Crossing Northern Italy - 21 Days

Day 1: Arrive in Venice, Self-Guided City Tour of Venice

Welcome to Venice! Upon arrival, a water taxi will take you from the airport to your hotel as you cruise the Venetian canals. Then start a self-guided walking tour in St. Mark's Square—Piazza San Marco—with its impressive Basilica San Marco (be sure to wear appropriate clothing for entering) plus the 600-year-old Doge's Palace, former home to the ruler of Venice, and the center of government during the Venetian Republic. Next, stroll over to the Grand Canal to view the iconic Baroque-style Bridge of Sighs and Ponte dell'Accademia, offering two of the most picture-perfect vantages of Venice and the canals.

Next, head along the Grand Canal to the Rialto Bridge and Rialto Market to browse this food market buzzing with local flavors (note that it shuts down around midday and is closed on Sundays and Mondays). Then explore the nearby district of Cannaregio, which has traditionally served as Venice's Jewish "ghetto" (made famous in Shakespeare's The Merchant of Venice). From Cannaregio's Fondamenta Nove, you can hop a ferry to Murano Island to witness the famous Venetian glass being made. Finally, head to a bar to celebrate the end of your first day with Italian wine and Cicchetti—the Venetian version of tapas.

Day 2: Guided Walking Tour & Private Gondola Ride

Immerse yourself more deeply in Venice with a walking tour that starts in Campo San Giacometto, an adorable square just a few steps from the world-renowned Ponte Rialto and the Grand Canal. The church here, San Giacomo di Rialtois, is the oldest in Venice (built in 421). At Campo San Bartolomeo, stop to admire the small Church of San Giovanni Crisostomo, with its beautiful altar built by Renaissance artist Giovanni Bellini. Your guide will then lead you through the maze of Venice's small alleyways before you reach Campo Santa Maria Formosa, boasting 11 bridges and numerous architectural masterpieces. 

Returning to magical St. Mark's Square for a grand finale to your walking tour with a classic Venice experience: a private ride in one of the city's world-famous gondolas. Be prepared for romance as you say goodbye to your tour guide and enter your gondola. Enjoy being paddled along the dramatic Grand Canal and the smaller side routes into the city's secret back canals, letting you more fully appreciate the history and beauty of this stunning city.

Day 3: Merano Mountains and Hiking

Day 4: Natural Swimming Bath Gargazon

This morning you can choose another hike in the Tyrolean Alps or through one of the four valleys that radiate out from Moreno. Or follow the easy one-hour Tappeinerweg (Tappeiner Trail), which begins in town and snakes along the hillside of Monte di Merano, offering a fantastic panorama over town. Or you might want to make a tour by e-bike to explore Merano and neighboring villages.

In the afternoon, you can soothe any weary muscles at the Terme Merano, a popular thermal spa with a wealth of indoor and outdoor pools, plus saunas and massage rooms. Or head to nearby Gargazzone, one of northern Italy's most charming villages, known for its massive Natural Swimming Pool of Gargazon, fed by naturally purified spring waters. Spend the balance of the afternoon exploring Merano's historic Steinach quarter, with its perfectly preserved 13th-century city gate and Middle Age facades, and the Portici di Merano shopping arcade, perfect for enjoying gelato and cappuccino in the sun.

Day 5: Stelvio National Park

Merano is the eastern gateway to the world-famous Passo dello Stelvio (Stelvio Pass), one of the most dramatic passes in the Alps for its incredible wall of switchback turns to the summit at 9,045 feet (2,757 m) elevation. Enjoy driving? Then you'll thrill to what is considered one of the best (and most challenging) driving roads in the world. Built in 1820–25, this engineering masterpiece features 75 hairpin bends (48 on the North Face approach from Merano), ending at the summit with an iconic panorama of the snaking road and gorgeous alpine setting below.

The road lies within Stelvio National Park, in the heart of the Central Alps. Pack your hiking shoes to explore the magnificent glacier-scoured wilderness along well-manicured trails that connect mountain farms, alpine villages, and glacial lakes. The Stelvio region is also an all-year skiing destination; a cable car leads from the pass summit to the ski slopes of Livrio. While hiking, keep your eyes peeled for fox, deer, ibex, chamois, and golden eagles. Enjoy the thrilling descent back to Merano for your final night.

