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47 Lessons from 47 Days on 3 Repositioning Cruises

Over the last 13 months, my family and I went on three repositioning cruises spanning 4 continents, 13 countries, and around 20 different ports.

Repositioning cruises are most commonly offered in the spring and fall when the cruise lines want to move their massive ships to ports about to experience a high season and away from ports about to experience lower demand.

Since the boat’s got to sail there anyway, they might as well fill it with paying passengers and line up some port stops. Lucky for you, future repositioning cruiser, the price you’ll pay per day tends to be lower on this type of cruise.

As we wrap up our third repositioning cruise in just over a year, I’ll share the lessons I’ve learned from them along with a hand full of other  cruises my wife and I have taken over the last twenty years.


Repositioning Cruise Number One

After Omicron, the world was opening up more and more, and my family of four decided to book a 13-day cruise from Galveston, Texas to New York City. Technically, we ended up in Bayonne, New Jersey, but it was a reasonable Uber ride to Midtown Manhattan from there.

Having the freedom to work (on this blog — my only “job” these days) from anywhere, we like to make cruising just a part of a larger trip. We started this one with a road trip through Canada to Boston where we caught a plane down to Texas. We spent a couple of days in Houston visiting the Johnson Space Center before taking a four-day beach vacation exploring the barrier island of Galveston.

On the back end, we spent 24 hours in New York City and then flew up to Boston where we picked up our vehicle.

After spending some time in isolation/quarantine at a relative’s cottage in Buzzard’s Bay, we returned to Boston and ventured on up to Maine to spend a week between Portland, Bar Harbor, and Acadia National Park before heading west on a more northerly route through Canada to return to our home in northern Michigan.

Additional ports on this cruise itinerary included Cozumel, Limon, Cartagena, George Town, Falmouth, Labadee, and Cape Liberty.


Repositioning Cruise Number Two

The second repositioning cruise of the year took place in November, bringing us back to The States just in time for Thanksgiving.

My wife is primarily Polish, and I’m Scandinavian with a healthy dose of Swedish, and we had been wanting to take our kids on a heritage trip to our respective homelands. We accomplished that before boarding this 16-day cruise from Southampton, UK to Fort Lauderdale, Florida.

After spending a meaningful week in and around Krakow, Poland, we spent five days in Stockholm, Sweden, four days in London, UK, and boarded a train to meet the Emerald Princess in Southampton.

Additional ports on this itinerary included Cherbourg, La Verdon, Bilbao, A Coruña, Lisbon, and Ponta Delgada in the Azores islands.


Repositioning Cruise Number Three

In mid-April 2023, we embarked on our longest cruise yet, an 18-day voyage from Sydney, Australia to Honolulu. By then, we had been traveling for over six weeks on a trip that started with WCICON in Phoenix followed by three and a half weeks in New Zealand and a week or more each in Tasmania and Sydney, Australia.

I was tempted to book the next leg or two of Royal Caribbean’s Ovation of the Seas as it continued on to Vancouver and ultimately Alaska, but after nine weeks away from home while having our next “forever home” built across the street, we were itching to get back home to see the progress and help move things along.

Additional ports on this itinerary included Bay of Islands (canceled due to weather), Auckland, Papeete, and Mo’orea.

The views from the upper deck as we sailed out of Sydney Harbor were unforgettable.



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Canceled Repositioning Cruises of 2020 and 2021

I was supposed to have two more of these lengthy cruises under my belt by now, but due to either a lab leak or an exotic animal market, a nasty virus decided to spread around the world and infect everybody. Our canceled travel plans pale in gravitas to what many others experienced, so I consider my family to be fortunate, but we didn’t make it to Asia as planned.

We had a 30-day cruise scheduled to take us from Los Angeles to Shanghai with many stops along the way, including in Hawaii, Guam, Japan, South Korea, and several stops in China.

We were going to return to The States eventually on a 15-day cruise crossing the Pacific, leaving Japan with several stops in the country, a brief stop in Russia, and finishing in Vancouver.

We had five months in between to explore Asia to our heart’s content, but it was not meant to be. Nevertheless, we did squeeze in one short cruise in late 2021 a few months after cruising restarted, and cruise lines are now back to full strength and occupancy with some enhanced infectious disease prevention protocols that should help not only with coronaviruses but also with others that tend to circulate easily on what some people like to call a giant floating petri dish.


47 Lessons Learned

Before we dive in, I want to emphasize that these are lessons that I’ve learned that apply to me and the way that I like to cruise. You may have different preferences and perspectives, and that’s perfectly OK. Let me know where I’ve gone astray in the comments!


