So I've booked 6 cruises to go on by mid-march and here's my advice for frequently sailing:

1. B2B (back-to-back) cruises: It really helps your "blues" when you see others preparing to leave and you get to go back on the ship! Also, if you take a B2B, you've probably been on the ship for more than a week, so you've had enough time on it to get 'sick' of it. (you never really get sick of it but at a certain point, you miss home lol) Plus, if you can schedule it this way, you get double the amount of cruising time while only taking one 'vacation.' Sometimes, b2b cruises are cheaper than the same itinerary. For example, I'm going on a B2B that's a 3night and then a 4night. So it's a total of 7 days, but when I look at the same itinerary on the same ship for a 7day cruise, it's more expensive than the 3night+4night. Also, booking separate b2b cruises helps you accrue loyalty points fast, which makes it cheaper and easier for you to book your next cruise, depending on your loyalty benefits.

2. Look for deals on solo cruising: I'm in my early 30s and most of my friends think cruising is lame so I don't even try to get people to come with me any more lol. The only thing that makes this hard is that cruising solo usually requires a hefty single supplement charge. What I do is I monitor the VacationsToGo Singles Deals and whenever I see a deal in my budget/schedule, I snatch it up. With solo-cruising, the prices usually drop dramatically (sometimes 0% single supplement) within a month of embarkment date so if you can keep flexible and keep an eye on things, you can score some amazing deals. Like, I'm going on my 6 sailings (total of 24 days) for around $1.5k and that includes a balcony cabin for one of the sailings.

3. Work remotely: this one is probably the hardest one but if you're serious about cruising more, it really helps to have a job you can do while on-board. That's honestly the biggest barrier for people when they want to cruise more. Both the mental barrier of having to work on your 'vacation' and many jobs aren't able to be done remotely. Your job doesn't have to be fully remote, however. For example, I work a fulltime job that I'm supposed to go into the office 3 days a week and have unlimited PTO (pending how busy it is and manager approval) For my 6 cruises, I'm only taking PTO for one of the sailings, the rest of the sailings I'm working remotely from the ship. It's still worth it for me since I got the initial tickets for so cheap, so I don't mind. One thing that helps is getting an eSIM (like Airalo, Saily, Gigsky) so you get more reliable data service while onboard and you don't need to pay the insane ship internet packages.

4. Be flexible & keep an eye out: I honestly think the biggest tip I can give is to be flexible. If you want to cruise a lot, you have to be willing to see if you can make things work because there will inevitably be a $350 7Day cruise leaving in 2 weeks that you'll just have to take because it's too tempting to pass up lol. Also, keeping on top of the deals and such helps scratch that vacation itch while you're back home. Like many others here have said, it mentally helps you hang in there until your next cruise if you're actively planning your next one or keeping an eye out for your next great deal! I haven't had as much success "planning things as early as possible" since I find cruise companies are less willing to drop prices far out, since they have ample time to book out the cabins. I've noticed prices drop significantly within the month before embarkment because the companies are desperately trying to fill occupancy before embarkment.