USVI-On-Line

My desire for a summer STJ trip is getting out of control.

I very nearly have my husband on board but only if it is a short trip, he is willing to entertain Wed to Sun.

It would be a keep-it-simple, no rental car trip. We have done this several times in the past and yes, 4 days is just enough. Beggars can't be choosers.

Because most flights I can find arrive 3:25 or later in the afternoon, I have the following brainy idea:

We can fly direct to SJU early in the morning (9:45 am arrival) and then take Cape Air to STT.

Getting to STJ too early to check in doesn't concern me, we will go to lunch or something to kill time if we can't check in early.

I am trying to use either miles or Amex points. Where I am running into a road block is with the Cape Air connection. I can get both legs on one ticket/code share.

My idea is to fly to SJU and purchase (in advance) seperate tickets on Cape Air and do the reverse on the return.

I am assuming if we do carry-on only we could stay within the secure area and proceed to the Cape Air departure area, avoiding the hike from baggage claim and the security lines. Make sense?

Are there any holes or potential problems I am not considering?

It seems too easy.....

PA Girl-- Here's the only problem. If you purchase two separate tickets and there is a problem with one flight and you can't make the next flight the airline will not fix it and you will be forced to pay any penalties and extra costs to rebook.

The airlines view tickets like these as two separate itineraries and therefore they are not accountable if they don't get you where you need to be in time to make the other flight.

I have done this for international flights. We usually use Amex pts to buy upper class tix on Virgin Atlantic to get us to Heathrow. Then we purchase separate tix to our final destination (in advance) from Heathrow to (fill in the blank: Florence, Edinburgh etc.).

When I do this I always allow lots of extra room for the connection to retrieve bags and check in again for the next flight. Obviously not an issue if you are carrying on.

But the first time we did this we booked the later daily flights on Virgin and they decided to cancel that flight and switched us to earlier flights on the way over and way back. Thus completely screwing up my itinerary so that on the return my flight to Heathrow wouldn't get there in time to make the flight back to the US.

At the last minute I had to purchase ALL NEW tickets on BMI to get us there in time. The cost was over $700 USD. Virgin never notified me of the change and since I was flying upper class I raised hell about the issue and they issued me a check for the costs incurred by having to rebook the other flight. But I was REALLY lucky.

Since then, when I book I always build in a ton of time between flights when booking two separate tickets like this. And the only reason I do it is to be able to use points to fly instead of paying $8,000 per ticket. So it's worth the risk to me.

Sorry for the long explanation but given the fact that the airlines have been all over the place changing flights and you're dealing with "island time" resulting in delays and flight cancellations, IMHO you would need to build in enough time to ensure that something went wrong you could still make the connecting flight on the separate itinerary.

In essence it would be enough time that - quite frankly - the 3:25 arrival on a single ticket is no longer that late.

So unless you are willing to risk it and have to buy replacement tickets at the gate if something goes wrong I would suggest playing it safe. If however you are saving a ridiculous amount of money on the tickets then go for it. Just be aware of the potential consequences.

Hope this helps.