Luxury Northwest Italy: Riviera, Piedmont, Valle d'Aosta & Lake Maggiore - 14 Day

Day 1: Arrive in Milan, Transfer to Portofino

Welcome to Italy! Arrive in Milan, where your private driver will be waiting to transfer you to Portofino, a delightful former fishing village nestled on the shores of the Italian Riviera. With its arch of colorful houses tumbling down to a historic port, the village is the epitome of laid-back Italian charm and style. Boutiques, galleries, and enticing cafés and restaurants line the narrow cobbled streets from the harbor. After a refresh at your hotel, head out to explore under your own steam.

The city's top sights include the statue of Christ of the Abyss, a memorial to Dario Gonzatti, the first Italian to use diving gear. Lying 56 feet (17 m) beneath the waves on the sea floor, you'll need to swim or snorkel to see it. If you'd prefer to stay on land, other notable sights include the 16th-century castle Castello Brown, which towers above the port, and the 12th-century Church of Saint Martin. When you've finished sightseeing, head to one of the town's impeccable restaurants and dine on exceptional Ligurian cuisine, washed down with a glass of the local white. 

Day 2: Free Morning in Portofino, Boat Tour to San Fruttuoso Abbey

It's a relaxed start to your Italy vacation this morning, and you'll have plenty of time to take in the sounds of the sea and church bells while enjoying a leisurely breakfast on your hotel's terrace. When you're ready, head out to see some more of Portofino. The town's seafront location and laid-back Mediterranean vibe have long made it a beloved destination for artists, writers, and lovers of the arts. The centrally-located Piazzetta, a meeting point for locals and visitors in the heart of the historic city, is great for a midmorning espresso and people-watching.

Stroll down to the port, enjoying the brightly colored houses and the refreshing sea breeze that passes through the town's shaded alleyways. The streets around the Borgo are filled with artisan workshops and hum with the handiwork of artists creating elegant patterns of bobbin lace—the perfect spot to pick up a few souvenirs or gifts for back home. When hunger strikes, settle in at one of the elegant restaurants that dot the harbor and serve excellent fresh seafood alongside the day's catch. 

In the afternoon, you'll take to the water for a private boat trip along the coast. Your destination is the Abbey of San Fruttuoso, and your journey starts as soon as you step onboard your gozzo, a traditional small wooden boat. In 30 minutes, you'll arrive at the medieval abbey; tucked into a cove and surrounded by lush vegetation, its remote location, only accessible by boat, made it a favorite hideout for pirate ships in centuries past. After a tour of the abbey, take in the views from San Fruttuoso Beach before returning to Portofino for a relaxed evening along the waterfront.

Day 3: Day Trip to Cinque Terre, Winery Visit & Ligurian Cooking Lesson

No trip to the Ligurian coast is complete without a trip to Cinque Terre, a famous section of the Riviera coastline renowned for its pastel-colored medieval villages that dot dramatic cliffs, incredible sunsets, and beautiful hiking trails that link the five famous villages. The best way to discover Cinque Terre is by train, and after breakfast, you'll meet your private guide and head to the station.

Your first stop is the town of Monterosso al Mare. The medieval center here remains nearly perfectly preserved, with its ancient tower houses and network of carrugi (narrow alleyways that lead from the sea to the cliffs above the town). Monterosso is also renowned for having the best granita (a semi-frozen dessert made from sugar, water, and local lemons), the perfect refreshing treat on a sunny day.

Your next destination is Manarola, a picture-perfect village famous for its plentiful grapevines and sweet sciacchetrà wine. This time, you'll swap the train for a 30-minute private boat trip to the town. Upon arrival, you'll be transferred to a traditional winery where you'll sip a special selection of wines and hear about Liguria's wine production history. Cap off your day with a private cooking lesson, where you'll learn the secrets behind the region's legendary homemade pasta and pesto. You'll return to Portofino in time for an aperitivo as the sun starts to dip. 

Day 4: Morning Trip to Genoa, Transfer to the Langhe Wine Region 

Wave goodbye to Portofino this morning and meet your driver for a one-hour transfer to Genoa. The birthplace of Christopher Columbus, this bustling, wealthy city has a rich seafaring history. You'll have several hours to explore the town's medieval center before reuniting with your driver, and the best place to start is Le Strade Nuove, a series of streets built by the Genoese aristocracy during the height of the city's financial power. Don't miss the Palazzi dei Rolli, a group of elegant Renaissance and Baroque palaces from the 16th and 18th centuries.

Grab lunch at one of the many international restaurants in the alleys near the harbor, then hit the road for your transfer to the Langhe Wine Region, a UNESCO World Heritage Site. This part of Piedmont is characterized by rolling hills, endless vineyards, medieval hill towns, and ancient castles.

Day 5: Truffle Hunting & Wine Tasting, Michelin-Starred Dinner 

Start your morning with a drive to Benevello to spend the day exploring the region's farming heritage. First up is a guided tour into the local woods in search of one of Piedmont's most famous natural resources, tartufi (truffles). You'll be accompanied by an expert truffle hunter (known as a Trifulau in local dialect) and his trusty four-legged companion, the Tabui truffle dog. After the hunt (and a chance to taste your freshly foraged truffles), you're off to visit a local cheesemaking farm that specializes in toma, a DOP Piedmontese aged cheese made using only raw milk from Langhe sheep.

