[princessnicki]

Originally Posted by RICO

You make some compelling points to retain the May dates -

1) The tickets to see the Red Sox - wow, awesome.
2) The weather in Florida in May is, in my opinion, a tad nicer than September when the afternoon storms and associated humidity kick in.
3) Fall prices could easily (but may not be) significantly higher in September to New England due to all those tourists coming to see the wonderful foliage - although that can be quite finicky and can easily move weeks either side.
4) Decent price on your existing flight tickets.
5) Time to play with until balance is due.

But then you say the 'mask issue' could be a deal breaker. Only you can answer this one because no knows what the crystal ball will tell us. Are you unable to wear it due to claustrophobia or some other medical issue, or simply unwilling to wear for 7 hours on a flight? The rectangular white/blue surgical-type masks are not (in my opinion) too bad to wear for lengthy periods, especially in an air-conditioned plane with the vent above facing directly onto you. Remember, you can take them off to eat and drink on the plane.

Personally, I'd stick with the original plan but, this being a diverse board, you will likely get differing opinions. Ultimately, your decision matters. Good luck.

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Thank you for the advice

The Red Sox are actually playing at home on the dates I want to move to in September (I thought the season finished in August!) so this has actually swayed us more towards September.

The weather does put me off on the Florida side but I was hoping it wouldn't bother us too much as we aren't doing the full-on Disney experience again until 2022.

I am just waiting for the flights to come out in October to compare but I am hopeful as the prices seem to be reasonable for all the dates released so far in 2021

Boston hotels might be a lot higher priced as you mentioned so we could look at renting an apartment if we decide on September

The mask issue isn't a medical thing, my husband wears one for work in a hot factory and its something we both wouldn't want to put up with on holiday so it's definitely a deal breaker. I guess things could change a lot by May.