We will ride through the heart of Tuscany on a tour that begins in Cortona, and then winds through the beautiful Val d’Orcia recognized by UNESCO as a “World Heritage Landscape” for its unique blend of human and natural environments. Over eight days we visit and photograph Pienza, Montepulciano, Montalcino, Siena and San Quirico. Prepare to explore the picture postcard landscape of Tuscany, one of the most beautiful regions in Italy.

This tour is early in the riding season for those of us who live in northern hemispheres. Photographing spring in the Italian countryside is a great place to get in those spring training rides, don’t you agree?

What to expect from the photography experience on this tour

This tour is designed to fulfill your photography bucket list shot for Tuscan landscapes, architecture and history. We will set a storyline to capture and look for throughout the trip, and of course we will be looking to create artistic images as well. Photography instruction will be provided at each photo location for those who are learning. A basic understanding of how to capture digital images with your equipment before you arrive will be helpful, but all levels of photographers and equipment are welcome. Group and individual instruction will be given freely.

What to Expect from the cycling on this tour

This tour has six ride days and will require a good to above average level of fitness to complete all rides. There is no mountain riding with sustained climbs but we do have three hilly days with 3,000+ feet (1,000 meters) of climbing. Please train and come prepared to ride. If you need to take a break from the bicycle or you are a non-riding partner who is coming along just for the photography stops, there will be comfy air conditioned transportation for you.

  • Tour Dates

    May 10 through 17, 2020

  • Departing from Cortona Italy

    Arrival airports Florence (FLR) or Rome (FCO)

  • Small Group

    12 guest max

  • Road Cycling

    6 riding days: 225 miles || 38 miles avg per day

  • Photography

    8 organized photo locations, instruction included, 1 photo review and editing session

  • Fully Supported Tour

    Ride each day at your own pace. Your photo gear will be transported to shot locations and luggage to the next hotel.

  • Pricing:

    $4,190 per person with double occupancy. Tour will run with 4 guests minimum. Early deposit guests (by Nov 5, 2018) will receive $200 off the total trip price.

Tour Highlights

  • Cortona to San Casciano dei Bagni – 47 mi (75 km)
  • “Val d’Orcia” to San Quirico – 37 mi (59 km)
  • San Quirico-Montepulciano Loop – 34 mi (55 km)
  • San Quirico to Montalcino – 49 mi (79 km)
  • Montalcino to Siena – 36 mi (57 km)
  • Montalcino-Castle Brolio Loop – 36 mi (57 km)

Daily Activity, Ride Info and Shot Locations

Take each day at your own pace. Transportation and schedule have been planned around capturing famous images from this region for your portfolio or personal enjoyment. Participating in photography sessions is always optional.

Day 1 - Arrive in Cortona

TEACHING PHOTO LOCATIONS: Streets of Cortona, Hermitage Le Celle

We are in the spectacular hill town of Cortona today looking over the Chiana River valley (the "Val di Chiana"). Cortona offers the perfect introduction to Tuscany since its founding as an Etruscan town dates to 600 BC. Come a day early to see the newly restored Etruscan Museum or the Diocesan Museum with its Fra Angelico paintings. We'll fit bikes and do a test ride late this afternoon and then have a photo walk before dinner together.

Day 2 - ride cortona to casciano dei bagni - 47 miles (75.5 km)


We pedal south today across the Chiana Valley to the spa town of San Casciano dei Bagni. San Casciano sits on the slopes of Monte Cetona, the northernmost of a series of extinct volcanoes in central Italy. Enjoy views looking back on your route from Cortona across the Val di Chiana. Enjoy a dip on the thermal pool overlooking the valley, or take a 15 minute drive to photograph a sunset view of the city and the valley before dinner together.

Day 3 - ride through val d'orcia to san quirico - 37 miles (60 km)

TEACHING PHOTO LOCATIONS: San Quirico, Sunset at Pienza and Capella di Vitaleta

We'll ride through Radicofani today dominated by its 11th century castle and continue through the Orcia Valley to Pienza, home of Pope Pius II. Pope Pius turned this tiny village into a showpiece of Renaissance town planning in the 16th century. Our hotel tonight is just inside the city walls. Photograph in the streets of Pienza on your own or take in a sunset landscape for group instruction. Take a walk around Pienza and sample the local wines and cheeses (we highly recommend the Pecorino that is wrapped in chestnut leaves and aged under a bed of ashes allowing for uniform drying and aging).


