Welcome to the Food, Festivals & Wine Tour, this is ITALY in a snapshot, action-packed and indulgent - an immersive, multi-sensory 10 day experience designed to thrill the Foodie, delight the Wine Enthusiast, and satisfy a Traveler’s search for bella Italia’s authenticity, culture, festivals and FUN!

The Highlights

Our adventure begins in BOLOGNA, Italy’s Food Capital and a Foodie’s paradise. Our first farm-to table experiences in the countryside are about flavor and behind the scenes secrets. Alessandro will guide us through the birth of a Parmigiano Reggiano wheel, the Cavedoni family will reveal the centuries old craft of barrique aged, prized Balsamics, and we’ll delve into the art of Prosciutto curing right at the source. Brains and bellies full.

From there we’ll travel to CHIANTI for several vineyard experiences and wine tasting. We’ll spend the afternoon with Stephen and Jen in the vineyard, check out Massimo’s Olive Oil, walk through a forest for a truffle hunt and get busy with a hands-on pasta making lunch with Camilla and Fabrizio at their family farmhouse. These are Tuscan treasures.

We’ll cross over to SPELLO and hike through green hills along olive groves and a Roman Aqueduct. In the evenings we’ll join local families and friends to watch the magnificent Flower Festival transform the town during an all-night celebration ending at dawn, when the cobblestone streets are blanketed in intricate floral mosaics. Too many photo ops.

Our last stop will be in ORVIETO, just in time for the centuries-old Medieval Festival and Procession in full regalia in celebration of Corpus Domini. Here we’ll also explore the green Umbrian countryside on E- bike with Paolo, pedaling quiet backroads to a forgotten village and vineyards truly “off the beaten path.”

Days & Experiences

June 1 • Monday • Day 1: Arrival & A Bite of Bologna

Benvenuti! Settle into our hotel in the heart of Bologna’s historic center, the Quadrilatero food district overflows with produce stands, artisanal delis, and cafés. They say gelato cures jet lag... worth a try. Late afternoon we’ll kick start our adventure with a welcome aperitivo in Piazza Maggiore, then a quick peak at the Basilica and short walk on glass floors above 2nd cent. BC roman ruins, before we enjoy our first dinner together, showcasing Bologna’s iconic flavors - Mortadella, Tagliatelle Bolognese and Tortellini. Raise a glass of Lambrusco or Pignoletto and toast to the days ahead. Salute!

Tuesday • Day 2: A Dream Day for Foodies

Let’s discover why Bologna is nicknamed la grassa - “the fat one” by checking out behind the scenes of three of Italy’s most treasured products: the golden Parmigiano Reggiano, the deeply complex Balsamic Vinegar, and savory mouthwatering Prosciutto. We’ll start at the dairy farms when the morning milk arrives, and the artisans begin the popular Parmigiano wheels’ very restricted process. On to a vineyard in Modena where the Cavedoni family have been safeguarding a 200-year-old balsamic tradition, where barrique-aged vinegars reach extraordinary depth and sweet-tart flavors. At the Prosciuttificio, we’ll follow each stage of the dry cured hams and richly flavored curing process. Despite too much tasting throughout the day, we’ll sit and enjoy a festive meal together with music and a few surprises before a restful ride back to this vibrant city for a free evening - explore, walk about and shop fancy shoes or bags of Tortellini.

Wednesday • Day 3: Truffles, Pasta Making & Chianti

We head south into the ruby land of Chianti and make our first stop at our friend Camilla’s farmhouse for a truffle hunt in the woods (with Tabu - the best dog). We’ll then prepare our own a fresh pasta lunch - Tagliolini Cacio e Pepe topped with our shaved truffles, dripping in the estate’s olive oil and accompanied with local wines. Continuing south, pause for a piazza espresso in Greve in Chianti town before arriving to Castellina in Chianti town and checking into our 14th-century farmhouse nestled among rose gardens. Tonight enjoy Chianti tasting at wine cellar under the town’s historic covered stone passageway, once used as defense from the cavalry below, during the legendary Florence- Siena Medieval rivalry.

Thursday • Day 4: A Day to Relax & Explore

Spend the morning relaxing at the villa’s pool overlooking the Tuscan valley or stroll through pedestrian Castellina’s main street lined with artisan shops of leather, linens, jewelry, ceramics. Visit the main church, where farmland protector St. Fausto rests in a glass case, or climb the Rocca fortress tower for the views and the small archaeological museum showcasing the Chianti area’s history from the Etruscans onward. This evening we gather at another local cantina for a delicious wine-paired dinner.

