photography holidays in italy Tuscany Holiday -

Since 2015, we’ve hosted unforgettable photography holidays in Italy. Join our annual Cortona retreats— where returning guests & new friends capture the timeless beauty of Tuscany.

Unleash your creativity in the rolling hills of Tuscany, where every meal, vineyard, and golden sunset provides inspiration for your photography. Explore ancient hill towns, sun-drenched olive groves, and charming streets on our photography holidays in Italy, capturing moments that tell Italy’s timeless story.

Over five unforgettable days in Cortona, immerse yourself in La Dolce Vita—refining your photographic skills, discovering breathtaking landscapes, enjoying delicious food and wine, and sharing laughter with fellow enthusiasts. Return home with a stunning portfolio of images and memories to treasure forever.

Our Photography holidays in Italy are priced economically, as Italy is a passion for Lillie and she sees this as an opportunity to retain this delightful region in her life.

Photography holidays in Italy - photographer silhouette

Photography holidays in Italy - vineyard dinner

Photography holidays in Italy - Photographer in Sunflowers

Photography holidays in Italy - high view of flag throwers

Photography holidays in Italy - photographers in sun hats

Photography holidays in Italy - Polenta festival

photography holidays in Italy - vineyard view

Photography holidays in Italy - Hotel Italia bedroom

Photography holidays in Italy - Hotel Italia entrance

The Accommodation

Location, location, location… Hotel Italia has all three!

Stay four nights in this beautifully restored 15th-century Palazzo, perfectly situated in the heart of Cortona—just steps from the charming Piazza della Repubblica. Enjoy hearty breakfasts made from locally sourced produce on the panoramic terrace, where breathtaking views stretch across the Val di Chiana to Lago Trasimeno, Montepulciano, and the Senesi hills.

With its elegant rooms, modern comforts, and unbeatable setting, Hotel Italia offers the ideal base for photography holidays in Italy—combining inspiring vistas, exceptional cuisine, and authentic Tuscan charm for an unforgettable experience.

View Available Dates and Book

Scheduled pickup and drop off from Perugia airport on holiday start day (Cortona is easily accessible from Rome and Pisa airports via train and we can provide adhoc pickup from Cortona station on holiday start day). Unscheduled airport and station transfers can be organised at an extra cost.
All scheduled journeys throughout our photography holidays in Italy (photography excursions and other trips)
4 nights single room occupancy with private bathroom at Hotel Italia or Hotel San Luca in Cortona (doubles available).
All breakfasts including morning coffee at the hotel.
3 evening dinners + wine.
4 lunches + wine (including 2 packed lunches).
Wine tasting evening.
All photography tuition (including morning workshops, other tuitorials, tuition when on excursion)
A professional guided historic tour of Cortona, Perugia or Assisi town centre and museum.

Itinerary for LSP Photography Holiday, Cortona 2023

Day 1 – Thursday: Arrivals and Welcome – Ciao Amici!!

Lillie, Charlie or a taxi will meet guests at Perugia Airport or alternatively at the Cortona train station if flying into Rome or Pisa.
12:30 Prosecco and seated lunch at Cacio Brillo in Piazza Signorelli and an introduction to the holiday by Lillie.
Leisurely stroll into Cortona and/or through the surrounding parks and olive groves. Keep cameras at the ready for those impromptu shots, and Lillie will be available for assistance and guidance.
Surprise visit to a wonderful private property with 180 degree views down onto Cortona and Valdicchiana
7:30pm Pre-dinner Prosecco on terrace at the superb La Loggetta restaurant https://www.laloggetta.com/en/ overlooking Piazza della Repubblica. An informal presentation by Lillie on photography and the more specific delights of photographing Cortona and the surrounding area.
Dinner on the terrace at La Loggetta overlooking the ancient Piazza and town hall.
Perhaps an after-dinner digestivo in one of the many café bars!

