Although an airport has (2005) been built at Anisakan, there is no civilian air service yet to Pyin Oo Lwin. The nearest airport, with connections to Yangon, He Ho, Bagan, Chiang Mai and other destinations, is Mandalay International Airport. It's a 90 minute drive away.
If you're going any distance, there's little alternative to the Toyota Taxi. Foreigners generally have to pay a premium, plus extra for the front seat. Four passengers is the limit, and four sharing get a better deal than four individuals. Try to find a driver with some relevant language skills, and you'll benefit hugely from local knowledge and ideas. Around $7 each, compared with $40+ if you hire a private taxi.
There are several taxi stations (known as 'taxi gates', locally), at the main market, four or five by the centre of town traffic lights, and three or four opposite the Shan market. They are all happy to do one day tours as well as longer journeys in the Hsipaw, Lashio direction. Hotels usually have 'friendly' taxis on call, though visitors might wish to ask around since prices will vary. Your hotel will probably use one of these taxi companies:
Soe Moe Aung, Bogkoke Street (Centre of town), (085-21500). From Mandalay: (02-60950)
Win Yadana, Bogyoke Street (Centre of town), (085-22490). From Mandalay: (02-35548). From Lashio: (082-23070, 082-23980)
Sein Myanmar The best taxi to and from Mandalay airport. Good drivers and cars. Reliable. (02-30128)
And several others
Most inter-city express buses do follow a timetable, but to reach more local destinations you will need to get some local knowledge in order to judge the departure time and place. Good air-conditioned buses leave Pyin Oo Lwin frequently for an overnight journey to Yangon at very reasonable prices. There are also direct bus services from Yangon to Lashio which passes through Pyin Oo Lwin daily. Many shops sell tickets. The bus station is a little out of town in the New Town.
It's possible to get tickets from the railway station to up-country destinations, and down to Mandalay. The timetable is fairly good. Time to Mandalay is about 5 hours. The world-famous Gokteik Viaduct is about an hour and a half's journey by train from Pyin Oo Lwin - not for the faint-hearted, though! The train timetable can now be found here.
Cheap, noisy, slow, cramped, uncomfortable but social. About 2 dollars and between 2 and 3 hours from Mandalay. You can hear the ticket collectors shouting for passengers at the Hilux stand near the Purcell Tower and opposite the Myoma Cinema: 'Man'lay, Man'lay!'
Most hotels offer bicycle hire at reasonable rates. A few also have motorbikes.
Except on the very rare very hot day, Pyin Oo Lwin and the surrounding villages can easily be explored on foot. For anything more than the town itself, however, you will need a guide. The lanes in the areas near the town centre are very rewarding for the curious and those interested in the history of the region.