“Experience Tuscany’s Val d’Orcia, where timeless landscapes and village life unfold in the golden light of autumn.”
DATES: – 27th October – 2nd November 2026: Tuscany (6 nights)
NOTE: We have an optional extension trip to Cinque Terre (3 nights) – 2nd November – 5th November 2026: Cinque Terre (3 nights)
LENGTH: 7 days/6 nights
COST: $5,495, single supplement available for additional $650 (a $300 discount will be applied if also booking Cinque Terre Extension)
- Initial Deposit is $2500
GROUP SIZE: 8 photographers (2 spots remaining)
COMPANION PROGRAM: This trip also has a Companion Program for the non-photographer. Pricing and details to follow
LEADERS: Buddy Eleazer, Leonardo Papèra
SKILL LEVEL: All skill levels, this is that rare location where high-quality cameras and iPhone will both deliver amazing photos and memories. Our focus will be improving your compositional skills during this workshop.
DIFFICULTY OF TERRAIN: These are old villages, expect some short walks on uneven cobblestone surfaces and some short walks in fields to get into position for shots.
Photographing in Tuscany’s Val d’Orcia in late October feels like stepping into a landscape suspended in time. Golden autumn light washes across rolling hills, where winding cypress-lined roads lead the eye toward centuries-old farmhouses perched on gentle rises. Morning fog hangs low in the valleys, softening the horizon and adding a dreamlike quality that makes each sunrise feel eternal. Vineyards, olive groves, and winding rows of cypress trees shape a countryside that has inspired artists for centuries.
The timeless beauty of this UNESCO World Heritage region is found not only in its sweeping vistas, but also in the intimate charm of its hilltop towns—Pienza, Montepulciano, and Montalcino—where stone walls, weathered piazzas, and quiet lanes speak of lives unchanged for generations. Just as captivating are the region’s hilltop towns—Pienza, Montepulciano, Montalcino—where stone streets and sunlit piazzas reflect a way of life that feels untouched by the rush of modern time.
Together, the landscapes and villages create an atmosphere that is both timeless and deeply photographic, offering endless opportunities to capture Tuscany’s enduring beauty. Every moment here invites a photograph that transcends the present, capturing both the grandeur of the Tuscan countryside and the enduring spirit of its villages.
In addition to being a fantastic time of the year in Italy, it is also a time of the year when the casual tourists have left, making this a much more relaxing trip during a season of extremely comfortable weather.
Please note that while we love the Val D’Orcia region of Italy, we think there is more that you MUST SEE during your trip. Specifically, we have an EXTENSION WORKSHOP TO NEARBY CINQUE TERRE to photo the coastline of Italy and the small villages that line it.
COMPANION PROGRAM FOR THE NON-PHOTOGRAPHERS
Please note that this trip also has a Companion Plan for the non-photographer. With many photo workshops, it is challenging to add a companion program that isn’t just an afterthought but rather a solid and exciting offering. THIS IS NOT THE CASE WITH ITALY.
This part of Tuscany is beautiful with too many options to leave a friend or partner behind. Companions can enjoy a parallel journey of flavors and culture—sampling world-class wines and olive oils, learning Tuscan traditions in a hands-on cooking class, visiting a pecorino cheese producer, and exploring the charm of local villages.
Whether behind the camera or immersed in the tastes and rhythms of Tuscan life, Val d’Orcia offers an experience where past and present meet in perfect harmony, leaving memories as lasting as the landscapes themselves.
At this time, pricing for the companion plan is still to be determined. Contact us for more details.
PHOTO WORKSHOP ITINERARY SUMMARY:
We are based for the whole week in Pienza, which some consider the prettiest out of all the hilltop towns around the rolling hills. This area, called Val d’Orcia, lies in the southern part of Tuscany. Some of the neighboring towns are Montepulciano, Montalcino, San Quirico d’Orcia; during the tour though, we will also visit San Gimignano and Siena!
Truth is that we never run two identical workshops – due to the weather, due to the light, due to the length of the days at any given time of the year and many other variables that come into play when dealing with outdoor photography.
Take this general itinerary for what it is – and by any means don’t think that we’ll stick to it at all times!