Cruising is a Great Way to Get from Point A to Point B

If you’ve got the time, cruising one-way toward home from a far-flung destination can be a fun and economical way to slow travel your way back.

Yes, a cruise typically costs more than a flight, but not necessarily that much more. You’ll also have all meals provided for the length of the cruise and hopefully a lot of fun as compared to being confined to a seat on an airplane.

Our repositioning cruises that crossed the Atlantic and Pacific Oceans cost us in the range of $1,000 to $1,500 a person, and we got more than a month’s worth of meals and entertainment along with them.


The Cruise Payment Can Fulfill a Credit Card Welcome Bonus

Most credit cards offering valuable welcome bonuses with values approaching $1,000 or more typically require you to spend $3,000 to $5,000 on the card in your first three months.

A cruise vacation may cover the minimum spend in one fell swoop.


Bring Friends and Make Friends

Life is more fun with friends. We’ve been joined by friends on many of our cruises.

If no one can make the same itinerary as you, it can be pretty easy to make friends. Share a table with others at the piano bar or themed pub. Offer to team up for trivia. Sign up for activities. Wear clothing with your favorite team’s logo. These can all be conversation starters.


Sign Up For Stuff

As above, participating in things around the ship is a good way to meet people and make friends. It’s also a good way to step outside of your comfort zone and maybe learn a thing or two.

Many cruises have enrichment lectures that are not all that different from a high school or college lecture, but you won’t be surprised with a pop quiz at any point.

Newer ships have lots of bells and whistles. Our most recent cruise had this North Star Experience that takes you up in a glass capsule some 300 feet above the ocean. They also had a skydiving simulator. We did both multiple times!


Loyalty is Rewarded

Just like airlines and hotel chains, the main cruise lines all have different loyalty programs. Over the years, we’ve cruised with five different cruise lines, but we have the most time on Royal Caribbean ships, and we plan to stick with them for most or all of our future cruising.

Why Royal Caribbean? For one, it’s a family-friendly brand that tends to skew a bit younger than some others. It’s also affordable without feeling cheap in any way. I’ve heard Carnival referred to as the Walmart of cruise lines. If that’s so, I’d say Royal Caribbean is more like the Target of the cruise industry.

The bigger reason, though, is the rewards program. We’re not far away from becoming Diamond members in Royal Caribbean’s Crown and Anchor Society (requiring 80 points or 40-80 nights aboard ships). You get double points when booking a suite, sailing solo, or during special promotions. I guess some people got quadruple points cruising solo during a post-COVID promotion.

Anyway, Diamond members get four complimentary beverages worth up to $15 apiece each day. For my wife and I, that could be a $120 daily benefit, although I’m more likely to drink $8 IPAs than $15 cocktails.


You Can Bring Some Alcohol On Board

Most cruise lines let you bring a couple of bottles of wine onboard per stateroom. In my experience, that “wine” can be a fancy bottled beer or even a tall can of beer. I suspect enforcement of these policies vary widely.

I’ve also known friends to bring a six-pack of canned beers through security without issue after visiting a port.  By friends, I mean me. Some cruise lines (like Disney when we sailed with them) fully allow you to bring your own, as long as it’s a reasonable amount.


The All-You-Can-Drink Package is Overkill

As you may have surmised, I enjoy a good beer, but I don’t like to drink every day. This is life, not vacation, even if it happens to be life on a boat. Even if I were to drink daily on a shorter cruise, it would take a lot of drinks for the economics of a drink package to work out in my favor.

I’m most familiar with Royal Caribbean’s beverage package options, but I don’t think they vary all that much from one cruise line to another. I’ve read that some cruise lines have a 15-drink daily maximum and others have no max. Like I said, overkill.

On Royal Caribbean, the unlimited package costs $70 or more if you buy before the cruise. Onboard, a Stone IPA is $8. I would have to average 9 of those a day to come out ahead financially. While that might sound like a fun challenge for a day or two, it’s certainly not a healthy one.

We actually had the drink package on our Princess cruise for 16 days. They had a crazy promotion where they gave you prepaid gratuities, internet, and up to 15 drinks a day for $25 a day. The gratuities alone are normally $15, so it was kind of a no-brainer. Now, we did have a good time, but when you tip your waistaff well, they tend to keep you well-hydrated, so to speak, and when there’s no additional cost to getting another round, there tend to be more rounds than necessary.


Nothing Good Happens After Midnight

See above. There are bars that will serve drinks until 1 or 2 am. Or so I’ve heard.

But nothing good happens after midnight.


It’s Not an All-You-Can-Eat Buffet

It is one actually, but you shouldn’t treat it like one.

