Best Small Group, Gourmet, Walking Tours

​​Best Umbria Small Group Walking Tour - 6 Days/5 Nights
For Active Travelers with a Spirit of Adventure ... Unpack just once! No hotel hopping!

Designed for seasoned travelers, first-time visitors, friends, couples, and solo travelers who want more than an ordinary sightseeing tour, our Best Umbria Small Group Walking Tour features the region's rich heritage through its delectable culinary traditions, precious artisans, hidden hamlets, ancient civilizations, medieval marvels, exceptional wines and so much more. The ultimate in small-group walking tours of Umbria, each day includes options for both walkers and non-walkers.

  • WHEN: 6 Days/5 Nights (See dates below)

  • WHO: Seasoned travelers, first-time visitors, couples, friends, relatives and solo travelers are all welcome on this tour (No single supplement fee!)

  • WHERE: Based at Il Colombaio, a historic, stone Umbrian farmhouse nestled in the countryside halfway between Orvieto and Città della Pieve - with daily side trips to medieval hill towns and castle villages throughout the spectacular green region of Umbria.  

  • WHY: The Best Umbria Small Group Walking Tour allows you to experience this famous region's culture, traditions and people as an insider (not as a tourist!), to learn more about the area's incredible history, artisans, artists, foods and wines, and to form lasting friendships with like-minded fellow travelers and welcoming Italians.

Umbria as an Insider
We live in this part of Italy, along with our Off the Beaten Strada team, and we KNOW Umbria. For more than 15 years we've been traveling and exploring the green heart of Italy, meeting friendly, welcoming Italians who are eager to create and host insider visits, experiences and activities for our guests. As a result, each carefully crafted small-group tour of Umbria allows you to experience an in-depth, insider's view of the region's irresistible traditions, culture and regional specialties.



Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by our private Mercedes Benz van service to the Italian countryside and your characteristic farmhouse accommodations, Il Colombaio. After check-in, and a friendly welcome, you'll have the opportunity to relax and settle in before enjoying a trip orientation and mini-tour of the grounds and historic casale with your Off the Beaten Strada hosts. Afterwards you'll have time to explore on your own before getting together for a cozy aperitivo hour followed by a delicious welcome dinner prepared by the talented Chef Adorno.

Dinner included

  • A Note to History Buffs: Agriturismo Il Colombaio lies just along the border between Tuscany and Umbria, an area rich with layers of history. Go back in time 3,000 years and you’ll find the first Etruscans here, go back 2,000 years and you’ll discover Romans, go back 1,000 years and you’ll witness the construction of castle towns, and go back 500-600 years and you’ll meet master artists who will soon ignite the Great Renaissance! 

Ferry to Isola Maggiore, island exploration walk (for non-walkers lace museum, church and exploring the village center), lunch on-your-own in Castiglione del Lago, castle visit, artisan shops, Panicale gelato stop
Breakfast and dinner included, lunch on your own

  • MORNING: After breakfast we'll make our way the shores of historic Lago Trasimeno where you’ll board a ferry to the charming island of Maggiore. Walkers will enjoy an scenic, explorative walk around the island perimeter, while non-walkers may visit the lace museum, church and explore the village on their own. Afterwards we’ll make our way back to Castiglione, perched along the edge of the lake, where you can enjoy lunch on your own.
  • LUNCH: On your own in Castiglione  
  • AFTERNOON: In afternoon we’ll pay a visit to the town’s regal castle fortress with sweeping views from its ramparts of the historic lake. You’ll also have an opportunity to visit the town’s many artisan food shop for some delicious samples LATE AFTERNOON: We continue to nearby Panicale - with its ancient, twisted olive groves and spectacular views over Lago Trasimeno - for an afternoon passeggiata (stroll) and a stop at our favorite gelateria!
  • EVENING: Aperitivo hour with wine pairings, followed by dinner prepared by the talented Chef Adorno
    • A Note to History Buffs: Lago Trasimeno is the site of the famous second battle of the Punic Wars where Hannibal devastated the Romans encamped there. It’s estimated that 15,000 Romans were killed - many forced into the lake itself - and the strategic ambush is still considered the largest in military history.


