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Tuscany and Venice, air/6 nights, from $699

Explore the picturesque hills of Tuscany, dotted with olive groves and vineyards, and then stroll along the mazelike streets and storied bridges of Venice.

The Real Deal: Round-trip airfare on an Alitalia carrier (arriving in Florence and departing from Venice); four nights at Fattoria degli Usignoli about 17 miles outside Florence; two nights at Hotel Plaza Venice-Mestre in Venice; two breakfasts in Venice; a midsize manual-transmission rental car for the week with unlimited mileage, from Autoeurope; rental car insurance; fuel surcharges; and hotel taxes, from $699 per person—plus taxes of $115–$150.

When: Nov. 2, 2009–March 21, 2010; add $60 for Nov. 21–28, Dec. 16–Jan. 6, Feb. 14–21; $240 for travel in September and October 2009.

Gateways: New York City; add $20 for Boston; $90 for Chicago, Miami; $102 for Houston; $173 for L.A.; $185 for Seattle; $188 for Denver; $191 for Phoenix; add-on rates may vary, and additional gateways are available.

The fine print: Taxes are an additional $115–$150 per person, depending on airline used. Based on quadruple occupancy; add $100 per person for triple or double occupancy; not available for solo travelers. Read before you book any Real Deal.

Book by: No deadline; based on availability.

Contact: Dooley Vacations, 877/331-9301, .

Why it's a deal: According to a recent search on Kayak, the lowest multicity fare— from New York City to Florence, and from Venice to New York City—was $594 with taxes for travel in early November (multiple carriers).

For an additional $220, the Dooley Vacations covers international airfare as well as six nights' accommodations, two breakfasts, a rental car for a week, fuel surcharges, and all taxes.

More: Upgrade to an automatic-transmission car for an additional $100 per person, which also gets you a wine-tasting tour at a historic villa. You can add a morning tour of Florence for $79 per person. Extra nights at the Hotel Plaza Venice-Mestre are $100–$150 per person per night, depending on season.