Trails of Italy: Walking the Vineyards & Villages of Tuscany & Piedmont

Fly overnight to Milan and travel to the town of Alba, set among the vineyards of Piedmont. Wedged between the Alps and the Mediterranean Sea, where cool mountain air meets sunny coastal climates, this region of rippling hills is known for producing some of Italy’s most prestigious wines.  After time to get settled at your hotel just steps from the Old City, gather for a welcome dinner. (D)

Set out on a loop hike through the spectacular vineyards of the Langhe, one of Piedmont’s World Heritage-listed wine regions. Begin by ascending to the hilltop village of Monforte d’Alba, where acclaimed Barolo appellation wines are produced from local Nebbiolo grapes. Hike along agricultural roads, passing medieval castles as well as ciabots, rustic stone shelters long used by Piedmontese vintners, to reach historic Barolo. Transfer to Bra, a hub of gastronomy associated with the Slow Food movement. You’ll have free time to try out one of the town’s excellent restaurants for lunch—gnocchi con castelmagno and panna cotta are local favorites. Return to Alba for a guided walk of the historic center, established by ancient Romans and today a hub of the region’s culinary specialties: fine wines, white truffles, and hazelnuts, as well as Ferrero chocolates, which originated here. Enjoy the evening at leisure. (B)

Hiking: 5 miles on country roads, village lanes, and dirt paths, with some elevation changes

Walking: 1 mile on paved and cobblestoned city streets

Head into the Montferrat wine region, the home of renowned Barbera d’Asti and Barbaresca wines as well as sweeter, sparkling whites. Today’s loop trail begins in the center of Costigliole d’Asti, following cobblestoned streets past the town’s historic castle before hiking country roads through vineyards and timeless hamlets. After your hike, visit a renowned winery for lunch and a wine tasting. Back in Alba this afternoon, enjoy free time to relax at the hotel or go on hikes in the surrounding countryside. (B,L)

Hiking: 6 miles on country roads, village lanes, and dirt paths, with some elevation changes

Journey south past the marble peaks of the Apuan Alps, crossing the Apennines and taking in the scenery as it shifts from Piedmont’s tight patchwork of vineyards to the cypress-topped hills of Tuscany. Along the way, stop in the town of Recco on the Ligurian coast to sample a beloved Italian street food that originated here: a flaky, cheese-stuffed flatbread called focaccia di Recco. Arrive at your home in the Tuscan countryside: a quaint agriturismo near San Gimignano that produces its own wine and olive oil. Enjoy free time to explore your surroundings and gather tonight for a dinner of regional specialties paired with local wines. (B,L,D)

Walking: 1-2 miles on country roads and vineyard paths

Today’s hike brings you through the hills of Chianti wine country, starting in the town of Greve, the center of the Chianti wine trade. Ramble through vineyards and olive orchards to a viewpoint overlooking the fortified village of Montefioralle, once a military stronghold and now designated one of Italy’s “most beautiful villages.” At a family-owned winery in Panzano where fine Sangiovese wines have been produced for 350 years, take a vineyard tour and savor a farmhouse lunch with wine pairings. Then head to the World Heritage-listed hill town of San Gimignano for a walking tour that follows a section of the Via Francigena, a medieval pilgrimage route leading from Canterbury, England to Rome. You’ll have time for dinner on your own in San Gimignano before heading back to the hotel. (B,L)

Hiking: 3-4 miles on country roads, village lanes, and dirt paths, with some elevation changes

Walking: 1-2 miles on paved and cobblestoned village lanes

Begin the day in the 13th-century gem of Monteriggioni, poised on the Via Francigena and considered one of the best-preserved fortified hilltop villages in Italy. Mentioned in Dante Alighieri’s Divine Comedy, Monteriggioni boasts all 14 of its original towers, which circle the hilltop like a crown. Hike a loop trail from the heart of the village through its outer walls and down into the picturesque pastures and farmlands below. Continue to a lookout point that offers stellar views of Monteriggioni’s castle and ring of ramparts. After arriving back in Monteriggioni, you’ll have free time for lunch. Return to the agriturismo for an afternoon at leisure. Toast your journey through Italy’s vineyards at a farewell dinner.  (B,D)

Hiking: 4 miles on country roads, village lanes, and dirt paths, with some elevation changes

After breakfast, transfer to the airport in Florence in time for your flight home. (B)