Tuscany Itinerary: 6 Fully Planned Days with Context

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Scenic View of the Tuscan Countryside

Scenic View of the Tuscan Countryside

Tuscany: the best known region in Italy for wine lovers, beautiful landscapes, medieval history and outstanding art and architecture. When you think of Tuscany, what is the first thing that comes to mind? For me it’s wine, but in reality, it’s so much more. Aside from sampling wines, cheese, olive oil and salami, Tuscany houses the cities of FlorenceSienaLucca and Pisa. Travelers often wonder if they should visit different parts of Tuscany as day trips from Florence or arrange a standalone trip. While both are great options, we’d never say no to 6 days in Tuscany. With that being said, the Context team crafted a perfect Tuscany itinerary for life-long learners and travelers. Join us in a 6 day Context Journey, Florence and Tuscany: Walking in History with Professor Kate Bolton-Porciatti where we’ll explore Florence and the surrounding countryside of Chianti for a blend of art, history, and walking in Italy.


Kate Bolton-Porciatti is a professor of Italian cultural history and music at the Istituto Lorenzo de’Medici in Florence, where she teaches BA and MA courses in the humanities. She also lectures at the British Institute, Florence, and at the Chigiana Music Academy in Siena. Kate has published extensively as an academic and a journalist; she is a music critic for BBC Music and a travel writer for The Daily Telegraph, UK. Before moving to Italy permanently in 2005, she was a senior producer and broadcaster for BBC Arts & Classical Music in London and has won prestigious Jerusalem and Sony Awards for her programs. She did her M.Phil. thesis in Italy, exploring the musical culture of early Renaissance Florence.

“As a keen walker and nature lover, it is a pleasure to wander through the hills of Chianti, exploring its flora, fauna, and culinary traditions that have evolved in symbiosis with the natural environment.  Above all, during stimulating conversations as we sip the exceptional wines of this area, I look forward to sharing our mutual passions for a cultural landscape that has been shaped to perfection by man and nature.” - KBP

While we’re in Florence, we’ll explore the historic city, narrating the story of how it grew from an ancient Roman castrum to a splendid Renaissance town - later chosen to be the first proud **capital city of the newly unified Italy. Together we will visit the Uffizi Gallery for an in-depth viewing of its paintings and sculptures, see Michelangelo’s David in the Accademia, and stroll through the beautiful Boboli and Bardini Gardens.

We’ll take in sweeping views of Florence from just beyond the medieval walls at the city’s oldest surviving church, San Miniato al Monte, where we explore the techniques of fresco, panel-painting, mosaic, intarsia, and sculpture – the artistic and artisan skills that ultimately defined the great Renaissance city in the valley below.


From there we journey together into rural Chianti to enjoy its scenery. On our walks through the verdant, vine-clad hills we’ll take in the historic abbey and hamlet of Passignano (surrounded by the noble Antinori vineyards), the medieval fortified castle of Montefioralle (family home of explorer Amerigo Vespucci), and the market town of Greve in Chianti, with its delightful arcaded piazza. Experience a private vineyard tour, wine-tasting, and a cooking class with Context on this Journey.

DAY 1: Arrival & Getting Settled

Once we’re all settled in, we will enjoy a local tour of our neighborhood and a traditional Florentine meal while we get acquainted with our fellow travelers and our expert, Professor Bolton-Porciatti.


At a Glance:

  • Arrive from the airport and check in to the hotel
  • Meet the group
  • Meet Professor Bolton-Porciatti for an orientation stroll
  • Welcome dinner together as a group

DAY 2: Renaissance Florence In Depth

On our first full day together, we’ll enjoy an in-depth tour of historic Florence, including the Uffizi Galleries and Michelangelo’s David, walking past all of the highlights of the city from the soaring Duomo to the picturesque Ponte Vecchio, putting the pieces of this magical place in context.



