Originally Posted by
diburning
Thank you everyone for the insight so far!
Do the repositioning cruises visit many ports or are they primarily days at sea? Part of the appeal of cruises to me, is the ability to visit many places. For example, there is a 4-day cruise out of Florida on Norwegian that only has one port stop in the Bahamas. It's not as interesting to me, although the price tag at $339 is very appealing.
I am somewhat flexible as far as my employer being ok with me taking PTO with at least a week of advance notice. I initially became interested in cruising when I read about Holland America's standby cruises (and I live near a port; not a particularly popular one, but cruise ships do start trips here!). (Holland America now charges a single supplement for standby cruises, making it less appealing than just booking a cheap cruise outright.
While I'm excited to see what a cruise ship is like onboard, the thing that appeals to me the most is being able to get off the ship in places where it would cost more than the cruise to fly to (ie caribbean destinations)
There are a few different ways to think about it and then you need to go from there.
Where are you located? If you are in FL you have a ton of flexibility in dates, if you live in Michigan, you need to fly to any cruise anyway. Personally I live in NYC area, so if its a shorter trip I look for dates that work and dont care about destination. We typically cruise without our 4 kids, so its about getting away while Grandma watches the little ones, destination does not matter to us at all. We would do 5 days to Canada or Bermuda, we almost never get off the ship so it doesn't matter. If its a longer trip, we will likely fly to Orlando where we can get more options of days, and then look for the dates that work for us (we are much more restricted in timing than it sounds like you are).
Do you care about number of ports or do you want to minimize days at sea, those are not always the same. We have done cruises from NY that do 3 days at a single port, and thats the only place it stops. You can also find 5 ports in 7 days, depending on from where and what ports.
Personally I like they layout of
https://www.cruisetimetables.com/ I find it very user friendly. Since I normally say "I can only go on December 9 from Orlando, show me all the options" its very quick and easy to find what I want. I always book using chase points, so I cant speak for their booking ease.