Drinking in the sunset and the Chianti at our friend Marco's farmhouse, we decided that a Tuscany walking tour couldn't be improved upon. Since he's a staunch Tuscan, he surprised us by saying, "Then you've never been to the Cinque Terre." So we went. They're not far, these five once almost unreachable villages that grow out of rock along the Ligurian Sea. For centuries, a connecting footpath was their lifeline, but for us it's the scenic route into a remote and vibrant coastal culture. Beforehand, we spend three nights in the parts of Tuscany we love best…complete with hilltowns that rise out of silver-green olive groves, homemade prosciutto and potato ravioli and the sunny vineyards of Chianti. Throughout, we'll explore the art history, and savor the food and wine. But in the end, will you prefer walking tours in Tuscany or the Cinque Terre? The good news is that because this trip gives you both, you don't have to decide.

DAYS 1-3 - FLORENCE / CHIANTI
We gather in Florence, before a short journey into Chianti leads to a private visit and tasting at one of the famed wineries, followed by a scenic walk to our hotel, a historic home that dates back to the 16th century (3 nights). In the nearby countryside, a walk past silvery olive groves culminates with a visit to a shepherd who shows how he makes sheep's-milk cheeses…and a chance to sample some of the traditional specialties. In the lovely Chianti hills, a vineyard walk ends with a home-cooked lunch and wine-tasting in the private cellars of Castello della Paneretta. San Gimignano, fortified with more than a dozen medieval towers, shimmers in the near distance as we approach along a rural footpath.

DAYS 4-5 - SANTA MARGHERITA
Along the Apuane mountains, we drive to Santa Margherita (2 nights), where our hotel overlooks the Ligurian Sea. By day, we walk to the colorful, isolated villages of the Cinque Terre—Monterosso, Vernazza, Corniglia, Manarola and Rio Maggiore—with time out for shopping or a picnic. (Or skip the walking, and take a little coastal train that runs between the villages.) A magnificent day's exploration includes the tiny monastery of San Fruttuoso reachable only by foot or boat, and is punctuated by a visit of Portofino.

DAYS 6-7 - FLORENCE
Back in Florence (1 night), our evening is capped by a memorable dinner at our favorite trattoria, where in one meal we enjoy the whole tapestry of Tuscan cuisine. Our final day is a glorious stroll that provides an insider’s view of the famed Renaissance city. Wandering through the ancient streets, you’ll see and learn about Brunelleschi’s incredible dome, the Ponte Vecchio, and Piazza della Signoria. We’ll graze through San Lorenzo, the Florentine’s main market, with its pyramids of produce, olives, breads, meats and more. And we’ve arranged for you to skip the long lines to see Michelangelo’s David.