DAY 1 – ARRIVAL
Pick-up: 10/10:30AM
Time to start our workshop together! On our first day, we will pick you up at the Florence (or Pisa) airport around mid-morning, so that we can start our drive to Pienza (our final destination, 1h45m drive from Florence) straight away.
Lunch: 12:30PM
As soon as we arrive in the beautiful Val d’Orcia, we’ll immerse ourselves into the rolling hills and we will have a lovely lunch in the countryside to set the right mood! You will have a first taste of Tuscany’s delicious cuisine.
Hotel Check-in & Afternoon Break: approx. 2:30/4:30PM
After our tasty lunch together, we’ll drive back to Pienza – the place where we’ll be staying for the whole workshop – to check in into your hotel and take a breath before hitting the road again.
Sunset Session: 5/8PM (depending on sunset time)
Our first official photography session together! Since it’s our first, we’ll have a longer session so that your workshop leader can assess your skills and give you the necessary notions to capture the golden light in the best possible way given the weather conditions of that day. The location we will probably visit is called “The Cipressi of San Quirico d’Orcia”, a classic of the area that we like to call “The Photographer’s Playground” because of the endless perspectives you can get there! See a few examples in the pictures below.
Dinner: 8:30PM
It’s been a long day: finally, we will have the chance to sit down and have a warm meal with some fine wine to end it in the best way!
DAY 2 – BELVEDERE, MONTEPULCIANO & BACCOLENO
Sunrise Session: 5:30/8AM (depending on sunrise time)
An early wakeup call waits for us: we will go out when the twilight glow is just starting to appear, so that by the blue hour we will already be set up and ready to shoot! During our first sunrise session we’ll visit the iconic “Podere Belvedere”, one of the places that better represents the landscape of Tuscany: a country house, endless rolling hills and cypress trees all over the scene.
Breakfast & Morning Break: 8/10:30AM
By the time we’ll be back at the hotel, I’m sure that you will be very much looking forward to having a nice breakfast and a bit of a break to gain some energies back.
Visit and lunch to Montepulciano: 10:30AM/2:30PM
Time to hit the road again and visit a different town out of all the marvelous ones in the area: today we’ll visit Montepulciano, famous for the Vino Nobile di Montepulciano (noble wine of Montepulciano) and obviously we won’t miss having a delicious meal in a winery!
Afternoon Break/Editing: 2:30/5:30PM
Depending on how tired we are, we might either take another break or do some post-production on the shots taken in the past couple sessions. Or maybe a mix of both!
Sunset Session: 5:30/8PM (depending on sunset time)
Another day, another sunset: at this “round” we will visit the infamous Podere Baccoleno, another popular house lost in the countryside a bit north from Pienza. This is actually one of the very few locations that it’s not in the Val d’Orcia but in a different area called Crete Senesi. That winding road is definitely an unmissable view of Tuscany!
Dinner: 8:30PM
Another long day has passed, nothing better than sitting down and having a delicious meal in the fabulous small city center of Pienza to wrap things up.
DAY 3 – COVILI, MONTALCINO & GLADIATOR HOUSE
Sunrise Session: 5:30/8AM (depending on sunrise time)
Another day, another early wakeup call! During our second sunrise session we’ll visit Poggio Covili, a lovely house on top of a hill with its characteristic straight cypress trees road: getting the low fog here with just the house peeking out is every photographer’s dream when visiting Tuscany.
Breakfast & Morning Break: 8/10:30AM
By the time we’ll be back at the hotel, I’m sure that you will be very much looking forward to having a nice breakfast and a bit of a break to gain some energies back.
Visit and Lunch to Montalcino: 10:30AM/2:30PM
Time to hit the road again and visit a different town out of all the marvelous ones in the area: today we’ll visit Montalcino, famous (yep, again) for the Brunello di Montalcino, another type of wine that they produce nearby.
Afternoon Break/Editing: 2:30/5:30PM
Depending on how tired we are, we might either take another break or do some post-production on the shots taken in the past couple sessions. Or maybe a mix of both!
