Starting to watch flights for our May charter. I can either fly AA from Chicago-Miami and land at STT @ 1:20 and ferry over ($307.00 one way plus ferry) and hit the island by 4 if the ferry Gods are working in my favor. thinks (travel time is about 6:45 hrs air travel time)
OR - I can fly Chicago to San Juan land at 1pm and connect on Seaborne to EIS at 2:10. That connection sounds too tight to me. I have only flown out of EIS to San Juan recently and do not recall the reverse process from years ago.
United has a flight Chicago-San Juan, land @ 1:30 / connect via Cape Air @ 5:30 and get into EIS @ 6:15 (487.00 or I can use miles) Down fall here is the long connection in SJU which makes it a 9.5 hr air travel time.
Have heard others comment on booking on one carrier to SJU and than either CA /InterC /Seaborne to EIS.....what are my risks? What would you do?
Also, how far in advance do you usually book for the best rate?

I have time to watch prices but would appreciate the opinions of others who have done SJU/EIS. I have done the ferry many times and its an ok option but we all know the downsides. I try to look at it as I have arrived on an island and now get a boat ride w a drink. cheers
Side note, I am traveling by myself and will have only carry on bags but one will have frozen food and will be a little heavy....which is why I am looking at the easiest option. Also, I am arriving a day before our sleep aboard to provision so I am not in a rush to get to the boat the day I travel but short is good!

Thanks for any and all suggestions.