I took my F18 through the Bronx last year. Not a problem. We do A LOT of real-time navigation when traversing that section of highway; I would not want to do it solo. We literally have 2 iphones and an ipad running in real time on two separate cell networks to avoid the traffic and have NEVER made the trip from Annapolis to Newport in under 10 hours. Getting through NY is the easy part. I-95 through CT is officially the worst road in the country; it was dead stopped at 1am last year. Parking lot every time we've gone through; remember, June is beach season for New Yorkers etc. and the close beaches are in NY, NJ, RI and MA. The mountain way around the entire NY corridor is recommended if you are traveling on a weekend.

Good luck with housing in Newport. Newport-Bermuda starts that same weekend and the week before is fully booked I'm sure. I can recommend staying on the Jamestown side and driving in. Worst case, Providence is a 45 minute drive to sail newport through downtown newport weekend traffic. Not terrible and liable to be far far cheaper.