Take Me To 04.20.2023

One Week in Milan and Lake Como

Intro Stay Highlights itinerary

For this seven-night itinerary, we’re taking you through the best of Milan’s refined urban landscape and Lake Como’s lakeside lifestyle.

Milan and Lake Como have long made a harmonious marriage when it comes to crafting Italy itineraries for honeymooners, vacationers in need of a reset, and multi-generational families alike. As two of the most beloved destinations in northern Italy, combining Milan and Lake Como makes for a fusion of urban sophistication and natural splendor. As the fashion capital of Italy, Milan dazzles with its upscale boutiques, refined dining, and architectural marvels. Meanwhile, Lake Como is nestled at the foothills of the majestic Alps and enchants visitors with its charming towns, exquisite villas, and pristine waters. With the help of our on-the-ground SmartFlyer travel advisors who recently returned from the region as Italy experts, as well as our friends at Lungarno Collection and Passalacqua, we’re here to show you how to blend city style with dolce far niente.

Kick things off with a stay at a brand-new hotel that blends old-world beauty with modern-day Milanese life at the heart of the fashion capital. While in Milan, you’ll be invited to explore (and shop) your way through the ins and outs of the Lombardy capital from its exclusive design houses to taking in architecture harking back to of the Italian Renaissance. Then, take a ride up north nestled in a private sports car to a villa shrouded in gardens that fully immerses you in the romance of Como. Our vetted selection of properties featured in this itinerary fully embodies the spirit of these complementary destinations. Whether it’s an elegant hotel at the heart of the fashion district or a restored villa with secret wine cellars and gardens, each accommodation is rich with history and accompanied by renowned Italian hospitality you’ll be sure to feel throughout each moment of your trip.

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Seven nights, eight days

We Love it For

Anyone looking to channel their inner fashionista and aesthetician.

Trip Style

An exploration of northern Italy’s buzzy metropolis and serene Lake Como.

Agent Notes

Pack your best and leave room for more: dressing to the nines for any and all occasions is the Milanese way.


SmartFlyer Picks

Portrait Milano

After undergoing an ambitious renovation, Portrait Milano preserves its historic structure while transforming it into a modern hub for hospitality, entertainment, and culture within the heart of Milan's fashion district. This hotel is housed within a former Archiepiscopal Seminary and isrecognized amongst the oldest examples of Lombard baroque architecture in the world. Portrait Milano overlooks the city’s Piazza del Quadrilatero, the largest public square in the fashion district, and is home to high-end boutiques and restaurants.



An escape to Lake Como takes on an entirely new meaning with this residential-style stay. A reimagining of a villa where Italian cultural juggernauts long ago lodged and were inspired, Passalacqua remains a place of wonder today after its restoration by De Santis family, owners of the beloved Grand Hotel Tremezzo. This hideaway along the fabled Lake Como coast is built around the art of villeggiatura, a long retreat to a single destination. Passalacqua features seven acres of gardens descending to a private jetty, swimming pool, and a spa signed by Dr. Barbara Sturm. From check-in to check-out, the Passalacqua team ensures that every guest's individual need is met – whether it's remembering your favorite dish to treating you to thoughtful gifts throughout your stay.



  • Gain exclusive access to Armani’s coveted collection at Armani/Silos Day 2
  • Climb the heights of the Duomo with a private pre-opening hours tour Day 3
  • Take a private boat tour through Lake Como Day 5
  • Learn the ancient art of silk painting from a local Como silk artist Day 6


1 Milan, Italy
Welcome to Milan

Begin your trip to northern Italy by touching down in the city of Milan. Known as the financial capital of Italy, high fashion, innovative art and design, and cultural landmarks that have touched the entirety of Western Civilization (Da Vinci Code, anyone?) will weave their way into your stay. After retrieving your bags, you’ll be met by your private driver who will escort you to the gates of Portrait Milano. This former 16-century Archiepiscopal seminary has now been transformed into a residential-style hotel by the Lungarno Collection, a chic group of Italian hotels owned by the Ferragamo family. Walking through the preserved seminary gates of Portrait Milano is like being transported into a private sanctuary where history meets the present day. From receiving your keys to walking into your suite for the first time, you’ll notice the many homages to Italian design in the form of various fashion-focused books and art pieces peppered across the property.

