If you are traveling then considering the advantages and attractions of the
destination makes sense. You can also pick a
destination where there is a lot of competition among different schools offering Day
Skipper courses.
I love British naval
history and eat up historical fiction along those lines -- O'Brian, Forester, Lambdin, Stockwin, etc. So for me, Portsmouth held a lot of appeal as a destination. Getting to tour the Victory was a highlight. And it feels like there are over a dozen competing Day Skipper schools. And flights into London are competitive vs other destinations offering Day Skipper.
The Solent is also a special place for sailors. We visited the Needles and spent a night in Cowes, among other charming towns on the Solent. Also got to navigate around my first chain
ferry and visit the site of the famous Bramble Bank cricket match.
We did get lucky with our
weather in May. Great winds from 10 - 20 every day. Never got to wear shorts, but also never had to break out the foulweather boots we packed all the way from
Seattle. And never had overpowering winds that kept us pinned at the
dock all day, which I have heard can also be an issue there at times.
I did the theory online through NauticEd and the practical with Nomad Sailing out of Gosport.