After a guided tour, you'll sit down with your hosts for a light lunch featuring plenty of farm-fresh cheese and an excellent glass or two of the local red wine. Speaking of wine, your day concludes with a visit to a historic wine cellar in the center of Barolo to learn about (and taste) its namesake red wine. You'll sip several different vintages amid idyllic scenery and relaxing views of the rolling hills before returning to your hotel with your driver.

Your day sampling Piedmont's gastronomy isn't quite over yet, as this evening, you'll sit down to dinner at a Michelin-starred restaurant known to hold one of Italy's most complete wine lists. Settle in for a memorable dining experience that's sure to be one of the highlights of your trip. 

Day 6: Tour Alba, Slow Food Experience in Bra

Enjoy a leisurely morning, relaxing poolside or indulging in a pampering massage at your hotel's spa. If you're an early riser, a private sunrise balloon flight over the Langhe countryside is a wonderful way to experience the region's lush valleys, tiny hilltop villages, ancient castles, and endless vineyards. Meanwhile, cycling enthusiasts could book a guided bike ride starting and ending in Cortemilia, a town notable for its many shady hazelnut groves.

Your plans for the afternoon are set. Make the most of northern Italy's impeccable foodie reputation with a private guided tour of Alba, a once-powerful city-state famous worldwide for its red wine, white truffles, and fabulous gastronomy. During Roman times, the city was known as Alba Pompeia, and over time, the city's buildings, from Roman origins to modern construction, have been built on top of each other. You'll head underground to see Alba's architectural Roman formations and still have plenty of time to sample a glass of the region's famed Barolo red wine. 

Afterward, you'll transfer to nearby Bra, a city famous as the birthplace of Italy's Slow Food movement. Started by Carlo Petrini in the 1980s, the movement aimed to defend local culinary traditions and a slower pace of life. Your destination is the restaurant where it all started. Over the next few hours, you'll feast on local specialties such as agnolotti (egg pasta stuffed with roast meat) and tajarin (homemade pasta noodles), followed by a hearty risotto and brasato al Barolo (a rich beef dish). Finish with the region's famous gianduiotto (hazelnut chocolate) before returning to your hotel.

Day 7: Transfer to Turin, City Tour & Exclusive Library Visit

You'll continue your tour of Italy's elegant north this morning with a private transfer to Turin. Known for its historic architecture, wide boulevards, and notable libraries, museums, and theaters, this captivating city has a buzzing café culture and rich history steeped in music and art. Check in to your hotel, and after a refresh, meet your guide for a private tour. You'll start in the Piazza Castello, where one of the buildings hides an architectural treasure: the San Lorenzo Church, a Baroque octagonal building with beautiful inner chapels and a soaring cupola with eight windows that allow sunlight to pour in.

Enjoy lunch at a historic café nearby and rub shoulders with the locals. Turin's cafés are legendary, with a long history of serving as the meeting place for artists, writers, and political refugees. When Turin found itself in the center of the struggle against Austria, several of the cafés became the headquarters of Risorgimento, Italy, where political theory and strategy were discussed over coffee. Speaking of which, you won't want to miss the famous local bicerin, an indulgent mix of chocolate, coffee, and cream. 

Refueled, you're all ready for this afternoon's highlight—a private tour of the Library of the Academy of Sciences. The library is typically closed to the public, but you'll get to visit the massive collection in the company of its creator. Founded in the 1700s, the library houses a vast array of literature: more than 250,000 books, 70,000 letters, 5,000 periodicals, 2,000 manuscript documents on the history of science, and a hundred drawings of industrial patents and maps. 

Day 8: Morning Tour of Sacra di San Michele, Home-Hosted Dinner

Spend your final day in the Langhe exploring one of the most recognizable symbols of the Piedmont region, the Sacra di San Michele. Considered one of Europe's leading examples of Romanesque architecture, the ancient monastery is strategically located amid snowcapped peaks on a pilgrimage route that runs from Saint-Michel in France to Monte Sant'Angelo in Puglia. Meet your driver at your hotel for the 45-minute drive to the monastery and begin your tour via the 243 steps that lead to the Doorway of the Zodiac, where you'll be met with panoramic views of the snowy Alps.

After several hours exploring the abbey, return to Turin, where the rest of the afternoon is yours to spend as you wish. History buffs should head to the Egyptian Museum, one of the city's main attractions and one of the largest Egyptian museums in the world, second only to Cairo's. Alternatively, visit the National Museum of Cinema, one of the city's architectural landmarks with a rooftop terrace perfect for sipping coffee and admiring the sweeping views of Turin against the imposing backdrop of the Alps. 

There's one last treat in store this evening—dinner hosted by a local family in their private home. After a warm greeting from your hosts, you'll be treated to an authentic Italian dinner consisting of a primo (starter), secondo (main course), and dolce (dessert). The conversation is guaranteed to be as good as the food as you share a delicious meal together and exchange insights into each other's cultures and lives. Buon appetito!

