This is the same tour that was originally scheduled to run in May 2020. We postponed a year to May 2021. Then after much consideration about the state of the world, travel in general, and life in Italy specifically; we determined that a fall 2021 date will provide the best experience for everyone. Our ground operations crew with Experience Plus has been amazing at communicating, rescheduling transportation, hotels and logistics, being flexible, and most importantly keeping their business running while keeping their staff and families safe.

Outside of the new dates; all of the tour details below are the same so if you downloaded a PDF with tour details in spring 2020, the locations, rides, and daily itineraries have not changed. I am finally looking forward to this tour with all of our original guests and the next two folks who are able to join us.

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 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 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.


    September 9 through 16, 2021

  • Departing from Chiusi Italy

    Arrival airports Florence (FLR) or Rome (FCO)

  • Small Group

    12 guest max

  • Road Cycling

    5 riding days: 155 miles || 31 miles avg per day

  • Photography

    10 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 on transfer days.

  • Pricing:

    $4,190 per person with double occupancy. +$550 for single occupancy (your own private room throughout).

Inquire About This Tour Before Making a Reservation Deposit

If you are ready to pay and join this tour you can make your deposit or final payment here.

Tour Highlights

  • San Quirico loop ride to Montepulciano - 30 mi (48 km)
  • San Quirico loop ride to Castelmuzio & Trequanda - 35 mi (56 km)
  • San Quirico to Montalcino - 23 mi (37 km)
  • Montalcino to Siena - 39 mi (62 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 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.

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, with slight potential for rain during this season. 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 and commercial projects I discovered travel photography and fell in love with the freedom to just have fun when I’m making photos. My projects now primarily focus on photography as art. I consult with corporate clients to decorate their spaces with artworks from their own employees.

I founded Intentionally Lost to combine passions for cycling & photography; and to experience the world with like-minded adventure travelers. I believe that you haven’t really traveled somewhere unless you get some of it on you.

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.

Inquire About This Tour Before Making a Reservation Deposit

If you are ready to pay and join this tour you can make your deposit or final payment here

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.

Southern Tuscany Cycling Tour and Photography Workshop