Following check-in, make your way to your lunch reservation at BeefBar. Conceived in Monte-Carlo, this bright and airy modern steakhouse spotlights a range of meat-based dishes curated from across the globe. Their Kobe beef and wagyu tacos are a must-try, with plenty of sharing options to accompany your own main course. We also recommend ordering a side of truffle mashed potatoes and a glass of mead to wash it all down.

After lunch, enjoy your arrival afternoon at leisure. Feel free to acquaint yourself with the local area by window-shopping through Quadrilatero della Moda, home to Milan’s primary concentration of world-class fashion brands. Portrait Milano’s Piazza also features two boutiques: Antonia features a curated selection of established brands and avant-garde names; SO-LE STUDIO was founded by Maria Sole Ferragamo and focuses on transforming recycled leather and brass into one-of-a-kind accessories.

Tonight, we recommend indulging in an apertivo at Portrait Milano’s 10_11 Bar before heading to your dinner reservation at 10_11 Restaurant. The mixologists here are masters of their craft; they are skilled at making unique herbal infusions based on your personal taste pallet in addition to a curated drink menu. Tonight’s dinner will be filled with classic Milanese delights. No matter what, you must order the pasta in bianco: prepared tableside, this best-selling delight blends parmesan cheese and egg whites to make a deliciously savory dish that warms the soul. Close out your first dinner in northern Italy with a saffron-based tiramisu, made from Milan’s signature herb.

2 Milan, Italy
Discover Milanese Fashion

Start off your first full day in Milan with breakfast and a morning at your leisure. This is the perfect opportunity to experience Portrait Milano’s state-of-the-art wellness activation: the Longevity Suite, set to open in fall 2023. Focusing on European biohacking and anti-aging, this spa’s menu of experiences is vast. The signature Longevity Checkup – a holistic, genetics-based examination of your current wellness routines followed by hyper-personalized treatments – is sure to start your day on the right foot.

Your lunch reservation today is at Terrazza A Riccione, a rooftop restaurant and bar perched on the Brian&Barry Building in Piazza San Babila. This spot caters to primarily a local crowd with many native Milanese regulars indulging in the bar’s specialty saffron drink as well as the restaurant’s rich seafood dishes. The linguini with lobster is a highlight, as well as the sardines with bread and butter.

Following lunch, your private guide will show you through the world-famous Quadrilatero d’Oro, the golden fashion rectangle that comprises the long parallel streets of via Montenapoleone and via della Spiga. From Gucci and Prada to Versace and Valentino, this neighborhood is lined with the flagships from iconic Italian brands. Thanks to your private guide booked by your SmartFlyer agent, you’ll also be provided VIP access to Giorgio Armani’s sanctuary, Armani/Silos. This art museum houses an exclusive selection of the fashion designer’s creations dating back to 1980 to present day. This is your chance to take in the Armani’s emblematic dresses, as well as sketches, technical drawings, and detailed descriptions of how each garment was crafted for some of the most renowned figures across the globe.

Your second night in Milan will take you through the city’s electric nightlife. Begin with a casual bite at Pizzeria Santa Lucia where you can have a bite of the same classic Neopolitan pizza that countless celebrities have tried throughout the restaurant’s history. The main attraction tonight is located high above the Milanese skyline: Terraza Aperol. Just a block away from the pizzeria, your SmartFlyer travel advisor can guarantee you entry to this bustling hotspot. Decked out in the brand’s iconic effervescent orange, you can dance the night away with a tasty spritz in your hand while looking out onto the magnificent Duomo nearby.

3 Milan, Italy
Experience Milan’s History

Following an early breakfast, your second day of Milanese delights begins with a private guided tour through the city’s famed sights and sounds. Your first stop will be a pre-opening private tour of the opulent Duomo di Milano. First estimated to have been constructed in 1386, this Gothic cathedral has been touched by various cultural titans from Pope Martin V to Leonardo da Vinci. Just crossing the preceding plaza and approaching its brilliant white towers is enough to take your breath away. And once inside, your guide will walk you through the vast breadth of Italian history stored within its walls. From original art to original music manuscripts, your private tour will take you through over six centuries of cultural artifacts. Cap off your visit here with fast-track access to the top of the cathedral, where you can climb the spires and look out on the skyline from new heights.

This stop offers a deep look into Milan’s multicultural history.

