City Guides

If you ask someone who’s been to Milan what they thought of it, you’ll probably get mixed reviews. Some will call it a day trip; others will say it was boring. Many skip it altogether in favor of cities like Florence, Venice, or Rome.

Spending four months living here showed me just how misunderstood Milan really is. Its beauty isn’t in checking off major sights (though there are a few worth seeing), but in what exists beneath the surface. Milan is a city for walking aimlessly — stumbling upon quiet plazas and leafy parks. It’s aperitivo and long dinners shared with good people and great food. It’s for fashion lovers and casual admirers alike, whether you’re browsing shop windows or taking in the city’s unmatched street style. It’s Lake Como just an easy day trip away, and luxury outlets waiting just beyond the city.

Milan is the kind of place that’s easy to call home — and even easier to miss once you leave. It stays with you, quietly, long after the trip ends.

This guide is meant to help you experience Milan the way I came to love it — slowly, without a checklist, and with room to wander.

Milan, By Neighborhood

As all big cities do, Milan has a plethora of neighborhoods to explore. Today I have chosen 4 to highlight (in no particular order) based on my experience there that will give you a well-rounded perspective of Milan’s landscape.

1. Brera

The Brera neighborhood is Milan at its most polished. Swanky, upscale, and understated yet glamourous. Brera is home to some of Milan’s most delicious food and the true luxury fashion scene. The Milanese elite don’t buy their designer bags in the Galleria; they shop in the quieter, more discreet boutiques tucked away in Brera. Beyond its restaurants and fashion houses, Brera’s cobblestoned streets are lined with small boutiques filled with clothing and art; curated, carefully chosen, and waiting to be discovered. Sometimes during fashion week, you might even stumble upon a free exhibit or a live art display, the kind that appears unexpectedly and disappears just as quickly.

✦ ✦ ✦ Brera Recommendations

2. Navigli

Navigli is the sparkling picture of Milan after dark. On the banks of sprawling canals, this district is the heart of Milan’s aperitivo and local nightlife culture. Whether it’s a fun cocktail with a spread of savory snacks, card games and a beer tower at La Fontanella, or dancing the night away, Navigli has something for everyone. Evenings here unfold naturally. Navigli is about atmosphere, spontaneity, and the kind of nights that don’t need much of an agenda.

✦ ✦ ✦ Navigli Recommendations

3. Centro Storico

Centro Storico is the Milan you expect to see from pictures. From the stunning white limestone Duomo to the light reflecting off the Galleria’s glass windows, this neighborhood sits at the center of Milan’s tourism. As the true heart of the city, much of Milan’s magic lives here. Take time to soak up the history, fashion, glamour, and shopping — and don’t forget to grab some gelato.

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A Taste of Milan

A few meals and moments that stayed with me long after I left.

Burrata with bruschetta & the legendary tiramisu at Osteria Da Fortunata

Weekend Plans

Seville is warm, colorful, and romantic. With tile and warm brick illuminated by golden sunlight, lush gardens filled with orange trees, and every corner bursting with flamenco culture, Seville feels like a fairytale town frozen in time.

The Moment

My most memorable moment in Seville was wandering through the stunning Plaza de España during golden hour and discovering some local flamenco dancers performing underneath the arches. We watched for an hour, completely mesmerized by the moment.

Plaza de España · The orange trees of Seville · The iconic tiled bridges

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The Plan

Seville is small and walkable — you can get almost everywhere on foot. This is a three-day weekend itinerary designed to move at a relaxed pace while hitting the city’s best moments. Further details on every place mentioned are provided at the bottom.

Friday — Arrive & Orient

Arrive late morning or early afternoon and drop your bags before heading straight into the historic center. Start with the Catedral de Sevilla — make sure to go inside. It is stunning, and it is also where Christopher Columbus is buried, which adds an additional layer of historical significance. Afterwards, climb La Giralda for sweeping views over the entire city. Then wander through Barrio Santa Cruz and soak in the gorgeous architecture and calm atmosphere.