Day 6: Visit Garda Lake

Now head south to Italy's largest lake—Lago di Garda—enjoying a mild climate and warm waters at the foot of the Alps. Its shores are graced by old Roman villas, medieval castles and monasteries, and charming villages. Focus your time this morning around Limone sul Garda, named for its lemon groves, on the northwestern shore—the Trentino coast—and popular with leisure boats and windsurfers. Explore this lovely town by walking the seafront promenade, or rent a bike to cycle the 3-mile-long (5 km) cliff-face cycle path suspended over the lake; then either relax or learn to kitesurf at Tifu beach.

Continue south to the twin lakeside town of Toscalano-Maderno, where you can explore such sites as the 11th-century Santuario di Madonna del Benaco church (built atop a Roman temple of Jupiter) and the waterfront Pieve Sant'Andrea church before visiting the majestic Vittoriale degli Italiana, in nearby Gardone Riviera. This bombastic architectural excess was created by proto-Fascist, Gabriele d'Annunzio, with classical piazzas, an outdoor theater, and a huge garden—today, the André Heller Botanical Garden—with water cascades. Continue to Peschiera del Garda for three nights. 

Day 7: Panoramic Cableway of Mount Baldo

The scalloped mountain range—the Prealpi Venete—that rises 6,600 feet (2,000 m) above Lake Garda's eastern shore is dominated by the peak of spectacular Monte Baldo. This morning head to Malcesine, a lovely town perched on a small promontory crowned by medieval Scaliger Castle (well worth your visit), and the Palazzo dei Capitani, with a beautiful garden overlooking Lake Garda.

Next, thrill to a ride on the Funivia Monte Baldo, a revolving cablecar that ascents from Malcesine to the snow-covered peak of Mount Baldo: the 360-degree panorama is memorable! Come prepared for an afternoon spent hiking. Mount Baldo is a popular destination for hiking and mountain biking along trails that fan out from the summit station, at 5,775 feet (1,760 m). You can even descend via a biking trail that augers back down to Malcesine. Feeling truly adventurous or in need of an adrenalin rush? Strap into a paraglider for a tandem flight down to Malcesine with an experienced pilot.

Day 8: Desenzano & Sirmione Walking and Boat Tour

Dedicate today to exploring the historic towns of Sirmione and Desenzano del Garda. Meet your guide in Desenzano and head to Villa Romana—the ruins of a lakeside Roman-era villa (dating from the first century BC) that boasts a well-preserved and vivid decorative mosaic floor, plus a hypocaust (underground hot-air ventilation system), and an impressive museum. Then enjoy a scenic boat ride to Sirmione, a medieval thermal spa town occupying a slender peninsula jutting to Lake Garda.

This afternoon you'll walk Sirmione's narrow and winding cobblestoned streets, stopping to admire such sites as the Church of Saint Maria Maggiore (famous for its painting of the Last Supper by the Veronese artist Domenico Brusasorci) and Villa Cortine, one of many grand villas overlooking the lake. Then, on to Castello Scaligero (Scaliger Castle), built at the end of the 13th century and reached via a moat with a little stone bridge. Finally, you'll visit the Grotte di Catullo, a Roman villa with thermal baths at the peninsula's tip.

Day 9: Bergamo & free relaxing afternoon on Lake Como

Today, head west to lovely Lake Como via Bergamo, stopping here to explore this charming Lombardy town in the foothills of the Bergamo Alps. Walk atop its 16th-century Venetian Walls encircling the upper old town (città alta), then explore the main plaza—Piazza Vecchia—with its 12th-century Palazzo della Ragione (note the arches decorated with animals) and cafés serving gelatos and cappuccinos. Don't miss the marble Cappella Colleoni chapel, the Basilica of Santa Maria Maggiore, boasting an overwhelmingly beautiful interior, and, adjacent, the equally lavish Cattedrale di Sant Alessandro (or Duomo).