Day 9: Afternoon Tour of Aosta, Transfer to La Thuile

This morning, you'll have time for a leisurely breakfast and stroll around Turin before checking out and meeting your driver for a transfer to your next destination, the Valle d'Aosta in the heart of the Alps. After a 1.5-hour journey, your first stop is the valley's namesake town, Aosta, a historic city with a fascinating Roman past that's also renowned for its excellent French-influenced cuisine. Settle in at one of the local trattorias and feast on specialties, including puff pastry filled with Valdostan fondue, venison with polenta, and rich beef stews braised in the local wine.

In the afternoon, you'll meet a local archaeologist to tour the city's Roman ruins. Key sights you'll see include the perfectly intact Porta Prateoria, which dates back to 25 BCE, the Roman Theater, with its impressive southern facade, and the Forensic Cryptoporticus, which dates back to the Augustan era. Part ways with your guide, and if you have time, squeeze in a visit to the Cathedral and the Collegiate Church of Saint Orso, both home to masterpieces of medieval art, with Ottonian frescoes, beautiful floor mosaics, and medieval cloisters. 

Back in the car, it's a short 45-minute drive west to your final destination, the ski town of La Thuile. Sitting below the Little Saint Bernard Pass at an elevation of 4,728 feet (1,441 m), the city is backed by dense forests, snowcapped mountains, and vast glaciers. Check into your luxury mountain resort, and the evening is yours to explore the charming town at leisure and soak up the Alpine views.

Day 10: Cableway to Monte Bianco, Alpine Life Tour

In the morning, meet up with a tour guide and head to see Monte Bianco (Mont Blanc) on the spectacular Skyway Monte Bianco cableway. The cableway consists of three ascending stations, the last of which, Punta Helbronner, sits at an altitude of 11,370 feet (3,365 m). You'll disembark at this final stop to marvel at the unparalleled 360-degree views from the circular terrace. After a look inside the Crystal Hall to see the jewels and gems of the Valle d'Aosta mountains, head to Bistro Panoramic for a memorable Alpine lunch and admire the sweeping vistas from the floor-to-ceiling windows. 

You'll spend your afternoon touring the nearby mountain villages of the Valle d'Aosta. Stop at Introd, a peaceful farming village in a scenic location between the Savara and Dora di Rhêmes rivers. The town was once a fief of the Barons of Sarroid, whose polygonal 13th-century castle and lookout towers still stand. Your guide will introduce you to several members of the local community, and over a coffee or glass of wine, you'll get a glimpse into rural Italian Alpine life. Return to La Thuile in the afternoon, where the rest of the day is yours to spend as you wish. 

Day 12: Transfer to Lake Maggiore, Visit the Rocco di Angera Medieval Fortress

After one last leisurely breakfast, join your driver for the journey east into the Italian Lake District and Lake Maggiore. Your destination for the next couple of days is the lakeshore village of Stresa; this one-time peasant settlement began its ascendancy to an exclusive holiday resort for Italy's aristocracy and bourgeois in 1748, when Stresa came under Savoy rule and entered a long period of prosperity.

Arrive at your hotel, and after settling in, the rest of the day is yours to explore. Stretch your legs with a hike up to Angera to visit the imposing medieval fortress of Rocca di Angera. Built in stages between the 12th and 14th centuries, the castle was of particular strategic importance for military and trade. Owned by the Borromeo family from the 15th century, the castle's museum houses a must-see collection of the family's priceless collection of dolls, toys, books, and board games from the 18th century.

When you've finished exploring, head back down to Stresa and pick from one of the lake's many excellent restaurants for dinner with a view.

Day 13: Motorboat Tour of the Borromean Islands

Spend the day exploring Lake Maggiore's prettiest corner: the Borromean Islands. A favorite with diplomats, intellectuals, and royalty, the archipelago comprises Isola Bella, Isola dei Pescatori, and Isola Madre. You'll board a private Venetian-style motorboat to reach your first stop of the day, Isola Bella. Originally a barren rock, the island is now a floating paradise of architectural and botanical treasures. In the company of a local guide, you'll explore the island's 17th-century Palazzo Borromeo and tour the palace's antique paintings, marble decorations, shining armor, and Flemish tapestries.

Next up is Isola dei Pescatore, the only permanently inhabited Borromean island and home to just 50 residents. It's a great spot to browse the handful of beautiful boutiques and grab a bite to eat at one of the island's restaurants, where visitors feast on freshly caught fish. After lunch, you'll head to Isola Madre, the largest of the islands and world-renowned for its elaborate botanical gardens. Marvel at the ancient wisteria, azaleas, and flowering camellias in the English-style garden, and don't miss the Kashmir cypress tree, the largest of its kind in Europe.

In the evening, you'll return to Stresa, where your night is free to dine on exceptional local seafood and raise a toast to your Italy adventure.

Day 14: Transfer to Milan, Depart

After one last coffee and pastry at breakfast, it's time to meet your driver and head to the airport in Milan for your flight home. Safe travels! 

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