For your first evening, visit the iconic wooden structure Metropol Parasol (also known as Setas de Seville) and see the iconic “I Love Seville” sign at the top. Getting a bird’s-eye view the first evening gives you a completely different perspective of the city. If you prefer a rooftop bar, La Terraza de EME or Antico Lobby offer similar perspectives.

The cathedral’s gilded altar · The tomb of Christopher Columbus

Dinner is around 8:30, so lean into the late schedule. For tapas, Eslava, Pan y Circo, San Marco, La Brunilda, and Bar Postiguillo Tapas are all solid options depending on the vibe you want. For drinks, El Rinconcillo is the oldest bar in Seville. Street flamenco is amazing and feels authentic, but you can also book a show — La Carbonería has a free show with a drink purchase and gets packed. There is also underground flamenco, or a traditional tablao where you can order sherry cocktails — wine from the south of Spain.

Saturday — Palaces, Parks & the Plaza

Start at the Royal Alcázar of Seville — book in advance. The gardens are lush and gorgeous and absolutely worth the reservation. From there, walk south into Parque de María Luisa and continue to Plaza de España. Don’t forget to take a ride in one of the Plaza’s iconic rowboats to give your feet a rest.

Horse carriages at the Plaza · Alcázar interior · Alcázar gardens

After the Plaza, walk along the river and stop at Torre del Oro for a quick visit before heading back toward the old town for tapas and drinks. Spend the evening at El Rinconcillo, explore Calle Betis, or bar hop and socialize.

Sunday — Slow Morning, Then Home

Sunday should feel slow. Visit Palacio de las Dueñas if you want one last architectural stop, or simply wander. Churros are a must — especially at Bar El Comercio. Leave in the evening and grab a taxi to the airport, which takes about 20–25 minutes.

Wandering Parque de María Luisa · Metropol Parasol

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The Details

Fly into Seville Airport and take a taxi, Uber, or the bus into the city center — about 20–25 minutes. The buses offer tap to pay, making public transportation affordable and easily accessible. Stay near the cathedral or in Barrio Santa Cruz so you can walk everywhere. Look for boutique hotels or Airbnbs with interior courtyards or rooftop views.

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A Quick Guide to the Places Mentioned

Sights Eats & Drinks Flamenco

Weekend Plans

Lisbon feels sun-washed and cinematic. Pastel buildings cascade down steep hills toward the Tagus River, yellow trams rattle through narrow streets, and tiled facades catch the light at every turn. The city offers beauty from every angle — from the blue water of the coastline, to hilltop overlooks featuring whitewashed buildings and terracotta tiled roofs.

The Moment

One of my most memorable moments in Lisbon was sitting at a viewpoint overlooking the city with a glass of sangria while the sun set behind the hillside of clustered clay rooftops. The river reflected the fading light, musicians played nearby, and the hills of Lisbon slowly turned warm orange as evening settled in.

A canopy of color over Lisbon’s streets · Azulejo-tiled facades · Cobblestones in Alfama

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The Plan

Further explanations of destinations mentioned in “The Plan” are provided at the bottom of this itinerary.

Friday — Arrive & Orient

Arrive Friday afternoon or evening and drop your bags before heading into Alfama, Lisbon’s oldest neighborhood. The streets here wind between concrete buildings and steep staircases, and it quickly becomes clear why Lisbon is known as the city of seven hills.

Start the evening at Miradouro de Santa Luzia, one of the most beautiful viewpoints in Lisbon. The terrace is lined with traditional blue and white tiles and shaded by bougainvillea vines, opening out to sweeping views of Alfama’s rooftops and the Tagus River beyond. Order a glass of sangria from the small kiosk nearby and find a place along the railing as the city begins to glow in the soft evening light. As the sun sets, musicians often gather and the atmosphere becomes quietly magical.

