If the plan includes taxis, hotels, rooftops, fine dining, or very short walks, heels may make sense. They can be worth it for the right dinner, wedding, event, or polished city night.

If your itinerary is full of cobblestones, hills, old towns, ferries, markets, stairs, or long strolls after dinner, heels may become more burden than benefit. A chic flat, sandal, wedge, or block heel will usually serve you better.

If heels are coming, keep it to one very versatile pair. They should work with multiple outfits and be comfortable enough to wear for more than twenty minutes outside the hotel room.

Paris, Milan, and New York can make a heel feel useful. Capri, Hvar, Santorini, Venice, and most old European towns may make you regret it quickly. The prettier the street, the less forgiving it usually is.

Some people can wear heels all night. Some people are over it by the lobby. There is no prize for suffering through vacation in the wrong shoes. Pack for the version of yourself who wants to enjoy the evening.