Most people aren't going to be very excited about he prospect, but we've done it three times. Once to Galveston, once to Tampa, and once to San Juan. I think the keys to doing this are:
1. Nonstop flights
2. Bring a decent amount of stuff in your carry on so you could survive if they DID lose your luggage
3. Book the ships's from airport to ship. They'll be ever so slightly more forgiving if you get stuck in traffic on the way to the ship.
4. Have good insurance.
5. Only do it if you really don't have another choice.
6. Do it only in good weather months. Obviously this depends on where you live.
7. Ideally do it with a major carrier from where you live so if you miss the flighty, there are theoretically others you can get on. For example I live in Atlanta and will only fly Delta.