Hilltop towns, ancient walled villages, fortresses, castles, medieval art…L’Umbria è magnifica!

Umbria, Italy

Tuscany’s neighbor, The Undiscovered Green Heart of Italy

An 11-day Cultural Immersion Excursion

Leave USA  April 7* – 18, 2025

*Arrive into Rome earlier to add on Dan and Deb’s exclusive Rome pre-trip. Details below

A journey into Italian culture, history, food, and wine.

First night in Rome and last night in ancient Rome’s port of Ostia

From $2,995

FIRST DEPOSIT upon sign-up.

See LOGISTICS PAGE for details.

Add some days in Rome with Deb and Dan before your Umbria Tour 

The Umbria tour starts in Rome. Why not add days and nights and enjoy the most historic city in the world? We have been to Rome 17 times and have organized many group tours there as well. We will offer you extra pre-trip days in this amazing city, personally led by us. The activities we will lead you to are unknown to most tourists.  And you will get to stay in an 18th century villa hotel! Add 2, 3, 4, or 5 days.. why not?!

                                        Kent and Kelsey on our Croation Coast tour a year plus ago…a great partnership.

We could not be happier!

For the third time we are pleased to partner on our Umbria trip with Kelsey and Kent, owners of Flights Wine Bar in Bend, Oregon. They have joined us twice in the past two years with an 11-day Croatian Coast tour (pictured on the left) and a Puglia, Italy tour.  Kelsey and Kent’s love of adventure and their style of travel mesh perfectly with our vision of immersion experiences. Their knowledge of wine is a valuable addition as well.  We happily extend a special invitation to all Flights patrons. Of course, all of our friends are welcome to join our Umbria tour. 

 Imagine a place of natural beauty, full of wonderful people, excellent cuisine,  unique wines, and unrivaled medieval art on 1,500-year-old castle walls. Imagine immersing yourself in this mythical locale for 9 days, having it permeate your mind, body, and soul in an unrushed journey. Imagine a region free of hordes of Instagram-tourists that have challenged and altered many of the world’s beautiful destinations. Imagine no more. Join Dan and Deb as they share an immersion experience of food, wine, walking, biking, and the dolce vita in the untrampled beauty of Umbria. This journey will be a breath of fresh air and you will come away refreshed and encouraged, knowing that there are still some authentic places remaining in the world to experience.

  • First night in Rome  in an 18th century Villa (up to 5 nights in Rome optional pre-trip) ,  Last night of tour in Ostia, the port of ancient Rome.

  • 8 nights in a 400 year old Borgo 4-star hotel

  • 19 meals included, some wine-paired

  • 2 cooking classes

  • Day-long bike ride on old railroad bed optional

  • Winery visits/ tastings

  • Private charter coach for all transport to/from Rome/Umbria and all daily touring

  • Full-day visits to Assisi and Perugia with tour and free time for lunch and dinner

  • Walking tours of castles and ancient walled villages

  • Accompanied by Dan and Deb. We don’t want to miss one second of this tour!

 Home in Umbria, the centuries-old Borgo Marmotta.

Spoleto Castle with amazing medieval murals.

   Umbria is an ancient region nestled between Rome to the south and Tuscany to the northeast. As with our other favorite Italian region, Puglia, we would describe it as “Tuscany without the tourists at half the cost.” It is a region of stunning mountains and vistas, filled with medieval castles and ancient walled villages. It is mostly known for the gorgeous city of Assisi, named after the animal-loving saint. Assisi is beautiful and you will have a full day and evening to enjoy it, yet Umbria is much more than its famous namesake. The beauty and intrigue lie in the harder-to-find villages and towns that are not included in most tours. Deb and Dan spent a week last spring getting lost. We fell in love with Umbria. We thrive on finding out-of-the-way authentic places that have not become mainstream. This is why we love Puglia (our other Spring 2025 offering) and have done six tours there. The same magical ingredients that make Puglia so marvelous are existent in Umbria..

We came away from our Umbria scout trip with a passion to organize a tour of cultural immersion in this historical, beautiful land. We want to share what we discovered with a small group of like-minded folks who seek the out-of-the ordinary tour experience, who want to absorb as much of the culture and history of a place that they can. If that is you, then join us as we return to See and Savor Umbria.

