Brigolante holiday rentals in Assisi, Umbria

Self-catering apartments in Assisi's town center and nearby countryside.

Fourteen Perfect Days: A Two Week Itinerary for Umbria

Over the past thirteen—gulp!  That can’t be right!—years welcoming guests at Brigolante, I have come to realize that about 95% of their queries are repeat questions.  Some of these I have template emails for (i.e. Do you have driving directions to reach you?), some of these I have pages in our welcome packet for (i.e. How does the washing machine work?), some of these I have Slowtalk for (i.e. What is the best credit card to use when travelling?), some of these I have local friends for (i.e. Where does one buy an accordian, anyway?).  And some of these I am gradually trying to answer here on my blog, which is why there is a drily-yet-concisely-entitled category called Trip Planning Tips for Umbria.

umbria italy

Among the most common travel advice guests require is help in planning an itinerary for Umbria, which is also one of my favorite questions to answer.  Here is a two week long suggested itinerary for visiting Umbria which throws in the crème della crème of the region:  art and history, towns and parks, food and drink, people and shopping.  It may not suit everyone, but feel free to use it as a guideline for planning your trip.

A couple of caveats:

Two weeks is the minimum amount of time you will need to properly visit Umbria, but I recognize that travellers have minor inconveniences like Jobs and Families which restrict their holiday time.  If you are only here for a week, check for a seven day itinerary here.

I am writing primarily for my guests, so I presume your base is Brigolante or, at very least, Assisi.  If you are staying in another town in Umbria, you will have to make some adaptations.

I presume you have a car.

I am neither for turtle nor hare travel, so each day has enough to keep you busy, with enough time left over to add/linger/meander/get lost/come home and relax.

Day One:  It’s Sunday so it must be Gubbio

Yes, I know you are chomping at the bit to visit Assisi, but believe me, Sunday is not the day to do it.  This is the most crowded day of the week, when day trippers from Tuscany and Rome fill up the parking lots and churches.  In fact, not only do I suggest you avoid visiting Assisi proper…I suggest you avoid driving through town altogether.  Instead, follow the winding provincial highway 444 from Brigolante to Gubbio (make sure to enjoy the beautiful drive through the Appennine foothills between Assisi and Gubbio).  This archetypical medieval walled town is a perfect place to begin to get to know Umbria.  Its roots are steeped in the ancient Umbrii people (the town houses the most important example of the Umbrian language on the Eugubine Tablets in the Civic Museum), passes through Roman civilization (there is a wonderful view of the town from the Roman Theatre in the valley below), and remains largely architecturally frozen in the middle ages.  Be sure to dine on truffles while you’re there, and work off your hearty lunch with a climb  (or, if you’re feeling lazy, the funivia car…no one will ever know) to the top of Mount Ingino where you can visit the sanctuary dedicated to Gubbio’s patron saint and enjoy the amazing views from the Rocca fortress.

Day Two:  It’s Monday so it must be Assisi

Ah, now we’re talking.  Assisi can get crowded with coach tours from late morning through the afternoon, so get yourself to the Basilica of Saint Francis as early as you can to enjoy the view, the church, and the famed frescoes virtually to yourself.  From here, leisurely spend the rest of the morning exploring the town (don’t miss the Roman temple in the Piazza del Comune and the surprisingly lovely museum under the Cathedral of San Rufino) and partaking in a little Italian culture by having a slow lunch.  In the afternoon, climb up to the dramatic Rocca fortress (be sure you make it to the “highest room of the tallest tower” for the best photos of your holiday), then hop back into the car to visit San Damiano and the Eremo delle Carceri.  These two shrines will give you a much better sense of who Francis was as a man and Saint than his opulent basilica ever can.  If you are a sunset person (I’m a sunset person), continue along the road past the Eremo to the top of Mount Subasio.  A little luck, the right weather, and a bottle of wine may just be the perfect storm for one of the most stunning sunsets of your life.

Day Three: It’s Tuesday so it must be Nature

You’ve had two towny days, it’s time to see the other side of Italy’s Green Heart:  her lovely parks.  Umbria has seven regional parks and one national park…a surprising number for one of the smallest regions in Italy.  You’ve already visited one of the regional parks…in fact, you’re sleeping in one as Brigolante is within the borders of the Mount Subasio Park (as is the entire town of Assisi).   Today I suggest you go further afield and visit one of the other parks in the region:   the Sibilline National Park with its breathtaking Piano Grande plateau.  There are a couple of hiking trails of varying difficulty—make sure you take a good map—or you can simply take a scenic drive along the spectacular winding road through the plateau, which is bloom from May to July but gorgeous all year round.  I also suggest you work in a visit to delightful Norcia (don’t waste your time with Castelluccio, which is much prettier from afar), a pretty town known as a foodie mecca for its tradition of truffles and charcuterie.  Ristorante Beccofino in Piazza San Benedetto is a perennial favorite for lunch or dinner.

