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Great Value Vacations: 110,000+ of our travelers served since 2011
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![Tuscany]()
Roundtrip Flights
Castle Stay
Car Rental
8 Days 6 Nights
Highlights
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A Tuscan Castle Escape: 8 days in the Chianti region with 6 nights at Castello di Montegufoni, a 12th-century castle, or similar.
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Share the Experience: Price is per person, based on a group of 4 travelers. Solo travel is in most cases available for an additional fee.
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Roundtrip Flights Included: Economy-class airfare to Rome (FCO) — carrier and government taxes & fees included.
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Car Rental for Your Stay: Manual-shift economy car for the duration of your trip, with an upgrade to automatic available.
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Explore at Your Own Pace: Florence, Siena, Pisa, and the vineyards of Chianti are all within driving distance.
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Not Included: Breakfast and meals, tours, upgrades, travel insurance, personal expenses, and property fees paid on site.
Travel Dates
Travel window: October 13, 2026 – September 15, 2027.
Book by: November 30, 2026.
Blackout dates: December 13, 2026 – January 5, 2027.
Travel dates, airfare, and inclusions are subject to availability — finalize the booking with Great Value Vacations as soon as possible to secure your preferred dates.
What You Get
Round-Trip Airfare
To Rome (FCO) from your choice of departure city
6 Nights in a Castle
Castello di Montegufoni, or similar
Car Rental Included
Economy car for the duration of your trip
Tuscan Countryside
Rolling hills, vineyards & medieval towns
With over 110,000 travelers served since 2011, Great Value Vacations handles the logistics so you can focus on the adventure. Choose your departure city and travel window, then get ready to explore the castles, countryside, and vineyards of Tuscany.
How To Book
1
Get Your Voucher
Purchase your voucher — one per person (4 or more). Pricing is based on a group of 4 travelers; solo travel is in most cases available for an additional fee.
2
Contact Tour Operator
Visit the Great Value Vacations special offers page, find your deal, then confirm your travel dates and departure city and enter your Groupon voucher code at checkout — or call (800) 495-4903 to book by phone (12:30–9pm Sat–Thu; 12:30–6:30pm Fri EST).
3
Finalize Your Booking
Once your booking is confirmed you will receive an email confirmation with your booking number and a direct link to Great Value Vacations' Traveler Portal where you will find important information and your travel documentation.
4
Receive Your Documents & Enjoy!
Your travel documents can be downloaded from the Traveler Portal from the time of booking up until 72 hours prior to departure. Everything is taken care of — just pack your bags and get ready for an unforgettable vacation to Tuscany.
Your Itinerary+
This is a suggested itinerary; sightseeing and activities are at your own pace and are not included unless listed in What You Get.
Your Hotel+
Castello di Montegufoni ★★★★ or similar
Montespertoli, Tuscany, Italy • 6 Nights • Standard Room (Room Only)
A beautifully preserved 12th-century fortress in the heart of the Chianti region, balancing medieval character with Renaissance elegance. Features an on-site restaurant and a swimming pool, about a 20-minute drive from Florence and 30 minutes from Siena.
Departure Airports+
Flights arrive into and return from Rome Fiumicino Airport (FCO). Available departure gateways and starting prices:
Prices shown are the lowest available "from" fares per person. Actual price depends on selected travel dates. Surcharges may apply for holiday-period departures. For departure cities not listed, contact Great Value Vacations.
Optional Tours & Upgrades+
Enhance your Tuscany experience with options available at time of booking:
• Florence Walk and Talk Tour: available to add at time of booking — visit Great Value Vacations for pricing.
• Fattoria San Michele a Torri Wine Tasting: available to add at time of booking — visit Great Value Vacations for pricing.
• Automatic Car Upgrade: upgrade from a manual-shift to an automatic car at time of booking.
• Extended Stay: options to extend your trip, including time in Rome and Venice, are available at time of booking — ask Great Value Vacations for details.
• Alternative Gateway: depart from a city not listed in the offer — pricing will vary; confirm with Great Value Vacations.
• Solo Travel: solo supplement pricing available — visit Great Value Vacations for pricing.
Know Before You Go+
Flights
Cabin class: Basic Economy. This itinerary includes 1 overnight flight. Airfare includes carrier and government taxes & fees. Baggage fees vary by carrier and are not included in the Groupon price.
Routing depends on availability and may include connections; connection count and layover duration vary by gateway and travel date — contact Great Value Vacations for details.
Car Rental
A manual-shift, economy-size rental car is included for the duration of your trip; an upgrade to automatic is available. The drive from Rome to Montegufoni is approximately 2.5–3 hours — be sure to choose a flight that allows time for travel so you arrive in time for check-in.
Check-In at Castello di Montegufoni
Check-in is not available after 6:00pm November through March, and after 7:00pm April through October. If arriving after those times, you must call the property for instructions to get your keys and reach your apartment, but no one will be available to assist.
Property Fees
The following taxes and fees are not included and must be paid directly to the property:
• Cash security deposit of €150 (refundable).
• Mandatory final cleaning fee of €60 for a one-bedroom villa, €70 for a two-bedroom, and €80 for a three-bedroom.
