Take Me To: A Refined Itinerary of Italy’s Northern Gems

Your Milanese adventure begins with a private car transfer from the Milan Malpensa Airport (MXP) that will deliver you to Casa Brera, a Luxury Collection Hotel. The hotel is ideally positioned beside Teatro alla Scala in the heart of the city’s historic center. Designed by celebrated Spanish architect Patricia Urquiola, the hotel sits on the pedestrian-only Piazzetta Maurilio Bossi. Take time to settle into your Milanese Suite, also designed by Urquiola, with a notable private terrace offering a view of Duomo di Milano. After you’ve settled in—and perhaps enjoyed a glass of Prosecco to say ‘cin cin’ to the start of your trip—head out to explore the city by foot, perhaps pausing in some of the shops of Brera as Milan’s elegance envelopes you.

Your first afternoon is dedicated to a true Italian classic: Campari. By late afternoon, it’s time for an aperitivo at the iconic Camparino in Galleria. Just a six-minute walk from the hotel, this historic bar sits amid the bustling Galleria Vittorio Emanuele II and has served Milan’s signature aperitivo since 1915, providing an excellent spot to toast your first evening in Italy while taking in its historic frescoes. After you’ve enjoyed your aperitivo, work up an appetite with world-class shopping: the Galleria is one of the world’s oldest active shopping centers. Your SmartFlyer travel advisor will work with the Casa Brera concierge to secure private appointments at the premier Italian fashion houses, including Prada, Gucci, Piumelli, and Versace.

From there, a private car will take you the ten-minute drive to enjoy dinner at Michelin-starred Procaccini, where contemporary Italian cooking is presented by Chef Emin Haziri, who’s considered “one of the most interesting figures” on the rise in the Milanese dining scene. From there, your driver will take you back to Casa Brera, located about fifteen minutes from the restaurant.

While your breakfast is included at Casa Brera, consider the temptation of easing into the morning like a true Milanese with an espresso and the popular maritozzo, a brioche filled with sweet cream, at Marchesi 1824. As one of the city’s most longstanding and celebrated pasticcerias, it’s a must stop while in town. The elegant café offers the perfect introduction to Milan’s enduring appreciation for craftsmanship, tradition, and taste thanks to its strong roots dating back to 1824 and conveniently, it’s located just a short walk from Casa Brera.

…independent galleries, artisan boutiques, and centuries-old architecture reflect the neighborhood’s creative spirit.

From there, your SmartFlyer travel advisor has arranged a walking tour through the historic Brera district specially matched to your interests. The guided walk follows Via Brera, where independent galleries, artisan boutiques, and centuries-old architecture reflect the neighborhood’s creative spirit. Alongside your knowledgeable guide, you’ll continue to the courtyard of the Pinacoteca di Brera to admire Antonio Canova’s striking statue of Napoleon before ambling through the tranquil Brera Botanical Garden, a historic green space once dedicated to the study of botany, medicine, and pharmacy. The experience continues along the streets of Via Fiori Chiari and Via Madonnina before arriving at Piazza Santa Maria del Carmine, home to the neighborhood’s beautiful fifteenth-century church. After the tour concludes, walk ten minutes over to lunch at Bice, a gem of the Brera neighborhood that specializes in Tuscan dishes. We love the risotto.

Return to Casa Brera in the late afternoon to unwind and refresh from your day exploring. As the sun begins to set, take in views of the city at Etereo, the hotel’s rooftop restaurant and sky bar. Relax beside the rooftop pool as you enjoy an evening aperitivo. Then, a car will take you the fifteen-minute drive to a private, after-hours viewing of Leonardo da Vinci’s The Last Supper at Santa Maria delle Grazie. Standing before the celebrated fifteenth-century mural offers an unparalleled window to Milan’s extraordinary artistic heritage before the city reveals another of its defining pleasures: exceptional cuisine. You’ll finish the day at Trattoria Torre di Pisa, where celebrated Tuscan fare is served up in the kind of classic dining room that feels synonymous with Italy.

