Photograph Tuscany with Diane Evans: September 25 - October 1, 2022

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Surrounded by sweeping vineyards, ancient olive groves and charming medieval villages, you’ll have the chance to practice your travel photography skills, as well as create memorable images as your magical Tuscan experience unfolds. With Diane’s expert guidance you’ll learn photography techniques to best capture the incredibly photogenic region, and its rich culture, while developing your own creative style along the way. Based at an Italian villa, each day brings memorable journeys with both 1:1 and group guidance with Diane. This is a not-to-be-missed opportunity!


  • Learn how to creatively frame your images for the most interesting and dynamic photos that truly reflect the beauty and culture around you
  • Become confident with creating photos in all kinds of light, knowing exactly which camera settings to use and when
  • Capture images of the mouth watering taste, smell, and beauty of the food and food preparation  – from olive grove to bruschetta lesson to plate.
  • Create a story with your images that not only expresses the spirit of your magical surroundings, but also of yourself
  • Understand how to approach the technical, practical, and creative aspects to create natural and unique portraits of people who you meet along the way
  • Develop your your own unique style of travel photography that truly expresses not just what you see but how it feels
  • Receive feedback from Diane on increasing the visual impact of your photographs throughout your time together

ABOUT Diane Evans

Diane is a photography mentor for creatively + culturally curious people who want to take unique photos of their global adventures. Through her simple yet thorough step-by-step methods, she shows adventurous souls how to turn down the volume of their inner critic, develop the confidence to be creative with their camera, and take travel photos that don’t just look stunning, but tell a stunning story.

In addition to her 1:1 coaching sessions and online courses, Diane’s extraordinary Tuscany workshop is designed to inspire you to move past technology overwhelm, connect with your creative side, and tell the story of your unique Tuscany adventures through amazing photos you’re proud to share.

You can learn more about Diane by visiting her website at PhotoFluent.


Day 1 ~ Sunday, September 25: Arrival Villa Poggio 

  • Highlights: Arrival from Rome Airport, orientation with Diane Evans, welcome aperitivo
  • Dinner

Upon your arrival at Rome Fiumicino Airport, our private drivers will transport you to the Italian countryside and historic Villa Poggio alle Trese. After some time to freshen up and recharge, you’ll enjoy a friendly welcome by your hosting team, followed by an overview of this amazing workshop with Diane Evans. Afterwards you’ll have some time to get to know your fellow trip participants, followed by a special aperitivo and welcome dinner prepared by your own private chef, Lorenza. 

Day 2 – Monday, September 26: Puscina Flower Farm 

  • Highlights: Puscina Flower Farm, tour & onsite mentoring with Diane, olive grove and vineyard walk, bruschetta-making lesson
  • Breakfast, lunch, dinner

This morning after breakfast, you’ll be heading to our friends’ family-run, organic flower farm with more than 500 varieties of flowers, situated in the heart of Tuscany’s wine country. Here you’ll enjoy a private tour and photography mentoring with Diane, as you capture the beauty of this Tuscan farm. Lunch follows, served up, rustic-style, under the ancient olive tree, and featuring specialties from the farm – including their own sheep cheeses, olive oil and wine.

In the afternoon, you’ll return to the villa for a bit of rest and relaxation before joining Diane for an on-site photography lesson along a countryside lane, flanked by vineyards and olive groves. Then it’s time for a walk through the olive grove to learn about the olive harvest, followed by an oh-so-fun fireside bruschetta lesson and olive oil tasting. Dinner follows, cooked alle brace (over coals).

Day 3 ~ Tuesday, September 27: Val d’Orcia, Pienza 

  • Highlights: Val d’Orcia, town of Pienza, photography mentoring with Diane, wine tasting
  • Breakfast, dinner

This morning, you’re off on an early start as our drivers will transport you on one of the most scenic drives in Tuscany, through the stunning Val d’Orcia and its classic Tuscan scenes of sheep farms, wheat fields and winding cypress-lined lanes. Here you’ll have the opportunity, with Diane’s expert guidance, to capture some gorgeous shots with the special morning light that is fabulously unique to Tuscany. Then it’s on to the lovely town of Pienza, and a break at a local coffee shop in the village, before exploring the village with local guide, Giulia – along with your camera. You’ll also enjoy lunch here on your own, at any one of the inviting trattorie.

In the afternoon, it’s back to the villa for some free time followed by instruction with Diane. Then it’s time to gather for a delightful wine tasting, with our own sommelier, Paola. Dinner this evening features some of Paola’s favorite wine selections.

Day 4 ~ Wednesday, September 28: Ficulle

  • Highlights: Walking tour of Ficulle, photography with Diane, ceramics demo
  • Breakfast, lunch, dinner

This morning, after a delicious breakfast, you’ll be heading to the Umbrian village of Ficulle, with its breathtaking views over the hills of Tuscany. Here you’ll enjoy a walking tour with plenty of opportunities to capture shots of panoramic views and winding, medieval alleyways. Then it’s time to make a stop at our friend, Fabio’s, fascinating ceramic shop, where you’re in for a treat as he demonstrates for you how Ficulle’s rustic cookware has been hand thrown for centuries. Afterwards, you’re invited for lunch in Fabio’s cozy trattoria, in his former wine cantina, where you’ll enjoy typical local dishes served up in Fabio’s ceramic cookware. What a fabulous food photography opportunity!