Day 2 – Friday: Under the Tuscan Sun Landscapes

First class begins after breakfast, meet Charlie & Lillie at 9am in the Hotel Italia lobby
Walk or ride in the minibus up to Torreone Bar for big views of the two valleys surrounding Cortona
Landscape Lesson, accompanied by coffee & pastries at Torreone Bar.
Stroll down the Localita Strada Torreone & pass the famous author Francis Maye’s house
Capture the views of Valecchie valley using aperture, perspective and composition creatively
Finish the walk in the ornate public gardens for further valley views framed by the Tuscan pines
Enjoy a typical wholesome Italian lunch down in the valley at Bar Pergo with a glass of the local Vino Novello… or perhaps two!
Go for an after lunch walk through picturesque Piazzano to capture breathtaking views of the Umbrian and Tuscan hills
Return to Cortona for a well-earned rest
30pm Meet Charlie & Lillie in Hotel lobby
Take the minibus to a Wine Tasting and Sunset photos at Palazzo Vecchio (https://www.vinonobile.it/en/ ) in the rolling hills of Be prepared to capture the golden hour views of Cortona high on the hill through the grapes and vines
After the sun has set, a splendid well-deserved Tuscan Dinner at Palazzo Vecchio vineyard

Day 3 – Saturday: The Hustle & Bustle of the Arezzo Antique Market

9am meet in the hotel foyer for a photography lesson in the Hotel presentation room
A short minibus ride to Camucia for a Pastries, cappuccinos with a talk and demonstration provided by the wonderful award-winning baristas at Café Vanelli. https://vannelli.coffee/
Arrive in Arezzo and capture the amazing antiques market that takes over the ancient historic centre.
Lunch at La Vigna Trattoria http://www.trattorialavigna.it/ . A 3^rd generation family restaurant cooking local produce in mouthwatering recipes to a standard that Nonna would happily give her stamp of approval!
Walk up through the winding and historic roads of Arezzo, capturing the hustle and bustle of the antiques market, a dream for all street photographers!
**Tonight gives you the choice of making your own plans for dinner, Lillie and Charlie are happy to make recommendations and help with the bookings.

Day 4 – Sunday: Olives, Sagra & fun!

Meet at 9am for lesson in the hotel presentation room
After the lesson, we head down to the village of Montecchio to capture the olive groves, Tuscan landscapes and hill-top castles.
Surprise lunch & Sagra – event photographers get those cameras ready. A local event that we will have unhindered photography access, great fun and superb local food
Return to Cortona from the splendid lunch adventure, for an afternoon critique of your holiday images
Meet Lillie in hotel presentation room with your SD cards or laptops for a fun afternoon, viewing & discussing one another’s favourite photos. Wine and snacks on hand J
30pm Finale: a splendid dinner at a Cortonese favourite, Dardano’s. Food, vino & ‘green sheeeet’ drink, that’s tastes a whole lot better than it sounds!
Lillie will present special ‘tongue in cheek’ awards

Day 5 – Sunrise, Cappucinos and Arrivederci!

Sunrise shoot @6am for those who are up for it.
Meet Lillie in hotel lobby at 6am for a short walk to Piazza Gariibaldi to capture the light as it spreads across the Valdichiana and Lago Trasimeno
Early breakfast and stroll into Piazza della Republica for some final shots and un caffé in Bar Signorelli.
Return to Hotel Italia to pack before the short drive to the airport or station.

Arrivederci, amici!

This itinerary is representative of what to expect: However, this itinerary is subject to change depending on availability, unforeseen circumstances, weather conditions and unexpected delays.

Our photography holidays in italy are priced with value in mind, as Italy is a passion for Lillie and she sees this as an opportunity to retain this delightful region in her life.
The 4 day vacation will be priced at £1,650 ($2200) based on 1 person in a double room (not sharing) inclusive of workshops, meals and tours. Flights not included.
2 people sharing a double room and both attending the photography courses will be £1,450 ($1950) per person.

Other configurations include sharing without attending the photography course Italy and family accommodation. These can be priced on request.

From the UK:

Ryanair fly from Stansted to Perugia daily in the summer. Multiple airlines including Ryanair, Easyjet, BA, Wizz and Jet 2 fly from different UK airports daily into Pisa, Rome and Florence

From the US:

There are direct flights from most major US cities to Rome daily, onward flight connections can be made to Perugia. Regular trains run from Rome to Cortona. We can provide pickups from Perugia Airport and Cortona/Terontola train stations. Please contact us for any queries.

