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I sail on cruise ships for a month at a time. Here are the surprising things and big mistakes I see passengers make

16 Feb 2023
Matt Hochberg

Most people take a cruise once a year at the most, but there are some people that cruise all the time, and they get to experience and see so much more of what cruising is all about.

Greg Brockman

Greg Brockman lives in Iowa, but manages to work in multiple cruises in a row to the point he will stay aboard a cruise ship for months at a time.

"Living in Iowa, it rarely makes sense to sail for just a week," he stated matter-of-factly as to why he will be on a ship for up to a month or longer.

How long does Greg actually cruise for?  He combines multiple cruises in a row, which is referred to by cruise fans as a "back-to-back" cruise because the voyages are consecutive.

B2B setsail passes

He's done six back-to-back cruises on 3- and 4-night sailings of Freedom of the Seas, as well as four back-to-back sailings on 6- and 8-night voyages on Explorer of the Seas in 2022.  That represents 4 weeks of cruising at a time.

In fact, Greg racked up 192 nights on a cruise ship in 2022.

Symphony of the Seas in Miami

With that many cruises at once, Greg has a lot experience with not only what Royal Caribbean has to offer, but sees what his fellow passengers do. It gives him an unique perspective on do's and don'ts of cruises.

I wanted to know more about what it's like to sail that much at a time, and what tips and advice he has for someone going on any cruise, regardless of length.

How do you pack for living on a cruise ship for a month?

SeaPass card

The logistics of living on a cruise ship for many weeks may seem daunting, but Greg has a few tricks.

"With my Crown and Anchor benefits of laundry, staying on for several weeks really doesn’t add much to the total luggage needed."

Read moreThe Crown and Anchor perks you should use on every Royal Caribbean cruise

Greg in Cozumel

His cruise ship packing strategy is centered on having a  core of clothes he can rely on, and then embrace Royal Caribbean's laundry services.

"Typically, I pack for 10-nights. Most of my cruise shirts are lightweight. I replace a shirt or shorts if one is damaged or wears out."

"I use Royal’s wash and fold service for everything except dress shirts, dress pants and blazers."

Packing for a cruise can be a struggle, even for the most seasoned cruiser.

Some people can actually manage to pack for a week-long cruise in just a carry-on, but it's easier said than done for most.

Odyssey of the Seas in the Mediterranean Sea

Inevitably, the question boils down to what is essential to pack for a cruise and it's easy to overpack. In a way, it is difficult to blame anyone for over packing because the longer the cruise, the harder it is to figure out just what clothing you will need.

Your luggage will have vastly different clothing in it if you cruise heads to the Mediterranean versus Caribbean or Australia.

Why cruise so much at once?

Greg on Odyssey of the Seas

Rather than cruise for many weeks at a time, Greg could spread out those cruises.  So what are the advantages of going on consecutive cruises?

"For me, one air flight and hotel on the front end saves over multiple trips," Greg pointed out.

"Also, my house sitter offers a discount for trips over 14 and 25 nights. So, that offers a savings."


I was curious if having the same restaurants and food choices was a problem, but Greg finds enough variety.

"Surprisingly, Royal does an amazing job in the main dining room to offer alternatives and “off-menu” meals to keep variety."

"Plus, each port offers alternatives for lunch."

Sun setting

Of course, there are negatives to all that cruising.

Greg admits being away from home for long periods isn't cheap, "The biggest downside for me is the credit card holds Royal places for onboard charges."

"I’m a casino player and sometimes have $2-3,000 charged to my SeaPass but pay down the balance with cash during the cruise."

"Royal can sometimes pre-authorize several times during the cruise and tie up much of a credit cards available balance. It can take 5 days for them to drop off. Sometimes requiring me to bring several credit cards to alternate between sailings."

Mariner of the Seas sailing away

As Greg has found, going on back-to-back cruises allows someone to maximize their airfare cost and get more out of a single vacation. This type of cruise allows you to get more bang for your buck by getting more time and experiences on the ship. Plus, you can often explore different ports and bring down the cost of travel by avoiding having to fly between cities.