TEACHING PHOTO LOCATIONS: Agrotourismo Belvedere, Poggio Covili, Agrotourismo Terapille and hills below Pienza

We spend this day photographing iconic views in the stunning Val d'Orcia starting with a 6 am sunrise. You can choose to do an unsupported ride to the Circle of Cypress or the spa town of Bagno Vignoni with routes we will provide. Or spend the day reviewing and practicing editing some of your photos with hands on instruction. In the afternoon we will drive out to capture golden afternoon light at a few bucket list locations.

Day 5 - Ride san quirico to montalcino - 42 miles (68 km)

TEACHING PHOTO LOCATIONS: Agrotourismo Baccoleno, Sant' Antimo Abbey, Streets of Montalcino

This morning starts with a ride on the ridgeline of the bare clay hills north of San Quirico. Cypress trees mark the entrances to isolated Tuscan farms on distant hills. The quaint village square in Trequanda is an excellent mid-morning cappuccino stop. Stop at Agroturismo Baccoleno directly on our route to photograph another famous Tuscan landscape in Crete Senesi. As we continue down the Asso River Valley, we leave the clay hills and ride through vineyards as we make our way to the Etruscan village and wine town of Montalcino. Today this town is famous for producing one of Italy's premier red wines, Brunello di Montalcino. Call it a day and head to the hotel or take an extra ride to the famous Abbey of Sant'Antimo. We have a special aperitif planned this evening.

Day 6 - Ride montalcino to siena - 36 miles (58 km)

TEACHING PHOTO LOCATIONS: Monte Oliveto Maggiore, Streets of Siena

The full beauty of the Tuscan landscape with the lush green fields and forests of the Orcia Valley and the barren clay hills of Central Tuscany unfold before us today as we leave Montalcino and pedal to Siena. We'll pass by the historic monastery of Monte Oliveto Maggiore and stop for photos if you wish. Then spin along the eroded chalk hills of the Crete Senesi. Siena remains Italy's best-preserved medieval city and rivaled Florence for dominance over Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls. We'll take a guided tour of the city later this afternoon and learn about the Palio, the horse race that takes place twice a year in the main square.

Day 7 - Ride siena to castle brolio and back - 30 miles (48 km)

TEACHING PHOTO LOCATIONS: Castello di Brolio, Streets and rooftops of Siena

You have the option today to take a rest from the bike and enjoy some sightseeing in Siena or join us on a loop ride into the Chianti hills. Not far from Siena is the famous Castle of Brolio or, "il Castello di Brolio." Brolio is the estate where the blend of wines that today make up Chianti was invented. This famous Tuscan wine is a blend of 70% Sangiovese, 20% Canaiolo and 10% Malvasia or Trebbiano wines. We'll be back to Siena in time for a final photo review and editing session and sunset photos around town before dinner together.

Day 8 - Tour ends in siena

Breakfast will be served and then we say our goodbyes and exchange info to share photos after we return home.

What’s Included

  • Fully Supported

    Including local guides, drivers, bike mechanic, baggage transfer, and camera gear transport to shot locations.

  • SAG Vehicle

    Ride in comfort in the SAG vehicle if you need a break from the bicycle.

  • Self Paced Rides

    Ride each day at your own pace. The route will be clearly marked, and an experienced ride leader follows the group for repairs, emergencies and keeps you from getting lost.

  • Lodging

    3 & 4 Star clean & comfortable accommodations.

  • Meals & Gratuities

    All breakfasts, 5 dinners with wine, guided tour of Siena, 1 wine tasting. All tips and gratuities at tour hotels and group meals are covered.

  • Photo Instruction

    Group and individual photo capture and editing instruction is covered in your trip cost.

  • Bikes Provided

    Use of a high quality Titanium road bike geared specifically to cruise the flats and help ease you over the mountains. Bikes come with an expandable rear rack pack if you want to carry your stuff, and a water bottle that is yours to keep.

What’s Not Included

  • Airfare

    Airfare or other transportation to and from the tour will be your personal responsibility.

  • Airport Transfer

    Information will be provided after booking with options for transport to & from our start & end points.

  • Some Meals

    Breakfasts and 5 dinners are included. Three dinners and all lunches will be your own responsibility.

  • Photography Equipment

    Guests are expected to bring their own photography equipment and to know how to use it.

