$699 – Italy Weeklong Castle Retreat w/Flights

TOP 20 - Sells out quickly!
Amy Thompson
Deal Expert
Frommer's notes how pleasant the weather is during spring and fall, calling it the best time to go.

The Deal

If you're looking for an idyllic Italy vacation outside the norm, Umbria is the perfect choice. Here's why we love this $699-per-person vacation:

  • The region evokes Tuscan landscapes of olive groves and vineyards but has fewer crowds
  • You'll spend the week at Castello di Baccaresca, a 4-star resort with stunning views of the rolling countryside
  • Easy day trips include Perugia -- an "enchanting" city with "a rambling maze of medieval streets" (The New York Times) -- and Todi, known for its "fairy-tale medievalism" (Rough Guides)
  • Car rental: You get your own set of wheels for 8 days; if you can't drive stick, you can upgrade to an automatic
  • Daily breakfast and dinners are included

Includes: International flights from the U.S.; 8-day manual car rental (automatic car available for an additional fee); 7 nights' accommodations with daily breakfast and dinner; parking.

Depart: From New York (JFK) or Newark, select dates September-March (depending on the departure city). +$100 for April 2020 departures, +200 for May 2020 departures and +$300 for July-August 2019 departures.

Additional departure cities: Boston and Miami are $799; Chicago, Fort Lauderdale, Los Angeles and San Francisco are $899; Oakland and Seattle are $999.

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

Book by June 26.

* Restrictions may apply. Prices are per person, based on two people sharing a room. Local city tax is not included; you'll pay at the hotel.


at Fleetway

When You Can Go

Select September-March dates; varies by city


$450 vs. booking on your own

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 646-417-9945.

  • Monday & Tuesday: 6 a.m. - 5 p.m. EST
  • Wednesday & Thursday: 6 a.m. - 7 p.m. 
  • Friday & Saturday: 6 a.m. - 4 p.m. 
  • Sunday: 6 a.m. - 5 p.m.

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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$699 -- Italy Weeklong Castle Retreat w/Flights

Top 20 Deal — Sells Out Quickly