After your final breakfast at Casa Brera, trade the vibrant energy of Milan for something more serene as your private driver transfers you to the idyllic shores of Lake Como. The scenic hour-and-a-half journey winds north toward one of Italy’s most celebrated destinations, where grand villas, dramatic mountain landscapes, and glittering waters define vistas. Upon arrival, check into the recently opened The Lake Como EDITION, on the lake’s western shore in the quaint village of Cadenabbia. Settle into your Penthouse accommodations, soak up your balcony view overlooking Lake Como, the suite’s ornate carpeting, soaking tub, and Calacatta marble finishes. When you’re ready for lunch, wander down to Renzo, the EDITION’s pergola-shaded outdoor spot serving carpaccio, fresh pastas, and Veal Milanese.

The perfect way to transition from the excitement of Milan into the slower, restorative rhythm of Italy’s most iconic lake.

Your afternoon is dedicated to restoration at The Longevity SPA. Inspired by the world’s Blue Zones—the five regions distinguished for their exceptional longevity—the spa blends advanced diagnostics, anti-aging therapies, biohacking technologies, and holistic rituals meant to enhance vitality, restore balance, and support long-term wellbeing.  For a signature introduction to the spa’s philosophy, experience the AÉRAS Ritual, inspired by Sardinia’s longevity traditions. The immersive treatment begins with a sea salt foot ritual, then a full-body exfoliation with Mediterranean herbs to prepare the skin for deep renewal. A restorative cork ball massage releases muscular tension while encouraging postural balance, and the experience concludes with an invigorating scalp treatment designed to boost mental clarity and restore energy. It’s the perfect way to transition from the excitement of Milan into the slower, restorative rhythm of Italy’s most iconic lake.

As the sun begins to set, head to Mistral for dinner, the Michelin-starred restaurant right on the waterfront in Bellagio. You will take the short, fifteen-minute boat ride from the hotel across the lake, where you’ll be dropped off at the restaurant’s private dock. Here, Chef Ettore Bocchia presents the finest seasonal ingredients through regional cuisine with Mediterranean influences. After dinner, your SmartFlyer travel advisor will have arranged another classic, Riva-style boat to provide seamless dock-to-dock transportation back to The Lake Como EDITION, allowing you to end the evening with one final journey across the moonlit waters of the lake.

Wake up to your first peaceful morning on Lake Como and enjoy breakfast on your terrace if you’re in the mood for in-room dining, or, at Renzo, for a different panoramic view. Either spot makes for an ideal setting to ease into the day, allowing you to take in the ever-changing light over the lake before setting off to explore one of Italy’s most iconic landscapes.

From The Lake Como EDITION’s private dock, you’ll board that classic mahogany speedboat to discover Lake Como from its most celebrated vantage point. Glide past elegant historic villas, picturesque harbors, and postcard-perfect villages as your captain steers you across the lake’s shimmering waters. Relax onboard as you soak up this quintessential vantage point showcasing the region’s eternal beauty. Then, after you’ve had the chance to relish the grandeur from the water, disembark at the docks in Bellagio, considered the “Pearl of the Lake.” Make time to stop at a cozy wine bar along the streets of Bellagio and to take in the colorful storefronts—we love Angolo DiVino. Your captain will pilot you back to the hotel afterward, for final golden hour views of the lake.

As evening falls, settle in for dinner at Cetino by Mauro Colagreco, the hotel’s signature restaurant, where the celebrated chef’s ingredient-led philosophy is expressed through an entirely bespoke tasting experience. There’s no selecting dishes from a menu here. Instead, you’ll begin by choosing a minimum of five wines from a curated collection. These selections become the inspiration for the evening, while the culinary team tailors its personalized seasonal menu to your tastes, and the wine—complementing, contrasting, and elevating each pour. Cap off your evening at Lobby Bar, where skillfully prepared cocktails and an effortless sense of occasion bring guests and locals together well into the night—and if you’re there on a Friday, you’ll catch some live music too.

