And of course you can throw some amex miles into the mix.. Or upper out and PE back.. PE is fine - I have done it many times and been happy. Upper is super - even better from Heathrow due to the clubhouse.
Assuming you know where you want to go it starts becoming somewhat easier. City, beach or both?
Virgin has a much smaller network so you be guided by that or award availability..
I good place to start is when and where and then phone up. The staff on the phones are excellent in my limited opinion - start of with a short list and take it from there.
The amex transfers are instant assuming you have sent one previously so maybe ping 1000 over to get that base covered and jump straight in .
Happy Travels.