In the afternoon, it’s back to the villa for some free time to relax poolside or take a walk before meeting up with Diane for this afternoon’s session of instruction. This evening you’ll enjoy aperitivo, together with your fellow travelers, followed by a delicious dinner prepared by chef Lorenza.

Day 5 ~ Thursday, September 29: Monteleone and Città della Pieve

  • Highlights: Truffle hunt and truffle tasting, walking tour Città della Pieve, pizza night
  • Breakfast, lunch, dinner

This morning after breakfast, it’s off to meet up with brothers, Andrea and Michele – and their amazing truffle dog – for an invigorating truffle hunt in the scenic forest that winds down the medieval hill town of Monteleone – with its stunning views across the heart of Tuscany. The photography opportunities are endless! Then it’s back to the brothers’ cozy restaurant for an oh-so-delicious truffle tasting and lunch, featuring local specialties.

Afterwards, it’s back to the villa for some time to relax and refresh, and perhaps take in some tips from Diane. Then, in late afternoon, our drivers will be transporting you to the town of Città della Pieve where you’ll enjoy a private walking tour, as you get to know this beautifully preserved historic village – including a stop in the cathedral, housing masterpieces by Renaissance artist, Perugino. You’ll also have time on your own, to explore and photograph with Diane, before heading to a private location for sunset shots and aperitivo. Afterwards, it’s off to a local pizzeria for wood-fired pizza.

Day 6 ~ Friday, September 30: San Casciano dei Bagni

  • Highlights: Roman baths and archeological site, Fonteverde Thermal Spa
  • Breakfast, lunch, dinner

This morning after breakfast, our drivers will transport you to the Tuscany village of San Casciano dei Bagni, situated on a panoramic hill top known for its hot springs. These luxurious waters have been used for thousands of years for their vast wellness benefits, and you’ll enjoy an astounding, private tour an archeological park where you’ll see the remains of Roman baths and an incredibly preserved temple.

Afterwards, it’s up to the main piazza of the town for a delicious lunch at our friend, Daniela’s, charming restaurant, before heading to elegant Fonteverde Spa for a soak in the mineral-rich, thermally heated pools – such a treat! Then it’s back to the villa for a special aperitivo and farewell dinner, prepared by our own chef Lorenza.

Day 7 ~ Saturday, October 1: Departure

Early morning departure for Rome Fiumicino Airport 

VENUE & ACCOMMODATIONS ~ Villa Poggio alle Trese

Your accommodations are beautiful Poggio alle Trese, a 17th century villa, nestled along the border of Tuscany and Umbria, near the town of Chiusi (Tuscany). The villa boasts a number of living rooms, sweeping terraces for dining or lounging, a swimming pool, an elegant breakfast room and a grand dining hall. Sleeping rooms are furnished with family antiques and offer either an ensuite bathroom or shared bathroom (max 2 guests per bathroom).  View photos of Villa Poggio alle Trese here.


  •  6 night stay at Villa Poggio alle Trese, reserved exclusively for your group!
  • Private transportation to/from Rome Fiumicino Airport on arrival and departure days
  • Private transportation service to/from all towns and sites included in the itinerary
  • All breakfasts
  • 5 lunches
  • All delectable dinners featuring regional specialties and accompanied by regional wines
  • Private, guided tours
  • Truffle hunting excursion
  • Wine tasting
  • Access to a private vineyard
  • Tour of Roman baths archeological site
  • Pizza night!
  • Entrance to Fonteverde Spa and thermal pools
  • Daily in-depth lessons, onsite mentoring, and photo feedback with professional photographer, Diane Evans
  • Instructions on what to bring and how to prepare for the retreat (to be supplied before the trip)


  • Camera Settings Toolkit to help you become more comfortable with your camera before you arrive (supplied before the trip)
  • $100 off Diane’s online Create Amazing Travel Photo group learning program (so your photography skills will be sharp and Ready for Tuscany!)
  • $50 off a 1:1 Coaching Session with Diane
  • A live, recorded, online critique and photo editing session following the retreat

Not included: Airfare, ground or water transportation outside of that listed in the trip itinerary, alcoholic drinks, wines or meals ordered “on your own”, gratuities for drivers and villa staff.

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up – like an unscheduled closing at a site or restaurant. If that happens, which it rarely does, we improvise to include something equally as wonderful and interesting. The quality of your experience is never at risk, as our team is committed to excellence, along with our vast connections of local Italians.

DATES & PRICE:  7 Days/6 Nights

  • Dates: September 25 – October 1, 2022
  • Trip Price:
    • $3,980 USD per person, Single Occupancy w/Ensuite Bath
    • $3,780 USD per person, Double Occupancy w/Ensuite Bath
  • $500 deposit is required to reserve your space on this trip, followed by 10 monthly trip payments (for a limited time)
  • Please see our Terms and Cancellation Policy.
  • Please see our FAQs and Covid-19 Updates.