Umbria is one of the most underrated regions in Italy. While all the popular travel lists tell you to go to Tuscany, Amalfi, Rome, Florence, and Venice, we have a secret for you - do yourself a favor and book a trip to Umbria instead! Umbria is a magical place that is still relatively well preserved from mass tourism - it has the most beautiful historic towns to spend long afternoons strolling through the winding streets, it has the same stunning rolling hills you see in Tuscany but at a fraction of the price and an even smaller fraction of the tourists, and the food is, well, it's some of the best food we've ever had! Not to mention the wine - omg the wine - the reds from Montefalco pair so perfectly with some fresh truffle tagliatelle pasta.
Top 3 Must-Do’s for an Umbria Itinerary
Walk along the ancient aqueduct in Perugia
Wander through the picture-perfect streets of Spello
Visit the walled fortress town of Orvieto built on a cliff
Duration: 4 nights
Typical Daily Cost for two people: $413 (excludes any required airfare to/from Rome)
Best Time to Go: April - October (we went in November and it was still lovely, although a bit cold)
Table of Contents
Umbria Roadtrip: Itinerary at a Glance
Day | Activities |
Day 1 | Pick-up rental car from Rome airport and drive 2.5 hours to Castello di Monterone just outside Perugia. Enjoy a relaxing dinner at the hotel. |
Day 2 | Spend the morning and early afternoon exploring Perugia. Stop at Terre Margaritelli for a wine tasting before heading back to the hotel for dinner. |
Day 3 | Wander through Assisi in the morning, followed by the picture-perfect town of Spello in the afternoon. |
Day 4 | Head over to the walled fortress town of Orvieto. Enjoy the hot tub and sunset back at the hotel. |
Day 5 | Drop off rental car and fly to your next adventure! |
Bonus Day: You can easily add an extra day to your trip to explore a bit of Tuscany - Cortona is one of our favorite towns in Tuscany and only 45 minutes away!
Just the Facts
Stay
Castello di Monterone: Italy has some of the most unique hotels we've ever stayed in, and for that reason, we spend a lot of timing researching the perfect hotel whenever we plan our trips to Italy. Our ideal Italian vacation really does revolve around the hotel - we want someplace that's set in the countryside with beautiful grounds to walk around, amazing views, and most importantly, fantastic food! Castello di Monterone ticked all the boxes and more. It's an actual historic castle and so incredibly well preserved. There's tons of common areas to hang out, drink a glass of wine (Montefalco red for the win!), play some board games, or relax in the pool, hot tub, or sauna. It's also perfectly located so we could easily grab a taxi into Perugia for dinner and drive to other towns to explore.
Eat
Ristorante Gradale: Hotel restaurant. Super convenient, but it has a limited menu so you probably won't want to eat here every night.
Ristorante Il Giurista (Perugia): Good for lunch or dinner, make a reservation. On the fancier side. The truffle pasta is amazing!
Civico 25 (Perugia): Our pick for best meal of the trip. Super cozy vibes, make a reservation. Two seatings a night. They own the bar next door so you can come a bit early for a drink while you wait for your table. Very creative pasta dishes. Natural wines.
Taverna Il Tiesto (Perugia): Casual lunch spot with good pasta
Trattoria Spadini (Assisi): Great lunch spot, traditional local pastas, good prices.
Orvieto lunch restaurants - all are comparable serving traditional Italian dishes
Drink
When we come to Italy, it's all about spritz's and wine. For the wines, we will typically always drink what's local to the region and our favorite wines in Umbria are from Montefalco. Specifically, we loved the 2016 Rosso Riserva and the 2018 Rosso from Adanti Winery in Montefalco.
2018 Rosso is available at the hotel
2016 Rosso Riserva was at Civico 25 in Perugia
Map
Detailed Umbria Roadtrip Itinerary
Day 1
Arrive at the Rome Airport in the early afternoon, pick up your rental car, and drive about 2.5 hours to Castello di Monterone just outside Perugia. The drive is very straightforward and mostly on the highway. If you're hungry on the way, we recommend stopping in the small village of San Gemini to grab some lunch - there is a free parking lot here and several traditional Italian restaurants to choose from right on the main street.
Once you check-in to Castello di Monterone, spend the rest of the afternoon relaxing (and don't miss the sunset over Perugia). The hotel is so unique and has a maze of rooms to explore throughout the castle. We particularly loved the roof deck that passed through the library, the patio overlooking the pool with Perugia in the distance, and the bar with a large fireplace and plenty of board games.
For dinner tonight, we recommend staying at the hotel. They have a very convenient restaurant right on site with great food and wine! One of the things we love about Italy is that dinner is always an event that spans multiple hours just relaxing and chatting over amazing wines, endless pasta, and good company.
Day 2
We recommend driving just down the road into Perugia today. We absolutely loved this city and were so glad it was only a few minutes away by car so we could explore it multiple times. Park your car in this paid parking lot at the base of the city and take the escalator inside Pincetto station up to the top of the hill (so convenient to avoid having to walk this hill!). From here, wander over to the Carducci Gardens for some amazing views of Perugia and the rolling hills in the distance.
Now the fun begins - go get lost in the streets of Perugia! You can start by walking along the main street of Corso Pietro Vannucci, and then turn down any side alleys and explore. Don't miss the main square Piazza IV Novembre - the architecture is stunning and it's a great place to have a coffee on the sidewalk and "people watch".