It’s no surprise that many guests choose to extend their stay after one of our unforgettable photography holidays in Italy. Cortona and the surrounding Tuscan countryside offer endless opportunities to relax, explore, and soak up authentic Italian charm. Spend extra days discovering Florence, Siena, or Perugia, strolling through medieval hilltop villages, or tasting world-class wines in the region’s celebrated vineyards. If you’re travelling from the US, a longer vacation allows you to fully embrace La Dolce Vita. Our team can assist with additional accommodation, personalized itineraries, and insider recommendations to ensure your extended stay in Tuscany is seamless, enriching, and truly unforgettable.

Book Now

Room Setup	Price	Includes
Single (double room, not sharing)	£1,650 ($2,200)	Contact us for details
Shared (2 people in double room, both attending photography)	£2,900 ($3,860)	Contact us for details
Other configurations (e.g., sharing without attending course, family accommodation)	On request	Contact us for details

Dates	Availability
Tuscany Oct 2nd – Oct 6th 2026 (Single)	Fully Booked	Fully Booked
Tuscany Oct 2nd – Oct 6th 2026 (Shared)	Fully Booked	Fully Booked
Tuscany Oct 9th – Oct 13th 2026 (Single)	Fully Booked	Fully Booked
Tuscany Oct 9th – Oct 13th 2026 (Shared)	Fully Booked	Fully Booked
Tuscany Oct 16th – Oct 20th 2026 (Single)	3 Places Available	Book Now
Tuscany Oct 16th – Oct 20th 2026 (Shared)	3 Places Available	Book Now

Lillie partners with her good friend Charlie Mitford for our photography holidays in Italy. Charlie lived in Cortona for 20 years, she is an accomplished event and vacation planner with enviable local connections and a deep love for Tuscany.

The historic Tuscan town of Cortona, perched on the Apennine foothills, offers breathtaking views across the Val di Chiana to Montepulciano—a must-see for any traveller in Italy. Its Etruscan origins remain visible in the ancient city walls built 2,000 years ago from Pietra Serena stone. Stroll medieval streets to discover charming Trattorias, enjoy the famous Chianina steak, and pair it with divine Cortonese wines.

Guests can also document local Summer and Autumn festivals, including the Cortona Medieval Festival in May and the Pierle Sagra della Castagna & Fratticiolla Country Festival in October. Notably, October’s sunshine consistently outshines May, making it a perfect time for photography.

Meet Your Tutor – Lillie

With over a decade of teaching experience, Lillie has led photography courses for prestigious institutions including The Photographers’ Gallery, The Nikon School, and her own successful photography tuition business. Holding a degree in Photojournalism and extensive experience as a professional photographer, Lillie brings both technical mastery and creative insight—making her the perfect tutor for our photography holidays in Italy.

Throughout your stay, Lillie will host four engaging morning workshops focusing on composition, light, and camera mechanics, followed by practical sessions capturing Tuscany’s breathtaking landscapes. One morning will begin early to photograph the serene sunrise, timed perfectly to the local weather.

Lillie believes confidence grows through hands-on experience, and there’s no better way to develop your skills than by immersing yourself in a relaxed, inspiring photography course in Italy surrounded by like-minded creatives.

Our photography holidays in Italy are designed to help students of all levels develop technical skills, creative vision, and confidence behind the camera. Each day combines engaging morning workshops with hands-on practical sessions in the breathtaking landscapes and historic streets surrounding Cortona.

1. The Exposure Triangle: Aperture, Shutter, ISO
Students learn to master camera exposure, understanding how aperture, shutter speed, and ISO work together. Discover how to blur backgrounds for striking street portraits, capture every detail of Tuscan landscapes, and work confidently in low-light situations such as medieval churches or evening festivals.

Aperture: portraits vs. landscapes
Shutter speed: motion and panning Italian street scenes
ISO: low-light photography without flash

2. Camera Functions & Settings
Students are encouraged to experiment with camera settings, controlling white balance in artificial light, locking focus for fast-moving subjects, and exploring black-and-white photography for a romantic Italian aesthetic. By the end of the course, participants have a thorough understanding of their cameras and confidence to create beautiful, self-directed images.

