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assisi umbria italy

Explore Umbria: Italy's Hidden Gem

June 24 - July 1, 2023

Starting at $3,685/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 stunning villa: a renovated 11th century church and 18th century farm house nested amongst hills in a peaceful valley, surrounded by meadows, woods, vineyards and olive groves.

Limited to 10 Guests and Guests 21+ years of age only



Benvenuti in Italia

Day 1: June 24

  • Arrive in Rome

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

  • Group dinner


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



Day 2: June 25

  • Chef prepared breakfast

  • Morning at your leisure

  • Lunch & wine tasting

  • 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: June 26

  • Chef prepared breakfast

  • Truffle hunting

  • 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: June 27

  • Chef prepared breakfast

  • Boating on Lake Trasimeno

  • Lunch near Lake Trasimeno

  • Dinner at Wine Estate Restaurant


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

Villa 17

Pool day

Day 5: June 28

  • Chef prepared breakfast

  • 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: June 29

  • Chef prepared breakfast

  • 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: June 30

  • Chef prepared breakfast

  • 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: July 1

  • Chef prepared breakfast

  • 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 villa living. Let us nip that in the bud right now - our villa is a renovated 11th century church and 18th century farm house.

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 villa sets the barefoot luxury standard for Umbria’s boutique countryside accommodation by pairing five-star urban comfort with rustic rural charm. The property is divided into two structures, the first the ancient church and the second the farm house.

Accommodations in the former farmhouse are all different. All have exposed stone, terracotta floors, wrought-iron beds, a mix of antique and period furnishings, and the perfect combination of memory-foam mattresses and an absence of television that make for a divinely restful night.

Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Umbria Villa
Villa 8
Villa 6
Villa 7
Villa 4
Umbria Villa

Terms & Conditions


$3,685 (USD) per person


Total price includes the following:

  • June 24 - July 1, 2023 (8 days/7 nights)

  • Accommodations (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 service providers and tCE host, and accommodations before June 24, 2023 and after July 1, 2023.


  • 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

    • December 16, 2022 - $1,350

    • March 16, 2023 - 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 December 15, 2022: $500 (Guest Deposit).

    • December 16, 2022 - March 15, 2023: 50% of vacation price per Guest.

    • March 16, 2023 and after: 100% of vacation price per Guest.


This trip is based on a minimum number of persons traveling. If this trip fails to satisfy minimum numbers by December 15, 2022, the trip may be canceled or rescheduled. In the event of cancellation due to not meeting the minimum traveler requirements, you will be notified on or after December 15, 2022 and will have the option to a) apply all fees paid to date to tCE for this specific trip toward a different tCE trip (trip credit) or b) be entitled to cancel your reservation and receive a full refund of all fees paid to date to tCE for this specific trip. Any applicable refunds will be returned to you by tCE via check or refund through the credit card used for payments. In no event will tCE be liable for any direct, consequential, compensatory, incidental, losses (including losses on booked flights), special damages, or any other damages, additional expenses, or amounts of any nature whatsoever as a result of any cancellations. We encourage travelers to wait to book their airfare until on or after December 15, 2022 once the trip is confirmed.


Explore Umbria Request

Please complete the below to express your interest in the Explore Umbria trip (June 24 - July 1, 2023). Please note, by submitting this form, you are not guaranteed a trip booking/reservation. Our team will contact you shortly to review any available options for this trip.

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