There are two types of people planning a proposal in Sintra: the ones who keep things simple and the ones who decide to combine the Monserrate ruins, dramatic ocean cliffs and a celebration dinner overlooking the Atlantic in the same afternoon. Jay very clearly belonged to the second one.

Planning a proposal or engagement session in Portugal? Discover the best proposal locations in Lisbon, Sintra and nearby, from iconic viewpoints to hidden beaches and cinematic coastal spots.

When Antonio started planning his proposal to Serena at Tapada das Necessidades, he didn't begin with flowers or candles. He began with a brown sofa. The sofa from their first home together.

Emily and Emiel travelled from Amsterdam to Lisbon expecting a few days of sunshine, good food and city exploring. What Emily didn't expect was a surprise proposal overlooking the rooftops of Alfama at Miradouro das Portas do Sol, followed by an engagement session through some of Lisbon's most beautiful streets and viewpoints.

When Sofia and Carlos travelled to Lisbon, they thought they were simply spending a few days exploring one of Europe's most beautiful cities. What Sofia didn't know was that Carlos had secretly planned a surprise proposal at Miradouro de Santa Luzia, one of Lisbon's most iconic viewpoints.

Jeff and Ali travelled from the United States to spend a few days exploring Lisbon. What Ali didn't know was that Jeff had secretly packed an engagement ring and was planning a surprise proposal at Castelo de São Jorge.

The morning started with that annoying “is it going to rain or not?” drizzle situation, but somehow the weather held long enough for Luís to pull off the sweetest surprise proposal for Andreia at Quinta de Santana. And him surprising her with her family waiting nearby to celebrate afterwards might have been one of my favorite reactions ever.