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assisi umbria italy

Explore Umbria: Italy's Hidden Gem

August 20 - 27, 2022

Starting at $3,200/person

 Sold Out: Join Our Waitlist 

The Best of Italy

Embark on a special discovery of Umbria, Italy. Known as il cuore verde or “the green heart of Italy," Umbria offers the best of Italy. Picture-perfect towns and authentic villages make you feel as if you’re in a different time period altogether. Rolling green landscapes are broken up only by immaculate vineyards and olive groves. And don’t even get us started on the glorious food and wine!

Umbria is a place where you can do as much or as little as you like. Go wine tasting, hiking, or truffle hunting, or simply sit back and soak up the views from our luxury villa: a renovated 11th century castle perched over one of the most spectacular panoramas of the Tiber Valley.

Limited to 18 Guests and Guests 21+ years of age only



Benvenuti in Italia

Day 1: August 20

  • Arrive in Rome

  • 1:00 p.m. - Transfer will depart at 1:00 p.m. from airport to our luxury villa in Umbria

  • Group dinner


What's included: airport transfer, villa room, group dinner & tips for dinner



Day 2: August 21

  • Breakfast at the villa

  • Morning at your leisure

  • Lunch & wine tasting at Chiesa del Carmine

  • Cooking class & dinner


What's included: villa room, breakfast, lunch & wine tasting, group cooking class & dinner, tips for lunch, cooking class, & dinner


A day of truffles

Day 3: August 22

  • Breakfast at the villa

  • Truffle hunting near Trevi

  • Truffle lunch in Trevi

  • Dinner at villa by our private chef


What's included: villa room, breakfast, transportation to & from Trevi, truffle hunting, truffle lunch, dinner at villa, tips for truffle hunting, lunch, & dinner


Explore Lake Trasimeno

Day 4: August 23

  • Breakfast at the villa

  • Boating on Lake Trasimeno

  • Lunch near Lake Trasimeno

  • Dinner at Il Caldaro

What's included: villa room, breakfast, transportation to & from Lake Trasimeno, boating on Lake Trasimeno, lunch, dinner, tips for lunch & dinner

Lounging by the pool in Umbria

Pool day

Day 5: August 24

  • Breakfast at the villa

  • Relaxing pool day at the villa

  • Lunch at the villa prepared by our private chef

  • Explore and have dinner in Gubbio

What's included: villa room, breakfast, lunch, transportation to and from Gubbio, dinner, tips for dinner


Wines of Umbria

Day 6: August 25

  • Breakfast at the villa

  • Wine Tasting & Tour: Visit wineries & sample the region's wine

  • Lunch during wine tour

  • Dinner at villa prepared by our private chef


What's included: villa room, breakfast, transportation to & from wine tour, entrance fees & wine tasting, lunch, dinner, tips for wine tasting, lunch, & dinner


Discover Assisi

Day 7: August 26

  • Breakfast at the villa

  • Guided Tour: Walking tour of Assisi

  • Lunch on your own in Assisi

  • Italian barbecue in the vineyards


What's included: villa room, breakfast, transportation to & from Assisi, walking tour, dinner, tips for walking tour & dinner



Day 8: August 27

  • Breakfast at the villa

  • Transportation back to Rome

  • 10:00 AM - Depart Umbria for Rome

What's included: breakfast, transportation to Rome

Eat & Drink

Live the Italian life as we enjoy local truffles, learn authentic local recipes, taste wonderful wines, and so much more.

All the Things

Here's an idea...instead of endlessly scrolling the web for experiences, we've actually done all of the work for you. Let us show you the real Umbria.


We get it. You might be anxious about castle living. Let us nip that in the bud right now - our luxury villa is a renovated 11th century castle.

More Inclusive Pricing

That means essentials like accommodations, most meals, basic bevvies, some really cool experiences, ground transportation, and Wi-Fi are included.


The Villa

Our luxury villa is situated atop a hill, overlooking the Tiber valley. This 11th century church and home offers breathtaking views over fields, rolling hills, olive groves, and vineyards. Meticulously renovated in 2019, this historic property boasts a large infinity pool, modern amenities, and well appointed bedrooms.

Villa pool view
Villa entrance
Villa kitchen
Pool view
Dining & living areas
Chapel at Villa
Aerial view of villa
Pool at villa
Living area
Villa views
Outdoor patio
Living Area

The Rooms & Pricing



$3,850 (USD) per person

Loft, King bed, En-Suite with Shower

Terms & Conditions


$3,200 - $3,950 (USD) per person


Total price includes the following:

  • August 20-27, 2022 (8 days/7 nights)

  • Accommodations (Luxury villa in Umbria)

  • One (1) shared villa room . Room options are based on a first-come, first-served basis. All pricing is per person and based on double occupancy. More than 2 people per room incurs additional charges.

  • Ground transportation as detailed in the trip itinerary.

  • Meals as identified in itinerary.

  • Tour experience, entrance, and guide fees Cooking Class, Truffle Hunting, Lake Day, Wine Tasting and Tour, Guided Walking Tour.


Not included in the trip costs are international and domestic airfare, meals on your own, alcohol unless noted, activities planned on your own, tips for lodging staff, and accommodations before August 20, 2022 and after August 27, 2022.


  • Price and availability not guaranteed until deposit is made. Price is in U.S. Dollars.

  • A $500 deposit per person is required to confirm a reservation at the time of booking.

  • A reservation is binding once deposit is made.

  • Deposits are non-refundable.

  • Payment Due Dates

    • Due Immediately - $500

    • March 31, 2022 - $1,250

    • May 20, 2022 - Remaining Balance Due

  • All pricing is per person and based on double occupancy. Solo travelers are welcome to book a room to themselves but must pay a single supplement based on room selection (Please email us at for information on single supplement options). Rooms with more than 2 people incur an additional charge which must be calculated upon request.


  • Cancellation requests must be made in writing to

  • Deposits are non-refundable.

  • Please refer to the Guest Contract for details on cancellations, payments, refunds, and other terms & conditions which are incorporated into this and every tCE trip.

  • Please note, that changes made to overall party size may result in a change to the rate.

  • We highly recommend the purchase of travel insurance. A great resource for comparing options and purchasing insurance is

  • Cancellation Fees:

    • From Date of Deposit through March 30, 2022: $500 (Guest Deposit).

    • March 31 - May 19, 2022: 50% of vacation price per Guest.

    • After May 20, 2022: 100% of vacation price per Guest.


Explore Umbria Request

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