Our Favorite Day Experiences
Strada Del Sagrantino
Strada Del Sagrantino
Strada Del Sagrantino
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Strada del Sagrantino Wine Day – boutique tastings, lazy vineyard lunch, optional olive oil/chocolate stop.
Tartufo My Love
Strada Del Sagrantino
Strada Del Sagrantino
Truffle Hunting + Farmhouse Feast – forage with dogs, cook + eat your finds, paired with local wines.
Di Borgo In Borgo
Strada Del Sagrantino
Di Borgo In Borgo
Medieval Town Hop – Assisi, Spello, Gubbio with artisan shops, frescoes, gelato + aperitivo built in.
Trasimeno Vibes
From Olive to Oil
Di Borgo In Borgo
Lake Trasimeno by Boat – island hop + fish lunch, optional Cortona wine stop.
From Olive to Oil
From Olive to Oil
From Olive to Oil
Olive Oil Immersion – grove walks, mill visit, tasting + cooking class.
Chocolate & more
From Olive to Oil
From Olive to Oil
Perugia Foodie Crawl – cafés, street food, chocolate tasting, sunset aperitivo.
Discover with WhenInUmbria
Spring Itinerary “Romantica In Tuscany” (3–4 Nights)
Day 1 · Arrival & Romantic Welcome
Arrive in the afternoon and settle into your suite before exploring charming cobbled streets and village life. At sunset, enjoy aperitivo in the historic piazza, followed by a candlelit dinner at a traditional trattoria featuring Lake Trasimeno cuisine and local wines.
Day 2 · Culture & Spa
Start the day in Arezzo, strolling through Renaissance streets as the city comes to life. Continue to Cortona for antique browsing and a Tuscan wine tasting. Return in the afternoon for a private spa experience with rock pool, sauna, and whirlpool.
Day 3 · Hidden Villages of Umbria
Discover authentic Umbria with a scenic drive through rolling countryside. Visit Città della Pieve, home of Perugino, with its flower-lined lanes and artisan shops, then explore Panicale, a beautifully preserved medieval village with sweeping panoramic views.
Day 4 · Slow Morning & Farewell
Enjoy a relaxed final morning — sleep in, linger in the piazza, or sip a last cappuccino as village life unfolds. Conclude your journey with a wine tasting in Montepulciano, savoring exceptional wines and unforgettable views.
October Itinerary “Harvest & Heritage” (3–4 Nights)
Day 1: Arrival & Autumn Welcome
Arrive in Umbria — maybe settle in around Lake Trasimeno, Montefalco, or Todi. Evening: Enjoy a relaxed dinner of truffle pasta or pumpkin risotto at a local osteria. Sip on a glass of Montefalco Rosso while watching the sunset over the olive groves.
Day 2: Olive & Grape Harvest Experiences
Morning: Join a harvest day at a local winery like Cantina Madrevite or Cantine Berioli — pick grapes or taste new vintages in the making.
Evening: Head to a nearby sagra (village festival) — October is packed with Frantoi Aperti, Sagra della Castagna (chestnut festival), and Sagra della Cipolla (onion festival in Cannara).
Day 3: Hilltop Villages & Autumn Festivals
Morning: Explore Bevagna or Spello with their artisan shops and medieval architecture dressed in fall colors.
Day 4: Slow Farewell
Morning: Enjoy a leisurely breakfast at your agriturismo with fresh bread, jams, and newly pressed olive oil.
Optional: Stop by Assisi for the feast of San Francesco (October 4) — a major religious and cultural celebration with parades, processions, and music.
Afternoon: One last countryside drive or lakeside walk before heading home, feeling like you’ve lived La Dolce Vita d’Autunno.
November Itinerary “Harvest & Food Focus” (4-5 nights)
Day 1: Arrive in Perugia/Assisi region, relax.
Day 2: Visit an olive-mill + participate in fresh-oil tasting (Frantoi Aperti region).
Day 3: Travel to Valtoppina (or nearby) for truffle fair, lunch with truffle dishes, explore countryside.
Day 4: Head to Perugia for EuroChocolate festival, stroll markets, chocolate tastings.
Day 5: Scenic drive through Umbrian hills, winery/olive estate visit, depart. and preferences of our clients.
December Itinerary “Festive & Cultural” (3-4 nights)
Day 1: Arrive in a small Umbrian town (e.g., around Lake Trasimeno or in central Umbria). Evening: stroll Christmas market & lights.
Day 2: Day-time visit to a village with “La Venuta” bonfires (Dec 9) if timing matches. Evening: enjoy a concert in a historic theatre.
Day 3: Food-focused morning: local winter produce (chestnuts, wild game if available). Afternoon: leisure & market visits.
Day 4: Optional extra concert, holiday event, or just relax with cozy winter ambience and depart.s and preferences of our clients.
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