We leave for Spain today, and the itinerary is finally finished. Which means I’ve reached the point where there isn’t much left to plan, but there is plenty left to question.

For part of our trip, I worked with two local destination specialists in Spain—these are the companies travel advisors use on the ground to arrange private guides, drivers and experiences that can be difficult to find or coordinate from home. I could have researched and booked many of these things myself, probably for less, but I wanted to see what their local knowledge and relationships could add. That was partly for my own experiences on this trip, and partly because I’m considering both companies for future client travel.

Throughout the planning, I made a number of decisions to pay more for private guides, private transportation and locally designed experiences rather than simply booking an option I could find on the internet myself. Some were about convenience. Some were about avoiding friction. And some were bets that the right person on the ground could create something I wouldn’t have found on my own.

I know why I made those decisions. I don’t know yet whether they were worth it.

Take the boat we have booked in Mallorca. It’s a private four-hour excursion from Port de Sóller on a 50-foot sailboat, with snacks, wine, snorkeling equipment and everything else we need for the morning. I could have booked a shared boat with similar inclusions for roughly a quarter of the cost. I’m fairly comfortable spending more when I understand exactly what the additional money is buying. In this specific case, a lot of it was about risk mitigation. I don’t particularly like shared tours. You may end up with people you enjoy, or you may spend four hours with people you would never voluntarily choose to spend four hours with. There may be plenty of space, or you may spend the afternoon negotiating for a place to sit or a bit of shade. I also evaluated the private options proposed by both of the destination specialists but they both departed from Palma. Our hotel sits just above Port de Sóller, so that would have added an unnecessary extra hour of transportation to a four-hour boat day. I paid more in order to remove all of those variables. Whether removing them makes the experience worth four times as much is something I can’t answer yet.

There’s another kind of premium I’m testing on this trip, and it’s harder to quantify.

Last year, a local destination specialist arranged a day for us in Valtellina that still stands as the best private excursion we’ve experienced. We spent hours walking terraced vineyards with Luigi, a member of a small wine cooperative I had never heard of, stopping at cellars built beneath enormous glacial rocks and eventually sitting down to lunch made by another cooperative member. I could not have planned that day myself because I didn’t know the people or the place well enough to know that experience existed. That is the level of access I’m looking for when I work with a good destination specialist.

I can find a private guide. I can reserve a winery. I can book a driver. What I’m paying someone else for is the judgment to know which guide, which winery, which sequence of stops, which person behind the scenes might turn a perfectly good day into one I never could have created on my own. Spain is going to test that.

And then there’s the itinerary itself.

Twenty-three days sounds generous until I count how many of them involve moving somewhere else. Including the international travel, seven of our days are transit days. We chose to fly some of the longer domestic stretches because it saved time on paper. But airports have their own friction: packing, getting there, checking bags, security, waiting, landing, collecting everything and getting to the next hotel.

Jerez is a day trip from Seville because I didn’t want to add another hotel change. But will one day there feel like enough? Granada has three nights. Seville has six. Rioja has four. Barcelona gets three at the end. Every one of those decisions made sense when I made it. I’m curious whether they still will once we’re actually living inside the itinerary I built.

The funny thing is that the trip looks very scheduled when I open the full itinerary, but I’ve deliberately left quite a lot of time to just explore without commitments. Most of Mallorca is ours to explore independently. Seville has real open time. Barcelona has one private sightseeing day and plenty we’ll do ourselves. The fixed experiences are surrounded by time for leisurely walks in neighborhoods exploring wine bars and local shops.

I’ve done something similar with dinner. We’ve mostly reserved dinners in Mallorca and Rioja because those were the places where I thought I was most likely to regret leaving it until the last minute. Everywhere else, we’re largely winging it. That could turn out to be exactly what we need after a long day with a guide. It could also turn into us standing outside a restaurant at 9:00pm, hungry, discovering that there are no tables available. I don’t know yet.

And I think that’s what has become interesting to me about this trip now that the planning is done. Not whether every reservation runs on time or every day unfolds exactly as scheduled. I’m much more interested in where paying more actually changed the experience, which things I could just as easily have arranged myself, whether the flights preserved more time than they consumed, and whether the blank spaces in the itinerary feel freeing or too loosely planned.

A few weeks from now, I’ll have answers. And probably a few decisions I’d make differently. I’ll report back from the other side of the itinerary.