering authentic places to stay in Tuscany's historic atmosphere. Engage with local artisans, participate in art workshops, or simply stroll and absorb the vibrant ambiance of this UNESCO-listed site.
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10. Maremma Coast: Untamed Nature and Authentic Beaches
The Maremma region boasts some of the most untouched beaches and natural reserves in Tuscany. For an active and social holiday, rent a holiday house or a villa near the coast and explore the pristine beaches, go horseback riding in natural parks, or indulge in fresh seafood at local trattorias. The Maremma is perfect for travelers who want to combine outdoor activities with local experiences such as birdwatching, hiking, or participating in seasonal festivals. Staying in short term rentals allows for flexible, experience-rich vacations, making it a top choice for energetic, experience-focused travelers.
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Enhancing Your Tuscany Holiday Experience
Beyond these hidden gems, Tuscany is filled with countless places to stay in Tuscany that cater to diverse interests and styles. Whether you're looking for a short-term rental in a lively town, a cozy countryside holiday rental, or a luxury villa with panoramic views, the region offers an experience for every budget and preference. Remember, the key to a memorable Tuscany holiday is immersion—engaging with local culture, tasting authentic food and wine, and participating in activities that excite your sense of adventure and social spirit.
For making the most of your stay, explore unique local experiences, things to do, and curated activities. From wine tours and cooking classes to outdoor adventures and cultural festivals, Tuscany is a destination that invites you to live, explore, and connect.
To find the perfect accommodations for your adventure or relaxing retreat, visit Search and Stay. Prepare for a fun-loving, experience-driven, energetic holiday in one of Italy’s most cherished regions, and create memories that last a lifetime.