Thanks obscure2k. As to the comments about Paris, I totally agree and kind of hinted at that in the original post. Although we love fine dining and would love to visit Paris, I don't think it would be the place to bring a newborn, and we'd probably not get the most out of the trip.
I love the beach holidays, so I will aim for that. We actually will be going to Maui for 4 nights in March (baby will be 5 months), for a friends wedding at the Sheraton. I guess that will be a good test run, and we'll be on a flight with several other friends sitting around us to give a little buffer zone. My parents will probably be going with us there as well, to help watch the baby on the wedding night, and rehearsal dinner night. I think the fact that we'll be going to Maui might steer my wife from wanting another 'purely' beach vacation, although I could do every trip to a tropical beach resort.
I think we will wait to book any travel or decide on a location until AFTER we have gone to Maui. That should give us a good idea if it's really something we want to do.
I'm leaning a bit towards Europe as a destination. First, my sister lives in Brooklyn, so I figure we can split up the trip/flight by spending 2-3 days visiting her in NYC. Then it's a much shorter flight from NYC to Dublin, London, Germany, Spain, ETC.
Does anyone have some advice on if splitting the trip like that is a good idea or bad idea? Is it easier to just do one long flight and get it over with, or split it up into two smaller trips?
People mentioned Spain earlier, and I started to look into it a bit. We'd probably be traveling in September or early October. How is Marbella or Malaga? I figure we can get our relaxing beach destination as well as a nice town/city to stroll and dine in. It seems that there's a lot of history, culture, dining, city life, etc to walk around in to please my wife, but also beachy too. We really enjoy just walking through towns, window shopping, grabbing quick bites at out door cafes, etc so I think that would be good there.