After lunch in Bergamo, continue to Y-shaped Lake Como for an afternoon of relaxation. Called "the pearl of Lake Como," the hillside town of Bellagio boasts an ideal position on the peninsula that splits the lake into two. During the next two days, you'll have plenty of time to explore Bellagio and its surroundings, but for now, turn down the dial with some sunbathing by your hotel pool in Bellagio or one of the many beaches that line the lake's shores. Or wander the pretty lakeside promenade and steep stone staircases lined with gelato bars, cafés, and restaurants.

Day 10: Kayak Tour from Bellagio, then Cycle the "Ghisallo"

Marvel at the beauty of Lake Como and the surrounding mountains as you enjoy a guided kayak tour of the serene lake this morning. You'll set out from Bellagio and paddle along Pescallo Bay, passing the Rockefeller cliffs, the manicured park atop Punta Spartivento, and the Grand Hotel Villa Serbelloni, a grand neoclassical hotel surrounded by formal gardens at the tip of the Bellagio peninsula. You can even opt to follow the route on a stand-up Paddleboard, subject to demonstrating sufficient experience and skill. Then it's time to relax by your hotel pool and enjoy a spa treatment.

In the late afternoon, cycle enthusiasts can mount up for a challenging bicycle ride of the Iconic "Ghisallo," the steep climb from Bellagio to the Shrine of the Madonna del Ghisallo that is traditionally the closing stage in the one-day "Giro di Lombardia" cycling race. Mere mortals can choose the much-needed assist of an e-bike, although you can still expect to pedal hard for the four-mile (6.5 km) climb up the peak! You'll explore the Santuario del Ghisallo and the adjoining Ghisallo Cycling Museum before cycling back to the lake.

Day 11: Free day in Lake Como

Today is at leisure for you to explore Lake Como according to your interests. You can opt to drive the perimeter road around the lake, stopping to explore the town of Como, including the 15th-century neogothic Duomo featuring sculptures of Pliny the Elder and the Younger; the late 16th-century Villa del Balbianello, in Lenno; Villa Capressa, with its lush gardens, in Tremezzo; Varenna, a pretty little fishing village with its Villa Monastero and lakeside Hotel Villa Cipressi (with a botanical garden open to the public); and/or the Museo Moto Guzzi, in Crebbo, displaying a century of Moto-Guzzi motorcycles.

Meanwhile, you might like to hop on a public ferry operated by Navigazione Laghi and explore the region from the water or take a guided 2- to 4-hour private taxi-boat tour. Alternatively, if you're feeling sporty, enjoy a few hours of water-skiing, skiff sailing, or kitesurfing or hike the mountains surrounding the lake. A good option is to follow the "Via Crucis" path from Lenno, with fourteen chapels, and end at the Sanctuary of the Madonna del Soccorso, a more demanding yet easy hike, is along the "Lariano Trail" on Mount Bisbino, above Cernobbio.

Day 12: Discovering Lago Maggiore

Next, head to Lake Maggiore for three nights in Stresa. The least crowded and most peaceful of northern Italy's lakes, sinuous Maggiore protrudes north into Switzerland. Stresa, on the lake's western shore, retains an elegant aura of the region's bygone late-19th century belle-époque decadence, when it was favored by bohemians from throughout Europe.

Upon arrival in Stresa, take the balance of the day to relax. Perhaps enjoy lazing by your hotel pool, indulge in a spa treatment, or take a stroll along the delightful waterfront offering fabulous views over the Gulf of Borromeo and the three Borromean Islands. Or you might want to take a water taxi to Reno to explore the Ermo Santa Caterina del Sasso, a 12th-century hermitage perched on the cliff face overlooking the Golfo di Borromeo.

Day 13: Knowing the Borromean Islands

Gazing out from the Stresa shoreline, the view is dominated by the three isles of the Borromean Archipelago: picturesque Isola dei Pescatori, the "floating" botanical garden of Isola Madre, and well-named Isola Bella. Madre and Bella are still owned by the Borromean family, who, since acquiring the isles in the 14th century, adorned them with lavish palaces and gardens. Explore the isles on a private guided tour by boat today, beginning with Isola Bella and its magnificently Baroque Palazzo Borromeo, surrounded by palazzos and terraced gardens enhanced by classical statues and shell-covered grottoes.

