The dreamy landscapes and golden light has drawn artists to Tuscany for centuries. Join us as we take a peaceful and sensory plunge into the world’s most beloved destinations and iconic photo locations: La Toscana!

A nature lover, history buff and foodie lover’s photographic dream, this unique experience offers countless picture-perfect moments and an exploration of all things wonderful in very specific areas within Tuscany: the illustrious Val d’Orcia and the Chianti hills.

We’ll focus on stunning landscapes and capturing the magic of this serene atmosphere, with its cultivated fields, flocks of resting animals and rural life, or of the ancient medieval villages perched on the hilltops. Most importantly, we’ll capture these places at just the right time, when the light is perfect!

Along the way, we learn about the production of olive oil, wine, preserved meats, honey and specialty sweets (and enjoy abundant tastings). You’ll photograph and absorb the rich, historical culture of the surrounding villages and cities. Our daily walks will take us through picture-perfect landscapes that reveal the land’s magical beauty, while our taste buds delight in tasting regional specialties, including the region’s renowned Brunello, Vino Nobile, Rosso di Montalcino and Chianti Classico wines.

The trip will be led by photographer Ossian Lindholm and Travel Vision Director Lauren Hefferon, a passionate Italophile who has three decades of Tuscan travel experience and expertise to share!

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What's Included

Trip Planning

  • Group airport shuttle at the start and at the end of the tour


On The Tour

  • Service of professional guides throughout the program
  • Guided visit to a local farm
  • 3 winery visits
  • 1 wine tasting


Accommodations & Meals

  • All accommodations
  • All breakfasts, 7 lunches and 4 dinners

Trip Highlights

  • Get daily photographic, hands-on instruction by renowned photographer Ossian Lindholm
  • Experience the Val d’Orcia and its stunning hilltowns, like Montalcino, Pienza and Montepulciano
  • Visit the local thermal baths of Bagno Vignoni, which were once enjoyed by the ancient Etruscans and Romans
  • Sip and savor the finest wines in the world in Montalcino
  • Visit a local, family-run winery that makes the famous Brunello wine
  • Experience an authentic, homemade Tuscan lunch in the private home of a local friend
  • And so much more!


Day 1: Florence Centro

Benvenuti a Firenze! Today, you arrive to Florence and check into our hotel. As we “follow the light” in the birthplace of the Renaissance, we quickly see that Florence has something for everyone: art museums and architecture, food and markets, stunning landscapes and sunset points, all soaked in centuries of history. 


Day 2: Transfer to Val d’Orcia

This morning, we transfer south to the “big sky country” of Tuscany as we enter the Val d’Orcia. This is quintessential Toscana: layers of rolling verdant hills topped with cypress trees, stone farmhouses and wide-open vistas that appear in Renaissance paintings and have been coveted by artists and photographers from around the world.


Day 3: Val d’Orcia: Montalcino & Brunello Wine

We begin with a gorgeous sunrise stroll to capture the sun-dipped layers of mist rising above the rolling horizon. After a delicious breakfast, we take a slow drive to the hilltop of Montalcino, which offers gorgeous views over the Asso, Ombrone and Arbia valleys. Next stop is a stop at a local, family-run winery that makes the famous Brunello wine, where we learn the secrets of Italian organic wine-making and enjoy a guided tasting of this prestigious wine.


Day 4: Val d’Orcia: Castiglione d’Orcia

Today after an early morning visit to the village of Castiglione d’Orcia, we tour a local farm that grows medicinal and aromatic plants. It’s the largest in the Val d’Orcia. The project is multi-faceted and eco-sustainable.The farm is self-sustaining in terms of energy and water and doesn’t use any chemical products.


Day 5: Val d’Orcia: Renaissance Pienza & Pecorino Cheese

This morning we take a leisurely walk from San Quirico to the beautiful town of Pienza. Lunch is held in the private home of our local friend Angela (a home cook). We meet her entire family, learn about and taste the different ‘ages’ of pecorino cheese, and sip wine on her terrazza overlooking Pienza. This will certainly make for an unforgettable Tuscan feast!


Day 6: Transfer to Chianti: Volpaia

This morning, we have a transfer to our villa base in the Chianti countryside. We then have a welcome aperitivo and lunch in the garden. And later, we review our photo goals and Ossian’s objectives for the week and head out to capture the magical Tuscan light on our first afternoon walk into the Chianti woods.


Day 7: Chianti: Castelvecchi & Surrounding Villages

This morning, we walk to Castelvecchi. We walk through vineyards, olive groves and across tiny streams, passing old and abandoned ancient mills, restored borghi (villages) and a tiny forest chapel. On this walk, we reach an elevation that allows views of the Valdarno, Chianti hills and the Casentino area of Tuscany. In the late afternoon, we visit a winery in Castello di Lamole. 


Day 8: Chianti: Castello di Volpaia

Today, our photo walk takes us to the top of local Monte Querciabella. The views reach the other side of Volpaia, offering spectacular views of Tuscany’s precious Monte Amiata. We pass through several tiny hamlets and Torniello Vineyard as we make our way along the famous battle boundaries between Siena and Florence provinces. Later in the day, we return to Volpaia for a mid-afternoon photo class.


Day 9: Arrivederci!

This morning, it’s time to say arrivederci to Tuscany! After breakfast, we have a 9 am transfer to Florence Airport. Interested in extending your stay in Florence, Rome or Venice? Check out our new city extensions!



City Extensions



Guide: There will be a local historian and sommelier that will take you around the center of Venice, do an overview tour of the important sites and then take you to tastings in Venice’s various bacari, small wine bars where you can taste a sampling of Venice specialties.

Optional: On day two, you can visit the gondola building and repair lot and take a gondola ride.

Meals: Dinners will be on your own, with an extensive list of restaurants provided by Ciclismo Classico (CC). You’ll also receive travel information for airports or continued travel in Italy.

Hotel: Belle Epoque (in the Cannaregio neighborhood)



Guide: On day one, there will be a local sommelier who will give you a welcome, overview visit, and a tour of the three main markets (including tastings of Florentine specialties), followed by an aperitivo.

Optional: Additional guided (or non-guided) visits of Uffizi, Accademia, Villa Bardini or other museums, which can be pre-arranged by CC for day two. An additional cooking lesson in a private home can also be arranged.

Meals: Dinners are on your own, with an extensive list of restaurants provided by CC. One lunch and all tastings are included. You’ll also receive travel information for airports or continued travel in Italy.

Hotel: Ad Astra (in the San Frediano, Oltarno neighborhood)



Guide: On day one, you’ll receive an overview of the neighborhood by a local guide, followed by a few tastings in one of the many markets.

Optional: A half or full day guided visit of Rome’s most famous monuments can be arranged by CC.

Meals: Dinners are on your own, with an extensive list of restaurants provided by CC. One lunch and all tastings are included. You’ll also receive travel information for airports or continued travel in Italy.

Hotel: Le Clarisse (in the Trastevere neighborhood)


Coming soon!




6-8 travelers: $6,095 pp

9 or 10 travelers: $5,695 pp

11 or 12 travelers: $5,395 pp

Single Supplement: Call

Length: 9 Days / 8 Nights

Ability Level: Easy

Start / End Locations: Florence / Radda in Chianti

2018 Trip Date: April 13-21