Going to Portugal
Portugal is one of those destinations where you genuinely cannot go wrong, but you can absolutely make the wrong choices if you're not careful about where you plant yourself. The country has exploded in popularity over the last decade, and with that has come a wave of excellent new hotels alongside the reliable classics. The question is always: Lisbon and the north, the Alentejo, or the coast?
If you want my honest read on where the real action is right now, Comporta is the answer. It has been quietly magnetic for years among Europeans who know things, and it's now getting the infrastructure to match the hype. A brand new property just opened there called Sublime Sand, and it's worth serious attention: 43 villas, each with its own pool, tucked into the pine forests and rice paddies that make Comporta feel like nowhere else in Europe. It manages to be genuinely luxurious without feeling like it's trying too hard, which is the whole spirit of the place. Comporta attracts people who could be in Saint-Tropez and actively choose not to be, and that tells you everything.
Lisbon itself rewards the traveler who resists the urge to stay in the obvious spots. The Bairro Alto Hotel remains one of the best in the city, full stop. It's right in the thick of things, the design is quietly magnificent, and the rooftop terrace at sunset will rearrange your priorities. For something with more of a grand dame feel, Bairro One in Chiado or the Four Seasons Ritz Lisbon (yes, that's actually its full name, distinct from the Ritz-Carlton brand) offer a kind of classic European luxury that the city does exceptionally well. Don't overlook the small design hotels in Mouraria and Alfama either if you want to feel embedded in the city rather than hovering above it.
For a few days of pure countryside decompression, the Alentejo is criminally undervisited by non-Europeans. The L'AND Vineyards resort near Montemor-o-Novo is a design-forward wine estate with rooms that open their ceilings to the stars, and the food and wine program is serious. Évora, the nearby UNESCO-listed walled city, is one of the most hauntingly beautiful towns in all of Europe and can be done as a day trip or a base in its own right. Portugal's interior moves at a pace that makes you feel like you've actually gotten away rather than just relocated your stress to a sunnier timezone.
One practical note: the Algarve is fine, but it belongs more to the European package holiday circuit than to what I'd call the real Portugal. If you end up there, stick to the western edge around Sagres and the Vicentina coast, where the landscape gets dramatic and the crowds thin considerably. Skip the Golden Triangle unless golf is your primary reason for existing.