Leave early. Casablanca traffic is worst before 9 am and from 5 pm. If you are taking a train, the first departures from Casa Port or Casa Voyageurs run from around 6 am. Aim to be in Tangier by midday so you have a comfortable afternoon to reach Chefchaouen before dark — arriving at night in an unfamiliar medina with luggage is never fun.
Book the Al Boraq in advance. ONCF seats — especially 1st class — sell out on weekends and public holidays. Book at oncf.ma or in person at Casa Voyageurs. The Al Boraq (TGV-class) takes just two and a half hours to Tangier; the conventional Intercité is slower at around three and a half hours.
Grand taxis fill up before they leave. At the Tangier grand taxi rank (near Place du Maghreb Arabe, not far from Tangier Ville station), you wait until six passengers have paid for their seats. If you want to leave immediately, you pay for the empty seats — typically 20–30 MAD per seat. A full taxi to Chefchaouen runs around 60–80 MAD per person (indicative).
The last stretch is winding. The RN2 into Chefchaouen climbs through the Rif Mountains on tight hairpin bends. If you suffer from motion sickness, sit in the front of the taxi and consider taking medication before the Tetouan–Chefchaouen section.
Cars cannot enter the medina. Your driver will drop you at one of the medina gates — Bab al-Ain is the main one. From there it is a five-minute walk uphill into the blue lanes. Hotels are used to collecting guests; if you are heavy-laden, call ahead and they will meet you.