I have done many Gulf Stream crossings and depending on the time of year and conditions, the Gulf Stream can get very nasty. In the summer time (and sometimes in the winter) it can be flat, but usually it is not and sometimes it is dangerous. From Miami to Bimini it is 090, but because the gulf stream is a river than runs north, there is a current and so you have to aim further south and crab your way across. The faster your boat goes the less influence of the stream will have. So, an O'Day 25 with a speed of maybe 3-5 knots might have a struggle. Motor sailing would help, but you have to make sure you have the fuel. Then it is a matter of the boat. An O'Day 25 is not classified as "offshore" and this is effectively offshore sailing because of the Gulf Stream peculiarities even though Bimini is only about 50 miles from Miami. It can be a rough 50 miles if you are in big seas. I have been on very large sailboats in big seas and much smaller sailboats and I was always happy that the boat under me was built with high quality standards designed to hold up to ocean travel. So, the most important thing is to watch for weather windows and go when it is favorable. If you have a two week vacation, then I don't recommend it because Mother Nature might not let you come back if there is lousy conditions for any length of time to catch that plane or get home on a certain date. You might have to wait for a week or so before you can go over and then have to wait the same wait to get back. Might make more sense to sail the Keys.