Puri Hotel in Melaka
When to go: Picking the right time to go to Melaka isn't so much a matter of the season as it is the time of week. Thanks to its location on the sea near the equator, the weather is warm and tropical with a chance of thundershowers all year long, so there is no time when it is really all that much 'better' weather-wise to visit Melaka. Instead, the city's position just a couple hours' drive from Kuala Lumpur makes it a popular weekend destination, making the city a lot more crowded on weekends and holidays than on weekdays. If you want to avoid these crowds (and some of the hotels charge more for weekends) then it's best to plan on making a mid-week visit to the city. However, there's one further complication: most of the restaurants and shops in Chinatown are closed on Tuesdays. Taking all that into account, my recommendation is to arrive on Tuesday or Wednesday morning.
How long to stay: Most people visit Melaka on a day trip from Kuala Lumpur. While you can see some of the highlights in just the few hours a day trip allows, it doesn't give you time to browse the shops or visit more than one or two museums. If you're really interested in soaking up the sights of the city, then I would suggest a three night stay which will give you two full days to look around. Spend one day around St Paul's Hill and the other poking around Chinatown.
Where to sleep: Most of the sights of Melaka are within easy walking distance of each other, so I think it's best to stay as close as possible to the historic areas. There are several small hotels in Chinatown as well as several around the fringes of the area. All are listed on the hotels page.
Getting around: As mentioned above, most of the sights are within easy walking distance of one another. You will only need transportation if you are staying too far away or want to visit some of the outlying sights such as China Hill or Portuguese Square. In such cases, a taxi will do and should never cost you more than RM 15 (3.05 USD). Note that Melaka taxi drivers have something of a bad reputation for over-charging and not using meters.
What to see: Melaka will appeal mostly to those with a keen interest in history and architecture. The specific things that will interest you are of course up to you, but the ‘don't miss’ sights would include the old town square, the ruins of St Paul Church and the Baba Nyonya Heritage House in Chinatown.