Monemvassia is a great place to wander. Sure, you'll get lost in the winding lanes, but how lost can you get on an island 480m (1,600 ft.) long and half as wide? The answer (at least at night) is: pretty lost. It's a good idea to wear good walking shoes, bring a flashlight, and save the 240m (800-ft.) ascent of the citadel (the best path up is marked on Odos Ritsos, the main street) for daytime -- preferably in the cool of the morning.
You might begin your visit at the Momemvassia Archaeological Collection (tel. 27320/61-403), in the former mosque on the Plateia Tsami (Square of the Mosque). It's open daily (except for Mon) from 8am to 3pm (sometimes later in summer); admission is free. The exhibits of local architecture and artifacts include some elegant old clay pipes; try to pick up a copy of the excellent guide The Castle of Monemvasia (3€), with its detailed map and explanations of the castle's elaborate fortifications.
From the citadel, there are truly spectacular views down to the red-tile roofs of Monemvassia, out across the sea and deep into the mountains of the Mani peninsula. While you're here, try to figure out how the 13th-century Church of Ayia Sophia (Holy Wisdom) was built not just on, but virtually over, the edge of the cliffs.
After exploring the citadel, you'll probably want a swim, so head down to the bathing jetty, signposted along the sea wall. En route, you'll probably pass through the main square again, with the church of Christos Elkomenos (Christ in Chains) across from a Venetian canon, as well as the Venetian chapel of Panagia Chryssafiotissa. The churches are sometimes locked; if locked, content yourself with the thought that the handsome stone houses lining Monemvassia's lanes are the real treat to see here.
The line of small shops along Ritsos Street, the main drag on "the rock," have thus far avoided the infestation of T-shirts and cheap museum reproductions so common elsewhere. Ioanna Angelatou's shop, next to the Byzantion hotel, has been here more than 20 years; it sells the deep-blue glassware made in Greece, jewelry, and well-done reproductions of antique woodcarvings and copper. Just inside Monemvassia's gate, Costas Lekakis has a good selection of books in English, including R. Klaus and U. Steinmuller's excellent guide Monemvassia (6€). Kelari has wines, including examples from the local Vatistas vineyards. Takis Papadakis at Kelari can often give you information on local rentals of rooms and small apartments (tel. 27320/61-695).
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.