Then glide over the waters to Isola Madre to roam its romantic garden, with its tall cypresses, topiary art, and a menagerie of avian species: white peacocks, golden pheasants, and (in the "House of Birds") parrots and songbirds. Finally, visit Isola dei Pescatori ("Fisherman's Isle"), the only continuously-inhabited island. Wander the narrow alleys and climb the steep rock stairs of this charming hamlet of stone houses (with upper balconies traditionally used for drying fish) and the Chiesa de San Vittore chapel. Dine on fresh-caught seafood at one of the idyllic lakefront restaurants before returning to Stresa.

Day 14: A Private Tour around Lake Orta and its Mounts

Overshadowed by its larger neighbors, little Lake Orta is relatively overlooked, and being just over a mile (a few kilometers) west of Lake Maggiore makes for an enjoyable excursion. Today's private guided tour begins with a hotel pick-up for the short drive to Orta San Giulio, a charming medieval fishing village whose narrow alleys spill into Piazza Motta. After exploring this lakeside gem, hop on a water-taxi for Isola San Giulio, a lovely little island topped by the Basilica di Orta. Dating back more than a millennium, it boasts superb frescoes and even a fossilized vertebra that legend says were those of a dragon slain by San Giulio.

After a lakeside lunch, you'll get to marvel at the panoramic view over the lake from the heights of the Sacro Monte di Orta (Holy Mount of Orta), a religious sanctuary (and UNESCO World Heritage Site) that you'll hike to along an ascending path dotted with 21 baroque chapels. Dedicated to Saint Francis, it dates back to the 16th century. Return to Stresa for the balance of the day to relax at leisure.

Day 15: Cinque Terre Trekking & Train Card, Hike Monterosso to Vernazza

Today head south to the Ligurian shore for four days exploring craggy Cinque Terre National Park, named for five small villages: Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore—connected by a dense network of coastal paths considered a paradise for hikers. You'll use the Cinque Terre Trekking & Train Card, which gives you free access to the hiking trails, unlimited train travel on the Cinque Terre Express trains on the Levanto-Cinque Terre-La Spezia line, plus local buses, reduced-price museum entry, and even guided tours.

The entire coastal trail, the "Blue Trail," between Monterosso and Riomaggiore is only about 7 miles (11 km) and can easily be done in one day, with stops at one or two villages along the route. However, the dirt trail (very dusty and hot in summer) involves a lot of steep climbs and descents, including staircase steps. Instead of tackling the entire distance at once, you can break the hike into smaller sections, combining short 1- or 2-hour hikes daily with other activities, completing the entire trail in stages.

• Monterosso–Vernazza (2 miles/3.5 km)
  
• Vernazza–Corniglia (2.5 miles/4 km)
  
• Corniglia–Manarola (2 miles/3 km)
  
• Manarola-Riomaggiore (1 mile/1.5 km)
  

Begin day 15 upon arrival in Monterosso, where after settling in your hotel, you can lace up your sneakers or hiking shoes (no sandals are permitted) for an afternoon hiking to Vernazza, where you can reward yourself with a delicious gelato at a seafront café.

Day 16 - Cinque Terre Trekking & Train Card; Swimming, Snorkeling & Boat Tour 

This morning you can take the train to Vernazza and hike along the coastal trail to Corniglia, the only one of the five towns that perch atop the cliffs. En route, you'll pass through many terraced vineyards. After a de rigueur gelato in Corniglia, descend the broad "Lardarina" staircase to the Corniglia train station for the return journey to Monterosso.

Spend the afternoon swimming and snorkeling (or scuba diving) in the warm waters of the Ligurian Sea, where exotic marine life is protected within the Cinque Terre Marine Reserve. Cliffs overhang the shore for most of the Cinque Terre coast, but Monterosso has two sandy strips suitable for sunning and bathing. Then enjoy a tour by traditional gozzo fishing boat along the coast, perhaps stopping at one or two of the villages. You might even opt for a romantic sunset sailboat trip.