At a Glance:

  • Breakfast at the hotel followed by a personalized introduction to the city’s Roman to Renaissance history
  • Visit the Medici’s Uffizi Galleries to see masterpieces of Italian art, including works by Botticelli, Caravaggio, Da Vinci, Michelangelo, Raphael, and Titian.
  • Experiencing Michelangelo’s David up-close with a leading art historian
  • Sightseeing around the Ponte Vecchio, Piazza della Signoria and the Duomo
  • Lunch together in a typical trattoria
  • Finish the day with a rooftop aperitivo as a group to enjoy panoramic views of the city
  • Guests will enjoy dinner on their own, tailored recommendations will be provided for lunch and dinner

DAY 3: Florentine Panorama:  From San Miniato to Boboli Gardens

In the morning we’ll visit the city's oldest church, San Miniato al Monte - a 1000-year-old showcase of the artistic skills of Florentine craftsmen. We'll spend the afternoon taking in the panoramic views of the city as we stroll through historic Renaissance-style gardens of Florence – such as the Bardini and Boboli. We’ll stop for lunch in a typical Florentine Osteria.


At a Glance:

  • Private transportation will convey us all together to San Miniato, above the city.
  • Guided by Professor Bolton-Porciatti, we’ll visit the church and enjoy a private tour of its artistic treasures
  • We’ll catch our breath as we take in the view at Piazzale Michelangelo
  • Stroll downhill via the Rose Garden into the San Niccolò artisan neighborhood and enjoy a narrated tour of the monuments we’ll pass
  • Lunch in the Oltrarno - a fashionable bohemian neighborhood where many Florentine artisans and craftspeople have their workshops
  • Afternoon visit to iconic Bardini Gardens and Boboli Gardens surrounding the Palazzo Pitti or opt to enjoy an afternoon at leisure on your own.
  • Guests will enjoy dinner on their own - tailored recommendations will be provided

DAY 4: From Florence to the Chianti Hills

We’ll enjoy a scenic drive through Chianti, and after leaving our bags at our countryside accommodation, we will set out on foot for our first walk in the hills – or our driver can convey guests who do not wish to go on foot. We will cover about 8 miles (13km) today on our circular route. In the evening we’ll enjoy a private cooking experience, led by a local chef.


At a Glance:

  • 1-hour drive from central Florence to Chianti in private vans with drivers
  • Leave luggage and set out on foot for a morning walk in the countryside with Kate
  • Experiencing the evocative views of the scenery and landscape of the Florentine hills
  • Touring the beautiful villages of Montefioralle and Greve
  • Lunch at leisure as a group in Greve and then we’ll make our way back to Villa Bordoni
  • Cooking class at Villa Bordoni with dinner

DAY 5: Walking to Passignano

On our final day together, we will once again take to the hills on foot and walk a total of 8 miles (13 km) to enjoy the flora and fauna of Chianti and to visit the historic village of Passignano, built around an ancient Benedictine Abbey.

In the evening we’ll enjoy a wine tasting and farewell dinner. We will come away from the wine tasting with a  deeper understanding of the role winemaking plays within Tuscany’s storied history.


At a Glance:

  • After breakfast at the hotel, we set out on foot to visit Passignano. For those who do not wish to travel on foot, transportation via private van will be available
  • Enjoying panoramic views of the idyllic countryside on our way to the Abbey
  • A leisurely picnic lunch
  • Free time to lounge at Villa Bordoni, enjoying the pool and additional amenities
  • Evening Wine Tasting excursion followed by farewell dinner

DAY 6: Departure

Travelers will depart from Villa Bordoni to Florence to continue their Italian journey independently – or our team will be happy to arrange airport transfers for flights home.

Join us

For more information, we invite you to explore our FAQ Page or get in touch about this Journey: Florence and Tuscany: Walking in History with Professor Kate Bolton-Porciatti. If you’re interested in meeting Kate, you can also spend a daywith her in Florence, or join her online.

Departure 1: March 17 - 22, 2022

Departure 2: May 12 - 17, 2022

Learn more about Tuscany and Florence, in person or online: