$799 – Italy: Weeklong Castle Stay in Umbria incl. Flights

TOP 20 - Sells out quickly!
Amy Thompson
Deal Expert
We love that this offer features flights, car rental and 4-star castle digs — all for under $800.

The Deal

Take a road trip through charming Umbria, a region that boasts olive groves and vineyards but has fewer crowds than Tuscany, with this 7-night vacation that saves over $450 versus similar packages.

Why we love this $799-per-person vacation:

  • Includes a weeklong stay at Relais Il Canalicchio, a 10th-century castle turned 4-star resort with stunning views of the rolling countryside
  • Covers flights, daily breakfast and a manual car rental (automatic upgrade available for an additional fee)
  • Easy day trips include Perugia — an "enchanting" city with "a rambling maze of medieval streets" (The New York Times) -- and Todi, which few places can beat for its "fairy-tale medievalism" (Rough Guides)
  • Explore wine country during peak season — both spring and fall dates are available

Depart: From Boston, Chicago, New York (JFK) and Newark; select dates April-May and September-October (depending on the departure city). +$100 for August departures; +150 for June departures and +$200 for July departures. Los Angeles and San Francisco departures are from +$50; D.C. and Miami departures are from +$100.

Customize your trip: When calling to book, upgrade your hotel rooms, add nights in Rome, the Amalfi Coast or even another European city (including flights), at an additional cost. See Fleetway's trip guide for additional information.

Book by Feb. 26.

* Restrictions may apply. Prices are based on two people sharing a room. Air and hotel taxes are covered, however the Italian tourist tax isn’t included. You’ll pay locally at your hotel upon arrival. Baggage fees vary by airline; check with your reservation agent when booking. Hotels are based on availability and are subject to change.


at Fleetway

When You Can Go

Select departures April-May & September-October


$488 vs. DIY pricing

How to Book

Continue to Fleetway

Visit Fleetway's website to see exact departure dates; call to book.

Book this deal by phone

Call Fleetway at 1-888-996-2127.

  • Monday & Tuesday: 6 a.m. - 5 p.m. ET
  • Wednesday & Thursday: 6 a.m. - 10 p.m. ET
  • Friday: 6 a.m. - 8 p.m. ET
  • Saturday: 6 a.m. - 4 p.m. ET
  • Sunday: 6 a.m. - 5 p.m. ET

About Fleetway

Based in the United Kingdom, Fleetway has 43 years of experience, specializing in vacations across Europe and the Mediterranean. A member of multiple travel associations, Fleetway has worked with Travelzoo since 2005.

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$799 -- Italy: Weeklong Castle Stay in Umbria incl. Flights

Top 20 Deal — Sells Out Quickly