Two paces. One of you wakes at 6 a.m. and one is alive at midnight, and a vacation will not change that. Give the morning person the early slot (the temple at 7 a.m., the market before it fills) and the night person the late one (the bar, the view after dark), and meet in the middle for lunch. Nobody apologizes for sleeping in or for leaving early.
One must-do each per day. Each of you names one thing per day that matters to you; the other comes along without comment. Everything else is negotiable. This is the rule that ends the “I thought you wanted to” conversation, because the wanting was said in advance.
The money conversation. Have it before the trip, not at the first restaurant. Decide whether you pool, split or take turns, whether the hotel upgrade comes out of the trip budget or is one person’s treat, and what the ceiling on a dinner is. Then stop talking about it. Waystop’s expense splitting keeps the running total so neither of you has to.
The one reservation. Every city has one meal or one slot that defines the week: a counter in Tokyo, a timed slot for a painting in Milan or Florence, the show. Those book weeks or months ahead and sell out. Pick one per trip, book it first, and build that day around it. The rest can be walked into.
The day apart. By day four, spend an afternoon separately. One goes to the museum the other has been dreading; the other sits in a café with a book. You come back with something to tell, which long days together tend to use up.
Honeymoon markups. Tell the hotel it is a honeymoon or anniversary when you book, in the notes field: the upgrade and the bottle cost nothing when they happen. The markup lives in the “honeymoon package”: the same room, a petal turn-down and a set-menu dinner at a price above the pieces. Price the pieces separately before you say yes.
When it rains. Plan the rainy day before the trip, not at the window: the covered market, the museum you were saving, the long lunch, the baths in Budapest or an onsen in Osaka, the food halls under the department stores in Tokyo and Seoul. Rain is the day apart if you want it, or the day you finally sit down.
At breakfast. Say the one must-do each, check the reservation time, and let the morning person leave first. Put the booking confirmation in Waystop’s Documents so the right phone has it, and if the plan slips, lunch is where you meet.