Wake to another leisurely morning at The Lake Como EDITION, and after breakfast, take a swim in the striking floating pool, which creates the satisfying feeling of gliding directly on the waters of Lake Como. Framed by teak decking, private cabanas, and comfortable loungers, it’s an idyllic place to relax while appreciating uninterrupted views of the encompassing mountains. For those looking to stay active, the fitness studio offers state-of-the-art Technogym equipment for cardio, strength, and functional training to break up the hours spent soaking up the sun and Italian wine.

Midday, you’ll take a private car or private boat to venture to the elegant lakeside town of Cernobbio, home to the legendary sixteenth-century Villa d’Este. One of Lake Como’s famed “Grand Dame” hotels, the historic estate is as much a destination as it is a landmark. Wander through its magnificent UNESCO-protected gardens and admire centuries of history, after a pause for lunch on the lakeside terrace while taking in sweeping views across the water. As evening approaches, continue to Michelin-starred Materia for dinner, a five-minute private drive from Villa d’Este. Here, Chef Davide Caranchini presents one of the region’s most exciting contemporary dining experiences. Strongly rooted in the traditions and seasonal ingredients of the Como area, his cuisine is equally defined by innovation, travel, and thoughtful experimentation. You’ll be whisked back to the hotel via a thirty-five-minute private drive along the lakefront, sated after another day of exploration.

Luxuriate in your final breakfast at EDITION Lake Como before readying for your departure as you set sights on your final stop. Your driver awaits for this four-hour private transfer, during which time you’ll trade alpine landscapes for the timeless beauty of Italy’s famous floating city. After transferring from the car to a private water taxi, you’ll check into your suite at the iconic The Gritti Palace, a Luxury Collection Hotel. Long favored by artists, writers, and discerning travelers, the historic hotel offers an elegant introduction to Venice. We recommend the Redentore Suite, the rooftop suite with its own plunge pool and unmatched views of the city. Here you can refresh after your travel day and watch the buzz of aquatic traffic below.

…impeccable service, historic surroundings, and unforgettable waterfront views set the stage for the final days ahead.

As afternoon unfolds, discover a side of Venice that few visitors experience through one of The Gritti Palace’s signature artisan encounters. For centuries, Venice has been lauded for its master artisans whose techniques have been passed from one generation to the next, preserving traditions that still define the city’s cultural identity. Working closely with local ateliers, The Gritti Palace’s Clef d’Or concierge team provides seamless and private access to many of these remarkable artisans, allowing you to step inside workshops that are rarely open to the public. Depending on your interests, your SmartFlyer travel advisor can organize a private visit or hands-on experience with renowned masters of textile weaving at Tessitura Bevilacqua, gondola oar and rowlock carving at Le Fórcole di Saverio Pastor, bookbinding with Paolo Olbi, woodcarving with Sebastiano Lunardelli, or silkscreen printing with Gianpaolo Fallani, among many others. Each encounter offers an intimate connection to the craftsmanship that continues to shape Venice today.

Return to The Gritti Palace as evening falls for dinner at Club del Doge, the hotel’s celebrated restaurant overlooking the Grand Canal. Showcasing refined Venetian cuisine prepared from the freshest seasonal ingredients, the restaurant provides a fitting finale to your first day in Venice, where impeccable service, historic surroundings, and unforgettable waterfront views set the stage for the final days ahead.

Begin your morning with breakfast at Gritti Palace before grabbing coffee beneath the arcades of Caffè Florian, the legendary café on Piazza San Marco that has welcomed artists, writers, and travelers since 1720. Just a short stroll from the hotel, it provides the perfect introduction to another day immersed in Venice’s rich cultural heritage before heading back to the property to experience one of the hotel’s most celebrated offerings.

For nearly fifty years, The Gritti Epicurean School has preserved and shared the traditions of Venetian cuisine. You will meet in the hotel lobby, then embark on the first stop of your cooking lesson, a visit to the historic Rialto Market alongside the hotel’s chef. Rialto is one of Italy’s oldest and most vibrant food markets. Here, you’ll discover the importance of seasonality, learn how to identify the finest local produce, and gather the ingredients that will later become your lunch. Along the way, stop at a traditional bacaro, a small wine bar, to sample classic Venetian cicchetti—the city’s beloved small plates—accompanied by a glass of local Prosecco.

