I went to Chefchaouen on my own in late March, arriving on a CTM bus from Tangier that cost 75 dirhams (about £6) and took just under three hours. The coach was clean, air conditioned and on time. The booking website was another story. I tried twice to pay online, both times the page froze at checkout, and I ended up buying at the counter in Tangier like apparently everyone else does. If you're going in spring or autumn, buy a day ahead. The good departures sell out.
There is no train to Chefchaouen. That caught me off guard. Your options are the CTM bus, a grand taxi for around 700 to 850 dirhams (£60 to £70) for the whole car, or a private transfer. I was solo, so the bus made the most sense.

Where I Stayed
I booked Dar Dadicilef, in the Souika quarter inside the medina. Two nights first, then extended to three because I couldn't bring myself to leave. It runs at around £30 a night in low season, more like £45 in high. The place is one of the oldest Andalusian houses in Chefchaouen, run by Abdou and his father, and they are the reason people come back. Abdou met me at the gate, carried my bag through the alleys, handed me a mint tea within five minutes and started drawing restaurant recommendations on a napkin. The room was blue. The walls were blue. The garden was blue. That sounds absurd written down but it felt completely right once you were inside it.

Breakfast was included and it was proper. Moroccan pancakes, honey, homemade cake, fresh juice, and more mint tea. I ate in the garden both mornings I was there, in full sun, and genuinely did not want to get up.
What I'd flag about staying inside the medina is the luggage situation. You get dropped at a gate and walk from there, uphill, on cobblestones. Some riads are fifteen minutes further in. Dar Dadicilef is close to Bab el Ain and Plaza Uta el-Hammam, which makes the walk manageable, but if you've got heavy bags or mobility issues, ask the riad how far they are from the nearest bab before you book anything. That one question will tell you more than any listing photo.
The building has steep, narrow staircases and no lift. That is standard here. If stairs are a problem, staying just outside the medina or close to the lower gates is the more sensible call. Dar Echchaouen, out on the Ras El Ma road, is the place people mention most for that. You trade the blue-alley feeling for a quieter setup with gardens and a pool in summer.
What I Actually Did
Walked. That is the honest answer for the first two days.

The medina is small enough that you can cross it in twenty minutes but disorienting enough that you won't. I got lost constantly, which turned out to be the point. Every wrong turn ended at a painted doorway, or a cat sleeping on a blue step, or a tiny shop selling jben, the local white goat cheese that you will not find in Marrakech. There was no plan and that was fine.
The one piece of timing advice I'd taken seriously was to go out early, and it paid off. The CTM buses from Fes and Tangier arrive mid-morning. By eleven, the lanes around Plaza Uta el-Hammam are packed. By half four, they thin out again. The early mornings and the late afternoons are where the town shows you what it actually is when the day-trippers leave.
On day two I walked up to the Spanish Mosque. It took about twenty-five minutes from the medina, starting at Ras el-Maa where the mountain water comes down at the top edge of town. Women were washing clothes there. A couple of kids were swimming. There were cafes with tables right next to the water. From there the path climbs, gets steeper and rockier in the last stretch, and opens out at the old mosque ruin on the hill. It was built by the Spanish in the 1920s but never finished because locals refused it. Now it is the standard sunset spot, and the view is the one you have already seen in photographs: blue roofs, the Rif behind, the whole valley laid out.

I will be straight about sunset though. The sun drops behind the mountains rather than setting over an open horizon, so you are not getting a dramatic fireball. What you get is the light changing across the whole town, warm and gold, and that is worth the climb on its own. It does get crowded up there. Go at sunrise instead if you want quiet. One reviewer described arriving early morning to find five other people and cool air. That sounds better than what I had, which was about sixty people and a lot of phone screens.
On the third day I took a grand taxi to Akchour, about forty minutes out of town, and hiked to the waterfalls. This takes most of a day and it is the thing to add if walking is your reason for being here. The trail follows the river through a valley, crossing stepping stones and narrow tracks. The path to the first cascade is about an hour. From there it gets rougher to reach the big waterfall. Wear proper shoes. Some of the crossings are slippery. You do not need a guide, despite what people at the trailhead will tell you. The path is followable.

Where I Ate
Bab Ssour, and then Bab Ssour again, and then Bab Ssour a third time.
It is a small, plain, family-run place in the medina. You eat on cushions, there are rolls of kitchen paper on the tables, and the owner, Said, will tell you what is good that day and remember your name when you come back. Harira soup costs about 7 dirhams (under 60p). Chickpeas with bread, about 20 dirhams (£1.60). Under two pounds for a meal. The goat tagine was the best thing I ate in Morocco, full stop. Reviewers name the bisarra, the white beans and the yoghurt. If you go on a Friday you can get couscous, which is traditional and apparently worth the timing. I missed it.

The terrace upstairs has a view over the medina that people describe as the best free thing in Chefchaouen. I sat up there with a mint tea after my second lunch and watched the light move across the blue roofs until I got cold.
The restaurants on Plaza Uta el-Hammam are where you go for the view of the Kasbah, not for the food. Every account says the same thing: have a tea there, then walk into the side streets to eat. Sofia is women-owned and gets named as the best in town for vegetable tagines and couscous. Lala Mesouda is the other home-style favourite. If you are vegetarian, Chefchaouen is the easiest place in Morocco to eat well. The mountain produce is the reason.
One thing I was not prepared for: alcohol is difficult. This is a conservative part of the country and drinking is simply not part of daily life. A few hotels have a discreet bottle of wine. Most places have nothing. If that matters to you, know it going in.
Who Should Go
Solo travellers. I felt completely safe the entire time, including after dark. Several other women I spoke to on the trip said the same. The haggling from shop owners exists but it is nothing like Marrakech or Fes. Nobody followed me. Nobody was aggressive. If you have solo travel experience already, this is one of the most relaxed destinations in Morocco.
Photographers. Obviously.
Vegetarians. See above.
Budget travellers. You can eat three meals for under five pounds. Hostels around Bab el Ain are the cheapest beds in town and almost every property at every price point has roof access.
Anyone who wants slow rather than a list of sights. There is a kasbah and a couple of mosques but this is not a city of attractions. It is a city of walking, eating and sitting on rooftops. If that sounds boring to you, it probably is not the right trip.

Who Should Think Twice
Anyone with mobility issues. The entire medina is built on a hillside. The streets are steep, uneven, cobbled and full of steps. The riads have narrow staircases and no lifts. This is not negotiable. If stairs are hard, research the flat-access options outside the medina carefully.
Anyone expecting nightlife. It does not exist here. The evening is dinner, then tea, then quiet.
Anyone coming with a lot of luggage who has not checked how far up the hill their riad is. You will be carrying it from the gate on foot, uphill. I saw a couple dragging a hard-shell suitcase over cobblestones for twenty minutes and they did not look like they were having a good time.
Day-trippers who want four hours and think that is enough. You can do it. Plenty of people bus in from Fes and get the blue alleys in the middle of the day. But you get the town at its most crowded, miss the early mornings and the sunsets, and leave before the part that everyone says is best. Two nights is the minimum. Three lets you add Akchour.
Practical Bits
Bring cash. There are ATMs in the new town below the medina but a lot of riads, cafes and stalls take cash only.
If you are coming between December and February, check your riad has heating. The Rif gets properly cold at night and a lot of these buildings were not designed for winter.
Book accommodation early for spring and autumn. The good places go months ahead.
And ask about the stairs before you book. That is the single most useful question in Chefchaouen.