On land, when you pay for the buffet, the natural tendency is to want to get your money’s worth. Once you pay the check and walk out that door, there’s no more crab rangoons for you, so you leave uncomfortably full of fried bread, sweet cream cheese and fake crab meat.

On a cruise ship, you can get three (or more!) meals a day at the buffet or order numerous main dishes in the main dining room.

Remember, though, that this isn’t a one-and-done kind of thing. You’ll have unlimited food the entire time you’re aboard, so there’s no reason to go overboard (figuratively or literally).


You Can Always Eat Something Somewhere

A saying we have in anesthesia is that “you can always give more.” The point being that it’s best to see the effects of an initial, perhaps somewhat conservative dose before giving another bolus, especially when performing sedation on a spontaneously breathing patient.

On the cruise ship, you can always eat more. Yes, you can order three appetizers, two main courses, and five desserts, but pace yourself. If you’re hungry later, there’s someplace on the ship serving food at all hours of the day and night.

I’m particularly partial to the late-night slice of pizza.


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Perks and Freebies Are on the Decline

I haven’t seen a fanciful midnight buffet in years. Lobster tails were only available for an extra fee on our most recent cruise. I haven’t gotten a complimentary Welcome Aboard or Sail Away beverage in over a decade.

I understand that perks like these vary among different cruise lines and ships, but the general sense I get from the chatter on cruise forums and Facebook groups is that freebies are decreasing across the board.

I see this as a good thing.

Hear me out.

These are cost-cutting moves that can help keep my costs reasonable and/or increase company profits. As a consumer of cruises and a shareholder of each of the three major cruise line companies, I welcome either outcome. There’s still plenty to like onboard, even if you have to substitute jumbo shrimp and salmon for the lobster.


It’s Possible to Stay Fit on a Cruise

Confession: I rarely found the gym, let alone set foot in it, on the early cruises I took. However, with these longer itineraries, I’ve found myself stopping in most days to hop on the treadmill and get my daily body-weight exercises done.

There are spin classes, yoga classes, and pilates classes, often for a fee. There are modern resistance training machines, dumbbells, elliptical machines, etc. A lengthy cruise with unlimited protein-rich foods and a well-equipped gym is actually a great setup for putting on muscle if that’s your goal.

You can also walk a lot. These massive ships typically have painted walking tracks. The loop on our most recent ship was 1/3 of a mile, and we often walked it while listening to podcasts. Deck 15 could sometimes be windier than Mount Washington, but you can always walk the halls and promenade areas.

I celebrated my 47th birthday in the middle of the Atlantic, and I got over 47,000 steps in that day.



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Elevators are Optional

To avoid being labeled as an ableist, I’ll reiterate that these are lessons I’ve learned that apply specifically to me. If you’re physically disabled or have arthritis or any number of other ailments that make climbing stairs difficult or impossible, you’ll be frequenting the banks of elevators, and I have no issue with that.

I do take issue with able-bodied me taking an elevator when the stairs are available, especially when I’m averaging 3.14 desserts a day, plus or minus a slice of pie. The least I can do to help counterbalance that caloric intake is to use my legs to get up and down the ship.

In the 47 days of cruising on my last three itineraries, I saw the inside of exactly zero elevators. Well, technically, since they’re mostly glass and often open when I walk by, I’ve seen their innards, but I haven’t stepped foot in one or ridden a cruise ship elevator in a very long time.

Making this pledge to myself has me climbing dozens of floors each day, and it’s another way I try to stay somewhat fit while cruising.


Cruise Line Excursions are the Most Expensive

When you travel as a family of four, the cost of every activity is quadrupled. There may be a child discount, but it’s usually not meaningful.

Occasionally, we’ll take a cruise line’s official excursion, but the handful of times we’ve done so, we’ve been underwhelmed. On the first of these three cruises, we went on a “Plantation Tour and Zipline Experience” in Jamaica. It set us back about $500 and 500 mosquito bites. As we’re waiting for the final zip line, our guide offers us the insect repellent he’s had with him the whole danged time.

In port, we’ll often do self-guided or app-guided walking tours, tip-based “free walking tours,” or we’ll just look for a beach within walking distance, depending on the location. We’ve also had some success booking excursions with local tour operators working near the port, and the price can half of what you might pay by going directly through the cruise line.


Onboard Credit Can Be Used to Pay Gratuities

Most bookings are granted some onboard credit through various promotions, and cruise line shareholders get additional credit (see more on that below).

You might assume that the credit must be used to pay for things like excursions, beverages, upgraded dining, or items in the ship’s shops, but no. You can use that credit to cover a portion of the daily gratuities, which are usually not included in your fare unless you got in on a promotion where you got “free” pre-paid gratuities (usually by paying more for the fare).