Sunset Session: 5:30/8PM (depending on sunset time)
On our third sunset together, we’ll visit Leo’s favorite location of the entire valley: the so-called “Gladiator House”, due to the fact that the originally shot a scene of “The Gladiator” movie of Ridley Scott there.
Dinner: 8:30PM
Another long day has passed, nothing better than sitting down and having a delicious meal in the fabulous small city center of Pienza to wrap things up.
DAY 4 – VITALETA, SAN GIMIGNANO & I CIPRESSINI
Sunrise Session: 5:30/8AM (depending on sunrise time)
On our third sunrise we will cover one of the most unique spots of the area: the incredibly photogenic Chapel of Vitaleta – a small church built on top of a hill in the countryside.
Breakfast & Morning Break: 8/10:30AM
By the time we’ll be back at the hotel, I’m sure that you will be very much looking forward to having a nice breakfast and a bit of a break to gain some energies back.
Visit and Lunch in San Gimignano: 10:00AM/3:00PM
A longer drive waits for us today: we’ll pay a visit to San Gimignano, 1h20m away from Pienza. One of the most incredible Tuscany towns from an architecture perspective, with its tall towers seen from miles away. Definitely a place worth the longer ride: they also have one of the best gelatos in the world – in case you are an ice cream lover!
Afternoon Break/Editing: 3:00/5:30PM
Depending on how tired we are, we might either take another break or do some post-production on the shots taken in the past couple sessions. Or maybe a mix of both!
Sunset Session: 5:30/8PM (depending on sunset time)
Tonight, we’ll capture another pretty country house called “I Cipressini”, just a minute drive out from Pienza. Another classic view of the area!
Dinner: 8:30PM
Another long day has passed, nothing better than sitting down and having a delicious meal in the fabulous small city center of Pienza to wrap things up.
DAY 5 – CORSANO, SIENA & MONTERONI D’ARBIA
Sunrise Session: 5:30/8AM (depending on sunrise time)
One of the many “pros” of opting for the 6 nights/7 days workshop is that you will get the chance to shoot not just the iconic and popular photography spots – but also the lesser known ones, the hidden gems, the ones that we personally found after years of experience in the area. We will dedicate this morning (and possibly also the next one) to some of those un-named locations – where you’ll be able to get some more personal and more particular shots.
Breakfast & Morning Break: 8/10:30AM
By the time we’ll be back at the hotel, I’m sure that you will be very much looking forward to having a nice breakfast and a bit of a break to gain some energies back.
Visit and lunch in Siena: 10:00AM/3:00PM
Siena is the capital (the province, technically speaking) of the whole rolling hills area – and by far the biggest city around here. Piazza del Campo, the Duomo and the gorgeous street views are just some of the things you’ll be able to see and shoot there!
Afternoon Break/Editing: 3:00/5:30PM
Depending on how tired we are, we might either take another break or do some post-production on the shots taken in the past couple sessions. Or maybe a mix of both!
Sunset Session: 5:30/8PM (depending on sunset time)
Tonight, we’ll drive up north again in the area around Monteroni d’Arbia (just south of Siena) to shoot some other beautiful rolling hills, lonely trees and country houses at sunset.
Dinner: 8:30PM
Another long day has passed, nothing better than sitting down and having a delicious meal in the fabulous small city centre of Pienza to wrap things up.
DAY 6 – TAVERNE D’ARBIA, BAGNO VIGNONI & VITALETA
Sunrise Session: 5:30/8AM (depending on sunrise time)
As we already mentioned when describing the previous day’s sunrise, we will visit some other less known locations far from the main ones (well, not really that far!): in case the weather has been bad in the previous days or you didn’t get the shots you wanted in a specific location, we might stop there again too!
Breakfast & Morning Break: 8/10:30AM
By the time we’ll be back at the hotel, I’m sure that you will be very much looking forward to having a nice breakfast and a bit of a break to gain some energies back.
Visit and Lunch in San Quirico d’Orcia & Bagno Vignoni: 10:30AM/2:00PM
No longer drives today: we will stay closer to Pienza and visit a true gem of the valley: Bagno Vignoni, a tiny town famous for its hot springs!
