We carry MedJet - we keep it active year round, whether we are cruising or not. For our World Cruise, we had to convert to the Expat policy since we would not be on US soil for more than 90 days. I don't know which cruise itinerary you are on, but the way it works is the 90 day clock is reset each time you set foot on US soil. I think you might be okay if this is the Grand Artic. Looks like exactly 90 days from Bar Harbor to New York!