3. Composition Techniques
Each day, students study inspiring works by famous photographers, learning composition rules and creative approaches to capture their own stunning images.

4. Light Mastery
Understanding light is key. Students learn to work with natural light, shade, and indirect sunlight, and experiment with flash for portraits and interiors. Lillie provides practical tips for identifying the best light on location to enhance every shot.

5. Project-Based Practice
Afternoons are dedicated to putting theory into practice across Cortona’s charming streets, medieval towns, and rolling countryside. Lillie offers personal guidance, helping students refine their compositions, select the perfect light, and elevate their photography projects.

By the end of this immersive photography course in Italy, students leave confident, inspired, and equipped to create images they will cherish for a lifetime.

Why choose LSP Photography Holidays in Italy?

Photography holidays in Italy are always inspiring, but a Lillian Spibey Photography Holiday in Italy offers something truly special. Designed and hosted by Lillian Spibey and Charlie Mitford, these carefully curated experiences combine exceptional photography tuition with privileged access to authentic Italian life. This is far more than a holiday — it’s a creative immersion into la bella vita.

Lillian Spibey Photography has been running photography holidays in Italy since 2015, drawing on years of personal experience living, working, and photographing throughout Tuscany and Umbria. Both hosts are deeply connected to the regions they share, ensuring every trip feels relaxed, genuine, and unforgettable.

Charlie has lived in Tuscany for 20 years, raising her family there and becoming fluent in Italian. Her local knowledge and extensive network — from restaurateurs and hoteliers to landowners and farmers — opens doors rarely available to visitors, giving guests unique behind-the-scenes access.

Lillie lived as a local while studying and working as a photographer in Perugia, Rome, and Cortona, where she met her husband. Her understanding of Italian light, culture, and landscape underpins the first-class photography tuition offered throughout each holiday.

Together, Lillian and Charlie have explored countless back roads, hidden valleys, and forgotten farm tracks far beyond the tourist trail. Their exceptional regional knowledge — and Charlie’s talent for discovering remote, little-known locations — ensures guests photograph Italy at its most authentic.

It’s this rare combination of expert guidance, cultural immersion, and insider access that makes Lillian Spibey Photography Holidays in Italy truly unforgettable.

Testimonials

Thank you so much for organising and running such a brilliant photography holiday in Tuscany last week. I had the most amazing time, thanks to the time and effort both Lillie and Charlie put into the week. I loved all the activities and the chance to try taking such a variety of photographs and it made such a difference having Charlie’s local knowledge and ability to speak fluent Italian. I still can’t quite believe how much we packed into every day. Getting back to work has been a real shock to the system!

Heather

I just wanted to say how much I enjoyed the Cortona trip and to send Lillie and Charlie a very big ‘thank you’

Malcolm

My first trip so all new to me, enjoyed everything we did.

Tuscany October 2025

Really enjoyed the flexibility to adjust to weather and also the group preferences.

Scarborough Sept 2025

I couldn’t leave it without saying a huge thank you to you and Charlie for a really informative, enjoyable and relaxing course. It certainly gave me lots to think about. We had great company, delicious food and probably more information than my brain could consume!

David

Very enjoyable. Excellent planning and operation!

Scarborough June 2025

The whole holiday was an excellent experience and certainly the best photographic course that I have been on. The organisation was excellent and I would like to thank Daniel and Lillie again for brilliant four days.

Scarborough June 2025

Thank you again for putting together such a fun packed and informative 5 days. I’ll get back to sorting my shots out – there seem to be a huge number!

Ian

I had not been to Tuscany before but with the range of sights, photo opportunities food and wine I think it is a fantastic venue. The local knowledge you and Charlie bring to it was invaluable.

Tuscany October 2025

I absolutely loved the trip – thank you for such a great experience.

Lillie and Daniel clearly put a lot of research and planning into the trip, so that you can provide photographic variety whilst also being able to be flexible to individual needs and desires.

For me the trip was filled with new opportunities and lots of laughter and fun with lovely people. I have come away with some lovely photos and the confidence to try more…. I will definitely be looking to be book more of your photography holidays.