There is a direct train from Portsmouth & Southsea to Winchester. South Western Railway runs it, and it takes about 53 minutes with nine stops on the way.
On the weekday timetable we checked, the direct train left Portsmouth & Southsea at 04:57, 05:55, 06:28, 06:55 and 07:29, then on the hour every hour from 08:00 to 21:00. The 21:00 was the latest direct departure we found.
That on-the-hour pattern is easy to work with, but it is only one train an hour. If you would rather not wait, a second pattern changing at Southampton Central left at around 27 minutes past most hours from 07:24 to 20:28 and took about 64 minutes, eleven more than the direct train. Between the two, there is something leaving roughly every half hour through the day.
Once the 21:00 has gone, the options get patchier. Journeys changing at Eastleigh left at 21:27 and 22:00 and typically took about 68 minutes, and a 21:46 changed at Southampton Central instead. After that the journeys stretch out: a 22:35 changing at Woking and Basingstoke took about 2h 15m.
So for a late evening in Portsmouth, aim for the 21:00 or one of the changes at Eastleigh or Southampton Central, and treat the 22:35 as a slow fallback rather than a normal train.
The road is quicker. The M27 route is 30 miles and takes about 43 minutes, around ten minutes less than the direct train, so the car wins narrowly if you already have one with you.
From Winchester station, the walk to the Buttercross on the High Street covers about 760 metres and takes around ten minutes.
Journey times and changes below come from the rail and bus timetables for Tuesday 1 December 2026. Weekend and holiday timetables differ, so check the day you travel.
From Portsmouth & Southsea on the weekday we checked: about hourly between 04:57 and 21:00.
By road it is about 30 miles from Portsmouth to Winchester, mostly via the M27 — roughly 43 min with clear roads. Car parks in Winchester are listed on the Getting Here page.