• Local tax of approximately €2 per person, per day for the first six days of your stay — applies only to adults over the age of 15.
• Heating fee of €20 per day for a one-bedroom villa, €25 for a two-bedroom, and €30 for a three-bedroom. Mandatory November through April; in other months, it applies only if the heat is used.
Gratuities, some local city taxes, daily housekeeping, and meals are not included. Fees vary based on accommodation type and are subject to change.
Passport & Visa
A valid passport is required for all travel to Italy. Check travel.state.gov for current entry and visa requirements before your trip.
Currency
Euro (EUR).
Language
Italian is the official language of Italy; English is widely spoken in tourist areas.
Age Requirements
Minimum age to check in: 18 years old.
Children's pricing: pricing will vary — visit Great Value Vacations for details.
Solo Travel
Solo supplement pricing available — visit Great Value Vacations for pricing.
FAQs
Does buying a Groupon voucher mean my trip is booked?+
No — purchasing the voucher does not book your trip. Purchasing a Groupon voucher entitles you to book a 'Limited Time Offer' vacation package at a rate specifically discounted for Groupon customers. After buying, follow the instructions in the How To Book section. Finish the steps as soon as possible to secure your preferred dates.
Are all travel dates available at the Groupon price?+
Not all dates are offered at the Groupon rate. Check the Great Value Vacations special offers page to see eligible dates. If your preferred date isn't available at the Groupon price, you may need to pay any additional amount at Great Value Vacations' checkout or adjust your travel dates.
If the departure dates show a range — how do I select my specific travel date?+
On the partner's checkout page, simply select the month of travel that includes your preferred departure date. You will then be presented with a calendar showing available dates and corresponding rates. Select the date that works for you and at the payment page enter your Groupon voucher code. If the date you selected is more than the Groupon voucher value, you can pay the difference with a credit card.
Can I travel from a different city than listed on Groupon?+
Yes — you can fly from any available airport, not just the ones listed on Groupon. Simply select any departure airport on Groupon and then change to your preferred departure airport at the merchant's checkout. Apply your Groupon voucher and the system will adjust the vacation package price accordingly.
Can I buy a voucher under my name and use it for someone else?+
Yes — your Groupon voucher is not tied to a specific traveler.
What type of rental car is included?+
A manual-shift, economy-size car is included for the duration of your trip, picked up at Rome Fiumicino Airport (FCO). An upgrade to an automatic car is available at time of booking. The drive from Rome to Montegufoni is approximately 2.5–3 hours.
Are meals included?+
No — this package is room only. Breakfast and meals are not included. Castello di Montegufoni has an on-site restaurant.
What time is check-in at Castello di Montegufoni?+
Check-in is not available after 6:00pm November through March, and after 7:00pm April through October. Be sure to choose a flight that allows time for the 2.5–3 hour drive from Rome. If arriving after those times, you must call the property for instructions to get your keys and reach your apartment, but no one will be available to assist.
What is the full cancellation policy?+
Your voucher is fully refundable to your original payment method or as Groupon Bucks until you submit your voucher to the merchant or within 3 days of purchase, whichever comes first. After 3 days and until the deal expiry date ("Book by" date), refunds for unredeemed vouchers are issued as Groupon Bucks. Once confirmed with the merchant, bookings are fully non-refundable and non-transferable unless the optional Travel Protection Plan is purchased at time of booking. All cancellations are subject to penalties; airfare is non-refundable after booking. Please refer to Great Value Vacations' Terms & Conditions for full details.
Fine Print
- Promotional value expires Nov 30, 2026. Amount paid never expires.
- Book by 11/30/26 or promo value expires.
- Limit 1 per person; may buy up to 3 additional as gifts
- Reservation required; travel dates, airfare, and inclusions are subject to availability
- Customers should be aware that if preferred dates are unavailable, Great Value Vacations will work with you to select alternate dates within the advertised travel window
- Additional fees may apply for certain departure dates
- Cancellations may incur penalties unless the Travel Protection Plan (9% of trip cost, including add-ons) is purchased; see full Terms & Conditions
- Airfare is nonrefundable after booking
- Must be 18+ to check in; credit card required at booking and check-in
- Baggage fees vary by carrier; airfare includes carrier and government taxes & fees
- Not all tours are handicapped accessible; contact Great Value Vacations at (800) 495-4903 for accessibility and solo travel pricing
- Passport required for all travel outside the U.S..
- Excluded from the pricing are mandatory fees payable directly to Castello di Montegufoni: final cleaning fee of €60–€80 (based on villa size), local tax of approx €2 per person per day for the first six days (adults over 15), and a heating fee of €20–€30 per day for stays November through April; a refundable €150 cash security deposit is also required
- Fees vary by accommodation type and are subject to change.
- Total price includes all other taxes and fees
- Before international travel, check the State Department for entry/exit requirements and US Embassy for COVID-19 advisories.
- Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.
- Learn about Strike-Through Pricing and Savings
About ✈ Tuscany: 8-Day Castle Stay w/ Air & Car Rental from Great Value Vacations
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