Day Four: It’s Wednesday so it must be Perugia

Umbria’s provincial capital may seem daunting, with its modern suburbs surrounding the historic center, but don’t be put off.  Find your way to the Piazza Partigiani parking lot and take the series of escalators passing through the underground ruins of the medieval alley of the city, which now form the foundations of the modern city above.  Have a good guide on hand; Perugia is full of interesting churches, monuments, and museums.  My favorites are the Galleria Nazionale dell’Umbria and San Francesco al Prato.  After lunch and a post-prandial stroll  (and a caffè and pastry at Pasticceria Sandri on the Corso),  take the afternoon to discover Umbria’s amazing array of artists and artisans who, for centuries, have produced some of the highest quality wares in Italy and the world.  Many, including my two favorites Laboratorio Giuditta Brozzetti, which hand-looms traditional Umbrian fabric and Laboratorio Moretti-Caselli, which paints stained glass, are workshop-museums where five generations of artists have occupied the same artelier.  Others, listed here, offer visits to their workshops.  There is no better way to return home with both a unique souvenir from Umbria, and an understanding of the region’s rich artisan culture and history.

Day Five:  It’s Thursday so it must be People

You’ve seen the towns (and the City), you’ve seen the nature.  Now it’s time to see the people.  Unfailingly, my guests name the day they took a tour and/or course as their most memorable day in Umbria and I can’t speak highly enough of some of the guides and instructors in this area. When you spend time with someone familiar with the local history and culture it gives you a chance to really get to know Umbria and its people in a way you wouldn’t be able to by simply visiting monuments. So plan a day preparing a traditional meal with a local cooktouring the small family-run vineyards, learning to hunt truffles (and how to use them in the kitchen), or painting your own majolica ceramics.  Alternately, get under the skin of a town or area with a knowledgeable guide.  I especially like Discovering Umbria for food and wine tours, and native Umbrians Marco Bellanca ( and Elizabetta Federici ( for cultural visits.  You won’t regret it.

Day Six: It’s Friday so it must be Todi and Orvieto

I can’t possibly send you home without having seen Orvieto’s cathedral.  It is, simply put, one of the most stunning churches in Italy.  You will be tempted to stop in Todi first, as it’s just off the highway, but push on to Orvieto passing along the banks of tranquil Lake Corbara.  Once there, first book your time for the Orvieto Underground tour in the Piazza del Duomo’s tourist office, then backtrack to visit the sumptuous Duomo.  Explore Orvieto under- and above ground, don’t miss the curiosity of San Pietro’s well, and make sure you have some excellent local white wine with your lunch.  Afterwards, head back to Todi and spend the afternoon in the small but surprisingly cosmopolitan center of this friendly hill town.  Take in the fabulous view over the surrounding rolling hills from the small public park along Via Ciuffelli and the quirky contemporary art boutiques in the center.  Have dinner here, because it’s an easy highway drive back to Assisi.

Day Seven: It’s Saturday so it must be Spello

One of my favorite towns in Umbria is Spello, which has much of the charm of Assisi with about 1/100th of the tourists  Yesterday you had a pretty long day that involved a bit of driving, so today you only need to be in the car for about 20 minutes. Spello is the next town over from Assisi along the S75 highway, though I suggest you take the old frontage road, which passes in front of Villa Fidelia—the Italian garden is worth a quick peek—and the much more interesting 11th century San Claudio church, whose delightfully off-kilter facade and elegant Romanesque interior has made it one of my off-the-beaten-track favorites (though you have to be damned lucky to catch it open to visitors).  Once in Spello, don’t miss the Pinturicchio frescoes in the Cappella Baglioni and the impressive Roman Porta Venere.  If you’ve been holding out to have a special meal, today is the day.  La Bastiglia, a four star hotel with an equally wonderful restaurant at the top of town, is one of the best restaurants in Umbria.  If the weather is nice, you can book an outdoor table overlooking the olive grove covered hills, or eat inside in the elegantly rustic (or is it rustically elegant?) dining room.  A meal to remember.  Otherwise, Spello is peppered with casual, friendly wine bars (my favorite:  the unfortunately named Drinking Wine) where you can have a light meal and wonderful vino.

