don't know the rest of your itinerary but I can help a little with San Juan. First, as to hotels, being San Juan, I would stick to a chain but cruise the internet for the best price. Makesure it's close to the port, then taxi fees will be low and you are in walking distance to Old San Juan. Take the horse drawn carriage ride thru Old San Juan. It is reasonable and romantic (even if you are alone). It is walking distance from the dock. You can't miss it. If you get a chance, if the ship offers it, take the tour to go see the world famous flamenco guitarist. I forget his name at the moment but I used to watch him on the Ed Sulivan Show when he and I were both very young. He is considered the world's best! The theater is very intimate, so no bad seats and you get a cocktail too. And for a single man, the girl dancers aren't bad either. If you get there before the shops close, the semi-precious stone Larimar from the Dominican Republic, is still a pretty good buy in San Juan. It is light blue and looks like it has clouds in it. Lovely and reasonable, set in silver. Alot of people hike up to the big fort but you'll get the best view and the best pictures from the cruise ship, either coming or going. As far as shore excursions go, we do both. I book from the ship if necessary, or I book independent if need be. It all depends on the circumstances. For instance, if the ship does not offer the tour I want, I do it on our own. Another instance is, if we have taken a tour thru the ship before and really thought it was worth it (such as the Sting Rays in Grand Cayman) then I will book thru the ship again. You can research it both ways and see what feels right. Yes, you can save some money on your own but on the other hand, the tours off the ship are designed to make sure you get back when you should. Don't ever want to miss the sailing. We will be in Cozumel on the Victory on Christmas Eve. We plan on going to Chankanaab Park to snorkel on our own (take taxis, pay entrance fee, rent snorkel equipment, rent a locker, snorkel) and watch our niece do the Dolphin Swim and explore the park. Then taxi back. And that's just the afternoon. Remember, shopping is also fun in all the ports even if you don't buy anything. Just to see what's out there and people watch as you go. Hope this all helps a little. If you post your other ports, I might have some more suggestions. (if you want them after all this)