Following your tour of the Duomo, make your way to your lunch reservation at Da Giacomo, a family-owned restaurant founded in 1958 offering a cozy, local atmosphere. People watching while sipping on one of their fine wines is a delight, not to mention their exquisite lobster pasta. After lunch, your private guide will treat you to a tour of Sforzesco Castle; originally designed by da Vinci, it has been meticulously maintained and now features five different museums. From homeware from the 19th century to fully preserved hospital wings, this stop offers a deep look into Milan’s multicultural history. For your final stop of the day, your guide will treat you to a sunset at the top of Teatro La Scalla’s panoramic terraces. This legendary opera house has hosted opera royalty since 1778 and continues to put on world-class productions.

Close out your evening at one of our favorite restaurants in Milan, La Gioia. With the help of your SmartFlyer travel advisor, securing a reservation at this highly exclusive restaurant is a breeze. But no trip to Milan would be complete without trying their cacio e pepe cheese wheel, prepared tableside with fresh truffles on top. We also recommend stopping by their cozy bar for a nightcap prior to returning to your plush accommodations at Portrait Milano for your final evening in Milan.

4 Lake Como, Italy
Milan to Lake Como

Your check-out at Portrait Milano isn’t just a simple alla prossima: it’s a whole experience that transports you to a new kind of beauty found in northern Italy. As you step out of your first hotel’s Baroque gates, you’ll be met by your private driver in a Maserati already prepared with hand-selected amenities courtesy of your next hotel: Passalacqua. On the hour drive, watch the soaring skyscrapers transition into a glimmering lakeside as you approach Lake Como where you’ll be first met with Passalacqua gated entrance and its lush gardens. Upon arrival, the hotel’s team will greet you in their own Passalacqua way; from micro-bouquets specially tailored for you by their on-site florist to an Aperol spritz in the garden, you’ll ease into the region’s knack for showing you what it means to embrace a life well lived. Keep an eye out for little surprises throughout your stay: the Passalacqua team is known to shower guests’ stay with small gifts, all proudly made in Italy.

Before doing anything, be sure to draw the curtains and let the breezy dolce far niente lifestyle completely take over.

The check-in experience is just the beginning of this magical first encounter with Passalacqua. Walking into your room, you’ll be met with the sweet sounds of soft, classic Italian music as you take in your uniquely decorated living space. Each room here is named after significant heroines from Bellini’s operas and is filled with lovingly restored vintage pieces from across the globe sourced by the De Santis family. The eclectic nature of these rooms evokes a particularly harmonious vibe; for example, your living room may feature pieces from across East Asia while your bathroom remains distinctly Scandinavian. Yet each piece finds its own place in your personal tapestry. Before doing anything, be sure to draw the curtains and let the breezy dolce far niente lifestyle completely take over.

Lunch today is on-property at La Double J, the renowned Italian brand’s first foray into interior design. While taking in the brand’s emblematic colorful prints that define the space, you can feast on freshly roasted lamb kebabs and pasta cooked over an open firepit. Zested with fresh lemons and topped off with a roasted pineapple dessert, this is the ideal way to kick off your time alongside Lake Como. Passalacqua also offers its guests one specially-curated experience per day. Today, we recommend continuing to indulge in your sweet tooth by partaking in a gelato-making experience. Whether it’s mango sorbet or classic dark chocolate, your personal confectioner will help you prepare the treat of your dreams. Want to save yourself for dinner? The Passalacqua team will make sure to store your masterpiece in their kitchen freezer and serve it up as an evening pallet cleanser.

Following lunch, we recommend heading to the hotel’s Moroccan-inspired spa for a massage. Like the rest of their staff, the wellness team at Passalacqua is keen on making sure your experience is highly personalized to your needs. Cap off your appointment with a tall glass of fruit-infused water before heading back to your room to get ready for dinner. Begin the evening with an apertivo at the hotel bar where you can enjoy a tasty cocktail accompanied by savory small plates. Dinner tonight is served in their cucina di casa back in their main building, fitted with live musicians every night. There are two must-tries here that every itinerary should include: an order of agnolotti – mini homemade ravioli stuffed with ricotta cheese – and a glass of Bràulio, the region’s local liquor. This coveted chilled amaro is popular amongst those in-the-know and can be served neat or fused into a cocktail of your choosing.

5 Lake Como, Italy
Sail the Lake

Begin your second day in Lake Como with a yoga class in their magnolia gardens, followed by a light breakfast filled with homemade treats including fresh pastries, finely cured meats, and honeycomb sourced from local apiaries. Afterward, your private guide will usher you through the hotel’s secret tunnels that open up to the property’s private docks where you’ll board Passalacqua’s own Aquarama for a motorboat tour of the lake. Along the way, your guide will point out the celebrity villas that dot the coast such as George Clooney’s private residence.

