We will ride and photograph in the heart of Tuscany on a tour that begins in San Quirico in the heart of beautiful Val d’Orcia. This region is recognized by UNESCO as a “World Heritage Landscape”. Over eight days we visit and photograph Pienza, Montalcino, and Siena. We end the tour in the photographer bucket list region of Cinque Terre. Prepare to explore the picture postcard landscapes of Tuscany and Cinque Terre, 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 tourThis 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 five cycling days. Three days have out and back distance options and two days are transfers to a new location. There is no mountain riding with sustained climbs but you can expect a lot of rolling hills and there are mountains to ride if you really want an extra challenge. Please train and come prepared to ride.
This tour is non-cyclist friendly
Non riding partners can relax or explore on their own during the days in San Quirico, Montalcino, Siena and Cinque Terre National Park. They will have comfy air conditioned transportation on the two transfer days to a new location.
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 CHIUSI and shuttle to San Quirico
TEACHING PHOTO LOCATIONS: Capella di Vitaleta, Pienza Cityscape
Chiusi provides the most direct train routes into the heart of Tuscany from either Rome or Florence. We will meet at Chiusi Chianciano train station and then shuttle to San Quirico where we will stay the first three nights. We’ll fit bikes and do a test ride then visit our first location for photos of the landscape around Pienza and we will photograph Vitaleta Chapel during sunset before returning to San Quirico for dinner together.
Day 2 - ride SAN QUIRICO TO MONTEPULCIANO, MONTICCHIELLO, BAGNO VIGNONI - 35 miles (56 km)
TEACHING PHOTO LOCATIONS: Pienza, Monticchiello, Podere Terrapille, Poggio Covili
Our loop ride today takes us through the wine village of Montepulciano and into the heart of the Orcia Valley. We will ride and photograph on the cypress road lined road at Monticchiello - it’s a good lookin’ curvy road that makes for good photos. This evening we shuttle thirty minutes from our hotel to photograph sunset on the rolling hills below Pienza and the cypres
Day 3 - ride THROUGH MEDIEVAL VILLAGES OF CASTELMUZIO AND TREQUANDA - 35 miles (56 km)
TEACHING PHOTO LOCATIONS: Bagno Vignoni, Sunset at Circle of Cypress
We have a loop ride north today through the authentic medieval Tuscan villages of Castelmuzio and Trequanda. The city square in Trequanda is an ideal mid morning coffee and cappuccino stop. Enjoy the afternoon in San Quirico on your own or shuttle 15 minutes to Bagno Vignoni to photograph this unique village; or enjoy the natural hot springs. We then drive to the Circle of Cypress for our sunset location at this landmark destination for photographers - a must visit photo location in Val d’Orcia.
Day 4 - RIDE SAN QUIRICO to SANT'ANTIMO ABBEY - 23 MILES (37km)
TEACHING PHOTO LOCATIONS: Podere Baccoleno, Siena streets, lifestyle and cityscapes
Wake early and walk 10 minutes from the hotel to photograph an iconic Tuscan landscape at Podere Belvedere, or take the morning for yourself. Ride 11 miles/18 km from San Quirico through vineyards lining the Asso River Valley to Montalcino where we will be staying this evening. Relax here for the afternoon or ride out and back to our afternoon photo location at Sant’Antimo Abbey. We ride back from Sant’Antimo to Montalcino, and settle into the hotel before enjoying a winery tour and sunset photos from the city walls overlooking the Orcia Valley. This town is famous for producing one of Italy’s premier wines, Brunello di Montalcino.
Day 5 - Ride MONTALCINO TO SIENA - 39 miles (62 km)
TEACHING PHOTO LOCATIONS: Agrotourismo Baccoleno, Sant' Antimo Abbey, Streets of Montalcino
We ride through lush green fields and forests of the Orcia Valley as we leave Montalcino and pedal north to Siena. We’ll pass by the historic monastery of Monte Oliveto Maggiore and stop for photos if you wish. We stop at Podere Baccoleno directly on our route to photograph another famous Tuscan landscape en route to our location for the next two nights in Siena. You’ll be transported back in time as soon as you enter the city walls. Siena is our best location for Tuscan streets, lifestyle and cityscape photos. We spend our afternoon and evening photographing on the streets, towers and walls of Siena.
Day 6 - Ride SIENA TO CASTLE BROLIO AND BACK - 32 miles (52 km)
TEACHING PHOTO LOCATIONS: Castle Brolio, Streets of Siena
We take a loop ride today 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. We will have your photography gear with us and spend time for an organized photography session walking around the castle together. We’ll be back to Siena in time for a final photo review and editing session and sunset photos around town.
Day 7 - no ride this day
TEACHING PHOTO LOCATIONS: Riomaggiore, Manarola, Vernazza in Cinque Terre Park
We leave Siena after breakfast and shuttle 3 hours to Cinque Terre Park. We will start the day at Riomaggiore; photograph there and then hike the trails of Cinque Terre Park to Manarola. After spending the afternoon at these picturesque seaside fishing villages we take a short train up to Vernazza to photograph sunset. We have a final short train ride (10 minutes) to Monterosso where our luggage is waiting. Settle into hotel rooms and then have dinner together to wrap up our trip.
Day 8 - Tour ends
Breakfast will be served and then we say our goodbyes and exchange info to share photos after we return home. Transfer to Pisa where you can visit the famous Tower of Pisa and Miracle Square, or continue on your travels or connect to a train to Rome or Florence. You can also choose to stay in Monterosso and explore more of Cinque Terre Park.
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
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
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
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.