Portugal

For wine country, Six Senses Douro Valley — a 19th-century manor above the terraced vineyards of the Douro, with the brand's European flagship spa. In Lisbon, Four Seasons Hotel Ritz is the city's grande dame, with its rooftop running track overlooking Eduardo VII Park. The two pair naturally into one itinerary.

May through October, with the September–October harvest the most atmospheric window — grape picking, cellar visits and golden light on the terraces. Summer is hot but glorious on the river; spring is green and quiet. Winter is the valley's dormant season.

The classic week: three nights in Lisbon for the city, then north to Porto and up the valley to Six Senses Douro Valley for three or four nights of wine, river and spa. We arrange the private transfers (or the scenic river-hugging train) and tastings at quintas that don't take walk-ins.

Not for the cities. The Alfa Pendular between Lisbon and Porto takes around three hours and is more comfortable than the motorway, so most clients take the train and pick up wheels afterwards. In the Douro we almost always arrange a driver rather than a hire car — the valley roads are narrow and switchbacked, and you will be tasting port. The Algarve and the Alentejo are the exception. Distances are real down there, and a lot of the quieter beaches sit at the end of unpaved tracks with no taxi rank anywhere near them.

Different holidays. The Algarve has the hotels, the golf, the direct flights and the restaurants, and the western stretch beyond Lagos still feels wild in a way the eastern resorts do not. Comporta and the Alentejo coast are quieter and more fashionable — cork oaks and rice paddies behind a great deal of empty sand, and about an hour south of Lisbon rather than a flight or a long motorway run. Want a proper beach week with things to do? Go south. Want somewhere to disappear for four nights after Lisbon? Comporta.

They do, and it will not be in the rate you were quoted. Lisbon charges €4 per person per night, capped at seven nights, with under-13s exempt. Porto is €3 on the same cap, and several Algarve councils add their own seasonal charge. You settle it at the hotel when you check out, and it applies to the Four Seasons Hotel Ritz Lisbon exactly as it applies to a guesthouse. Small money against the cost of the trip, but it lands at the desk on your last morning and it catches families out.