These daily gratuities are automatically applied to your onboard account. Technically, they’re optional, but you have to choose to opt out and you’d have to be one lousy human to deny these hard-working people a bit of a wage supplement when you know they’re not paid very well to begin with.

Using your onboard credit to cover gratuities doesn’t impact what the crew gets from you, and you can always give more (which we do).


Shareholders Get Additional Onboard Credit

We had $750 in additional onboard credit on these three cruises as a result of being shareholders in the cruise lines’ parent companies. Owners of 100 or more shares get additional onboard credit of $50 to $250 per stateroom depending on the length of the cruise.

There are three major publicly traded cruise line companies, and as of June 2023, you can buy 100 shares of each for a bit over $10,000. If you leave out Royal Caribbean, you can buy 100 shares each of Carnival and Norwegian for about $3,000 total.

I own very few individual stocks, but I own RCL, CCL, and NCLH, ensuring that I’ll be awarded with additional onboard credit on many popular cruise lines — most lines you’re familiar with are owned by one of these three. Viking and Disney are exceptions.


Tip Above and Beyond the Normal Gratuities

How are cruises so affordable? And why are there so few Americans working on these ships? The answer to both questions is the same. The pay is quite low for how hard these people work.

On most cruises, gratuities of about $15 per person per day are added to your bill automatically, and we don’t board a ship without at least a few hundred dollars more to tip the people that take care of us.

Tip on every drink, and tip your stateroom attendant and dining room waitstaff well. That money will do so much more for the hard-working crew members, many of whom leave their families and young children behind for many months at a time, than it will for you.


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Don’t Forget to Ask For Your Discount(s)

I’m not as familiar with other loyalty programs, but one thing that Royal Caribbean’s Crown and Anchor Society gives its members is some discounts on drinks. These will not be applied automatically; you must ask for them.

For example, on our recent cruises, we were entitled to 50% off of two beers (or wines) and 10% off a third one. Expect to pay full price for each drink if you don’t ask them to apply your discount.

A Great Entertainer Can Make the Cruise

On our most recent cruise, the piano player who entertained the Schooner bar guests most nights was pretty lame. His song list was repetitive, and his piano playing was almost always accompanied by a track with percussion and other instruments.

I honestly think he was just hitting the play button to play the original recording most times while singing along and pounding out some chords. A glorified karaoke singer who had his own show for three hours a night. Rubbish.

The guitarist in the English Pub, on the other hand, was quite talented with a unique voice, but he was battling a URI and strained vocal cords for much of our cruise.

On the first of our three recent repositioning cruises, we were fortunate to have one of the best piano bar entertainers I’ve ever seen on land or sea, and I’ve been to more than a few piano bars. He would take all kinds of requests and mash them together into one track. He always kicked off the evening with a themed set list, and when I requested our wedding song  (Ben Folds’ The Luckiest), he didn’t know it but promised to learn it. He played it for us on our last night of the cruise.

If you ever come across Alan Taemur playing in the Schooner Bar or in London somewhere, check out his show!


Upgraded Dining Is Better, But Is It Worth It?

On a recent cruise, we were offered a complimentary upgrade one evening to the restaurant of our choice. We chose Chops Grille, the upscale steak and seafood restaurant.

I’ll admit that the meal was outstanding, but I don’t know if it would be worth the $35 or $39 per person upcharge as compared to eating in the main dining room.

There is a certain sameness to some of the dishes served in the main dining room, but it’s rare to be served a dish I genuinely don’t like, and when that happens, another dish can always be ordered at no cost.

If you and your travel companions are true foodies, I can see the benefit of trying out the various specialty restaurants. The upcharge is definitely much less than the full price of a comparable meal on land (in most countries, anyway). For my family and I, though, the value’s probably not there. We’ll splurge at another time when we don’t have a tasty complimentary option.


There are Few Kids on Certain Cruise Lines

If you pay attention to their marketing and amenities, you can tell that lines like Royal Caribbean, Disney, and Carnival cater to families. Other cruise lines do not.

Our boys were the only kids in the 12 to 17 age range on the entire Princess ship coming over from the U.K. to Florida in the fall. Our longer itinerary from Sydney to Honolulu in the spring had about 100 of them.

I hear that Holland America has a reputation for catering to an elderly population, and when we cruised Celebrity to Alaska for our honeymoon years ago, the two of us brought the average age of the cruise down substantially. I’ll never forget the condescending “shipmate” of ours who asked if our parents paid for our vacation. No, sir, I was actually able to afford the trip myself on a physician’s salary, but thanks for asking.


