12th Century Tuscan Castle Vacation with Car Rental and Airfare - Montagnana, Italy

9-Day Tuscan Vacation with Airfare and Car Rental from Great Value Vacations. Price/Person Based on Quadruple Occupancy.

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Romantic Tuscan Vacation with Stay in 12th-Century Castle

On this 9-day vacation from Great Value Vacations, you can sample Tuscan wines and cheeses, stand before Michelangelo’s David, and tilt your head in line with the Leaning Tower of Pisa during a stay at a 12th-century hillside castle. We’ve listed some of our favorite highlights below. This vacation includes:

  • Round-trip airfare from New York (JFK), Boston (BOS), or Chicago (ORD)
  • 7 nights' two-bedroom/one-bathroom apartment accommodations in a 12th-century castle: Castello di Montegufoni in the Chianti countryside
  • Manual-shift midsize car rental for the duration (groups of three will receive a compact-size car; groups of one or two will receive an economy-size car)
  • €60 final cleaning fee

View the full itinerary here.

Montegufoni Castle

Montegufoni Castle (Castello di Montegufoni in Italian) is a relic from the 12th century, built just before the Italian Renaissance. Situated amid the rolling hills of Tuscany, the castle is just 14 miles outside of Florence. You’ll be staying on the castle grounds, in an apartment equipped with an en suite bathroom and a kitchenette. From here you can walk into town to purchase the Chianti region’s namesake wine.

The castle has a prized room frescoed by Italian Futurist Gino Severini. The work, known as La Sala delle Maschere, or “the room of masks,” depicts characters from Italian commedia dell'arte masked theater. The castle estate features an outdoor pool and a restaurant that serves authentic Tuscan food prepared with locally sourced ingredients.

Day-Trip Ideas: Florence, Pisa, and San Gimignano

While you’re staying at Montegufoni Castle, hop into the included rental car and check out some of these nearby attractions.

Florence: The birthplace of the Renaissance and one of the world’s most beautiful cities, Florence is just 14 miles away. Climb Il Duomo di Firenze—the Florence Cathedral—to see the city in all its splendor, or marvel at Michelangelo’s David at the Accademia di Belle Arti di Firenze.

The Leaning Tower of Pisa: This world landmark is just an hour’s drive west of the castle. While in Pisa, you can study up on 20 other historical churches or explore the campus of the University of Pisa, which dates back to the 12th century.

San Gimignano: This walled medieval hill town is known as The Town of Fine Towers for its magnificently preserved Romanesque and Gothic architecture. The town is equally popular for its white wine, vernaccia di San Gimignano.

Frequently Asked Questions

How much would it cost to fly from an airport not listed as part of this deal?
Call Great Value Vacations at (800) 495-4903 for additional pricing options from any departure airport not listed on the Groupon Getaways deal page.

Can we extend our trip before or after the promotional dates for the deal?
Yes, for an additional fee you can arrange for that over the phone when you redeem your vacation.

How do I find out if the dates I want to travel are available?
After your purchase, call Great Value Vacations at (800) 495-4903 for the most up-to-date availability.

What happens if I buy the Groupon and my travel dates are not available?
If Great Value Vacations is unable to book the stay you want during the available dates and before the book-by date, Groupon will refund your purchase.

Does my child need a Groupon, and can they stay in my room?
All travelers age 2 and over are required to purchase a Groupon. Different occupancy arrangements can be requested with Great Value Vacations at the time of reservation.

Is the price advertised available on every date?
Airfare subject to availability. Additional fees may apply for some departure dates. Contact Great Value Vacations for details.

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What You Get

  • 15 options available, including departures in May, June, July, August, September, October, November, or December 2014 from New York (JFK), Boston (BOS), or Chicago (ORD)
  • Click here to see all options and departure dates.

Note: all options priced per person and valid for a Travel with a Group package (four Groupons required), or pay an additional fee to travel with fewer than four: $1,000 to travel solo, $300/person for groups of two or three. Read about package structures here.

Policies and Fees

For all options, book by: 4/18/14

  • Cancellation policy and fees: all cancellations subject to fee up to Groupon price unless Great Value Vacations travel insurance is purchased; insurance cost is 8% of trip cost (including add-ons purchased at time of booking). Airfare nonrefundable after booking.
  • Taxes: local tax of €1/person for the first 6 days of your stay not included
  • Additional fees: airfare subject to availability. Additional fees may apply for some departure dates. €25 heating fee per day (if used) not included. Refundable €150 deposit due at check-in.

Read the Fine Print for important info on travel dates and other restrictions.


  • 12th-century Tuscan castle located 14 miles from Florence
  • Driving distance from Siena, Pisa, and San Gimignano
  • Signature restaurant specializing in Chianti recipes
  • Outdoor pool
  • Free WiFi

The Fine Print

  • Book by 4/18/14 or promo value expires
  • 1/person, +unlimited as gifts
  • Reservation required, inclusions/airfare/airline subject to availability
  • Additional fees may apply for some departure dates
  • Fee up to Groupon price to cancel unless Great Value Vacations travel insurance is purchased (cost is 8% of trip cost including add-ons)
  • Airfare nonrefundable after booking
  • Must be 23+ to rent car and 18+ to check in
  • Credit card required at booking/check-in
  • Baggage fees may apply and vary by carrier
  • Airfare includes carrier and government taxes & fees
  • $1,000 fee to travel solo, fee of $300/person for groups of two or three.

Other Details

Hotel Policies

  • Check in: 2:30 p.m. to 6:30 p.m. (€50 fee for late check-ins)
  • Check out: 10 a.m.
  • Parking: free
  • Rollaways: not available
  • Smoking policy: no smoking inside the property
  • Pet policy: pets are not allowed inside the property.
  • Accessibility: handicap-accessible rooms are not available.
  • Room upgrades: not available

Getting There

  • Round-trip airfare is included from New York (JFK), Boston (BOS), or Chicago (ORD) to Rome (FCO). Flight time is approximately 8 hours from JFK, 7.5 hours from BOS, and 9 hours from ORD.

Traveler's Tips

  • A passport is required for all travel outside the U.S.
  • Before international travel, always check the State Department's website for important info on the destination and its entry/exit requirements.
By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.

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