Spend Fall in Italy eating, drinking wine and learning photography.

One week dream tour of Tuscany in a private van. Equal parts food, wine, photography.

We drive, you enjoy. Limited to just six guest. We’ll visit Orvieto, Pienza, Bagno Vignoni, Montepulciano, Montalcino and Siena.

Oct 1-8, 2025 (Groups of 5 or more can pick their own dates)

All flights lead to Rome… 

Day One:
We’ll pick you up at your hotel or airport and begin our journey into the heart of Tuscany. Our first stop is the hilltop fortress town of Orvieto, where we’ll enjoy a delicious lunch and a guided walking tour through its medieval streets and underground caves.

From there, we continue on to the stunning village of Pienza, where we’ll check in at the stylish and serene La Bandita Hotel (www.la-bandita.com). After settling in, we’ll take a relaxed stroll through the charming streets of Pienza before dining together at La Bandita’s acclaimed restaurant.

Throughout your Italian photo safari, Kelly Fajack will help you refine your photography skills — focusing on lighting, framing, and composition. You’ll learn to confidently use manual camera settings, putting you in control of your creative vision. There will be ample one-on-one instruction covering techniques such as motion panning, the rule of thirds, and effective use of polarizing filters.

After the tour, each guest will also receive a one-hour private Photoshop session via screen share, once you've had time to select your best shots and reflect on your visual story.
A scenic view of the Tuscan countryside with rolling hills, cultivated fields, and scattered trees, viewed from a stone house with a garden patio hosting people sitting under a trellis. 
Day Two:
We’ll start the day with a morning photo walk through the charming streets of Pienza, capturing its Renaissance architecture and sweeping valley views in the golden light. Next, we’ll tour Pope Pius II’s summer residence, a stunning example of 15th-century design and papal opulence.

Lunch will be at the beloved Trattoria Latte di Luna, known for its rustic Tuscan fare and warm hospitality. After a short break back at the hotel, we’ll venture to the peaceful spa village of Bagno Vignoni to unwind in its natural thermal mud baths, surrounded by cypress trees and rolling hills. We'll stay in Vignoni for a relaxed, local dinner in town, soaking in the quiet magic of the countryside.

Day Three:
Enjoy a relaxed morning to sleep in, stroll, or photograph the quiet beauty of your surroundings. In the afternoon, we’ll join the charming Chef Paolo Coluccio for a hands-on cooking class where he’ll share the secrets of local Tuscan cuisine and the regional wines that complement it.

After our culinary adventure, we head to the medieval hilltop village of Montepulciano — a paradise for wine lovers and photographers alike. We'll explore the ancient streets during a guided photo walk, then settle in for an unforgettable dinner at the renowned La Grotta, one of Tuscany’s most celebrated dining experiences.

View of a historic Italian square with tall clock tower and castle-like building made of red bricks, surrounded by old stone buildings and shops with people walking and shopping. 
Day Four:
After breakfast, we pack up and head to the wine mecca of Montalcino for a scenic walking tour and lunch at the lovely Albergo Il Giglio. After lunch, we continue on to the stunning medieval city of Siena, where we’ll check in at the luxurious Grand Hotel Continental. You’ll have free time to explore the city’s historic piazzas and winding alleys before we gather for a memorable dinner at Grotta di Santa Caterina da Bagoga, a local favorite known for its traditional Tuscan flavors.

Day Five:
We’re up early for a drive to the postcard-perfect village of San Gimignano, famous for its medieval towers and breathtaking skyline. After a guided tour and lunch at Ristorante Fuoriluogo, we put the cameras down (or at least switch to wine mode) for a relaxing afternoon of wine tasting throughout the hills of Chianti. In the evening, we return to Siena to unwind and reflect on the day’s indulgence.

Day Six:
We’ll pack up and head to the town made famous by Under the Tuscan Sun — the enchanting Cortona. Enjoy a guided tour and history lesson of this ancient hilltop village, which actually predates Rome. We'll have lunch at the charming La Loggetta, followed by free time to wander the walkable streets, soak in the views, and shop or sip at your leisure. In the evening, we’ll dine at the cozy Taverna Il Gozzoviglio before settling in for the night at the elegant Monastero di Cortona.

Day Seven:
You have options!

Stay and enjoy Cortona at your own pace.
We’ll arrange transport to a hotel or airport in Rome or Florence.
Keep the adventure going with a custom extension — we’ll help design the perfect add-on to your journey.
Price: $4,900 (double occupancy) / $5,800 (single).
Includes lodging, meals, excursions, ground transportation, and tours.
Airfare, alcohol, and travel insurance not included.

Tuscan photo gallery

  • Sunset over a mountainous landscape with fog in the valleys, view from a village with stone rooftops and a church bell tower in the foreground, and a mountain in the distance.

    Val d'Orcia

  • Hanging cured meats and sausages at a deli or butchershop, including whole hams, salamis, and pork cuts on display.

    Eat local

  • A stone house with a castle turret surrounded by trees in a rural landscape with rolling hills and mountains in the background.

    Hills outside of Pienza

  • View of rolling hills and mountain in the distance through an open window with brick walls.

    Sarteano

  • Pizza with fresh arugula and cherry tomatoes on a crust.

    Pizza

  • View of historic Tuscan city rooftops with a tall clock tower under a partly cloudy sky.

    Siena

  • A lively outdoor cafe scene in front of an old stone building with pink flowers on the windows and an Italian flag hanging from a balcony. People are sitting under large umbrellas, dining and chatting, with a person walking past.

    Pienza

  • Modern bedroom with a white four-poster bed, black leather armchairs, a brick wall, and a window open to the outside.

    La Bandita Pienza

  • Black and white photo of historic buildings with a clock tower on the right side, featuring arched windows and a flag hanging below.

    Pienza

  • A group of people sitting around a rustic wooden table outdoors during sunset, with a waiter presenting a plate of food. The table is set with glasses, plates, and utensils, and lush greenery is visible in the background.

    Chef Paolo Coluccio

  • View from an ancient terrace with tall stone columns, overlooking a rural landscape under a blue sky with some clouds.

    Pienza

  • People walking up the stone steps outside a historical European cathedral with intricate architecture and striped marble on the facade, under a clear blue sky.

    Siena

  • Sunset over rolling hills and vineyards in a rural landscape of Italy with houses in the foreground.

    Montepulciano

  • A wooden outdoor table set with a large oval platter of sliced prosciutto and cheese, two small vases with flowers, a glass, a plate with a teal napkin, and an empty wine glass.

    Local eats

  • A sunny street scene in a European village with old buildings, potted plants, people sitting at an outdoor cafe, and a clear view of the countryside in the background.

    Pienza

  • A narrow alleyway framed by an archway, with buildings on either side, leading to a scenic view of trees and rolling hills with three people walking toward the horizon.

    Montepulciano

  • Santa Maria Novella, a historic brick town hall with a tall clock tower, under a cloudy sky at sunset, located in Florence, Italy.

    Siena

  • Black and white landscape of rolling hills with a group of tall, slender trees on a small rise, under a cloudy sky.

    Tuscany