Childcare is Available

No matter the age, there’s a place where you can drop off your baby / toddler / preschooler / grade schooler, etc. Teenagers also get their own space, entertainment, and programming, but they’re free to come and go as they please, whereas younger kids generally need to be checked in and out. Certain cruise lines (Royal Caribbean, Disney, and Carnival) will presumably have more robust children’s programs.

Our boys have really enjoyed meeting kids their own age and taking part in the activities lined up just for them and their peers. Most kids do.

In our experience, this has all been provided at no additional cost, but I’d recommend checking with your particular cruise line ahead of time.


We’re Good at Trivia

On the Princess cruise, we and our travel mates took part in quite a few trivia contests, and they actually give out real prizes to the winners, usually a bottle of ship champagne. Halfway through the cruise, we started giving our winners’ bottles away to the runners-up or other people we liked.

Royal Caribbean rarely gives away much more than a certificate and a highlighter, and I picked up a couple of those on our most recent cruise.



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We’re Bad at Bingo

We got some free play on a recent cruise. Not only was bingo boring, but it was really well-attended by some serious bingo enthusiasts who packed their own stampers to mark the spots.

Never were we even close to winning, but at least we were losing ship money that was created from thin air.


Some People Were Born to Complain

“I ordered my steak medium-well. This is medium.” “I’m never eating in here again.” “We’ve been here 15 minutes and I haven’t gotten any of the three appetizers I ordered!”

Some people suck, and we somehow keep getting seated near them. On a ship with so many food options, if you don’t love the food or the service, get over it and find some food somewhere else. Or save your comments for the survey. There’s no need to berate the servers or chefs, who, by the way, probably haven’t had a full day off in months.


Pack Light

On these most recent trips, we’ve combined our cruise vacations with weeks or months of other travels, so what we bring with us has to serve us in many capacities and climates.

I can’t say that I’ve missed not having formal attire or different outfits for Disco Night, Eighties Night, Tropical Day, and so on.

The bare necessities for me are a pair of flip-flops and closed-toed shoes, pants and shorts (or convertible pants), and some short and long-sleeved shirts, preferably with a collar on at least one. Throw in some moisture-wicking gym clothes that can double as truly-casual casual wear.

I know the packing list from most women will look a lot different, but my wife’s list looks a lot like mine. Add in some regular and sport bras, some laundry soap, and a small portable fan.



Learn to Do Laundry in Your Stateroom

Why the fan, you ask? It will expedite the drying of hand-washed clothes, and when you’re traveling for two-plus weeks and packing light, room-based laundry can be a necessity if you don’t want to spend hundreds of dollars to launder clothes worth dozens of dollars.

Princess ships have small laundry rooms with washers and dryers, but on most ships, the only laundry option that’s not true DIY is to pay $25 to $35 or more to have a surprisingly small bag of clothes laundered and folded. I’ve heard they use very high heat; friends have had their clothes ruined.

I must thank my wife for keeping us in clean clothes by doing a small load most days. The process is to soak the clothes in the sink or a basin (the champagne bottle holder can work well) with some laundry soap. Agitate a bit. Rinse thoroughly. Wring out. Lay flat in a dry towel, roll it up and squeeze, and then hang it somewhere in the room.

We’ve used a short rope to create a clothesline in some rooms. Most recently, we used all the hangers in a large closet to hang the clothes to dry. This process works quite well, but with a family of four, laundry has to be done at least every other day, and daily works better. There’s only so much space to hang things to dry.


Pack Magnetic Hooks

You can get some really strong magnets with mug hooks on Amazon, and these are handy to have on board. Your doors and perhaps a few walls will be made of metal, and you can post important papers, hang swimsuits to dry, and these things can come in really handy. They take up almost no space (ours are about 1/2 inch long), and they come with us on every sailing.


There Won’t Be Many Electrical Outlets

You might think the solution is a power strip, but the cruise lines tend to forbid these, and based on the tables I’ve seen full of them at the disembarkation ports, I know they’re not afraid to take them away.

To be able to charge all of your devices and run your clothes drying fan, you may need creative solutions. A universal adapter can be handy, as there may be separate US and EU outlets, and it’s nice to be able to use both.

I also recommend a charging adapter with numerous USB outlets (4-6), and if you may be able to get away with a power “cube” with additional outlets if it’s not in the shape of a typical lengthy surge protector.


Make it as Formal as You Want

My top hat goes off to the ladies and gents who dress to the nines and bring the proper formal wear and outfits for each and every themed night. You all look amazing; you really do!

I do not. Please be happy that I bothered to zip the pant legs back onto my convertible pants for formal night. I might also be wearing a shirt with long sleeves and/or a collar, but don’t count on both on the same evening.

