Centered around Florence and encompassing such storied towns as Siena, Montepulciano and Arezzo, Tuscany is one of Italy’s most fabled regions, known for its gorgeous countryside, vineyards, old-world charm and coastline.

  • Perfect for
    Families | Foodies | Romantics | Ultimate Indulgers
  • When to go
    March-May | June-August | September-November
  • Ideal length of stay
    1 Week

Designing Your Journey

Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.

  • 1 Week: Essential Tuscany-LP

    1 Week: Essential Tuscany

    An ideal Tuscany itinerary combines outings with more relaxed activities all while based at Indagare Adored properties. Here is just one example of what our destination specialists can create for you.

    • Days 1-2: The Tuscan Spirit

      Upon arrival in Tuscany, ease into the spirit of the region with a private cooking lesson and learn how to make homemade pasta, sauces and various other Tuscan specialties. Another favorite activity in Tuscany is setting off on a bike or horseback ride, through the forests, on winding lanes and along fields, which, depending on the season, might be bursting with sunflowers. Get a recommendation for a winery to visit en route. Our favorite hotels in Tuscany have excellent spas and feature treatments utilizing local beauty products.

    • Day 3: Special Experiences

      Indagare can arrange special, insider experiences ranging from making your own olive oil or going truffle hunting to visiting a town featured in many movie sets and, of course, wine tasting to your heart’s content.

    • Day 4-5: Day Trips

      Tuscany is bursting with tiny towns to explore on half-day or full-day trips from your hotel. Favorite locales include Cortona, the setting for Under the Tuscan Sun, Montepulciano and Montalcino, wine-making meccas, Pienza, a fairytale-like walled city and the historic Siena, home to the twice yearly palio horse race.

  • Member Stories

    “Our guide in Tuscany was tremendously knowledgeable and great with our kids. Our favorite activity was a visit to Cortona, our guide’s hometown!”
    L.C., member since 2017
  • Member Stories

    “We loved our villa at Castiglion del Bosco! The pasta-making experience Indagare arranged was seriously so much fun. The chef could not have been nicer and we made a delicious lunch that was then served to us in the restaurant downstairs.”
    Megan H., member since 2015
Indagare’s Amelia Osborne Scott
“In Tuscany, whenever possible, visit a weekly market, small family-run food stores and farm shops and put together picnic meals of crusty bread, pecorino, prosciutto, tomatoes, olives and wine. These are always my favorite meals when I’m in Italy. Alternatively, appeal to a winery, restaurant or your hotel for a small spuntino, or snack, which will inevitably result in a great meal of nibbles.”

What To See & Do

Ready to go and in need of expert trip planning? Contact us today.
Indagare Insider, Trudie Styler
“Our ideal morning in Tuscany is a very laid-back one! Everyone will trickle down for a buffet breakfast on the terrace. Sting is often first up and practicing guitar in his favorite shady spot. We’ll chat and read, sunbathe, and Sting and I usually work out, doing some yoga or Pilates. At lunchtime everyone convenes at the great long table under the huge oak tree for a lunch of pastas and salads.”

What To Read

Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.

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