Borgos are  farm homes from the days of large estate farms. Most date back centuries. Borgo Marmotta has been in Federico’s family for generations. It has been transformed into a gorgeous 4-star resort in the middle of the stunning Umbrian countryside. Federico has agreed to open a few weeks earlier than normal just for our group. We will have the entire property…. all just for us! This will be a unique experience you will thoroughly enjoy.

Umbria has been inhabited for millennia. Ancient castles, fortresses, and walled villages abound as well as many “borgos”.  Borgos are centuries-old homes that were centers of agricultural endeavors. Some of these borgos have been turned into amazing 4-star hotels. We have found a gem of a borgo for our stay. Borgo Marmotta has been in the family of Federico for many generations. This borgo has been transformed into a lovely refuge. It is just large enough for our group. We will be the only ones there. We have procured the entire property. There is a huge bonus: We will stay in Borgo Marmotta the entire 8 nights of our stay. It is perfectly situated for exploring this region of Umbria. There will be daily exploration trips to castles, villages, cities, and wineries, all of which are no further that 40 minutes from Marmotta. The kitchen of this borgo is excellent and will offer up cuisine typical of the region for all of our breakfasts and six of our dinners. We will have two hands-on cooking experiences with the chef. Frederico’s borgo is exquisitely authentic and perfectly located. 

                                                                     You will have at-your-leisure time at the Borgo. Spend some of it here!

Day by day Itinerary for entire Umbria Tour

Day 1 ~ April 7    Leave USA on overnight flight. Arrive in Rome on April 8. Note that IF you are adding on days in Rome on our customized Dan and Deb’s Rome adventure, you adjust the departure date according to how many extra days you are doing. Click link below for Rome details.

Day 2 ~ April 8  Arrive in Rome, take taxi to included hotel night. You are on your own that day and night.

Day 3 ~ April 9   After your included breakfast at the Villa, we will depart on our private charter bus for the start of our Umbrian adventure. We will journey to our first “Wow” moment of the tour, the medieval walled town of Spoleto. The highlight will be our tour of the 1,100 year old castle that has some of the best medieval mural walls in the world. Then our first meal together, featuring food typical of Spoleto at Trattoria del Festival, including wine. After lunch, a short drive for our check in at Borgo Marmotta. Settle in, pre-dinner welcome drink, then our first included dinner at Marmotta.

Day 4 ~ April 10 Off to a charming walled village of Bevagna after a leisurely morning at Borgo. We will leave at @10:15AM arriving at Bevagna at 10:45. You will have some time to explore. At noon, we will have a typical lunch (included in your tour) in Bevagna paired with some local wines. Then we will meet our guide, Maura, for our walking tour. On this tour we will visit some artisans who will show us how medieval merchants made candles and paper! After tour, we head for a stop at Carapace winery, an archctuctural marvel with excellent wine, specializing in Sargentino wine, a must-try! You will be free to purchase on your own a tasting our just buy a glass of what you want. Return to Borgo.

Menu for included wine-paired lunch at the most charming husband and wife owned restaurant EVER!

Antipasto: Potatoes tortino with cheese cream and truffles
First : Cappellacci  (“Hat pasta, typical of the region) 
Second: baked Pork “Porcona”

Included dinner at our Borgo.

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Option, afternoon of Perugia day below:

“Under the Tuscan Sun”… A visit to the village of the movie and a visit to a spectacular winery for a tasting.  $65 

note: Everyone is signed up automatically. If you do not want to participate, you must advise before Jan. 21.

Day 5~ April 11 Perugia is in no way second-fiddle to Assisi. We visited it for the first time on our scout mission and were stunned. The well-preserved medieval buildings replete with great painted murals were beyond our expectations. You will have a guided walking tour of the highlights and then free time. Time for lunch on your own. Then our bus takes us to the Tuscan village of Cortona, made famous in the film Under the Tuscan Sun. On the way to Cortona, we will stop at one of our favorite wineries in all of Italy for a tour and tasting. Upon arrival to the charming Cortona, you will have the remainder of the afternoon to explore on your own. We will return to our Borgo where a fabulous 4-course dinner (optional) prepared by chef just for us will be awaiting you. See trip page for details.

Return to Marmotta @7:00 PM FOR SOMETHING SPECIAL!

DINNER: Federico’s chef at our Borgo has a feast of typical regional delights planned for us. Four courses of amazing!    