Day 17: Cinque Terre Trekking & Train Card, Pesto Cooking Class

Regional Ligurian cuisine may not be well known outside Italy, except for being the home of pesto sauce, which originated in Genoa around the 16th century. Today, learn all about the secrets of Ligurian cuisine with a Cinque Terre food and wine tour that includes a one-hour cooking class. You'll pick your ingredients from a vegetable garden, then learn how to create local dishes, including using crushed garlic, basil, and pine nuts blended with Parmesan cheese and olive oil to make pesto sauce. Now enjoy your creation with fresh bruschetta and a platter of cured meats and cheese, plus a glass of local wine.

Your class with two engaging young Italian cooks will take place in Manarola, perfectly positioned for you to work off the calories by hiking the Blue Trail to Corniglia (or even as far as Vernazza), from where you can catch a bus or train back to Monterosso. 

Day 18: Cinque Terre Trekking & Train Card, Wine Route and Tasting Experience

Today, combine your last hike—between Riomaggiore and Manarola—with a late afternoon tour of a local vineyard and winetasting with the vintner. You might spend the morning relaxing by your hotel pool or on the beach at Monterosso before taking the train to Riomaggiore, the most southern Cinque Terre village. From here, walk the Via dell'Amore ("Lover's Lane") coastal trail, a flat and easy walk, although it is often closed due to landslides; in that case, you can choose a much higher, steeper, and more demanding trail—the Via Beccara—offering breathtaking panoramas.

Arrive in Manarola with time to relax before meeting in a cantina for a short walk through the vineyards that stairstep up the mountainside above town. Taste Cinque Terre Doc white, red, and sweet Sciacchetra dessert wine in a cozy winery, accompanied by local delicacies, before returning to Monterosso.

Day 19: Free day in Cinque Terre

Today you have the entire day at leisure to do as you please. That could mean more sunning, snoozing, and/or snorkeling down by the shore. A languorous massage and spa treatment. Alternatviely, you may like to rent a kayak and get active paddling along the Ligurian coastline. Guided kayak tours begin in Monterosso, but you can also rent kayaks in Vernazza, Manarola, and Riomaggiore—a chance to reach hidden caves and coves with otherwise inaccessible (and therefore deserted) beaches.

History and architectural buffs might head to Riomaggiore to hike a zigzagging trail to the hilltop Santuario di Nostra Signora di Montenero (Sanctuary of Our Lady of Montenero). Situated at an elevation of 1,115 feet (340 m), it offers a fabulous panoramic view in all directions. Or, hike south from Riomaggiore to Portovenere (5 hours), the only other town along the Cinque Terre coastline. Although not technically one of the official Cinque Terre villages, Portovenere is no less idyllic and was awarded UNESCO World Heritage status. It enjoys a stunning location at the tip of the peninsula, studded by the Chiesa San Pietro chapel.

Day 20: Cinque Terre to Milan, Best of Milan Walking Tour

This morning transfer to Levanto to take the high-speed train to Milan, where you'll transfer to your hotel. After time to relax, meet your guide for a shared three-hour walking tour of Milan's main sights and landmarks, starting at the Duomo—Milan's official, and ornately gothic cathedral. Then head to the ornate 19th-century Galleria Vittorio Emanuele II shopping plaza, with its equally awe-inspiring glass ceiling. Exit into Piazza della Scala and the renowned La Scala opera house. You'll then explore the bohemian Brera district, teeming with hip boutiques, bars, and restaurants.

Next, walk a short distance west to Renaissance-style 15th-century Sforza Castle, hosting museums on themes ranging from ancient and Egyptian art to musical instruments. Finally, you'll finish with the tour's highlight: a visit to the former Dominican convent of Santa Maria delle Grazie for a skip-the-line admission to view Leonardo da Vinci's "Last Supper" fresco. Measuring 15 feet (4.6 m) high and 29 feet (8.8 m) across, the masterpiece is still in its original place, on the wall of the refectory, where da Vinci painted it in tempera and oil between 1494 and 1498.

Day 21: Depart Milan