Derbent (Russian: Дербе́нт dyeer-BEHNT) claims to be the oldest city in Russia with historical documentation, with a history stretching back more than 3,000 years. Occupied by the Arabs, Persians and later the Imperial Russian empire, the city is a UNESCO World Heritage site. This is the site of the quasi-historical "Gates of Alexander," and a massive fortress that overlooks the Caspian Sea
There are two daily commuter trains from the regional capital of Makhachkala, one departing 10 a.m. and another departing 5:20PM, journey time is around three hours.
From Moscow there are departures on Mondays, Thursdays and Saturdays, leaving from Moskva Paveletsky station at 6:05PM and arriving two nights later at 6:40PM. A second class sleeper ticket costs around 3,500 RUB. Other Russian cities with rail connections includes Saint Petersburg (59 h), Rostov-on-the-Don (25½ h) and Yekaterinburg (64 h). International connections includes Kiev (56 h) and Minsk (65 h). Long-distance trains heading to and from Baku stopover here.
There are frequent marshrutkas from Makhachkala's South bus station, leaving several times an hour, taking around 2 hours and costing 170 Rubles.
From Azerbaijan, the car crossing is at Samur/Yarag-Kazmalyar. After clear immigration, it's about a 45 minute drive to the city. Expect to pay around 800 rubles for a full taxi or a 200-300 roubles for a place in a shared car or van.
Derbent's star attraction is the sprawling hilltop Naryn-Kala Citadel complex, which boasts impressive, powerful stone towers and walls. There has been a fortress here since very ancient times and sections of the current structure date back to the 6th c ad. The Khan's Palace entrance building, housing the modest site museum, is from the 16th-18th c. Guided tours are available in Russian. Entrance is 100 rubles/50 rubles for students.
There are also some well preserved sections of the defensive City Walls running from the Citadel down towards the sea.
Historical attractions include the baths, the cisterns, the old cemeteries, the caravanserai, the 18th-century Khan's mausoleum, as well as several mosques. The oldest mosque is the Juma Mosque, built over a 6th-century Christian basilica; it has a 15th-century madrassa. Other shrines include the 17th-century Kyrhlyar mosque, the Bala mosque and the 18th-century Chertebe mosque.
Standard southern Russians are available in town – expect kebabs, BBQ and soups. A couple more upscale restaurants such as the Restaurant Monte Carlo offer sushi, while burgers and pizza are sold at the local cinema.
Cafe Randevu serves decent shashlik and other Caucasian dishes.
Hotel Europe, III Интернационала, 23А. A small comfortable mid-range hotel.
Derbent's on the sea, so the main routes are either north towards Makhachkala or south towards the Azeri border.