Slow Travel in Tuscany and Umbria

Advisor - Jennifer Schwartz
Curated By

Jennifer Schwartz

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  • Arts & Culture

  • Boutique Travel

  • Couples Travel

  • Italy

  • Tuscany

  • Local Culture

  • Local Food

  • Entertainment

An Italian building with red and pink flowers.
Curator’s statement

Take it easy when traveling in Tuscany and Umbria. Meander through the Italian countryside and coastline, stopping along the way to explore the villages, medieval cities, timeless coast and rolling hills of endless vineyards.

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Where to stay in Tuscany and Umbria

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Castello di Casole

La dolce vita brought to life on 4,200 acres of fairytale Tuscan countryside.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Hotel Cipriani, A Belmond Hotel, Venice

It’s hard to rival the glamour, history and setting of this Giudecca Island icon, prized for its lagoon views, famed cocktail bar, enchanting gardens and pool.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Villa San Michele, A Belmond Hotel, Florence

Hilltop property in a former 15th-century monastery with elegant rooms and villas.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

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Advisor - Jennifer Schwartz

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Things to do in Tuscany and Umbria

A meandering old Italian street.

Take a Tuscan Wine Tour, or two, and visit the vineyards of Podere Poggio Scalette, Tenuta Carobbio, Ca' Di Pesa, Tenuta Degli Dei, Montevertine, Le Miccine and Castello di Ama.

Visit Siena, this medieval city has preserved its character into the modern age. The city is built around the Piazza del Campo and blends into the surrounding landscape. Walking along the 15th century streets will transport you back to this era. Besides the Duomo and Palace, there are old world markets and boutiques to explore and if you’re hungry, just past the Piazza del Campo, up a narrow alleyway and housed in a former grocer’s shop, Osteria Le Logge is worth a stop.

Visit the port town of Porto Ercole on Mont Argentiono. This fishing village retains its old world charm with its picturesque beaches, luxury hideaways and gorgeous landscape.

Make time for Perugia, a lively city, which isn’t on the map for a lot of tourists. There are ancient foundations which contrast with modern cafes and boutiques. There’s a big chocolate culture, it’s home to the Perugina chocolate house and host of the Perugina EuroChocolate Spring festival.

Get to Assisi, a hilltop town in Umbria, with lovely views and its pinnacle being the massive Basilica of St. Francis. There are Roman ruins, and a number of less imposing religious monuments.

Stop at Spello, a picturesque and floral village with narrow cobblestone streets. Worth visiting during the Infiorata festival when the streets are transformed into mosaics of petals.

Places to eat & drink in Tuscany and Umbria

A fine dining establishment in Italy.

Tuscany and Umbria

20 Posti - Small Mediterranean bistro with great dishes.

Villa Pigano - Gorgeous setting for elevated Tuscan fare.


Osteria Le Logge - Classic osteria serving upscale Tuscan dishes.

Osteria Il Carroccio - Solid restaurant with a great vibe.

Panzano in Chianti Panzanese - Make the trip. It’s beyond good, and I had the vegetarian menu!

Porto Ercole Il Pellicano - Stop in at this iconic hotel for a bite.

Perugia L'Officina - Upscale creative cuisine.

Assisi Trattoria Pallotta - Family run trattoria serving regional fare.

Spello Osteria del Buchetto - An intimate family run trattoria, great setting.

Need to Know

Looking for more travel inspiration? Check out my guide, Guide to Picturesque Picnics in and around Rome.

Advisor - Jennifer Schwartz

Travel Advisor

Jennifer Schwartz

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This guide is part of our ongoing series on travel to Tuscany.