It's always worth asking for a hotel upgrade. If you feel shy about asking at the front desk or calling the hotel ahead of time, a simple email to the right person can do the trick.
Photo by Skaneateles Suites.
Conde Nast Traveller offers this "secret". Look up the hotel on TripAdvisor and look for replies to reviews from the hotel. The general manager's name should be there. While the article says the email address is listed there, in my search I only found names. But that could be all you need to find out the manager's email address.
You can send a personal email about how much you're looking forward to spending time in the hotel for your (real or fictitious) special occasion. Hopefully, the manager will reply with a free upgrade or other free perks.
An Easy Way to Get a Better Hotel Room [Conde Nast Traveller]