Our Favorite Day Trips
Strada Del Sagrantino
Strada Del Sagrantino
Strada Del Sagrantino
.jpeg/:/cr=t:0%25,l:16.66%25,w:66.68%25,h:100%25/rs=w:388,h:388,cg:true)
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.
Discovering the World with WhenInUmbria
October Itinerary “Harvest & Heritage” (3–4 Nights)
December Itinerary “Festive & Cultural” (3-4 nights)
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 h
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)
December Itinerary “Festive & Cultural” (3-4 nights)
October Itinerary “Harvest & Heritage” (3–4 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
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)
December Itinerary “Festive & Cultural” (3-4 nights)
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
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.
Welcome to WhenInUmbria!
Subscribe to have access to exclusive information on our vacations, tours and retreats!