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2026 Tuscany Landscapes & Hill-top Villages

Italy Workshops
2026 Tuscany Landscapes & Hill-top Villages image

May 16 - 23, 2026

About this trip

This is the Tuscany that tourists don't get to see.  Unpack and settle into our 15th century  farmhouse resort, a little village actually with its own pools, restaurant and private apartments.  

See and photograph the most famous landscapes and villages of the Val d'Orcia, pilgrimage sites for photographers from all over the world.  Add to that secret locations that we've discovered in our 25 years photographing this region. 

Being immersed into the culture of small local trattoria dining, visits with local characters and villages devoid of tourism better informs your photographs and enriches your Tuscan experience. 

Inspiration is guaranteed!

YOUR HOSTS

Drake Busath - American Travel and Portrait Photographer 

Gabriele Angelini - Italian Pro Photographer and licensed guide 

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SMALL GROUP 6-12 Guests

This tour has a minimum group size of 6.   You will receive a notification when the trip is confirmed.

You can check the TUSCANY TRIP PAGE to see if the minimum has been met and who's going.  Or you can inquire here

Booking Your Trip

Costs & Inclusions
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You are one click away from the trip of a lifetime!

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Trip Payment - $4950 per person (double occupancy)

Secure your booking with a $500 deposit. The balance payment is due 120 days prior to your trip departure.

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Inclusions

  • Accommodations 7 nights

  • All breakfasts plus 5 special meals

  • Master Photographer instruction

  • Full time guide

  • All Local Transfers

  • Departure Airport Transfer

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Exclusions

  • Arrival to Florence, Italy

  • Travel Insurance

  • Hotel Incidentals

Overview

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Overview

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About this trip

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YOUR HOSTS

Your Hosts

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Instructor

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Drake Busath, Master Photographer

Drake founded Italy Workshops in 1999, bringing his passion for Italy and photography to a wider audience. Over the past five decades, he has either lived in or visited Italy frequently, immersing himself in its culture, history, and landscapes. Fluent in Italian, Drake has developed a deep affection and intimate understanding of the country. Hundreds of photographers have joined him on what he describes as a “personal Renaissance,” exploring the rich and diverse regions of Tuscany, Umbria, Liguria, Venice, Lake Como, the Dolomites, Puglia, the Amalfi Coast, and Sicily. Through his workshops, Drake offers a unique blend of artistic inspiration and cultural discovery, making each journey a memorable experience.

View Drake’s Images

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Local Host and Guide

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Gabriele Angelini, Instructor and Guide

Gabriele Angelini, Italian photographer and publisher from Imola, near Bologna, is known for his big smile, infectious passion for street photography, and deep knowledge of Italian photographic history. Former photography instructor at the University of Bologna, he has worked for years as a photographer in Tuscany and knows the region intimately. He enriches every journey with unique cultural insights, local connections, and a love for Italy’s traditions. Living in Emilia Romagna, the heart of classic Italian cuisine, he’s the perfect guide to pair unforgettable images with equally unforgettable food and wine.

View Gabriele's portfolio

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Map

1. Florence

Florence, Metropolitan City of Florence, Italy

2. Siena

53100 Siena, Province of Siena, Italy

3. Buonconvento

53022 Buonconvento, Province of Siena, Italy

4. Crete Senesi

Via Goffredo Mameli, 34, 53041 Asciano SI, Italy

5. Val D'Orcia

3H75+HQ, 53027 San Quirico d'Orcia, Province of Siena, Italy

6. Pienza

53026 Pienza, Province of Siena, Italy

7. San Quirico d'Orcia

53027 San Quirico d'Orcia, Province of Siena, Italy

8. Monticchiello

53026 Monticchiello, Province of Siena, Italy

9. Montefollonico

53049 Montefollonico, Province of Siena, Italy

Day 1-3

San Gimignano / Siena
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MEET IN FLORENCE

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Transport Florence to San Gimignano

DepartureSaturday, May 16, 20269:00 AM
DestinationSan Gimignano10:30

9:00 AM- Meet us in Florence at Piazzale Michelangelo to load up the vans and head to San Gimignano (about 1 hr)

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Transport to Siena

DepartureSaturday, May 16, 20262:00 PM
DestinationSiena3:00 PM

After lunch continue with us to Siena

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Walking / Shooting Tour in Siena

Stroll the perfect medieval town with our favorite local guide Claudia. Soak in the beauty and rich history.

