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For the love of fashion and excellent espresso, head to Pasticceria Marchesi. The cafe’s been serving amazing pastries and coffee for 191 years but recently underwent a facelift. Locals and tourists alike have more reason to drop by the iconic Milanese hotspot now that Prada acquired the cafe.  The historic appeal is bolstered with the luxurious Prada touch, as seen from the green walls to the well-dressed staff. For a taste of the past, don’t forget to order a cup of espresso and Pannettone, which is a must when going to Milan!

A few steps away from Marchesi is another well-known (and Louis Vuitton-owned) Caffè Cova. The 200-year-old establishment is another favorite thanks to its wide selection of dainty pastries and filling sandwiches. The espresso with whipped cream is an absolute must-try — it’s a deceptively simple drink that’s hard to recreate at home.

For a sweet pastry and cappuccino breakfast, head to Trussardi. Often frequented by the young banking and fashion set and for good reason: the food selection is surprisingly robust and enticing. From espressos to after-work cocktails, they have it. Nibbling on a brioche while looking at its good looking neighbor — the Teatro alla Scala — is not a bad way to start the day.

For artisanal breads and pastries, head to Princi, a beloved Italian institution. For a delicious Italian cheesecake and cappuccino, stop by this cafe and enjoy the relaxed atmosphere. It’s a great place to stop by if you’re on holiday with friends or family who all want different food options. From pizza to finger sandwiches, they have it all. It's also a good starting point for wandering around town: it's conveniently located near Duomo, a magnificent structure and definitely a must-see in Milan. With 4 stores in Milan, you don't have a reason to miss sipping espresso in this Milanese favorite.

For a memorable end to your Milano trip, step inside the Bastianello, which is another must-visit. Known for its delectable aperitivos and sumptuous desserts, you’ll be hard pressed to decide which to order first. Don’t forget to add a frothy coffee to accompany your meal of choice.
 

Photo courtesy of Pasticceria Marchesi, Caffe Cova, Trussardi, Princi, and Bastianello.

1. Jenny of tsangtastic.com

What we love about Jenny: Looking for stylish Instagram pages? Check out @tsangtastic. It's hard to miss her photos when scrolling through one's feed. She has a certain style that just stands out: edgy yet feminine but always streamlined and chic. This globetrotter is definitely worth the follow.

A post shared by Jenny Tsang (@tsangtastic) on May 5, 2016 at 8:22pm PDT

FW 2015 Collection on Jenny.

2. Ashley of blondecollective.com

What we love about Ashley: everything about @ashbegash is easy and carefree. Her writing is fresh, her style is uncomplicated, and her smile draws you in. We adore how she made the Gabardin boots uncomplicated and daytime-worthy.

A post shared by Ashley | Blonde Collective (@ashbegash) on Jul 22, 2016 at 10:36am PDT

Ornella on Ashley:

3. Heidi of wishesandreality.com

What we love about Heidi(@wishes_reality): she inspires women (especially working gals and moms) to dress up in easy-to-live-in clothes but with a twist. It’s exciting how she puts together pieces and how they just work. Case in point: leather and lace plus our Malta pumps.

A post shared by Chicago Fashion + Lifestyle (@wishes_reality) on Feb 22, 2017 at 7:18pm PST

Malta on Heidi:

4. Kathleen of carriebradshawlied.com

What we love about Kathleen(@carriebradshawlied): She has mastered the art of fun dressing. So it’s safe to say that her style is fun and colorful, but always tasteful and modern. She never fails to inject a bit of charm into her looks as evident in the way she paired mom jeans” with the Jolandra. Not to mention that her blog is such a fun read as well.

A post shared by Kathleen (@carriebradshawlied) on Feb 3, 2017 at 3:38pm PST

Jolandra on Kathleen.

Why: It’s only a 1 hour train ride from Milan. So if you’re already in Milan, why skip Lake Como?