DAY 3: CITTA DELLA PIEVE ...Click to View the Complete Itinerary

Behind the Scenes
What makes the Best Umbria Walking Tour so special are the Italians artisans, history buffs, winery owners, pasta makers, herbalists, nature lovers, art experts, culinary enthusiasts and so many others, who welcome our guests like family and generously share their culture, traditions and best-kept secrets. Their vast, first-hand knowledge of Umbria has helped us create the BEST, most culturally rich, small-group walking tour of this region!


  • 5 nights stay in a historic, family-run Umbrian farmhouse accommodation with individually decorated rooms, ensuite bathrooms, elegant restaurant, stunning panoramic terrace, swimming pool, indoor and outdoor lounging areas and so much more. (Note that single occupancy sleeping rooms with ensuite bathrooms are available with no single supplement fee!)
  • Private Mercedes Benz van service to/from Rome Fiumicino Airport upon arrival and departure 
  • Private Mercedes Benz van service to/from all towns and sites included in the itinerary
  • All buffet-style breakfasts with a multitude of delicious choices, plus teas, juices and made-to-order Italian coffee
  • Two delicious lunches featuring regional specialties and accompanied by Umbrian wines 
  • All gourmet, chef-prepared dinners featuring regional specialties and accompanied by Tuscan or Umbrian wines 
  • Ferry ride to/from Isola Maggiore
  • Castle and fortress visit Castiglione del Lago
  • Truffle "hunt" with local tartufaio 
  • Visit and tasting with truffle expert
  • Tour of olive press and private olive oil tasting
  • Vineyard tour and private wine tasting
  • Pasta-making lesson (optional) 
  • Bruschetta -making lesson
  • Guided countryside and village walks (with options for non-walkers)
  • Visits to cathedrals, museums and historic sites
  • Tour of "hidden" 12th century Abbey
  • Organic toiletry products 
  • Entrance fees to all sites included in trip itinerary
  • Daily itinerary overview with Pamela Haack
  • Daily accompaniment with trip host, Pamela Haack, and/or Off the Beaten Strada team hosts or guides
  • Restaurant gratuities

Not Included: 
Airfare, travel insurance, transportation outside of that specifically listed in the trip package. Gratuities for Il Colombaio cleaning and serving staff.

Please note:
Sometimes small changes must be made to the itinerary due to inclement weather, changes in venue or other circumstances beyond our control. Rest assured that any itinerary alterations will be minor.


2018 Dates

Select your preferred dates upon booking.

  • ​April 24-29
  • May 8-13
  • ​September 11-16
  • October 23-28

How to Book

  • Our online booking process is easy and secure. We accept all major credit cards. Should you wish to pay your trip balance by check, please contact us by email at
  • We require a $500 deposit upon booking, $100 of which is nonrefundable, but always applicable towards alternate tour dates should you need to reschedule.
  • Upon booking you may select to either pay a trip deposit of $500 or to pay your trip balance in full.
  • Immediately after booking you will receive a confirmation of your payment and we will reserve your space on the tour. 
  • Beginning 120 days prior to the trip start date, you will be automatically be sent email reminders to pay your trip balance (if you have not already done so). Your trip balance must be paid in full no less than 90 days prior to the trip start date.
  • Click "Book It Now" below, and let's get started! 

Early booking discount SAVE $400 per person - good through August 1, 2017


Please note that a $500 deposit is required to book your space on this tour, $100 of which is nonrefundable, but always applicable towards other tour dates or towards an alternate tour. 





Who should join the Best Umbria Small Group Walking Tour?
Seasoned travelers, Italy first-timers, couples, friends and solo travelers are all welcome on this tour! Although the tour is geared towards those who love to walk, and includes easy to moderate walks each day, optional activities are included for non-walkers, as well.  

Why is this tour offered only a few times per year?
We know from experience that less is actually more. We are committed to keeping our small group tours authentic, so rather than running the same tour over and over again throughout the year (which can feel contrived and less genuine) we choose to run tours only on select dates. This keeps things fresh and special for our guests!  

