Spend four nights in Chiusi at Villa Il Patriarca, a small hotel that has been restored from its previous incarnation as a patrician house -- a.k.a. home of royalty. Montepulciano, a charming Tuscan hill town, is within driving distance and offers plenty of old cathedrals, art, and churches to view. Italy in November -- when this deal sees its lowest prices -- typically ranges in temperature from the high 50s to low 60s.
Why is this a good deal? A Kayak search revealed that a nonstop flight to Rome starts at $862 per person (with taxes) for the first departure date in November. The hotel's published rates in November, including taxes and breakfast, are $225 per night. The total price for the hotel and airfare, if booked separately, would come to $1,312 per person. A car rental with a manual transmission adds another €211, (about $304 total or $152 per person with taxes), according to an Avis search.
If you booked the hotel, airfare, and rental car separately, it would come to about $1,464 per person. You may be concerned because this is $67 less than the package price ($1,299), which totals $1,531 with air taxes. However, when you consider we haven't factored in the wine tasting, the wine cellar tour, or the dinner at the hotel's on-site restaurant, you're most likely going to come out ahead.
Trip Type: Air-inclusive and independent, with the exception of the wine cellar tour, which is guided.
What the Quoted Price Gets You: Round-trip airfare from New York-JFK to Rome, four nights in a superior double room at Villa Il Patriarca, a five-day car rental, breakfast daily, one dinner at an old Tuscan osteria, an English-speaking guided tour of an old wine cellar in Montepulciano with a special wine tasting, and airline fuel surcharges.
What Else You'll Have to Pay: Airline taxes and fees of about $232 per person
Book By: As soon as possible to ensure availability
When: Nov. 3, 10, 17, 24
Single Supplement: $499
Other Details: Feel like learning something new in the kitchen? Add a two-hour cooking class from $175. You can also extend your stay from $129 per night or upgrade your room to a junior suite (from a superior room) from $99 per person per night, based on availability. Other departure dates are available, too. Rates are highest (from $1,899) in the summer, and drop to $1,399 and $1,499 for much of September and October. If you've saved up your frequent-flier miles, you can book this trip for a land-only price of $899.
All prices are per person and, if lodging is a component of the package, based upon two people traveling together (unless otherwise noted). The prices listed are general starting rates; see "What Else You'll Have to Pay" for details about associated taxes and fees. Base-prices, taxes, and fees can vary based on point of departure and time of travel. Blackout dates may apply. Trip add-ons like sightseeing tours and meal plans may also increase the price. Check with the tour operator for additional gateways and any single supplements, which is the extra cost that a solo traveler would pay to book the deal.