Day Eight:  The Day of Rest

Even God himself kicked back once a week, and (if I may remind you) you are on vacation, after all.  So after a week of high powered touring, take it down a notch for today.  Catch up on your laundry, hang out in the garden and power your way through one of those books you packed, grab our maps and hiking information and take a walk through the countryside around Brigolante (you can pick up the famous Franciscan trail virtually from our front door, or simply follow the road uphill past vineyards, olive groves, and pastures until you get to Costa di Trex at the top).  Slow down and enjoy the passage of time.  After all, as the great James Taylor once said, that is the secret of life.

Day Nine:  It’s Monday, so it must be Lake Trasimeno

You’ve been landlocked for over a week now, so now it’s time to head to water.  You’re back on the road again, but don’t panic because Lake Trasimeno is an easy 45 minute highway drive.  Castiglione del Lago is a lovely town to visit, and from there you can take the regular ferries to Isola Polvese or Isola Maggiore in the middle of the lake.  Trasimeno is a mud-bottomed lake and—frankly–not one of my favorite places to swim, but there are certainly pretty sandy beaches near Tuoro and Passignano if you want to stretch out and enjoy the view (notice how the countryside has become more gently rolling as you near the Tuscan border).  One of my favorite spots for dinner in Umbria is Rosso di Sera in San Feliciano, where you can enjoy the beautiful sunset over the lake.

Day Ten:  It’s Tuesday, so it must be Spoleto

One of my favorite places in Umbria to have a quiet drink is the Bar Tric Trac in Piazza del Duomo…if you manage to get there when the sun is setting and the swallows are circling the Duomo’s stately belltower, you are in for a golden Umbrian moment.  Austere Spoleto was saved from centuries of provincial backwaterism by the world reknowned fine arts festival Due Mondi, and now is center to a thriving cultural scene. Don’t miss walking across the dizzying medieval Ponte dei Torri acqueduct which spans the Tessino ravine more than 80 meters below.  As the wind makes the grass in the meadows below move like waves in a green ocean, stand near the edge, spread your arms, and understand for just a moment what it must feel like to take flight.  (But not too near the edge…this towering structure is one of the top destinations for spurned lovers who have decided to meet their maker.)  On your way home, take a minute to stop at the delightful Fonte del Clitunno and nearby Roman Tempietto.

Day Eleven:  It’s Wednesday, so it must be the Valnerina

I have often waxed lyrical about the Valnerina, because this dramatic corner of Umbria inspires waxing.  Today you will explore the Nera River Regional Park, winding your way along highway SS209 which skirts the Nera river and runs under steep mountainsides where tiny hamlets perch precariously.  Stop by the beautiful Marmore waterfalls and the gorgeous San Pietro in Valle abbey (check their quirky opening hours carefully)…two of the best kept secrets in Umbria.  Visit some of the creche-like villages along the river valley:  Arrone, Vallo di Nera, Scheggino, Sant’Anatolia di Narco, Cerreto di Spoleto.  You won’t be so much scratching your head as to why these towns are so empty, but more likely surprised that these miniscule, remote centers are still inhabited at all.  If you are drawn to the truly strange and wonderful, visit Ferentillo’s mummies or Castel San Felice’s 12th century San Felice in Narco church, where the facade is decorated with a bass relief of the Saint ridding the locals of a troublesome dragon.  We call it an allegory today, but if you visit the Valnerina on one of her more brooding, misty days the presence of a dragon doesn’t seem so farfetched.

Day Twelve:  It’s Thursday, so it must be People

I know, I know.  I keep harping on the People thing, but I know of what I speak.  I can’t encourage you enough to take the time to really under the skin of Umbria with a knowledgeable instructor or guide.  If there was something that caught your eye from Day Five (the most common combination with my guests is a wine tour one day and a cooking class another day—we must really attract foodies here), go ahead and consult that list again.  Otherwise, there are some wonderful area guides who offer itineraries that would be hard to reproduce without their insider expertise.   I especially like American Elizabeth Wholey’s Artisan Tour, Anne Robichaud’s (another American) FestaTours, and native Umbrian Alessandra Pettinelli’s Underground Tour.  You won’t regret it. Again.