Menu   $49*

Typical Antipasto from the region, cold cuts cheese and local specialties

A pasta course: Stringozzi (tipica pasta from Spoleto) with Spicy tomato sauce 

A Meat course: Ginea fowl roll stuffed with cheese and Potatoes cream

Dessert: Tiramisu

No wine included. You order whatever beverages you want.

      *Note: As with all our optional meals, this has been added to your tour. If you do Not want this, simply notify before January 21 and we will remove it from your tour.

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Day 6 ~ April 12    Assisi is the crown jewel of Umbria in many people’s book. Famous for being the home of Frances of Assisi, the animal and nature-loving mystic, lived here centuries ago. A huge cathedral stands at the top of the city in remembrance of him. You will have a guided walking tour of the highlights and then free time. a lot of free time.  Time for lunch, meandering, shopping, sipping wine. Your day, your call.

   At 5:30 we will leave Assisi and  go straight to Restaurante  Palazzaccio, which is about 10 minutes from our Borgo. Debbie and I ate there one night on our scout mission. Two words: charming and delicioso! We will have a three-course meal awaiting our group.  The exact menu t.b.a.  The cost will be around $45 without wine. This is an optional meal, not included in your tour cost. You can of course opt out, but keep in mind that Borgo kitchen will not be available this night. So if you want dinner, you can join us (highly recommended!) or you can dine on your own wherever you choose in a nearby restaurant. You would take a taxi to/from on your own. If you do not want to have any dinner, our driver could return you to Borgo, but it will be a hungry option! Your call. Our take: join us! It is going to be a lovely meal in a lovely family-owned typical restaurante, a definite enhancement to your immersion into all things Umbrian! 

*Note: As with all our optional meals, this has been added to your tour. If you do Not want this, simply notify before January 21 and we will remove it from your tour.

Day 7 ~ April 13   A visit to an olive oil borgo, Marfuga, for a tour and tasting, then off to a beautiful winery Arnaldo Caprai for a tasting with lunch included. Early to Mid- afternoon return to Borgo for free time.  

Included Brogo dinner.

Day 8 ~ April 14  You choose: A chill morning at Marmotta to enjoy the grounds, have a lunch, then a cooking class in the afternoon. Included Borgo dinner that evening.

OR

OPTIONAL BIKE RIDE ALONG ABANDONED RAILROAD BED! If you are a competent bike rider this is for you!  An all-day ride thru gorgeous scenery from Spoleto to Borgo Cerreto, with a lunch along the way. $179 for everything, including lunch. But you must sign up for this before time of final payment, late January. 

Day 9 ~ April 15  We are visiting today one of the most beautiful villages in Umbria: Spello. We will arrive at 10 AM for a walking tour with Maura and a colleague. Then, OPTIONAL addition: a typical wine-paired lunch at LA BASTIGLIA in Spello. It will be on their amazing panoramic terrace.

Cost: $35*    Or you can do lunch on your own. 

*Note: As with all our optional meals, this has been added to your tour. If you do Not want this, simply notify before January 21 and we will remove it from your tour.

After our lunch, you can enjoy Spello at leisure on your own. 

Depart for Borgo late afternoon.  

Special event before dinner: Dan’s daughter Jillian is a level 3 som and she will offer a wine tasting of some of her favorite grapes of the region, right at the Borgo… fun! 

Included dinner at Borgo.

Day 10 ~ April 16     Staying local… Leisurely morning, then a 1.5-mile round-trip walk or short van ride to the 1,100 year old castle/fortress that towers above Marmotta.  We will have a local guide tell us the scoop about this amazing place. Then it is back to Borgo for a lovely picnic lunch with wine on the grounds. Then we will have a cooking class followed by your included Marmotta dinner.

Day 11 ~ April 17  We will say Ciao to Umbria in the morning and will return to the Rome area for our last included hotel night. But here is where it gets interesting! We are going to travel about 20 minutes south of Rome to the port town of Ostia. This was the ancient port for the Roman Empire and the ruins there are awesome. We will do a guided archeological tour of Ostia Antica and then proceed to our 4-star hotel. You will be a short distance from the sea with plenty of good restaurants to choose from for your last dinner of the tour. Cool bonus: Ostia is MUCH closer to Rome airport, with only a 15 minute taxi ride.