By car: 97 km down Simferopol highway, turn right towards Serpukhov.
Located at a point where two rivers Oka and Nara merge, this city was a capital of the Serpukhov princedom during Troubled times. For the first time, it was mentioned in 1328 in the letter of Ivan Kalita, who was doing an inventory of his property. The most famous Serpukhov prince was Vladimir Andreevich, who received a nickname Brave for participation in the Kulikov fight. In 1483 the princedom was finally attached to the Moscow area. Many trade routes went through Serpukhov, in a local museum among others they name a Great Silk Road. Due to constant enemy attacks, a fortress was constructed in the city.
Almost nothing is preserved from the times of the Serpukhov princedom, except for the Red Hill, the remains of the Kremlin on the bank of Nara river. Once monastery walls were 8 m high, now all you can see on the hill are few lonely stones with the remains of loopholes sticking out of the ground. The monastery was taken apart in 1934, and monastery stones were used at the construction of the Moscow subway. Now Troitsky Cathedral (1696) towers on the hill; there is a branch of a Local History museum inside. The exposition is generally devoted to architecture of the city. If you go down the hill from there, it is possible to see the small river Serpeika (regional specialists believe that the form of a channel - a sickle (Russian: serp), and the form of the Cathedral mountain - an ear (Russian: uho) gave name to the city). At a corner of the Soviet and Kalugskaya streets there is a restored church of Nikoly White which was constructed in 1857 on a place of an ancient temple. Going down the Kalugskaya street towards Lenin square, it is possible to glance at the territory of Raspyatsky monastery through a white gate and to approach the dilapidated cathedral of the Crucifixion (1751). Other two monasteries in the city, Vladychny and Vysotsky, are in better condition. In front of the entry of the Vysotsky Monastery there is a viewing platform, from there you can get an outlook on the part of the city on the opposite bank of Nara and located slightly to the left Vladychny Monastery.
Two monasteries, divided by the river, were established almost at the same time: female, Vladychny, by Metropolitan Aleksy in 1360, male, Vysotsky, by Sergy Radonegsky in 1374. In Vysotsky Monastery you can find a five-domed cathedral of the Conception of the Virgin (the end of the 16th century) and Nikolay Chudotvorets church (the beginning of the 17th century), but they are usually closed. To get into the Pokrovskaya church, where services are usually held, you might need to wait in line. The reason of such popularity is an icon called “Undrinkable Bowl”, to which people address their prayers, hoping to recover from alcoholic dependence. To get to the Vladychny Monastery on the opposite bank it is better to use a car. Oldest of the constructions which have been preserved here: dining hall with the tent-like Georgievskaya church (1599) and the Sacred gate with the church of Feodotiy Ankirsky (1599). The towering five-domed Vvedensky Cathedral was constructed in the beginning of the 17th century. Now the monastery is being restored little by little, though, in comparison with Vysotsky monastery, it is in a very dilapidated condition. In the History And Art museum (ph.(4967) 35 26 70, 35 17 53, Chehova, 87) there is an excellent collection of pictures by Shishkin, Savrasov, Ayvazovsky, Repin, Levitan, Polenov and also an admirable collection of European art.
You can get a bite in the city in the restaurant «Rus'» (ph.(4967) 72 66 02, 2nd Moskovskaya, 2/20, opened every day 11.00-0.00) or in unexpensive, but pretty decent cafe «Tolstopuz» on Revolutionary square.