Where do we meet on the first day of the tour?
Trip participants will rendezvous together for group transportation at Rome Fiumicino Airport on the first day of the tour. Once you have registered for the trip you will receive specifics regarding where and how to meet.

Where and when does the tour end?
On the final morning of the tour our drivers will transport you, along with the rest of the group, to Rome Fiumicino Airport where the trip officially ends. Arrangements can also be made to transport you to a hotel in Rome.

Would you recommend a stay in Rome before or after the tour?
Absolutely! Our guests often extend their stay in Italy with a night - or a few nights - in Rome. We're happy to share a link to our favorite boutique hotel, as well as a top site for booking sightseeing tours. 

What documents do I need to travel to Italy?
A valid passport is required to travel to Italy from the United States or Canada. If you do not have a passport, we recommend that you apply for one as soon as possible. If your passport expires within 6 months of the tour start date, be sure to renew at your nearest passport office.

Should I obtain travel insurance?
Yes, we highly recommend that you obtain travel insurance. If you must cancel your participation in an Off the Beaten Strada tour, retreat or workshop for any reason whatsoever - including health reasons for yourself or a family member at home - cancellation fees will apply. Travel Insurance - specifically trip cancellation insurance - can cover some or all of these expenses.

If you miss a specified group pick-up and transfer due to a delayed, cancelled or missed flight or for any reason whatsoever, you are responsible for arranging and paying for your own transportation to the tour venue. Travel insurance - specifically trip cancellation or trip interruption insurance - can cover some of all of these expenses.

Note: Terms and coverages vary depending on the specific insurance carrier. Carefully check the specified terms and coverages before purchasing your policy. We suggest that you contact your travel agent for recommendations and price quotes. 

How should we dress during the tour?
We recommend packing comfortable, casual clothing that includes breathable fabrics and items you can layer - plus versatile shoes. No formal attire is necessary, however, we suggest smart casual at dinner. No shorts, gym shoes or workout attire at dinner, please. 

What kind of walking can I expect?
From medieval hill towns to countryside lanes, Umbriais a region for walkers! Our tours are designed for active travelers with varied walking abilities and include daily leisure walks in hill towns for all tour participants, along with scenic, countryside walks for avid walkers. For those who enjoy getting in some extra steps, optional additional walks are offered most days. 

Our scenic, countryside walks are rated easy to moderate, are taken at a moderate pace so as to enjoy our surroundings, and include a scenic island walk, village ring walk and olive grove walk. Since we'll be walking on countryside lanes, along vineyards and through olive groves, you can expect dust, dirt, loose stones and uneven terrain. Proper walking shoes are a must. 

For non-walkers, options include shopping, museum visits, on-your-own exploration, cooking lessons and/or leisure time. 

All tour guests can expect to walk in hill towns and villages with uneven, stone pavement and steep avenues, as well as from our Mercedes Benz vans to restaurants, vineyards and historic sites. Our tours are not recommended for those with foot, knee, hip, back or breathing problems, or any other health issues that would impede their participation in the tour.     

What can we expect for our meals?
Italian culture is inseparably entwined with its food, which is why we carefully hand select restaurants, meals and menus for each day of the tour that include the very best regional dishes made of fresh, locally grown ingredients - often organic. Our in-house chef serves up regionally inspired, traditional dishes that just beg to be savored. Our guests rave about the meals!

Are wines included with meals?
Yes, excellent wines are included with all lunches and dinners, with the exception of any meals taken on your own.

What items will be offered at breakfast?
Breakfasts include both Italian and North American selections, such as freshly baked cornetti and marmalade-topped crostate, as well as eggs, cold cuts, cheeses, tomatoes, yogurts, breads and fresh fruit. Gluten free items are also available, along with a wonderful selection of Italian coffees, from espresso to cappuccino to macchiato. 

What are the accommodations?
Accommodations are 
Il Colombaio, a historic farmhouse on the border of Tuscany and Umbria.