When I’ve taken vacations that were solely cruise vacations, I’ve packed suits, Hawaiian shirts, and polyester shirts with massive collars original to the 1970s. Lately, that hasn’t been feasible given our pre and post-cruise travels, and in my experience, I’ve been fine without them.

I’m sure some finely dressed people have scoffed at our sadly ordinary attire, but these are probably some of the same sad saps who send their food back with pointed feedback for the chefs.


Beware the Paparazzi

Speaking of optionality, you don’t have to have your picture taken 8 times a day. The photographers are set up all over the place, and for a price, you can take home lots of pretty pictures, but you can easily bypass these paparazzi types.

I feel like they’ve become less bothersome over the years, at least. I remember the Carnival guys and gals making people wait and making everyone feel like their pictures were mandatory.

They’re not.


Expect Crappy Internet

This is going to sound a lot like a complaint, and it is one, but if you go in with low expectations, you’ll be less likely to be frustrated by the slowness, frequent disconnectedness, and sometimes wholly unavailable internet on the ship.

Royal Caribbean ships have been equipped with Starlink, but the speeds are still throttled and shared with hundreds of others. Random disconnects still happen, although maybe not as frequently as on other ships.

On our Princess cruise, there were 48 hours where the wifi connection gave no internet whatsoever. Other days, the internet speed rivaled that of a 14.4 mbps dial-up modem.

If reliable internet is important for your job, you’ll want to use some vacation days rather than try to work remotely. Even on the best days, you’re probably not doing Zoom calls with video feeds.

Pro tip: crack your door open to improve the wifi connection. Our cabin steward loaned us a doorstop for the length of our most recent cruise, and our connection would improve from 2/4 to 4/4 bars on the wifi signal with the door open 6-8 inches.

The App May Be Only Slightly Less Crappy

Given the budgets of the cruise lines, it’s surprising how glitchy their apps can be.

I don’t like to complain, so I’ll leave it at that.

Use a Travel Agent… No, Really!

A travel agent can get you extra perks and in some cases, better pricing than you’ll be able to find on your own.

The only times I’ve used a travel agent in the last 30 years are when booking cruises and once for a Disney vacation, although that was an online agent that I didn’t really interact with.

Our travel agent has spent hours on hold with the cruise lines for us, straightening out complicated scenarios when scheduled itineraries were delayed or canceled due to the pandemic. We always have a welcome gift from her waiting in our stateroom.

This is one scenario in which I don’t recommend booking direct. If you do, you’re likely missing out on some goodies and/or savings.


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Find Your Oasis

There are a lot of busy places on the ship. People constantly coming and going, throwing towels down to reserve seats, queuing for soft serve ice cream or pizza, that sort of thing.

Find somewhere far away from those places where you can always find a comfortable seat and perhaps a little peace and quiet.

It might be the nightclub during the daytime. It could be a lesser known outer balcony area, library, or unoccupied conference room.

It’s nice to have a place on the ship other than your stateroom where you can go and feel at ease without the hustle and bustle of the pool deck or promenade.


The Ship is as Important as the Stateroom

Personally, I think many people focus too much on the room they book and not enough on the ship they choose. We’ve been in balcony rooms, outside rooms, obstructed view rooms, and inside rooms. On a recent cruise, we upgraded ourselves to a front-facing room that was nearly double the size of a typical room.

Regardless of the room, we’re not spending much time there outside of sleeping hours, so it really doesn’t matter much what type of room we get. If sleep is the most important factor, an interior room guarantees that you won’t be awakened by exterior light. Yes, we like to see the ocean, but there are plenty of places all over the ship to do that.

What matters more to me is the rest of the ship. What are the public spaces like? What unique amenities does it have? What do they have that’s geared to kids and teens?

On our recent cruises, we’ve taken advantage of a free skydiving simulator, surf wave simulator, bumper cars, mini golf, indoor and outdoor movie theaters, and this capsule reminiscent of the London Eye that takes you 300 feet up in the air.

I have yet to cruise on one of Royal Caribbean’s Oasis Class ships, the largest ships on the seas, but that’s something I’d like to do on one of our next cruises.


There’s a Benefit to Scheduled Dining

For one, dinner might be the only time we see our kids all day if it’s a sea day.

The scheduled dining times are also coordinated with the event schedule, so there’s usually not much entertainment going on at dinner time, especially if you opt for “early” dining, which we always do.

Many ships now offer flexible dining times, but from what I’ve seen, that means waiting in a line, hoping to get a time that works for you on that particular evening, and a level of uncertainty that doesn’t do you any favors.