Afterwards, wander Alfama’s narrow streets and find dinner nearby. For traditional Portuguese petiscos and a chance to hear live Fado, Bela is one of the authentic, laid-back spots locals point you toward — the kind of place where the music feels spontaneous rather than staged. Parreirinha de Alfama is another classic, tucked on a quiet street corner that most people walk past without noticing, coming alive at night with local fadistas. If you’d rather skip the show and just eat well, Farol de Santa Luzia is a reliable seafood spot right in the heart of the neighborhood, and Antiga Wine Bar is a well-reviewed spot in Alfama for petiscos and wine. Book ahead if you can — evenings fill up fast.

Rossio’s iconic wave-patterned cobblestones · Colorful riverside installations along the Tagus

Saturday — Castles, Trams & the Historic Center

Saturday is perfect for seeing Lisbon’s main sights. Because the city is built on steep hills, walking around can feel like a bit of a workout, so this itinerary is intentionally designed to move downhill through the city.

Start the morning high above Lisbon at Castelo de São Jorge, the hilltop castle overlooking the city’s red rooftops and the Tagus River. The views from the castle stretch across the entire city and are one of the best ways to understand Lisbon’s layout. You’ll also likely notice the castle’s resident peacocks wandering the grounds, bringing colorful life and charm to the historic ruins.

From there, walk downhill toward Miradouro de Santa Luzia and the surrounding streets of Alfama before hopping on Tram 28, Lisbon’s famous yellow tram that winds through the historic neighborhoods. The ride itself is part of the experience as it climbs steep hills and squeezes through narrow streets. In its charming vintage style, Tram 28 gives an authentic introduction to Lisbon’s architecture and sights.

Depart Tram 28 near the center of the city and wander Rua Augusta, Lisbon’s lively pedestrian shopping street filled with cafés, boutiques, and street performers. Continue walking until the street opens up beneath the Arco da Rua Augusta, the monumental arch that frames the entrance to Praça do Comércio.

Praça do Comércio is Lisbon’s massive riverfront square, surrounded by warm yellow buildings and opening directly onto the Tagus River. Spend some time here wandering the arcades or sitting along the water before finding a rooftop bar or riverside terrace for sunset drinks.

At some point during the day, make sure to stop for a Pastel de Nata, Portugal’s iconic custard pastry. The flaky pastry and caramelized custard filling are one of Lisbon’s most famous treats and are best enjoyed warm with a coffee.

One of Castelo de São Jorge’s resident peacocks · The castle walls · Climbing Lisbon’s steep hills by tram

The column of Dom Pedro IV rising over Rossio Square · Portuguese ceramics for sale along the streets

Sunday — Slow Morning & River Views

Sunday gives you an opportunity to pick your pace. Start the morning with brunch at Dear Breakfast or another café nearby, then wander the hills of Lisbon one last time, stopping at viewpoints or streets you might have missed earlier in the trip.

If you want one final scenic moment before leaving, walk along the river near Praça do Comércio or take a short ferry across the water. From the river you get a clear view of the 25 de Abril Bridge, Lisbon’s red suspension bridge stretching across the Tagus.

Leave Lisbon in the afternoon or evening and head to the airport or train station.

Sunday morning coffee · A quiet Alfama side street

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The Details

Stay in Alfama, Baixa, or Chiado so you can easily walk to Lisbon’s main sights. Alfama offers the most atmospheric experience, with winding streets, historic buildings, and viewpoints tucked between staircases.

One thing to know is that many of Alfama’s streets are too narrow for cars, which adds to the charm but can make arrivals a little adventurous. You may need to walk the last few blocks to your hotel over cobblestones and steep hills, but the tradeoff is a quieter neighborhood that feels completely different from the rest of the city.

Lisbon Airport is about twenty minutes from the city center by taxi or Uber. The metro is also simple and affordable if you are traveling light.

Lisbon’s hills are part of what makes the city so beautiful, but they also mean exploring can feel like a bit of a workout. Comfortable shoes make a big difference.

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Guide to the Places Mentioned