Your first stop will be for lunch at Passalacqua’s sister hotel, Grand Hotel Tremezzo, the grand dame of Lake Como seeped in over one hundred years of history. Famously known for its distinct orange facade, this hotel is also home to the only restaurant in collaboration with the renowned Da Giacomo. Where this restaurant differs from its Milan outpost though is in its immaculate seafood offerings. With an orange Aperol spritz in hand, indulge in the fried seafood appetizer followed by spaghetti with clams. Their fresh sea bass is also salted, crusted, and cracked tableside for you so that you’re guaranteed the freshest bites possible. After lunch, pop into Grand Hotel Tremezzo’s boutique store, “Sense of Lake,” filled with Passalacqua goodies and signature Aqua Como products, from candles to skincare.

Choose your own adventure for the afternoon. You can opt to remain lakeside at Grand Hotel Tremezzo’s buzzy Beach Club or retreat back to your abode at Passalacqua to unwind in their lush hotel grounds. A hidden gem we love is Passalacqua’s new rose garden where you can sip on rose-infused gin with book in hand. Your dinner reservation tonight is located at Kitchen, a gourmet restaurant nestled by a private park. Their saffron risotto is immaculate, and be sure to also order their beef filet or foie gras and cap off your night with their chocolate souffle.

6 Lake Como, Italy
Ride Through the Como Countryside

This garden is laden with blooming vines and a romantic 18th-century mansion.

Kick off the day with a freshly-made breakfast prepped and adjusted to your tastes by the hotel team (before you can even think to ask). The first half of your day will find you on a private Ferrari ride. Your driver will race through the remote towns perched across the lakeside, some of which have served as the backdrops for popular silver-screen favorites like Hitchcock’s Pleasure Garden. Your first stop today will be at the Balbianello for a private guided tour. Famously known for its appearance in the Star Wars and 007 franchises, this garden is laden with blooming vines and a romantic 18th-century mansion. The mansion’s interior is adorned with historical maps, travel tools, books, and previous art pieces for guests to peruse.

Today’s lunch is at your leisure. You can either request your private Ferrari driver to make a stop along the coast for a pasta break or opt to return to Passalacqua for a midday refresher at La Double J. For the rest of the afternoon, you’ll be driven up the winding mountainsides to Monte Bisbino for an exclusive silk-making experience. With origins dating back to the 15th century when the Duke of Milan planted mulberry trees across the lakeside, your private instructor will teach you the art of silk painting. Together, you can craft a scarf from start to finish before enjoying an apertivo prepared by a private chef. Enjoy a night at your leisure as you’re driven back to your slice of Lake Como heaven.

7 Lake Como, Italy
Embrace Dolce far Niente

For your final day in northern Italy, we invite you to spend the day at your leisure. For those hankering to explore, a sky tour of Lake Como is a thrilling way to learn about the region. Your SmartFlyer travel advisor will help charter your own private seaplane via the longest-standing seaplane company in the world, with views of the neighboring Alps and a touchdown in Bellagio for lunch and shopping. For those who elect to stay grounded, the Passalacqua staff will set up a private picnic for you within their gardens. You can also spend the day enjoying a few games of bocce ball or tennis, as well as a full day lounging poolside and diving into the clear, warm waters.

To send you off for your final night, the hotel staff will invite you to their hidden wine cellar. Upon entering, you can watch the magic of Lake Como’s culinary world come to life. Throughout the evening, Passalacqua’s chefs are preparing all your meals tableside from freshly sliced prosciutto to their aged cheeses. For your antipasti, try the parmesan wheat followed up with Milanese risotto topped with freshly shaved black truffle for your primi piatti. Their salt-encrusted fish and mixed veggies make for a dreamy main course, finished with homemade tiramisu with goldplated chocolate (or perhaps the homemade gelato you crafted on your first night on the lake!). Afterward, dance the night away with their DJ at the pool before finishing with a nightcap at La Double J.

8 Home
Return home

For many of us, arriving and departing from northern Italy is enough to bring tears to our eyes. However, Passalacqua’s team will make sure you’re sent home with a little piece of paradise. Whether it’s a favorite recipe or a small token from the region, no request is too big or small. Reminisce as your private driver transfers you back to Malpensa Airport and your plane’s wheels leave the tarmac. And as you do, be sure to let your SmartFlyer travel advisor know how to plan your next great escape to Italy.

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