When you dine at a fixed time every day, you’ll also eat at the same table and have the same waitstaff throughout your cruise. If you have a standard drink order, they’ll have it ready for you when you arrive. There were always three glasses of chocolate milk already made up when we arrived every evening after we ordered them the first night.


Go to Shows With an Open Mind

Pretty much every evening, there will be live entertainment of some sort in the main theater. It might be a Broadway-style song and dance number, a comedian, a juggler, a musician, a contortionist, or any combination thereof.

I don’t go to 100% of them, but I’ll bet I attend eight or nine out of ten. Even when the description doesn’t sound that enticing or just not my cup of tea, I’ll usually give it a shot, and more often than not, my expectations are exceeded.

That said, if you begrudgingly agree to go to a show that you’re convinced you’re going to hate, you’re bound to hate it. I try to go in with an open mind, and if I’m not enjoying myself, I’ll leave early. Most shows only last an hour or less, so it’s not a huge commitment either way.


You Can Teach an Old Dog New Tricks

A person can learn a lot on a cruise ship. Knowing how to fold a napkin to look like a flower or how to make a couple of towels look like a puppy dog are not important life skills, but they’re fun party tricks to have up your sleeve when hosting a dinner or overnight guests. Many cruises will teach you how to do both.

You can pick up other skills and activities, like “surfing” the Flo Rider wave, playing pickleball, and different types of dances like line dancing or the Thriller dance.

Longer cruises also have educational or enrichment talks where lecturers might cover any variety of topics from geography to natural science to history… basically any topic that might be of interest to an audience that cruises. On the Princess cruise, the first enrichment talk was all about famous shipwrecks, including the Titanic, an interesting choice for a transatlantic sailing.


The Theater is in the Front… or is it the Back?

These huge ships can be disorienting. You’d think that by day eleven, navigating within the boat would be second nature, but no.

With up to 20 decks and various theaters, sports courts, pools, dining rooms, buffets, bars, and shops, it can be the last day of the cruise, and I’ll find myself heading to the aft when I should be heading to the bow based on where I think I’m supposed to be going.

I’ll add that none of us are born knowing that bow, starboard, aft, and port are maritime names meaning front, right, back, and left. I remind myself that aft comes after the bow, and that port and left are both four-letter words ending in “t,” so they’re clearly the same thing.

Patience is a Virtue (That I Don’t Have)

The best part about vacationing with a cohort of a few thousand guests whose average age is 93 is the incredible speed at which everyone moves.

By incredible, I mean incredibly slowly, and it’s not the best part, but the worst. Adding to the fun is the fact that the corridor leading to your room is four feet wide at best, so you can’t just leisurely stroll past Dutch and Irma to get around.

I’m clearly exaggerating on the average age. There are also plenty of younger, able-bodied people who are capable of walking at a moderate pace and will do so but then abruptly stop in the middle of a pedestrian thoroughfare, stairwell, or other super-convenient place.

Don’t get me started on the people that constantly walk the wrong way in the dedicated running loop on the outdoor track. On our last ship with 3,900 passengers, there were 3,899 people doing exactly that the one time I tried to run for several miles outside.


Robots Can Mix Drinks

I was mesmerized watching Mix and Mingle, the two robotic drink makers in the Bionic Bar aboard Ovation of the seas. They swung their arms about in rapid fashion, pulling mixers and liquors from a large selection suspended above them, shook or stirred their concoctions, and poured them out into a waiting cup, delivering whatever preset recipe or custom drink order the guests had requested.

I can’t comment on the quality as I’m more of a beer guy, but it was sure fun to watch the robots work.


If You Want a (Good) Seat, Arrive Early

Our first two repositioning cruises were only at about two-thirds capacity, so there was always plenty of seating. Our most recent cruise was more full, and I was reminded of the importance of arriving early if you want a good seat, or in some cases, any seat at all.

I’m not just talking about the main stage performances in the theater. There was rarely an open seat in the Schooner Bar when the piano player was performing, and scheduled trivia filled the place up just as much, if not more.

If a show or performance is important to you, I would recommend arriving at least 15 to 20 minutes beforehand. Also, be wary of saving seats. It’s a common practice that is officially discouraged, and I’ve seen some passengers, probably emboldened by an unlimited drink package, just about throw down in fisticuffs over someone saving good seats for their friends.


Bookmark Cruisesheet.com to Find Cruises

Most websites that claim to find you discount cruises are just poorly designed search engines for cruises that collect referral fees or travel agent fees when you book through them.

Cruisesheet.com makes money the same way, but it’s much better organized and more powerful, with many search filters and a handy visual representation of the price of cabins on each cruise over time. The site was created by frequent traveler and renowned pick-up artist Tynan, an interesting fellow to say the least.

