How much time to allow at SJU for connecting to EIS

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. (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.
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.

If you're doing carry-on only, connecting on the way down is pretty easy. You don't have to leave the secured area and can go directly to the Seabourne gate. I do 1.5 hour connections frequently and have not had issues. 1 hour would work if everything is on time and you're sitting near the plane door. I would do the 1:10 connection but it's not long enough to be comfortable for many people.

Going home, you'll need more time because you have to clear immigration, collect bags, clear customs, recheck your bag, and clear TSA.

I would be fine with the 1:10 connection on the way down. Seaborne codes shares with AA so they will transfer your checked bags.

Jason, how close is that Seaborne gate at SJU? If I book everything on AA they have to get me there right LOL


NC Sailor ~ Thanks...I normally do not check my bags but may check the one with the meat. My connection in Miami usually involves a long walk and not lugging a heavy bag sounds nice. I just always worry that everything makes it there with me.

I would do the United flight. Less stress and I like to find the empanada place in the Seaborne terminal and have one for lunch along with a beer. Absolutely love flying into Beef Island over St. Thomas. Only way I do St. Thomas anymore is if it’s a lot cheaper.

Thanks I think you've pushed me into making the decision to head for the empenadas! With 2 inexperienced travelers in tow, if we can go to SJU and avoid checked baggage it sounds a lot less stressful for all concerned and any reasonable extra expense would be worth it.

On the way down, an hour is enough (on one ticket). United generally codeshares with Cape Air. The new Seaborne counter is right next to Margaritaville.

4 hours is more time then I'd typically want to hang around in SJU, but given those options, that's what I'd go with. 1:10 is probably enough time, if everything goes well. If you are late at all, then it can become a problem. With the 4 hours, you have plenty of time, even if there is a delay. And since your 5:30 flight is Cape Air, it is possible you might be able to get on an earlier flight if there's room. So doing that, I'd go check in with Cape Air first thing and then see about food after depending on what they say about flights.