The Ultimate Romantic Trip to Tuscany and Umbria: Hidden Gems

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Angela Marini
Curated By

Angela Marini

  • Tuscany

  • Italy

  • Food & Wine

  • Arts & Culture

  • Couples Travel

  • Romantic

Advisor - The Ultimate Romantic Trip to Tuscany and Umbria: Hidden Gems
Curator’s statement

There are places you visit… and places that feel like they were made for love. A romantic journey through Florence, Umbria, Orvieto, and Tuscany isn’t just a trip. It’s a slow, cinematic love story unfolding across sun-washed hills, Renaissance art, candlelit trattorias, and vineyard sunsets. Whether you’re planning a honeymoon, anniversary, or spontaneous escape, this part of Italy feels designed for romance.

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Where to stay in Tuscany & Umbria

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Things to do in Tuscany & Umbria

Orvieto

  • Explore the ancient medieval streets, get lost in alleyways that lead to charming piazzas and hidden treasures. Oh, and don’t worry if it is raining—just grab your umbrella and go. Orvieto feels even more special in the rain.

  • Discover the underground! Tunnels and underground pathways are a secret world beneath the streets!

  • Visit the artisans and small local shops for treasures.

Umbria

  • Stay in a medieval castle or monastery surrounded by vineyards and olive groves.

  • Go truffle hunting in the woods around Norica and wine tasting in the many local vineyards. Although they might not be as well-known as Tuscan vineyards, they are just as fabulous.

Florence & Tuscany

  • Take a cooking class in one of the many markets and cooking schools in Florence. Or have your travel agent arrange a cooking class in a local home with a nonna.

  • Visit the lesser-known towns of Pitigliano, Sovana, and Sorano, which are known as the “tuff towns”. These villages are carved into volcanic rock. Walk their narrow streets and discover ancient Etruscan tunnels.

  • Rent a vintage convertible through the rolling hills, cypress-lined roads, and vineyards, giving you the freedom to explore hidden gems at your own pace. Stop at small towns and vineyards along your route and have a long, leisurely lunch in a small village.

Places to eat & drink in Tuscany & Umbria

Coro

  • Casa del Vin Santo - Ristorante Braceria Firenze: Loved local favorite with traditional Tuscan fare and a warm, lively atmosphere. Great for long dinners together.

  • La Buchetta Food & Wine Restaurant: Highly rated spot blending wine culture with Tuscan cuisine—perfect for a romantic dinner.

  • Mezza Luna: Cozy trattoria in the historic center, perfect for casual yet delicious pasta, bruschette, and local wine.

  • Trattoria del Moro Aronne: A beloved classic with traditional Umbrian dishes, fresh pasta, and hearty local flavors and is ideal for a relaxed lunch or dinner.

  • Coro: Refined and intimate fine dining in the heart of Orvieto, perfect for a special dinner with creative Umbrian cuisine and local wine. It also happens to be in my favorite hotel in Orvieto.

Need to know

This trip offers a slow, meaningful journey through Umbria, Orvieto, Florence, and Tuscany and is perfect for travelers seeking something fresh and unexpected, yet comfortably familiar.

Angela Marini

Travel Advisor

Angela Marini

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For more inspiration and insider recommendations, visit our Tuscany page.