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.


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


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.


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.

Southern Tuscany Cycling Tour and Photography Workshop