Very good questions. We have spent about a year cruising in the Med and a substantial amount of time traveling on land (usually by rental car). I agree that most of my fellow Americans would be more satisfied on a cruise line that caters to Americans and Brits. Hence you should be looking at RCI, Princess, HA, Celebrity and Carnival among the mass market cruise lines. There are also Oceania and Azamara which is a stop above these lines and offers excellent smaller ship (700 passenger) cruising. There are also great luxury lines such as Seabourn and Silverseas for those not on a budget. We tend to favor cruises that begin and end at different ports since you can better maximize your trip by spending a few extra pre and post cruise days in different countries. However, the round trip voyages (these are usually shorter 7 day itineraries) can save you a few dollars with airfare. You should carefully compare the price of doing your own air against the price of cruise provided air. As to hotels we can always find better deals on our own than cruise packages...but you must also factor-in the cost of transfers to and from ships. Isolated ports such as Civitavecchia (for Rome) can add a more than $150 for transfers...while places such as Barcelona are pretty cheap when using taxis. As to itineraries this is purely personal preference. If you enjoy ancient ruins you would want ports such as Naples (Pompeii) and Kusadasi (or Izmir) for Ephesus. If you want sun and sand than the Greek Islands are a great destination. If you want major cities there are many different options that can get you to places such as Rome, Paris, London, St Petersburg, Copenhagen, Berlin, etc. Another option is to take a river cruise on rivers such as the Rhine and/or Danube. You also need to understand that a European cruise will cost a lot more money for excursions than a Caribbean cruise...so budgeting can be a major factor. Hopefully this post will get you thinking and doing some homework.