Luxury Day Trips from Cortona, Tuscany 

Private Tours with Driver & Personalized Experiences​

Discover the Essence of Tuscany — Your Way, in Style

Welcome to Do It in Tuscany’s curated Day Trips — where we design exclusive, private day tours from Cortona and surroundings that feel less like transportation and more like an unforgettable Italian journey.

Whether you want world-class wine tasting, scenic hilltop villages, or Renaissance art and architecture, we create bespoke experiences tailored to your interests, pace, and style.

With over 10 years of local expertise, we personally match each guest with the destinations, wineries, and cultural highlights that best fit their interests.
This is not a standard tour.
This is Tuscany, curated just for you.

Each day trip may include: 
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✔ Professional private driver with luxury vehicle
✔ English-speaking guide on request
✔ Flexible itinerary customized for you
✔ Authentic local experiences — not cookie-cutter tours

From world-renowned vineyards to charming medieval towns, explore Tuscany your way, with comfort, confidence, and insider insight.

Why Choose Our Luxury Day Trips from Cortona​

Tuscany is more than a destination — it’s a feeling. And the best way to experience it is with a private driver and guide who knows every hidden vista, historic alley, and exceptional winery

​Cortona is perfectly positioned between Tuscany and Umbria — making it the ideal base for exploring:
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  • Montepulciano & Brunello wine country
  • Val d’Orcia’s iconic rolling hills
  • Siena’s medieval beauty
  • Florence’s Renaissance masterpieces
  • Assisi and the spiritual heart of Umbria

With a private driver in Tuscany, you avoid train schedules, parking challenges, and large tour groups.
Your day flows naturally, at your pace.
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  • Door-to-door pickup from your villa or hotel
  • Luxury vehicle (Mercedes sedan or van)
  • Flexible itinerary
  • English-speaking driver or licensed private guide upon request

Our Most Requested Luxury Day Trips

Private Wine Tours from Cortona

Explore Tuscany’s most celebrated wine regions with exclusive tastings at boutique wineries.

​Options include:
  • Montepulciano (Vino Nobile)
  • Montalcino (Brunello)
  • Chianti Classico
  • Hidden family-run estates
We arrange private cellar visits, vineyard walks, and reservations for unforgettable farm-to-table lunches.

Perfect for couples, anniversary trips, and wine enthusiasts.

Val d’Orcia & Tuscan Countryside Experience

This is the Tuscany you imagine — cypress-lined roads, golden hills, and timeless villages like Pienza and Montalcino. We design scenic routes with panoramic stops, artisan shops, and authentic trattorias away from tourist crowds.

Ideal for photographers and travelers seeking the iconic Tuscany landscape.

Florence, Siena or Orvieto Private Day Tour

Experience art, history, and architecture without feeling rushed.
  • Private guided walking tours available
  • Reserved museum entry upon request
  • Insider recommendations for lunch and local cafés
Return to your villa relaxed — not exhausted.

 Hidden Gems of Tuscany

For returning travelers or those who prefer authentic local life, we suggest:
  • Arezzo
  • Lake Trasimeno
  • Small hilltop villages off the typical tourist routes
  • Artisan food producers and olive oil mills
These are the experiences most visitors never find on their own.

Orvieto - ​Art, Architecture & Timeless Umbrian Charm

A stylish private day trip from Cortona to Orvieto—visit the magnificent Duomo, enjoy free time in the medieval center, and savor an easy Umbrian lunch at your own pace.

​Lake Trasimeno - Scenic Views, Lakeside Villages & Authentic Umbria​

Surrounded by hills, vineyards, and olive groves, Lake Trasimeno is Central Italy’s largest lake and home to three islands, including inhabited Isola Maggiore. Enjoy a relaxed private day trip from Cortona with panoramic stops, charming villages, and the comfort of a private driver—an authentic escape from the crowds.
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What Makes Our Luxury Tuscany Tours Different?

Many companies offer transportation.
We offer curation.
We take the time to understand:
  • Are you wine lovers or art lovers?
  • Do you prefer structured guidance or relaxed exploration?
  • Is this a honeymoon, a family vacation, or a milestone celebration?
Then we design your day accordingly.
Our guests often tell us this feels like exploring Tuscany with a knowledgeable local friend — but with the comfort of a luxury service.

Frequently Asked Questions

Are your drivers English-speaking?
Yes. We work with professional English-speaking drivers, and licensed private guides can be added for in-depth historical tours.
How long are the day trips?
Typically 6–8 hours, but we customize timing based on your preferences.
Is this suitable for families?
Absolutely. We adapt pacing and activities for children and multi-generational groups.​
Do you offer fully custom Tuscany itineraries?
Yes. Many of our guests combine several day trips into a personalized Tuscany travel plan.

Plan Your Luxury Day Trip from Cortona

Whether you dream of sipping Brunello at sunset, wandering through Siena’s piazzas, or discovering hidden countryside estates, we will design a day that reflects your style and interests.

​Contact us to begin planning your private Tuscany experience.