I live in San Juan, and offer the following thoughts:
1. Plan to take the taxi trip from the airport, which will cause less headache than waiting for the Princess organized transfer, believe me. With luggage, you should get their for $25, as previously posted. The drive is not far, and you will feel it expensive for the distance. Keep in mind that SJ is an extremely populated area, small in size. We meausure distance in driving time, not miles. I recommend that you DISCUSS THE TARIF BEFORE YOU GET IN THE CAR. The goverment in PR
regulates taxis and the fares that they can charge. At the same time, I've heard unbelievable ripoff stories. If it sounds like too much, (more than $30) look for another one.
2. When you get to San Juan, make sure you have your baggage claim tags in hand as you leave, as they are required to exit baggage claim.
3. Keep in mind that once you leave baggage claim area, you will not be permitted re-entry into the buidling. Porters are hard to get, so if you are loaded down, be prepared.
4. As you exit, you should find a taxi stand outside the terminal, or cars lined up. There will be no problem getting your ride with no more than a short wait, unlss you have the bad fortune to arrive with six or seven planes at the same time.
5. Consider staying in Puerto Rico at least two or three days following your trip. It is the true high-light of any Southern Caribbean cruise. Sadly enough, many visitors view it only as a point of departure for their trip, and jump back on a plane when they get back here. If you want to see true beauty, you must drive into the interior of the Island. Roads are very good, overall, and the trip well worthwhile. There are a number of charming guest houses that offer great rooms at low rates. I can provide names, if you wish.
6. Be prepared for the possibility of rough seas. Keep in mind that the hurricane season is not over until the end of November. Although a storm is unlikely, you may experience a tropical wave which implies pelting rain and higher seas. Oct. is very unpredictable--could be clear for two weeks, could rain every day for some time. If it does, it will not ruin your trip, unless a true storm.
7. It is hard to tell you what to do without knowing where you are going. If you go to Barbados, I highly recommend the horseback riding. I did this last Nov., and it was the highlight of the trip. Incredible scenery, fresh air, and great people.
8. If you go to St. Croix, you can rent a car cheaply and drive the entire Island. Most people don't know it, but the Point Udall Monument is there, which marks the eastern most point of US Territory. Take your photo, and you'll remember it forever. Buy liquor, if you wish, at the discount food club store that is on the main road, left side, just out of Fredricksburg, I believe. We got deals there that were unbelievable, while others bought in tourist traps.
9. If you go to St. Lucia, go to the Tetons and the volcano--try to get a boat tour there, instead of driving. We rented a car and drove the 2 hour + drive ourselves, only because we know Island mountain driving. The Island is lush and green, and very beautiful.
No matter what, you can't go wrong with a Caribbean cruise. Weather will still be hot, as the winds are starting to shift, but still unpredictable.
I wish you a wonderful time! Let me know if there is anything more I can do to be of assistance.
PS If the pic comes out, it was taken on the north central coast late last saturday afternoon. Couldn't resist it since I hadn't seen a double rainbow in years, and never in PR