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Lisbon: Cobblestones, Custard Tarts, and the Charm Offensive

  • allie4354
  • Apr 24
  • 3 min read


Your slightly over-the-top, highly accurate, and lovingly luxurious guide to Portugal's coastal capital






So You’re Going to Lisbon. Prepare Your Legs (and Your Appetite).

Lisbon is a city that says, "Sure, wear your chicest shoes" and then introduces you to the steepest hills this side of San Francisco. It’s a place where the tiles are more photogenic than you, the food is better than you remembered, and the weather is sunny enough to question your commitment to returning home.

This is your go-to guide for three days of luxurious meandering, scenic funiculars, and enough pastries to justify a second suitcase. We’ll cover where to stay, what to eat, what not to miss, and how not to die on a cobblestone while looking for azulejos.


Where to Stay: The Bougie Triangle

Tivoli Avenida Liberdade

This sleek, stylish landmark sits on Lisbon’s fanciest avenue and knows exactly how cool it is. The rooftop bar, Sky Bar, has views that make your cocktail 40% stronger and your Instagram 80% more liked. The rooms are crisp, modern, and spacious enough to lay out every outfit you brought "just in case."

Four Seasons Hotel Ritz Lisbon

If the Four Seasons were a person, it would be a charming diplomat with impeccable posture and a preference for fresh flowers in every room. Overlooking Eduardo VII Park, it’s the perfect place to recover from sightseeing by getting a massage while watching the sunset. Also: the breakfast buffet could end wars.

Palácio Príncipe Real

The boutique option you’ll want to gatekeep. Set in a restored palace, this hotel gives "Lisbon royalty on a wellness retreat" vibes. With leafy courtyards, a hidden pool, and just enough antique furniture to feel cultured, it’s ideal for travelers who like luxury with a splash of charm.


Things to Do (That Don’t Require an Oxygen Tank)

  • Ride Tram 28: Yes, it’s touristy. Yes, it’s crowded. But you’ll see half the city for under €5 and it’s way cuter than a tour bus.

  • Belém: Visit the Jerónimos Monastery, wave at the Torre de Belém, and of course, eat an irresponsible amount of pastéis de nata at Pastéis de Belém. They're warm, flaky, and slightly spiritual.

  • Alfama: Wander. Get lost. Follow the sound of Fado. Accept that you’ll be climbing uphill no matter what direction you go.

  • Time Out Market: A glorified food court? Sure. But one that includes Michelin-starred chefs and perfectly cooked octopus. So.

  • Sintra: A day trip, but it might just be the most magical thing you do. Castles! Fog! Mossy stone staircases! It’s basically a Disney set with better pastries. Visit Palácio da Pena, Quinta da Regaleira, and have lunch at Tascantiga for tapas with a view.


Where (and What) to Eat

  • A Cevicheria: Tiny, hip, and covered in octopus decor. Order the pisco sour and thank us later.

  • Taberna da Rua das Flores: Small plates, big flavor, no reservations—go early.

  • Cervejaria Ramiro: Technically a beer hall, spiritually a seafood temple. Garlic butter clams, tiger prawns, and a steak sandwich for dessert. (Not a typo.)

  • Pasteis de Belém: Again. Because it’s worth listing twice.


3 Days in Lisbon: Your Glamour & Tiled Glory Guide

Day 1: Welcome to the Hill Workout

  • Check in and caffeinate.

  • Stroll Avenida Liberdade for boutique shopping and shade.

  • Ride Tram 28 to Alfama. Get lost, find wine.

  • Sunset cocktails at Sky Bar (Tivoli).

  • Dinner at Taberna da Rua das Flores (go at 6 PM or bring a good book).

Day 2: Belem and the Custard Pilgrimage

  • Visit Jerónimos Monastery and Torre de Belém.

  • Eat all the pastéis at Pastéis de Belém.

  • Lunch near the waterfront.

  • Museum hop (MAAT or Berardo Collection).

  • Dinner at A Cevicheria.

Day 3: Castles, Markets & Mellow Goodbyes

  • Day trip to Sintra (early train or private driver if you’re feeling fancy).

  • Explore Palácio da Pena and Quinta da Regaleira.

  • Lunch at Tascantiga.

  • Return to Lisbon for shopping or Time Out Market grazing.

  • Farewell dinner at Cervejaria Ramiro. End with a steak sandwich.


Final Thoughts: Don’t Overpack. Do Overeat.

Lisbon is one of those cities that manages to be effortless and grand at the same time. Between the history, the food, the hills, and the hospitality, you’ll leave with sore calves, a full camera roll, and a deeply committed love of custard.

Just remember: pack light, wear sneakers, and never say no to another pastél de nata.

 
 
 

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