GemmaTuscany is the heart of romance, where rolling hills meet golden sunsets, and vineyards stretch as far as the eye can see. If you are looking for a getaway that blends charm, history, and tranquility, Tuscany offers the perfect backdrop. From my own personal experience, the region has a magical way of slowing time, letting you truly savor every moment with someone special. Whether you dream of staying in a medieval villa tucked in a hillside village or a countryside estate surrounded by olive groves, Tuscany has it all. Let me show you eight beautiful villas that make for unforgettable romantic retreats.
1. Villa La Massa – Florence’s Riverside Elegance
Villa La Massa sits along the Arno River, just a short drive from the cultural treasures of Florence. This historic villa, dating back to the 16th century, offers rooms with frescoed ceilings, antique furniture, and views of the lush gardens.
Why you will love it: The villa’s riverside location is perfect for romantic walks at sunrise or sunset. You can enjoy a private wine tasting in the estate’s cellar or take a cooking class together in their Tuscan kitchen.
Must-do experiences nearby:
- Stroll across the Ponte Vecchio in Florence.
- Visit the Uffizi Gallery for Renaissance art.
- Take a private boat ride on the Arno River.
Villa La Massa is ideal if you want a balance between peaceful countryside living and access to city culture.
2. Borgo Santo Pietro – A Luxurious Countryside Escape
Nestled in the heart of southern Tuscany, Borgo Santo Pietro is more than a villa—it’s an experience. With a Michelin-starred restaurant, a spa, and beautifully landscaped gardens, it offers luxury and intimacy.
Why you will love it: The villa blends privacy with elegance. Imagine lounging by the pool with a glass of Chianti while the rolling hills stretch around you.
Things to explore nearby:
- Visit the medieval town of Pienza for stunning architecture.
- Explore Montepulciano’s wine cellars for some wine tasting.
- Take a hot air balloon ride for breathtaking views of the Val d’Orcia region.
Based on my overall experience, staying here feels like stepping into a fairytale, yet it’s grounded in comfort and sophistication.
3. Castello di Casole – Medieval Charm and Modern Comfort
This 10th-century castle has been transformed into a luxurious retreat while maintaining its historical charm. Castello di Casole sits on a vast estate, offering olive groves, vineyards, and gardens that feel straight out of a postcard.
Why you will love it: Each suite combines medieval architecture with modern comforts. Private terraces allow you to watch the Tuscan sun set over the hills, creating a romantic ambiance that is hard to match.
Must-see nearby attractions:
- Explore San Gimignano, the “Town of Towers.”
- Take a cooking class to learn traditional Tuscan recipes.
- Wander the vineyards and enjoy wine tours on-site.
This villa is perfect for couples who want both history and luxury in one place.
4. Villa Cora – Romantic Splendor in Florence
Located near Florence, Villa Cora offers a glamorous experience with its opulent interiors and beautiful gardens. Originally a 19th-century mansion, it has been restored to provide luxury accommodations while retaining its classic charm.
Why you will love it: The villa features rooms with antique furnishings, marble bathrooms, and stunning views of the Boboli Gardens. Romantic dinners under the stars in the private garden are unforgettable.
Activities to enjoy:
- Visit the Florence Cathedral and climb the Duomo for panoramic views.
- Explore the Boboli Gardens and Pitti Palace.
- Enjoy wine tasting at a local vineyard nearby.
From my own personal experience, Villa Cora is ideal for couples looking for a mix of cultural exploration and indulgent relaxation.
5. Villa Le Fontanelle – Tuscany’s Hidden Gem
For couples who love privacy, Villa Le Fontanelle offers a secluded escape near Florence. Surrounded by olive groves and cypress trees, this villa provides a peaceful retreat with breathtaking views of the Tuscan countryside.
Why you will love it: The villa has a private pool, spacious terraces, and cozy interiors perfect for quiet moments together.
Things to do nearby:
- Explore the Chianti wine region and sample local wines.
- Take a scenic drive through the Tuscan hills.
- Visit Florence for a day trip to enjoy museums and historic sites.
This villa is a haven for couples seeking a serene and romantic environment.
6. Villa Medicea di Lilliano – Historic Charm with Wine and Views
Located in the Chianti region, Villa Medicea di Lilliano combines history, elegance, and a love for wine. The villa, dating back to the Renaissance, sits atop a hill offering panoramic views of vineyards and olive groves.
Why you will love it: The villa has beautifully restored rooms, a private chapel, and terraces ideal for sunset views. Wine lovers will adore the private wine tours available right on the estate.
Must-visit nearby spots:
- Explore Greve in Chianti, a charming Tuscan village.
- Take part in olive oil and wine tastings at local estates.
- Enjoy hiking trails with breathtaking countryside views.
Based on my overall experience, staying here combines culture, history, and intimate relaxation seamlessly.
7. Villa Vignamaggio – Iconic Countryside Retreat
Villa Vignamaggio, famously associated with the Mona Lisa, offers a romantic escape in the Chianti hills. Surrounded by vineyards, gardens, and centuries-old olive trees, this villa exudes authenticity and charm.
Why you will love it: The villa offers spacious suites, private pools, and the chance to explore historic vineyards. Evening walks through the gardens and tasting estate wines make it a perfect romantic retreat.
Things to explore nearby:
- Discover Greve in Chianti’s artisan shops and cafes.
- Join wine tours in the surrounding Chianti vineyards.
- Take cooking classes to experience traditional Tuscan cuisine.
This villa captures the essence of Tuscany and is ideal for couples who love history and wine.
8. Villa Celsa – Classic Tuscan Elegance
Set near Siena, Villa Celsa is a luxurious retreat offering classic Tuscan charm with modern amenities. Surrounded by cypress trees, vineyards, and gardens, it is a perfect spot for romance and relaxation.
Why you will love it: Each room has unique interiors, terraces with stunning views, and access to the villa’s private pool. You can enjoy long walks, wine tastings, and quiet evenings under the stars.
Must-do experiences nearby:
- Visit Siena’s historic center and Piazza del Campo.
- Explore Monte Oliveto Maggiore Abbey.
- Enjoy private wine tastings and culinary experiences in nearby estates.
From my own personal experience, Villa Celsa offers the perfect balance of seclusion and accessibility to Tuscany’s most beautiful spots.
Planning Your Romantic Tuscany Retreat
When choosing a villa in Tuscany, consider what type of experience you want:
- Countryside Peace: For private moments and nature walks, villas like Le Fontanelle or Medicea di Lilliano are perfect.
- Luxury and Indulgence: If you prefer high-end amenities, spa services, and fine dining, Borgo Santo Pietro and Villa Cora are ideal.
- Historic Charm: Castello di Casole and Villa Vignamaggio offer a deep dive into Tuscany’s history and architecture.
Tips for your romantic escape:
- Book well in advance, especially during peak seasons (spring and fall).
- Rent a car to explore the scenic countryside at your own pace.
- Plan wine tours and local culinary experiences to make your trip unforgettable.
- Take time for slow mornings, picnics, and sunset walks—these are the moments that stay in memory.
Tuscany has a way of making you feel like time slows down. From my own personal experience, every villa offers a unique story, a different view, and countless moments to share with someone special. Whether you are sipping wine in a vineyard, strolling through historic towns, or simply relaxing by a private pool, Tuscany is more than a destination—it’s an experience that stays with you forever.
This guide showcases eight villas that perfectly combine luxury, history, and romance, each offering something unique. Exploring them is not just about where you stay, but how you feel, what you discover together, and the memories you create in the heart of Tuscany.
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.