We are HUGE DCL fans .....
However.... we have kids that are are 1.75 and 4.... and even without kids DCL has strong merit. They do a superior job then about half their competitiors with service and they come in at the 90th percentile for cabin szie and ships condition for the money. But their port schedule is sort of stale after having sailied only twice with DCL ~ but even with the pluses and minuses we're scheduled to go again on an Eastern 7 nite DCL sailing this September.
We have sailed to most major ports in Carib and our type of wanderlust has us eagar to see other ports. Especially the southern routes or - frankly - anyplace we have NOT visited before. BUT - IF we were your shoes then we would take the NEWEST ship you can find with the ports of greatest interest - more or less forget the line as most of the non-Disney "majors" blurr together somewhat. The order of the day is whether you want to focus on the PORTS or the SHIP. Ideally you should combine elements of both in a decision.
What they say in stereo-typing some lines is somewhat true - HAL has an older crowd, Disney has lots of kids and Carnival has a younger and active set - but the rumors are NOT 100% true as YOU should set your own pace and lead a private parade. Frankly we enjoied the variety we encountered with various lines - and it did not give us much pause when we were not quite matched up with a similar crowd. IE - on HAL we were among the younger 20% easily - but that did not stop us from doing all sorts of active tours and activities. Heck - I vaguely recall we even tried bingo... an overrated experience if you ask me. Especially so since I didn't win anything!
Among our FAvORITE destinations are San Juan + most of the SOuthern Carib ports. AND... in turn among the least interesting ports are the Western Carib ports. Yes - they are fun but in the past they seemed to be too HOT and they had the wrong type of commercialization for our tastes.
If we were you - we would fly into San Juan 2 or 3 days early and make a full visit to the island - stay at the Wyndham for the nite life environment ~ OR ~ stay at the RItz around the corner and walk to the Wyndham. The Ritz has a GREAT conceriege level - really superior snacks through-out the day and worthy of a go nowhere else type of stop - which may be counter to going PR. BUT - rent a car and cruise around - the old town has decent shopping and a nice Dooeny and Bourke outlet (if that's your thing).... plus if being slightly off beat is your thing - then try the out of SJ hotels. It is after all just another big caribbean city.
But - back to cruising.... yeah - go for the newer ships - you'll note they ALWAYS charge more for those. And as for large or small (or midsize).... we've sailed all sorts over the past 2 decades (we're just 41) and we like each sort for different reasons. If you have not tried it all - they we encourage you to TRY IT ALL!
Have you ever considered a Windjammer cruise? Those ships really exemplify the small ship expereince - but in a UNIQUE and affordable way. And on the other hand you should get around to sailing one of those huge Adventurer class RCCL ships. We have YET to get on one of those but just looking at the brochures we can sort of tell what it would be like. Windjammer will NOT let you sail unless your kids are at least 6 (I think). So if you have 2 kids about 3 years apart - then it will be a DECADE before they will even let you go!
Order a Windjammer brochure soon BEFORE you become pregnant - so you have a chance to do it TWICE or more if you like it. I for one have never done one before but folks that we identify most with talk about it in glowing terms. Almost as loyally as Disney cruisers IMHO. Once you have kids then you'll be doing DCL almost exclusively (or at least a few times) for nearly a decade - that is - if you read these boards much you'll see the REASONS why folks do it.
BTW - DCL and NCL are the only cruise lines I know of that scale their rates for kids. IE - young infants are welcome AND they charge almost nothing or in fact DCL charges ZERO for infants - just pay port charges. And as the kids age the rate goes up gradually. Now the only other line we know of that has similar treatment is Raddison Seven Seas but their adult rates are fairly stiff. Easily 2 or 3x DCL rates. RSS compares to Crystal and Seabourne in adult cost and quality of vacation... supossedly.
Besides that - after you've surveyed the cruise and travel options of all sorts - then you'll settle into the precise trips that were landmark experiences for you. No one BUT YOU can decide that. Who knows what passions and memories will turn up as the sweetest moments of your various escapes?
At any rate - "get around town" before the kids "show up" - and of course - having kids has been THE MOST fuifilling experience for my spouse and I. That is entirely another adventure with indescribable rewards and experiences!
Adios!