Find that out, then tailor your trip that way.
I'd also lean more towards 5 nights/4 days - the travel days are stressful enough without planning activities.
Earlier this year I saw a deal on travel from NYC to Tuscany for a week - wife said No. We ended up going to Florida for two weeks. Flew to Key West, drove here and there, flew back from Jacksonville. Only 6 nights in motels - most with friends & relatives.
Not sure I'd pick Freeport as a destination. Bermuda would be good.. Cuba could be interesting.. Lots of nice places right in Florida.