We are traveling to southeast England in June. Picking up a car in Dover, driving to Rye for a few nights and then to Portsmouth for 2 nights . My husband wants to then drive up to Winchester and drop the car off there after touring the city, then taking the train to Victoria Station to be in town late afternoon. Is this a reasonable idea or too much logistics? We've been to England several times, but never the south.
Yes, it would work assuming your car rental company has a branch in Winchester, and it is open.
Lots of other places to stop at between Rye and Portsmouth (Arundel, Chichester, . . . ).
- Check your hotels have parking, especially the ones in Portsmouth and Winchester (or drop car off before touring city).
- Trains from Winchester go to London Waterloo station, not Victoria.
What are you planning to do in Portsmouth? If you're keeping to the main sights of the Dockyard and Southsea Seafront (including the D-Day museum) then a car will not be required and parking is quite expensive likewise Winchester which is quite compact and can easily be toured on foot. The centre of Winchester comprises of a lot of one way streets and scarce parking. Winchester can be reached by train from Portsmouth Harbour and from Winchester to London.
However, if you plan on visiting outside of Portsmouth, perhaps Portchester Castle, the Royal Armouries museum at Fort Nelson, Southwick House and the plethora of small, attractive villages on the route to Winchester then a car would be the best option. This would probably be my choice. Two nights in Portsmouth will be more than adequate to visit the Historic Dockyard and the Southsea sights thereby giving you some time to visit the wider area. Portsmouth is a heavily populated island, it is a gritty port city that doesn't offer much outside of the naval history, much of the city is urban and unattractive as a result of the heavy bombing during the war.
The quieter, more pleasant and residential areas north of the city (where I live) don't offer much for visitors although the line of forts running along the top of Portsdown Hill are very interesting, most notably Fort Nelson which offers free admission.
https://royalarmouries.org/venue/fort-nelson/
My recommendation would be to leave Portsmouth and visit Portchester Castle www.english-heritage.org.uk/visit/places/portchester-castle/, which will probably occupy an hour or two and then drive the short distance to Fort Nelson for another hour or so. I would then opt to take the country drive to Winchester rather than the motorway, taking in Southwick, Soberton, Droxford, Corhampton and, if the timing is right, stop for lunch in Exton at The Shoe Inn, www.theshoeexton.co.uk.
From here I would take a little diversionary route to include West Meon and Bramdean before heading to Winchester. Drop the car off as soon as you get to Winchester and tour the city on foot.