Back-to-back cruises can be especially beneficial if you are looking to visit multiple ports or take an open-jaw sailing. With a back-to-back, you don’t have to worry about flying from one port to another - instead, you stay on board your cruise ship and enjoy all the amenities it has to offer while visiting several ports in succession.

Two ships docked in Cozumel

For example, if you are cruising in the Caribbean, many ships alternate between Eastern and Western Caribbean itineraries, meaning that with a back-to-back cruise you can experience both sides of the region without having to deal with costly flights or extended stays in one city.

In addition, back-to-back cruises allow for great savings when it comes to airfare costs since they require fewer flight tickets than traditional cruises do. Since back-to-backs last longer than regular cruises, they offer more time onboard which helps justify the airline price tag. Not only that but they also provide travelers with ample opportunity to explore all the ports and attractions available at their destination - allowing them to make their trip as memorable as possible. 

Planning many cruises

Two cruise ships at CocoCay

Picking out the perfect week-long cruise is its own challenge for many, but trying to coordinate multiple cruises in a row has its own set of challenges.

Anyone planning a cruise must consider the ship, itinerary, cabin and so many other factors.  New cruisers can struggle with navigating the myriad of choices. 

Read more8 questions to ask yourself before picking a cruise ship

Quantum of the Seas cabin drawers

When cruising as long as Greg does, he relies on the cabin selection as being a primary consideration, "I usually pick the cruises by where I can keep the same cabin back-to-back."

"I also try to follow crew I know that will be onboard. I have a few Cruise Directors, Hotel Directors and others I keep in touch with throughout the year."


Choosing a ship and itinerary is always a subjective choice, so it's important to prioritize the aspects of the voyage that are important to you.

You'll start off with the price, destination and length, but quickly you may find yourself choosing a cruise similar to Greg: considering which restaurants, shows, or activities are available on one ship over another.

Read more: Picking a Cruise Line and Ship

With so many places around the globe to choose from, it can be difficult to know which itinerary is best for you. 

For first-time cruisers, it’s important to pick a sailing that offers a good balance of sea days and port days. Too many days at sea or too many days in port can make for an exhausting vacation, so look for an itinerary that provides plenty of variety and chances to experience both the open sea and exciting ports of call.

A typical cruise will include several days at sea, during which you’ll enjoy amenities like swimming pools, spas, fitness classes and themed activities onboard the ship. You’ll also have your pick of delicious restaurants, bars and lounges where you can kick back and relax after each day of exploration. At night, take in the dazzling entertainment shows or dance the night away in the ship’s disco. Days at sea are just as fun as any other part of a cruise – so don’t skimp on them! 

But port days are equally important when planning your itinerary. After all, these destinations are what makes cruising so special! From historic European cities to exotic Caribbean islands, there are countless amazing places to explore while sailing around the world. 

Ultimately though, it doesn’t matter if you choose a short weekend getaway cruise or a month-long journey around the globe – as long as you make sure there is a healthy mix of both sea days and port stops included in your itinerary!

What do you wish other passengers did differently?

Drink vendor

When you sail for weeks at a time, it's easy to pick up on trends among other passengers. 

I asked Greg what stands out to him in observing other guests across his sailings.

"When you spend a lot of time onboard a ship you start to see the ship as the crew’s home. They live there and will be onboard long after passengers who sail once are long gone."

"It’s sad how disrespectful passengers are when they are actually guests in someone else’s home. Passenger frequently act entitled: 'it’s my vacation, I’ll do what I want.'"

Read more8 things some cruisers do that annoy everyone else

There's no excuse for being rude to any crew member, and it's an absolute faux-pas for anyone. 

Matt started Royal Caribbean Blog in 2010 as a place to share his passion for all things Royal Caribbean with readers. He oversees all the writers at Royal Caribbean Blog, and writes a great deal of content on a daily basis.  He has become one of the foremost expert on a Royal Caribbean cruise.

Over the years, he has reached Pinnacle Club status with Royal Caribbean's customer loyalty program.

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