Day Thirteen: It’s Friday, so it must be Bevagna and Montefalco

Okay, I was kind of stuck on Friday because it’s the last guaranteed day of daytripping (some of you won’t be able to squeeze in your last visit somewhere on Saturday because your spouse pounced on cheap airline tickets while late-night online surfing nine months ago and didn’t notice until it was too late that it involved being at the Rome airport at 4 am tomorrow) and there are still about 50 wonderful things to visit.  See caveats.  But I couldn’t in good conscience send you home without getting to know two of my favorite villages in Umbria:  Bevagna (the perfect town to visit if your calves are aching; it’s in the valley!) and nearby Montefalco (perhaps my favorite small town in Umbria.  Art, architecture, food, wine, views, textiles…Montefalco is all that is wonderful about this region in one convenient little package.)  Start in Bevagna, making sure not to miss the medieval workshops, and end your day in Montefalco, from where you will certainly want to watch the sun set over the Umbrian valley.  I love L’Alchimista for dinner.

Day Fourteen:  It’s Saturday, so it must be Your Bucket List

This is your last day, and a bit of a wild card since you may have all the time in the world or you may have to make a dash to your next destination.  Fill this last day/half-day/quarter-day/final two hours by choosing one thing off your Umbria bucket list that you didn’t get to earlier.  Some suggestions:  choose one of the Most Beautiful Villages in Umbria in which to say goodbye to this enchanting region;  head to Deruta if you are interested in seeing this famed artisan majolica production; take a tour of the Perugina chocolate factory on the outskirts of Perugia and stock up on Baci for home; check out the Roman ruins of Carsulae near Narni; if you have the stamina for one more church, work in Lugnano in Teverina’s Santa Maria Assunta or the moving Madonna del Bagno near Casalina.  You’ve come full circle–from your first Umbrian town to your last, with the best of the region along the way.  May you bring back a little piece of Italy’s Green Heart in your own.  This is not goodbye, but arrivederci!


  1. Jane |

    Rebecca, what an excellent gift this is to your guests (well, others, also.) You have guaranteed a wonderful Umbria experience to anyone who trusts you and follows your guide. And…I am really looking forward to our short time with you next summer. Will send dates soon.

  2. Lisa Barr |

    I just wanted to take a moment to tell you how much I have enjoyed your writing over the years, first through Slow Travel and more recently, your blog and various guest sites. We have been traveling in Italy for 20 years now, with plans to return as soon as able. Having spent two weeks this summer in Umbria, I especially enjoyed looking at your itinerary with a more informed eye. We just did our first “big group in a villa” trip–14 people in all–so Brigolante wasn’t large enough for all of us, but we want to spend more time in Umbria, and will keep you in mind for our next family trip. (We also know Lynn and Joe Guardino, who recently stayed with you.) Meanwhile, do keep writing–you have many fans back here, and if I can’t actually be in Italy, I can still read about it, especially from someone with a nuanced understanding of the country and a fair measure of wit. Happy holidays.

    • rebecca |

      Lisa, I can’t tell you what a pleasure it was to receive this note! Really, you made my day (week, month, etc) and if you do make it back to Umbria please get in touch so we can at least meet for a cappuccino. Thanks, again, from the heart….

  3. Dave |

    Hi Rebecca,

    This is a superb itinerary, which I ‘followed’ on a recent trip to Italy. You may mention this elsewhere, but as you know the stop in Orvieto ought to include an attempt by visitors to see Luca Signorelli’s frescoes in the Cathedral. Michelangelo himself travelled on foot and by horseback from Rome (1508, age 33) to study them before commencing work on his Sistine Ceiling, such was the more senior artist’s reputation at the time. [Luca worked on his masterpiece 1499 – 1502, finishing at age 56.] While these frescoes contain some gruesome scenes they are stunning to behold. His work on the lower walls themselves reveal some accomplishments unprecedented in the history of art – a must see.

    • rebecca |

      Dave, I can’t tell you how happy I was to hear you followed the itinerary and were pleased with it! I wholeheartedly agree with you regarding the Signorelli frescoes (which, by the way, were recently restored so even that much more stunning)…so much is said about the breathtaking facade and little about the fabulous art inside! Thanks again, Rebecca

  4. Greg Aikey |

    Gubbio was fantastic – and not crowded on a Saturday. The city has that wonderful feel attained by having extremely well cared for historic buildings. In general, the stairways and side streets in these historic cities – Gubbio, Assissi, Montefalco, etc. – were so much fun to photograph.

  5. Greg Aikey |

    Rebecca, thanks so much for all the wonderful advice on visiting Umbria. I planned a good portion of our trip’s activities around your recommendations. As you can see from my various posts, both my wife were thrilled with your advice. You hit it out of the park!