Old San Juan in Two Nights, Mostly After Dark

Old San Juan is roughly seven blocks by nine. You can walk from one end to the other in about twenty minutes without hurrying, which sounds like an argument for a day trip and is in fact the opposite.

The old town holds about eleven thousand residents and, on a heavy day, several times that number of visitors, most of whom arrive in the morning and leave in the late afternoon. The city that exists after they go is the city worth booking a room for, and you cannot get to it on a day trip by definition. That is the entire case for two nights here, and having now done both versions, I would not go back to the other one.

01Getting there late is fine

My flight landed after eight, which on any other trip I would count as a wasted evening. Here it was the best decision of the trip, because the ride into the old town takes about twenty minutes and I was walking on wet blue cobbles by half past nine with almost nobody around.

The stones underfoot are the first thing anybody mentions and they earn it. They are a deep blue grey, they were originally ballast, and after a shower they hold the light from the street lamps in a way that makes the whole grid look like it has been varnished. It had rained about an hour before I arrived. I spent the first night doing nothing except walking the same six streets in different orders.

That is a real recommendation, incidentally. On a two night stay the first evening should have nothing planned in it at all.

The old town holds about eleven thousand people and, on a heavy day, several times that many visitors. Almost all of them leave by six.

02Day one, and the shape that worked

The shape I would repeat is simple: forts in the morning, shade in the middle, streets in the evening.

The two great stone fortifications sit at either end of the old town, and both are best in the first two hours they are open. Not for the light, though the light is good, but because the walls are wide open to the sun and by eleven the exposed sections are genuinely hot. The scale of them is difficult to convey. Ramparts that go on for hundreds of yards, layered defensive terraces stepping down toward the water, and a green field on the seaward side where the wind comes straight off open ocean.

I walked between the two of them along the outer wall in the morning, which took about forty minutes at a slow pace, then dropped down into the grid when the heat arrived.

The middle of the day belongs to shade. The streets here are narrow enough that one side is always in shadow, and the buildings are two and three storeys with wooden balconies that overhang the pavement. I ate lunch, sat in a plaza for an hour, went into a small museum mostly for the courtyard, and read for a while. On a two night stay it is tempting to fill the middle hours with something, and I would argue strongly against it.

03The second evening is the point

If the first evening is for wandering, the second is for staying out.

Around six the tone of the whole place changes. The cruise passengers have gone, the day tour groups have gone, and what is left is a small residential city that is out on its own streets. Doors that were shut are open. There is music from at least two directions at any given moment and none of it is being played at you. Tables appear on pavements that were too narrow for tables an hour earlier.

I sat in a plaza from about eight until close to eleven and covered maybe three hundred yards in that time. That is the correct pace for this. A cat with a serious territorial claim worked the perimeter. Somebody was tuning something. Two men had an argument about baseball that lasted longer than my dinner and appeared to be entirely recreational.

The photographs I kept from this trip are almost all from these hours. Warm interior light coming out through open shutters, pastel walls that go strange and lovely under sodium lamps, and the cobbles doing their thing again.

04Practical notes worth having

Everything in the old town is walkable and you should walk it. Bringing a car into the old streets is a way of turning a pleasant stay into a parking problem, and the grid is small enough that walking is faster in practice.

The hills are real, though. The town sits on a rise between two water frontages and several streets are properly steep, with cobbles polished by three centuries of use. They are slick when wet. Shoes with grip matter more here than in almost any other small city I have stayed in, and the elegant footwear plan should be reconsidered.

Hydration is not a joke in this climate. The heat is not extreme but the humidity is, and I got through more water than I expected on both days without doing anything strenuous.

On timing: check whether large ships are in port on the days you are there, because that single fact changes the daytime feel of the streets more than anything else. It does not change the evenings at all, which is the other argument for the two night version.

05Where the old town stops

Worth knowing that the old walled town is a small piece of a much larger city, and the rest of San Juan is not this. Twenty minutes away there are beaches, high rise districts, and a completely different pace, and none of it is a substitute for the seven by nine grid.

On a two night stay I would not try to see both. The old town rewards being lived in for forty eight hours far more than it rewards being ticked off in an afternoon on the way to somewhere else. Save the rest of the city for a longer trip and let this one be about a small number of streets in the dark.

06Would I do it again

Yes, and in exactly the same shape. Land late, waste the first evening on purpose, do the forts before the heat, hide in the shade through the middle, and then give the second evening everything.

The one change I would make is to book the room inside the walls rather than a short ride away. I did not, and the twenty minutes back at the end of each night was the only friction in an otherwise frictionless two days. In a place where the whole argument is about being present after everyone else has left, being able to walk upstairs at midnight is worth paying for.