Returning to The Gritti Palace, step into the warm, country-style kitchen of The Gritti Epicurean School, where you’ll don an apron and learn to prepare an authentic three-course Venetian menu under the guidance of the hotel’s expert chefs. From perfectly cooked risottos and handmade pasta to classic regional desserts, each dish grants a deeper understanding of Venice’s culinary traditions. The experience concludes with an unhurried lunch accompanied by regional wines, allowing you to enjoy the fruits of your work while overlooking one of the most storied cities in the world.

Such an intimate experience is a hard act to follow, but now it’s time to hit the streets and waterways of Venice to take in some of the city’s best shopping experiences. Take a private taxi directly from Gritti Palace’s private docks to Giberto, the highly celebrated store of Murano glass designer Giberto Arrivabene Valenti Gonzaga on Venice’s Rialto Bridge. From there, walk the ten minutes to Legatoria Polliero for stunning printed paper goods and pick up bespoke designs from Anselmo Polliero. In this same area of the city, you’ll find the mask shop Talia Venezia and the Iranian artisan shop Kooch. Finish the day with dinner at Ristorante Da Ivo, a legendary family-run Venetian restaurant—best known as George Clooney’s favorite restaurant in the city. Take the five-minute walk along the moonlit streets of Venice to return to Gritti Palace.

Leave the intricate canals of Venice behind for a day and venture further to explore the extraordinary beauty of the Venetian Lagoon in true Gritti Palace style. Step aboard the hotel’s private Riva Aquariva Super Il Doge, an iconic expression of Italian craftsmanship and the spirit of la dolce vita. Handcrafted by Riva, the legendary Italian shipyard founded in 1842, the speedboat offers one of the most unforgettable ways to experience Venice from the water.

Step aboard the hotel’s private Riva Aquariva Super Il Doge, an iconic expression of Italian craftsmanship and the spirit of la dolce vita.

With a route tailored by The Gritti Palace’s Clef d’Or Concierge, discover the lagoon’s diverse islands, landscapes, and centuries-old traditions, navigating the waters at your own pace with the help of your captain. Lasting between four and eight hours depending on your preferences, this private journey presents the ultimate expression of Venetian exploration. Travel north to Murano, where generations of master glassmakers preserve a centuries-old craft, or visit Burano, known for its brightly colored houses and exquisite lace-making traditions. Continue to Torcello, one of the oldest settlements in the lagoon and where Venice’s remarkable story began, with its peaceful atmosphere and ancient landmarks that give you a peek into the city’s earliest history.

For a different perspective, explore the quieter southern reaches of the lagoon, navigating historic fishing routes between Malamocco, Pellestrina, and the lively seaside town of Chioggia. Alternatively, uncover Venice’s spiritual heritage with visits to the islands of San Francesco del Deserto, Torcello, San Lazzaro degli Armeni, and the magnificent Basilica of San Giorgio Maggiore. Whether focused on art, history, craftsmanship, or hidden corners of the lagoon, each Riva Yacht Experience is uniquely curated to reveal a side of Venice that few others have the opportunity to discover.

For your last night in Venice, your SmartFlyer travel advisor has secured a reservation at Osteria Alle Testiere. Again, you’ll depart from the private docks of Gritti Palace to be dropped off at Calle Del Mondo Novo. From there, you’ll go into a quiet side street to be seated at one of the most coveted tables in Venice. Be sure to order the catch of the day for the full experience. It’s a cinematic finale to a perfectly crafted masterpiece.

Whether you’re planning to continue your European adventure or jet home, departing from Venice will be a breeze. A private transfer from Gritti Palace will take the twenty-five-minute drive to Marco Polo International Airport. Your SmartFlyer travel advisor can arrange a direct flight back to the States—both Delta and United offer daily direct flights between Venice and numerous East Coast cities.