Pskov — the ancient capital is not well prepared for tourism, but is rich in sites; its Krom (medieval citadel) is very impressive, it is circled by monasteries—including one which is Russia's oldest, and the city is full of small, old churches
Gdov — a medieval town famous for its churches, which were destroyed in an act of cultural vandalism by the German Wehrmacht, but are being carefully restored
Izborsk — a town 30km to the west of Pskov with a huge, ancient fortress, surrounded by a modern day park
Pechory - a town just 8 km from the border of Russia and Estonia, famous for its great Orthodox monastery.
Porkhov — a small town with a fortress constructed by Alexander Nevsky in the 13th century
Sebezh — a small town most interesting for its 17th century baroque, Polish built, Roman Catholic cathedral, which has been reconsecrated as an Orthodox cathedral
Velikiye Luki — the second largest city in the region; the principal attraction is the estate-museum of composer Modest Mussorgsky, outside the city
Inside the Krom of Pskov
Pushkinskie Gory (Pushkin Hills) - a former Pushkin's mansion and its surroundings converted into a large open-air museum with breathtaking scenery and traditional Russian ethnic elements. An excellent weekend destination.
An ancient region of Russia which once constituted its own republic, Pskov Oblast is a great weekend trip or longer from Saint Petersburg. Tourist infrastructure is at best rudimentary, although one would expect this will change in the near future, but the region has lots to see for an adventurous traveler or a traveler with a good guide. Pskov, the capital, is without a doubt the principal attraction and likely the only stop for most travelers, but it might be a good plan to get out of the city and check out nearby Izborsk.
Two daily buses depart for Pskov from Novgorod at 08:30 and 16:00.
Trains from Saint Petersburg are unfortunately very inconvenient—they leave around 03:00 and arrive in Pskov four hours later. A better option is to hop on a bus from Petersburg's Vitebsky Vokzal; there are 15 buses bound for Pskov daily and they take about 5 hours to get there.
There is a daily overnight train from Moscow which leaves around 20:00 and arrives in Pskov around 08:00.
Pskov is a common last stop in Russia for visitors traveling overland to the Baltic states.