Afternoon Break/Editing: 2:00/5:30PM
At this point of the workshop – you already had a few editing sessions with your instructor, but today as it’s your last full day here we’ll do one last post-production session to select some of the best shots you’ve taken throughout the workshop and possibly to give you some helpful critique on them.
Sunset Session: 5:30/8PM (depending on sunset time)
Our last sunset together: time flies! Depending on the conditions, we might visit the Chapel of Vitaleta (yes, the one we shot from far away a couple mornings back) and shoot it from up close, as you can see from the images down here!
Dinner: 8:30PM
Your last full day of the workshop is just finished, time to celebrate the (hopefully) amazing time we had together in front of some pasta and wine!
DAY 7 – DEPARTURE
Sunrise Session: 5:30/8AM (depending on sunrise time)
We are mentioning one last sunrise in the itinerary, even in our very last day: since you’ll probably have to pack things up and get ready for your trip back home, you are 100% free to decide whether you’d like to go for it or maybe just sleep in and get ready a bit later. Our recommendation is to see how the weather looks like and then decide.
Breakfast & Check-out: 8:00/9:30AM
Time to pack everything up, get some “juice” for the trip back home and start our drive back towards the airport!
Drop-off: 11:00AM/12:00PM
We hope most of you will be joining us for our EXTENSION TRIP TO CINQUE TERRE. For those that do not wish to join further, after a 1h45m drive back to Florence, it’s unfortunately time to say goodbye: your instructor will help you take the luggage into the building and wish you a safe flight back home!
COMPANION PLAN
For those traveling as companions, Val d’Orcia offers a rich tapestry of experiences beyond the camera lens. Days can be spent savoring the flavors of the region through wine tastings at renowned Tuscan estates, sampling the area’s celebrated olive oils, and joining in a hands-on cooking class that brings the traditions of Italian cuisine to life. A visit to a local pecorino cheese producer reveals the artistry behind one of Tuscany’s most beloved specialties, while guided explorations of the hill towns—Pienza, Montepulciano, Montalcino, and others—invite travelers to wander cobbled streets, explore historic piazzas, and soak in the timeless atmosphere of village life. This companion program balances food, culture, and discovery, ensuring a journey as rewarding and memorable as the photographic adventure itself.
WHAT IS INCLUDED:
- Lodging – 6 nights in Tuscany (Val d’Orcia area) nicely positioned relatively to our photo spots
- Airport Transfers – We will pick you up at the airport and drop you back off at the airport
- Meals – Breakfast included
- All Transportation – All transportation included while in Italy via 2 9-seater vans with guides/drivers. No need for a rental vehicle
- Entrance Fees – Misc. entrance for the shooting locations
WHAT IS NOT INCLUDED:
- Gratuities – Gratuities are not included
- Meals –
- Lunch – During the trip, we will stop at local restaurants for lunch, which is not included in the overall cost
- Dinner – We can always have our meals together, but everyone will pay for its own. Guests will still be able to enjoy the typical Tuscan food and we will always take everyone to our favorite restaurants in the area. We have chosen to exclude dinners as every guest has different preferences.
- Alcohol – Alcohol is not included
- Transportation from your home to Florence, Italy
- Travel Insurance is highly recommended
Cost for Tuscany is $5,495, single supplement available for additional $650
- Initial Deposit is $1650
Cancellation Policy for This Trip:
- Up until 6 months before: only the deposit is non-refundable
- 3 months before the tour we ask for the outstanding balance
- From 3 months before till the departure date: no refund is possible unless the guests can find a replacement for their spot, in which case we can return the full amount to them at any time.
To Book your space, please contact Buddy Eleazer at buddy.eleazer@gmail for information on sending your deposit.
As the days in Val d’Orcia draw to a close, the region leaves an impression that feels as lasting as the landscapes themselves. The gentle light of late October, the stillness of mist-filled mornings, and the quiet rhythm of life in the hill towns linger in memory long after the final photograph is taken. Each image—whether of sweeping hills glowing at sunset or of narrow cobbled streets worn smooth by centuries—becomes more than a record of place; it becomes a reminder of Tuscany’s timeless spirit. To photograph here is not only to capture beauty, but to step briefly into a world where past and present exist in perfect harmony.
