The Real Deal: Six nights' accommodations, breakfast daily, and maps and directions for the walking tour, from $1,189 per person—including taxes.
When: Through Oct. 31, 2008.
The fine print: Taxes, breakfast daily, luggage transfers throughout the trip, and maps are included. Estimated additional costs for transportation/transfers throughout the walking tour are €6 per person for bus tickets and, if day three and four fall on a Saturday and Sunday, €20 per person for taxi fare. Based on double occupancy; subtract $110 per person for triple occupancy; single supplement is $410. Airfare is not included. Read these guidelines before you book any Real Deal.
Book by: No deadline; based on availability.
Contact: Air France Holidays, 800/237-2623, airfrance-holidays.com.
Why it's a deal: The $1,189 rate breaks down to about $198 a night, and it includes taxes, accommodations, breakfast, luggage transportation, and access to a local contact person for questions and emergencies. In addition to being able to negotiate lower rates through relationships with various hotels, Air France Holidays will also save you the time it takes to reserve rooms at each stop throughout the tour—which is especially helpful during the busy high season from June through September.
Trip details: The package includes six nights' accommodations at various traditional three-star inns in a room with standard amenities. As no transportation is included in this trip, except for luggage transfers, you'll depend on public buses and/or taxis to supplement your self-guided walking tour.
Maps and notes to help guide you as you explore the Tuscan countryside will be waiting for you at the hotel on the day of arrival. While there is no formal orientation, the tour operator will drop by on the first day to offer advice or answer any questions you may have. The terrain throughout the tour is a mix of dirt roads, rocky paths, and city streets, including many moderate and a few steep inclines and declines.
You'll begin in the medieval town of Siena, 43 miles south of its rival city, Florence. If you arrive early, you can explore historic sites like the Piazza del Campo, the main shell-shaped piazza that hosts the Palio horse race each July and August. You could even squeeze in a climb up its 14th-century tower, Torre del Mangia, which overlooks the terra-cotta rooftops and church spires below. The Duomo and the Museo Civico, where the works of Sienese painters Simone Martini and Ambrogio Lorenzetti are on display, are among the city's other sights.
Spend the night in Siena at the 59-room Hotel Minerva and then take a private taxi ride to a Benedictine monastery, Monte Oliveto Maggiore, where you'll find Renaissance frescoes by Luca Signorelli and Il Sodoma.
Afterward, you'll set out for Montalcino, a small town with a big reputation for its wines (think Moscadello di Montalcino, Brunello di Montalcino, Rosso di Montalcino, and Poggio alle Mura). This is the longest walking stretch of the tour—about six hours—and allows you to take in the semidesert landscape of the Crete Senesi, where the Sienese and Florentines fought at the Battle of Montaperti.
Your two-night stay in Montalcino at the 12-room Il Giglio hotel includes a three-hour hillside hike to the abbey of Sant' Antimo, a French-Lombard-style Romanesque church, followed by a bus ride (or a cab ride, if it's a Saturday or Sunday) back to the hotel.
From Montalcino, proceed on foot for about four hours to Bagno Vignoni, known for a thermal pool where Lorenzo de' Medici is said to have bathed. Spend the night at the Albergo Le Terme hotel before continuing on a nine-mile walk to Pienza, the birthplace of Pope Pius II.
You'll spend the night in Pienza at the 40-room Hotel Corsignano and then take a final three-hour hike to Montepulciano, a Renaissance town known for its Vino Noble. You'll spend the last night at Montepulciano's 51-room Hotel Granducato, and then leave after breakfast the following day.
Air France Holidays gives you the option to extend your stay in Siena for an additional $125 or more per room per night. For more tips on what to do in the area, visit the official Web site of the Italian tourism board.
Getting there: Airfare is not included. We priced out sample fares to Florence, the capital of Tuscany, located about 43 miles from Siena, where the trip begins, and 74 miles from Montepulciano, where it ends. According to a recent search on SideStep, the lowest round-trip fares for a departure in mid-October start at $878 from Chicago, $904 from Houston, $934 from New York City, $1,092 from Miami, and $1,170 from L.A. (all on multiple carriers).