Little Details

Skimmed this community. Searched hippocampus+damage, hippocampus+damage+memory, anterograde+amnesia, anterograde+amnesia+treatment, anterograde+amnesia+coping, encephalitis+amnesia, anterograde+amnesia+school, anterograde+amnesia+homeschool

Time: Modern day.

Setting: Anycity, Anystate, USA

This is for an RP, not a story, but this is an awesome community and I was hoping someone could help me with this character. He is, tentatively, a 17-year-old male who lives with his grandfather and a year or two ago had the bad luck of contracting an arbovirus, which led to encephalitis, which led to some brain damage.

I want him to have a hard time forming new memories without getting rid of that completely -- like a mild sort of anterograde amnesia -- but I'm not sure if what I have in mind is reasonable.
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If this doesn't work at all, it's not a huge deal, but I'm hopeful... Sorry for so many questions!

Googled: Sea Travel in Ancient Rome (and found this: http://www.csun.edu/~hcfll004/travel2.html, but doesn't have the itinerary I'm looking for). Crystalinks was vague.

Time: Imperial Rome in the first century CE

Basically, I have a character going by boat from Syracusa, Sicilia to a fictional city roughly 40 miles north of Rome (Google maps tells me that it's probably situated around present-day Ladispoli aka Alsium.)

It's a merchant vessel.

1) Are there any months of the year where such a boat simply would not sail, given the risk of storms? I'm getting a bit confused trying to think in terms of the Julian calendar.

2) About how long could such a trip be expected to take?

3) What sort of accomodations would be provided for passengers on-board the vessel? If it makes a difference, the merchant has a 15-year-old orphaned niece. He's sending her to live with his youngest brother, in this fictional city, thinking that her prospects of marriage will be better there.

ETA: Thanks so much for your help! Based on the comments here, I've been reevaluating a few things. For one, I think I'm going to have the girl's parents be cousins. That would make the maternal uncle also a paternal relative. Closest relative geographically speaking, if not by blood. For another, the 'jilting over the lack of dowry' is done. Her betrothed is some eight years older and currently in the military but native to the city to which she's being sent.