Then enjoy a welcome dinner in one of the most iconic restaurants of Siena for our first taste of true Tuscan cuisine.

And yes! Wine and beverages are always included.

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Two nights in Siena with balcony views

Check inSaturday, May 16, 2026
Check outMonday, May 18, 2026
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Wine Tasting in an Etruscan Cellar

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Day 4-7

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World famous landscapes of Val d'Orca and Crete Senesi

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San Galgano Abbey

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Check in at our favorite farmhouse in Tuscany

Check inTuesday, May 19, 2026
Check outSaturday, May 23, 2026

Just south of Siena is our farmhouse stay: Borgo Pieve a Salti. Drake has hosted workshops here each year since 1999. We're pretty sure you'll feel at home here the way we do.

Begin each day with a farm-fresh breakfast and 360 degree views you won’t believe.

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Hilltop Villages: Pienza, San Quirico, Montecchiello

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Landscapes of the Val d'Orcia

The rolling hills of the Val d'Orcia cover an area coveted by landscape photographers world wide.

We'll stop to photograph the most famous views at prime times, but also our favorite secret locations.  

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Cooking Class at a Storied Trattoria

The owners of an iconic Tuscany trattoria have agreed to host us for a private cooking class and a great lunch. In addition to learning cooking tips, this is an opportunity to create culinary images and portraits of the chef.

If you're not into the class, you'll find lots to see in this special village of Montefollonico. Just don't miss the lunch.

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Crete Senesi

Dive deeper into villages and landscapes of the Crete Senesi, much less traveled but equally jaw dropping for photographers.  A working monastery with wine tasting, meet ups with local characters and true Tuscan meals dot this itinerary and make it an authentic visit you won't forget.  

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Day 8

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Buonconvento / Siena

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Check-out our favorite farmhouse in Tuscany

Check outSaturday, May 23, 202610:00 AM
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Buonconvento, the real thing

Wrap up our week with a relaxed morning in Buonconvento, our "home town" just 5km from our farmhouse.

Tourists don't know about this place and we like it that way.  Meet some great old characters and experience truly authentic Tuscany lifestyle.

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Farewells / Siena Train Station

DestinationSaturday, May 23, 2026 3:00 PM

We'll help you with train tickets from the Siena Station to Florence ( 1 hour direct train) or anywhere else you're headed.

Come Hungry

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Eating Well Improves Your Photography

In Italy, eating well, or "mangiare bene," is essential to the travel experience. Each region boasts its own specialties, so we take the extra time to discover the best little trattorias where you can enjoy authentic local cuisine.

Dining family-style and asking for a variety of the chef's recommendations is a favorite way to share meals with our groups. Everyone gets to taste everything and enjoy as much as they like.

Of course, wine and soda are included with our meals.

Immersing yourself in a local region's culinary traditions enhances your photography, making it more informed and authentic.

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Pre-Workshop - Florence Extension

May 14-15-16. 2026
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Three Days with a Local Photographer

Join pro photographer Gabriele Angelini as he shows you his favorite spots.  Visit the most photogenic sites, meet local artisans, and indulge in local cuisine as you can only do with a local friend.

See Gabriele's work  

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4 Days / 3 Nights

DepartureOrta San GiulioSunday, Oct 12, 20259:00 AM
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Highlights

  • Discover the secret corners of Venice

  • Meet talented local artisans

  • Explore the colorful Island of Burano and more in the lagoon

  • Visit the most photogenic locations at the optimal times of day

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Inclusions

  • Full time guide

  • Welcome dinner

  • All. entrance fees

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Exclusions

  • Arrival to Florence

  • Accommodations (see recommended Florence hotels below)

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Hotel Suggestions in Florence for Pre-Workshop Nights (Copy)

There are a multitude of hotels and B&B options in Florence. Here are a few in which we've had good experiences:

Hotel Calziauoli 4*

Albergo Firenze 3*

Hotel De Lanzi 3*

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Arriving to Florence

We recommend flying to the Florence FLR Airport. A 15 minute taxi gets you to your hotel in town.