Bikes Available for This Tour

Our ground operator for this tour is ExperiencePlus! The first US-based bicycle tour operator in Italy and now one of the oldest and most well-respected bike touring companies based in the US. Shipping or flying with a bike is expensive and finding quality bikes in international locations isn't always a given. Fortunately they have been doing bicycle touring for over four decades now, they know what makes a good touring bike and have custom built bikes perfect for multi-day touring.


Frame: Titanium with carbon fork


-Shimano 105 2x22: Compact crank 24-50 and 11-32 cassette

-Sram Rival 1x11: 40 chainring and 11-42 cassette

Tires: 700x25

Made by Nevi, an Italian manufacturer, or Van Nicholas, a Dutch company, both of whom specialize in custom made titanium bikes, these bikes are built for cycle touring, not racing. This means that the longer head tube and fork column, and the slightly shallower head tube angle, will have you sitting pretty for a full day in the saddle yet able to take advantage of all that titanium provides a road bike - stiff, light and nimble.


Frame: Titanium with Carbon Fork

Gearing: Shimano SLX 3x10: 24-32-42 and 11-34 cassette

Tires: 700x25

Experience Plus titanium hybrid bikes are lightweight and optimized for road usage so are essentially a road bike with a flat handle bar. These custom made bikes come in both a standard and mixte (step-through) frame and are a great choice if you prefer low gears (like a mountain bike), a more upright riding position, and easier to reach brake levers. To ensure customized comfort and avoid numb hands or tired forearms while cycling our Hybrid bikes are equipped with Ergon GP touring grips.

What to Bring
  • Camera, lenses, tripod and bag to carry them.
  • Laptop with your choice of photo editing software. Laptops will be available for editing and backups if you don’t want to travel with your own.
  • Your own cycling shoes and pedals, any bike bags you like to ride with, your bike helmet.
Weather and Kit

Expect warm sunny weather between 60F (16C) and 75F (24C) during the days. Mornings and evenings after sunset can be chilly before 10am; around 45F (6C). Bring layers, not heavy jackets.

I am happy to discuss any aspect of your riding and photography kit with you. Please email me any time with questions or Schedule a time to chat using my Calendly scheduler.


Your personal bags will be carried by the support vehicle throughout the event. If traveling with your own bike; we strongly ask that your bikes be transported by bike bags (semi-rigid/soft). Please do not arrive to the event with rigid bike travel boxes. Support vehicles will not be able to stow large solid bike boxes as well as all luggage throughout the event.

Fitness & Training

You should be capable of riding comfortably up to 50miles/80km in a day over hilly terrain. Please arrive ready to ride. Don’t let us or yourself down. Train to ride.

Your Tour Leaders

Kevin Wenning


After many years of client work in studio & commercial projects Kevin discovered travel photography and never looked back. He founded Intentionally Lost to combine his passions for cycling & photography; and to experience the world with like-minded adventure travelers.

His projects now focus on photography as art and on educating anyone who picks up a camera to find their vision and voice. He consults with corporate clients to decorate their spaces with artworks from their own employees. He can approach any subject  from an editorial, commercial or artistic perspective; and he hates writing about himself in the third person.

ExperiencePlus! was the first US-based bicycle tour operator in Italy and is now one of the oldest and most well-respected bike touring companies based in the US.  As multi-lingual, bicultural and dual citizens (Italian-American), current owners - Monica and Maria Elena are thrilled to be leaders in their industry as they have elevated the profile of their company into the "next generation" of adventure and active travel companies.

Working with local companies is always important to me, and it's our good fortune to travel with one of the best bike touring companies in the world showing us around the country they call home.

I’m happy to talk with you in person to answer any questions. CLICK HERE to schedule a time to chat using my Calendly scheduler. I do calls via Skype or WhatsApp

Cancellation & Refund Policy

We understand that sometimes it’s necessary to change your plans. These policies apply if you need to cancel:

All cancellations are subject to a minimum of a $100 service charge. If you cancel and your spot is otherwise filled, you will be refunded the full amount you have paid (minus the $100 service charge). However if you cancel and your spot is not filled, the following applies:

  • 120 days or more: full refund minus $100 fee
  • 90 days or more: 50% refund
  • 60 days or more: 30% refund
  • Less than 60 days: no refund

Requests for refunds must be submitted in writing. There is no refund for travelers arriving late or unexpectedly leaving a trip.

How would you improve on spring in Tuscany Italy? Explore Val d\'Orcia on a cycling tour and photography workshop guided by professional photographers. 

#biketour #italy #cycling #traveltour #travelphotography