For most people, a cruise is a week or so vacation and then it's back to reality. For Greg Brockman, a cruise is more like his second house.
He spends roughly six months onboard Royal Caribbean ships, booking a series of cruises in a row in a sort of "binge" to stay onboard for weeks at a time before a brief return home.
Naturally, people have questions about how he can manage to do this. Greg isn't retired and still works.
Here’s what Greg says about the reality of living at sea for months at a time, including the perks, the drawbacks, and the strategies that make it possible.
Do you get tired of visiting the same places?
Royal Caribbean ships tend to repeat the same itineraries often. While the cruise line welcomes repeat cruisers, the sailings aren't designed for someone to effectively live onboard.
"When it comes to traveling onboard ship, after several weeks, it feels more like home than living in a floating hotel room," Greg says.
He picks a ship based on what it offers to maximize his time onboard, "You look for entertainment options, dining options, and local activities that are appealing and align with your interests."
Even if the ports repeat, the experience changes. "Although the ports might be the same, consecutive cruisers can attest, there can be a dramatic difference in the experience based on your fellow passengers. Some crowds are more active and outgoing than others."
How Greg pays for all those cruises
You might be wondering how he can afford to pay to cruise for half the year, and the casino is his secret weapon.
You can earn complimentary cruises by gambling enough in Royal Caribbean's casino, and he maximizes that perk.
"The casino plays a huge role in my ability to travel as much as I do on the budget I set for myself," he explains.
"I took 100% of my cruise fare as my budget for the casino and I played just enough to earn a complimentary interior cabin. Then I stop playing."
From there, he uses "Pay Now, Book Later" to lock in future freeplay, then books consecutive cruises.
"It’s cheaper to pay to upgrade to a balcony than play the points, unless I am on a big winning streak," Greg says.
According to Greg, the casino loyalty program has let him cruise "30+ sailings a year for usually far less than 50% of the cruise fare."
The casino does require 200 points on comp cruises to keep the offers coming, but Greg has even “earned the cruise certificate completely on their money and spent none of mine."
Working from a cruise ship
Since Greg isn't retired, he still needs to put in work and he does it from onboard.
For the last three years, Greg has worked as a real estate trainer and coach. Since most of his job can be performed remotely, he's able to take Zoom meetings and phone calls from the ship.
He gets free internet packages from both his Pinnacle status and casino perks, which not only keeps him connected but reduces the out of pocket costs.
Sometimes, he even works from unconventional spots: "Occasionally, I was able to use vacant rooms in the conference center in a pinch, with guest services approval."
Greg believes cruise lines could take this further: “With more and more careers offering remote work options, Royal could get a jump on ‘Remote at Sea’ to accommodate a growing number of remote workers."
Do you get sick of the food?
"The food can be tricky, but there are so many options," Greg explains. He cycles between specialty dining, the Main Dining Room, Windjammer, and other restaurants like Cafe Promenade, or Park Cafe.
"With more cruises come more Crown and Anchor points. I’m fortunate to have Coastal Kitchen access on Oasis, Quantum, and Icon Class ships," he says.
He claims the chefs sometimes even go off-menu for back-to-back guests: "They have offered some custom dishes and meals they do not often make."
Over time, his eating habits shift, "After 7–10 days onboard, I’m less interested in breads and the pizzas, but find I am eating more often but far smaller portions."
"It’s been a few days since anyone has starved on a cruise ship, and I find I am skipping the cookies for a banana, kiwi, pineapple, or other fresh fruit option."
The drawbacks of cruising so much
It's not all rainbows, unicorns, and Sorrento's pizza when you cruise for an extended period of time.
One downside is trying to balance his social life at home versus onboard, "I have land friends that never cruise, and then I have fellow travelers who I see onboard. This can strain relationships with both over time if you don’t work to try to maintain both."
Cruise friendships, he says, are "the most forgiving for not staying in touch directly."
Being apart from his dog is also a negative to how much he travels, "I have a dog at home — Sasha, named after a Royal Caribbean ice skater I met on Liberty — a 6-year-old Samoyed that I leave with friends while I’m gone. That is also why I break up my trips into 3–6 week blocks so I can spend time with her."
And just like his friends at home, cruising means being apart from family, "My sister and husband have visited me on various ships, including the recent 8-night Northern European Cities sailing on Independence on June 19, 2025. My mom stayed on with me for the next two. My brother and his family joined me on Ovation for an Alaska sailing.”
Crew members matter even more when you're onboard so often
Being on a cruise ship for such a long period of time has afforded him the opportunity to get to know a lot of crew members, and he values those friendships.
"The bonus on top of the amazing travel adventures are the friendships I have with crew," Greg says. "Some even play a role on which ships I book because I know the Hotel Director or the Cruise Director onboard."
He’s also a self-professed Royal Entertainment junkie, "In November/December 2024, I spent 6 weeks on Allure and watched almost every showing of Mamma Mia."
When he boarded Independence of the Seas this summer, "I was recognized by 3 crew members I have sailed with in the past. There is a complete feeling of relaxation when you see a familiar face."
