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Italy
From $5,150 per person
9 Days | Customizable
A curated journey through Tuscany and Northern Italy blending countryside charm, Renaissance Florence, and the design-forward energy of Milan. This itinerary is fully supported with private transfers and rail logistics included throughout, ensuring a seamless experience between regions.
Your Journey at a Glance
Stay:
9 days, 8 nights
Meals:
Daily breakfast + select culinary experiences
Accommodations:
3 boutique properties
Departs from:
Florence Airport
Destinations:
  • Siena, Italy
  • Florence, Italy
  • Milan, Italy
Included Activities:
  • Full-day Volterra & Colle Val d’Elsa tour
  • Private Tuscan cooking class in Siena
  • Dante literary experience
  • Florence walking tour with Uffizi Gallery
  • Florentine craft & cuisine tour
  • Milan secret walking tour
+ 3 more
Gallery
The Itinerary
Lemon tree in villa garden with manicured bushes.

Day 1–3

Siena: Tuscan Countryside & Hill Towns

Arrive at Florence Airport where you are met for a private transfer included to your Tuscan countryside hotel in Siena. Settle in and explore medieval hill towns nearby. A full-day guided excursion to Volterra and Colle Val d’Elsa is followed by a hands-on Tuscan cooking class highlighting seasonal regional cuisine.

  • Villa Scacciapensieri (or similar)
  • Breakfast + cooking class meal
Historic Volterra skyline with medieval architecture and sky.
Women cooking together in rustic kitchen setting.
Sunny courtyard of multi-story residential building.

Day 4–6

Florence: Renaissance & Living Culture

Enjoy a private transfer included from Siena to Florence. Explore the city through immersive experiences including a Dante literary walking tour, a guided Uffizi Gallery experience, and a final day focused on artisan workshops and Florentine cuisine.

  • Hotel Orto de’ Medici (or similar)
  • Breakfast
View of tower through historic columns, Florence, Italy.
Florence cathedral dome against blue sky with clouds.
Elegant hotel room with checkered decor and plants.

Day 7–8

Milan: Design, History & Hidden Corners

Transfer included to Florence train station for first-class rail included to Milan. Upon arrival, a private transfer takes you to your hotel. Discover Milan’s hidden side on a guided walking tour through courtyards, historic streets, and architectural gems.

  • Hotel Matilde Boutique (or similar)
  • Breakfast
Milan Cathedral at sunset, Italy
Charming narrow alley with rustic brick walls

Day 9

Departure

Private transfer included to Milan Airport for departure.

  • Breakfast
Scenic sunset over Tuscan countryside vineyards.

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