Where to stay:

Il Sereno: Elegant, relaxed, and done in muted colors, this hotel is a hotel of our time. Forget the antiques and heavy velvet drapes; here you’ll find custom furniture handpicked by no other than Patricia Urquiola who’s a favorite in the interior design world. If you see a particular furniture you like, just ask: it might be available for sale.

Where to eat:

Osteria del Gallo: Tucked away in a narrow pedonale, this family-run restaurant serves simple, home-style meals. The locals give this place their seal of approval and for good reason: It’s been operating for 35 years, churning out excellent food on a daily basis. We recommend the cheese focaccia and don’t be shy to try their selection of local wines.

Il Gatto Nero: If you want to eat with a view, high up in the mountains overlooking Lake Como is the famed Il Gatto Nero. Need a reason to go all the way up just to eat? George Clooney gives this place his seal of approval by frequenting this restaurant.

Interesting info: If you see George Clooney walking the streets of Italy, it’s because he has a house on Lake Como — Villa Oleandra — but it’s said that he’s selling it. Madonna, Brad Pitt and Angelina Jolie are also said to have houses in the area.

Recommendations: If touring Lake Como by private boat, we recommend booking a few months in advance to get the best deals. 

Why: It’s photogenic, charming and has a lot to offer that even the rich and famous frequent it.

Where to stay:

Hotel Splendido is the hotel of choice for the selective traveler. Here, the terrace is elegant, the pool is always enticing, and the service is nothing short of exceptional. There’s a reason why Hollywood’s elite have chosen this hotel as their destination of choice.

Eight Hotel: If you want a cozier vibe, this is a good choice. Nestled in a quiet part of town, it’s also a short distance to the harbor and restaurants.

Where to eat:

Ristorante Puny for simple fare done well, and served by exceptional staff to boot. Order the Pappardelle Portofino. It’s worth a try.

Trattoria da Pezzi is a family-run restaurant, at close-by town Santa Margherita, that’s been serving good food since the 60s. Try the calamari fritte and cold veal — simply wonderful.

Recommendations: Make sure to bring a good pair of sandals. When sunbathing is not on the order of business, explore the footpaths at a leisurely pace. We recommend going to the Benedictine abbey at the tiny bay of San Fruttuoso. Abbazia di San Fruttuoso is heaven on earth, but it takes a good 2 hour walk from Portofino. You can also get there by boat.

Why: Paradise to sun worshippers, scuba divers, and food enthusiasts, many forget that Pantelleria is only 9 miles long and 5 miles wide. Here the wine is always flowing and local flavors are served with gusto. Expect only the most exceptional dishes done with local flair.

Where to stay: We recommend staying at a typical stone villa called dammuso. Search a rental via Solopantelleria.

Where to eat: Wherever you choose to eat, make sure to pair it with passito wines and to try the local capers. 

Recommendations: Circle the island by boat, travel inward by car, or take a leisurely pace and enjoy the sunset while taking a walk. There’s a reason why A Bigger Splash was filmed here — the place seems suspended in time and there’s always someplace interesting to explore.  

Why: For the discerning traveler who wants to enjoy exclusive nightlife spots, shop at designer boutiques, and relax at luxury spas, Porto Cervo is the place to be.

Where to Stay:

Petra Segreta is an oasis perched on a hill. It’s the best hotel for a relax weekend but it’s also a great starting point for all your exploring needs.

Where to eat:

San Lorenzo is a proper Italian restaurant that serves delicious suckling pig served on a bed of myrtle leaves. Book ahead of time in order to reserve the suckling pig — it’s well worth it.

Recommendations: Echo the stylish interiors of Italy’s best villas with luxurious silk tops and crisp culottes. Finish with satin or suede sandals for a clean and minimalist take on Italian glamour.

Main photo by jarekgrafik. Lake Como images by Villa Serbelloni, Matus Kalisky, and Nico Franano. Portofino images by jarekgrafik, and Hotel Splendido. Pantellaria images by Sikelia Luxury Hotel, and Pantelleria Hotel. Porto Cervo images by Colonna Resort, and Hotel Cervo. Outfit image via polyvore.com.