While making our way through the brightly-colored (steep) streets, I said to one of my travel companions that Lisbon was probably the most beautiful city I've ever seen. Not much has changed. With delicious wine and even better views, Lisbon and the surrounding area is an amazing destination.
EXPLORE
Sintra is a half-day excursion outside the city, but probably the best thing we did while in Lisbon. A quick train ride will land you in the lush mountain landscape where this UNESCO World Heritage Site sits. While the Pena National Palace and Moorish Castle are popular attractions, if you only have time for one sight do not miss Quinta da Regaleira. This former noble estate is beautiful but its grounds are the true fantasy -- full of waterfalls, grottos, hidden wells, towers, and caves all fit for discovery.
Tuk tuk ride to Alfama Distric is honestly the best way to get up to the historic area surrounding Castelo de S. Jorge. While the famous yellow tram is a bit unreliable, a friendly tuk tuk driver is on every corner. Wander the cobblestone streets near the 11th century Moorish castle for shopping and bites.
Fado at A Tasca do Chico is a good way to experience fado, without too much commitment. Fado, the traditional Portuguese musical narratives, starts around 8:30 -- so get there early to grab a table and order a wine before the show starts.
Ribeira das Naus Lisboa is a seaside stop tailor-made for sunset-watching -- with live music and tinto drinking.
SHOP
A Outra Face da Lua combines vintage shopping with a quaint cafe. Stop in for coffee, stay for the wild bright 70s printed dresses and glittery handbags.
Conserveira de Lisboa is one of many sardine shops across the city, but this one does it with style. Filled with locals, this shop has sardines stacked from floor to ceiling, each wrapped in a gorgeous illustrated paper cover (who knew sardines could be so pretty?). I'm not a fan, but my dad eats them like candy.
EAT
Bar Terraco Santa Luzia has the best view of the city. Tucked back in a vine-covered courtyard, this tiny terrace bar offered delicious vino verde (green wine made from young grapes) and olives, a stellar happy hour stop. Be advised it's cash only.
Pizzaria Lisboa a foodie coworker told me this was one of the best pizzas she'd ever tasted, and she wasn't wrong. Terrific dinner spot for groups, be sure to order the molecular pizza with the special explosive olives!
Confeitaria Nacional is one of a couple historic bakeries that claim to be the original creators of the famous custard tart known as pastéis de nata (or pastéis de belém). No matter the true inventor, these treats can be found most places in Portugal. Confeitaria Nacional is a beautiful bakery that's been around for more than 180 years.
Cafe A Brasileira in the Chiado neighborhood is a nice late-night stop. End your day with a port wine night cap and some people watching.
STAY
Airbnb on Rua Augusta this picturesque boulevard is filled with outdoor dining spots and opens up to Rossio Square to the north and the oceanfront to the south. Walkable to many things and easy access to transit.