Depending upon how you like to vacation cruises can be very busy (or not). Most cruise lines offer a lot of different activities during the sea days and evenings while in port.
For that reason, I brought a lot of petite coronas along on my cruise, so if I wanted a cigar and did not have a long time, I could still enjoy a small cigar and not feel rushed. I brought the Padron Principe Maduro, the Illusione 68 Bambone PC, and the Fuente Hemingway Short Story and WAOMs.
I also brought a few larger sticks for when I had a couple of hours to really enjoy a cigar. I don't know how much you smoke, but I brought enough for 5 cigars a day with the idea that I would not bring any back. It worked for me.
Figure out how many sticks you want to "average" in a day and bring that amount. If you don't have enough space in your cigar caddy, pack your cigars in a double-bagged zip-locks -- as long as you can store the cigars some place where they will be protected and not squished and a zip-lock will keep them fresh for 5 days. Or you could pick up a larger caddy at
www.cheaphumidors.com 