For lunch, you can decide between Ristorante Settimo Sigillo (a more traditional Italian sit-down restaurant) or Taverna Il Tiesto (a more casual pasta spot). Either way, be sure to order as much truffle as you can - Umbria is known for their truffle!
After lunch, walk over to the Medieval Aqueduct of Perugia - this was our favorite part of Perugia (besides the food, of course). You'll get some absolutely beautiful photos as you walk along the top of the aqueduct.
If you have some extra time in the afternoon, we recommend driving over to Terre Margaritelli for a wine tasting and cellar tour - you can book a visit beforehand on their website. It's only about a 15 minute drive back to the hotel, so why not buy a bottle of wine after the tasting to enjoy in the hot tub over sunset at the hotel! Enjoy the rest of the evening at the hotel and have dinner at the hotel restaurant again tonight.
Day 3
Today you'll be exploring 2 towns in Umbria - Assisi and Spello. Start the morning with a 30 minute drive to Assisi - this town is the birthplace of Saint Francis and is an incredibly popular pilgrimage destination (this means it can be very crowded, but we still think it's worth a visit). One of the things we distinctly remember about Assisi is how impressive the town looks from the road leading up to it - it's something you really need to see with your own eyes!
Park your car in this paid parking lot and walk up to the Basilica of Saint Francis. Wander around the rest of the town, walking towards the absolutely picture perfect Piazza del Comune.
For lunch, we highly recommend going to Trattoria Spadini - it's a super cute traditional Italian restaurant with delicious handmade pastas. After lunch, work off that pasta by walking up the hill to Rocca Maggiore - this is an old fortress that overlooks the entire town, and the panoramic views are totally work breaking a bit of a sweat on the walk!
In the mid-afternoon, wrap up your time in Assisi and drive just down the road to Spello (this was our winner for most photogenic town of the trip). You have two options for parking your car - either at the bottom of town (this parking lot) or the top of town (this parking lot). We opted for the bottom lot, but it really doesn't matter which you choose. Spello is a tiny town, so just wander along the streets and stop for a coffee and some Italian pastries/cookies (we loved this cafe). If you parked at the bottom lot like we did, be sure to walk all the way up to the top parking lot for some great views of the countryside before driving back to the hotel.
For dinner tonight, we recommend you take a taxi into Perugia and go to Ristorante Il Giurista - this restaurant is a bit more upscale and the food is incredible (make a reservation a few days ahead). We especially loved the pasta dishes - we ordered three (be sure to order the truffle pasta)! And a little surprise bonus - they serve an insanely good olive oil here produced by Quinta Luna. To get back to the hotel, you can ask the restaurant to call you a taxi.
Day 4
Next up on your tour of the cutest towns in Umbria, we bring you Orvieto! Orvieto is the farthest town from your hotel, so be prepared for just over an hour drive. Driving to Orvieto was a memorable experience - Orvieto is perched on top of a cliff and our first thought when we saw the town was, "I really hope we don't have to drive up that cliff!". Thankfully for everyone, that's not the case (phew!) - there's a very convenient parking lot at the base of the cliff and you can simply take the interior escalator up into town.
Orvieto is another town where the best way to explore is to just wander around the confusing maze of streets. At some point, be sure to stop at the Duomo di Orvieto - this is one of the most beautiful and intricate duomos we've seen (and so photogenic).
For lunch, you'll be spoiled for choice. Orvieto has some incredibly good restaurants to choose from so here are a few options, all serving traditional Italian food: Mezza Luna, Trattoria la Palomba, or Osteria da Mamma Angela. After lunch, you can either spend some more time wandering around Orvieto, or drive back to the hotel and relax in the hot tub or sauna.
For dinner tonight, we highly recommend taking a taxi into Perugia again and going to Civico 25 - this was our pick for best meal of the trip (be sure to book a table a few days ahead). They do 2 seatings a night, the food is super creative, and the wines are incredible. They also own the bar just next door so you can come a bit early for a cocktail or spritz before dinner (or after dinner).
Bonus Day in Tuscany
Lucky for you, Umbria and Tuscany are neighbors, so you can easily add an extra day to your trip to explore a bit of Tuscany - one of our favorite towns in Tuscany, Cortona, is only 45 minutes away!
Start the day out in Cortona and park your car in this parking lot - this is a super convenient lot with escalators leading up to town. Just like the towns in Umbria, Cortona is best explored by just wandering around the adorable streets. For lunch, stop at one of our favorite restaurants, Taverna Il Gozzoviglio, and get the pistachio & pancetta pesto pasta!
After lunch, go up to the Fortress of Girifalco to see an incredible 360 view of Tuscany. Now, you have options for getting up to the fortress - you can walk, like we did, to burn off those pasta calories, but we will warn you...it's only about a 20 minute walk, but it's straight uphill. If that's not your jam, then feel free to just drive your car up.
Day 5
That's it for Umbria! Drive back to Rome, drop your rental car off and catch your flight to your next adventure.
Cost Breakdown (2 people for 4 nights)
Note: Flights to/from Italy are not included in this cost breakdown.
Hotel - Castello di Monterone | $750 |
Rental Car (includes gas, tolls, insurance, parking) | $250 |
Lunch | $160 |
Dinner (2 entrees, 1 app, bottle of wine) | $280 |
Drinks (1 extra drink per person per day) | $80 |
Wine Tasting | $50 |
Taxis to/from Perugia for 2 Dinners | $80 |
Total | $1,650 |
Daily Cost for 2 people | $413 |
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