Friday • Day 5: Through Tuscany, Vineyards & Olive Oil

Crossing Tuscany on our way to Spello, we stop to visit our friends Stephen & Jen. Strolling through their vineyards we’ll learn more about cultivation and blending before a delightful wine tasting lunch under the gazebo. Next, we tour Massimo’s olive oil farm to learn about production and (hopefully) pick up some take-home tins from the latest, freshest olive harvest. After checking into our 4-star hotel in Spello, we’ll enjoy a slow town orientation walk, as we do in each town, to find this tiny medieval town’s main historical sites before your free evening.

Saturday • Day 6: A Hike-Filled morning & A Flower-Filled Night

This morning you can enjoy a beautiful, guided walk through the outskirts of town, past silver olive groves and wild red poppies, along an ancient Roman Aqueduct offering endless Umbrian views. Follow the well-marked trail back to town anytime or continue up to the hilltop village of Collepino – your choice. Tonight the Flower Festival begins. Families gather to sketch their elaborate designs onto the cobblestones and pluck a zillion flower petals. At sunset the magic starts, the town transform into a busy, collaborative hive of pure joy as everyone works through the night to complete their masterpieces. After dinner we’ll join the town’s festivities for one of the most enchanting nights you’ll ever experience.

Sunday • Day 7: 2 for 1 Festival Celebration

You probably stayed up late, but you’ll probably still wake early to catch the sunrise over the just finished, incredibly vivid and colorful floral “carpets” all before neighboring towns and the Bishop arrive to bless them. Now we move on to Orvieto, drop our bags at our hotel off the main piazza, to go find the perfect viewing spot in front of the Duomo - just in time for the spectacular Corpus Domini Medieval Procession - a glorious pageantry of velvet robes, trumpets, banners, and swirling flags. After our group lunch, enjoy the rest of your free day exploring Orvieto in party mode, with background sounds of the parade as it cris-crosses from piazza to piazza.

Monday • Day 8: E-Bikes, Countryside Villages & Wine

After breakfast we’ll saddle up with our guide Paolo for an e-bike tour through the quiet Umbrian countryside. Our first stop is to explore the charming, tiny town Civita di Bagnoregio. We’ll leave bikes below and cross the dramatic pedestrian bridge suspended over a gorge to reach the ancient town entry. On our return to Orvieto, we’ll stop for “refreshments” at a wine estate featuring outstanding local reds and the fresh and fruity local Orvieto white. Free evening to relax our biking thighs.

Tuesday • Day 9: The Last Day of La Dolce Vita

Spend your final day enjoying Orvieto, the center is pedestrian only and lined with shops including Orvieto’s popular colorful ceramics. Or visit any of the cultural treasures such as the spiral Well of St. Patrick’s or the 12th-century Torre del Moro. Early evening we’ll enjoy a guided tour of Orvieto’s Underground, where ancient Etruscan tunnels and caves reveal centuries of evidence, lives lived, carved in the hill’s tufa stone. Just across the piazza, we’ll marvel at the magnificent Duomo, including the San Brizio Chapel’s stunning artistic depictions of Heaven and Hell. Tonight’s farewell dinner features Antonio’s legendary Pasta Carbonara, often described as a spiritual experience in itself! One last toast - È stata una bellissima esperienza!

June 10 • Wednesday • Day 10: Arrivederci!

Assistance for shared transfers to your points of departure – train stations or airports. Buon viaggio!

Numbers & Details

  • $4,220 per person, land only, in a shared double occupancy room. Single Supplement + $722

  • 9 days (+ departure morning), 9 nights in centrally located 3/4 star hotels and B&Bs

  • 8 Breakfasts, 4 Lunches and 4 Dinners (with wine)

  • Starts: 4pm, Monday June 1, 2026. Ends: 11 am, Wednesday June 10, 2026

  • 4 Town Guided Orientation Walks to sites of interest: Bologna, Chianti, Spello, Orvieto

  • 3 Entry Tickets: Basilica of Bologna, Orvieto Duomo, Civita di Bagnoregio

  • 3 Wine Tastings with a mix of vineyards and cantinas.

  • 2 Remarkable Festivals: Spello’s International Flower Festival & Orvieto’s Corpus Domini

  • 2 Italian Aperitivo Hours

  • Full Day Food Tour for Parmigiano, Prosciutto & Traditional Balsamic

  • Truffle Hunt (with a good dog — Tabu!)

  • Hands-On Pasta Making Class

  • Guided Hike (Spello to Collepino optional)

  • Olive Oil Production Visit

  • E-Bike Tour (guide, helmets, and van assistance)

  • Not Included: Airfare, organized transfers to/from airport and travel insurance.

This is not a typical “Vatican-Gondola-Limoncello” loop. The activity level is high and each varied experience has been carefully selected, crafted for your deepest APPRECIATION and ENJOYMENT for Italy’s flavors, authenticity, culture and breathtaking beauty!

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