I typically use Cruisesheet to find a cruise, and once I’ve selected an itinerary, I ping our travel agent so she can book it for us.


Have a Plan to Fill Downtime

When it’s Day 15 of an 18-day itinerary, you’re fresh out of ports of call to visit, the disco trivia has lost its appeal, and you’ve already mastered folding towels into weird-looking animals, you’re going to need something to do.

Come prepared with whatever you would normally do to fill downtime. Many cruise ships have small libraries, but you’re better off bringing your own reading material. Pack a Kindle or a physical book if you’re a reader.

If you’re more of a listener, remember that the internet will be expensive and crappy, so download your podcasts and audiobooks before you embark.

You can always spend more time at the gym or on the walking track, and if you have the all-you-can-drink package (which I still don’t recommend), you can always opt for drinks by the pool.



You Might Get Sick

The term “floating petri dish” is a little harsh and woefully inaccurate because there are no scientists actively looking for disease on the ship, unlike a petri dish which is literally put under a microscope. I get the feeling that the cruise lines would rather not know about your illness unless you reach the point where you actually need medical treatment. They don’t like making the news for that reason. The major cruise lines all hire a ship doctor, although I’ve never had a reason to visit one.

It is true that whenever you have thousands of people living in close proximity, transmissible illnesses can thrive. Most commonly, viruses or bacteria that cause gastrointestinal or upper respiratory symptoms are the culprits. Think norovirus, rotavirus, influenza, and varicella.

In recent years, a particularly nasty coronavirus made its way around the world a few times over, and cruise ships were not spared. My family and I managed to evade the virus for over a year, but after our repositioning cruise in the spring of 2022, we all tested positive. Having been vaccinated and boosted, our symptoms were mild to none, and we only tested out of courtesy to relatives we were planning to visit afterward. One of the four of us was positive for COVID on an antigen test, but a follow-up PCR test showed that all of us must have contracted it at some point on board. It wasn’t that surprising; we heard a lot of coughing and sneezing as we made our way up the eastern seaboard in the final days of the cruise.


Some Pandemic Inspired Changes are Welcome

Like many non-medical industries, the cruising industry was brought to a standstill during the pandemic. When they did begin sailing again in the summer of 2021, a number of changes had been made, some of which have survived to the present day.

Hygiene had been a focus because of norovirus and its friends, but the coronavirus made hygiene a top priority like never before.

While mask-wearing is now optional, passengers are more likely to don a mask when experiencing symptoms of respiratory illness (or surrounded by others who sound ill).

Hand hygiene is also stressed more than ever before. Sanitizing gel stands are everywhere, and there’s a mandatory soap-and-water hand washing station at the entrance to the Windjammer buffet on Royal Caribbean ships. Are the “washy washy” shouting staff members annoying? Absolutely. But they’re also effective and probably necessary. People display different hand washing behavior when they’re not being watched, and I know this as a man who uses public restrooms. It’s gross, I know, but true.

Another pandemic-era change that appears to be permanent on Royal Caribbean ships is one that makes me especially happy. Those with Diamond or higher level status in the loyalty program used to get a couple of hours of free drinks in one lounge each evening. They closed these lounges as they reopened (though they’re now open again), opting instead to award higher-status passengers four or more free drinks that can be enjoyed anywhere on the ship at any time of day. We’re just a few short cruises (or one long cruise) away from that coveted free-drink status!


Frequent Cruisers are Proud of Their Frequent Cruising

When you’ve accumulated a whopping 700 points on Royal Caribbean ships, which represents nearly two full years of cruising (or one year of cruising in suites or during a double points promotional period), you are a Pinnacle Club member.

Apparently, Pinnacle Clubbers get a free cruise, some Royal Caribbean swag, and most importantly, at least to some people, a golden plastic nametag identifying you as a Pinnacle Club person. I noticed that some people wear this pin wherever they go, day in and day out, ensuring that everyone knows they’ve dropped something close to, if not exceeding, a six-figure sum on Royal Caribbean itineraries over the years.

One guy on our last cruise sported a large Royal Caribbean logo on his calf. I’m not kidding.

Others have big magnets they put on the exterior of their stateroom doors with silly sayings based on nautical themes. My favorite is the chalk board or dry erase board announcing whose room it is. “Vince & Margie” written in erasable ink or chalk in case things don’t go so well between the two of them and one or both names need to be changed before the last port of call is reached.

I’ve thought about having my own golden plastic nametags made with my name and “Pineapple Barnacle Club” or something similar written on them. Short of spending a couple years on board, I don’t know how else I’m ever going to look so cool. [Note: Pineapple replaces with Barnacle because it seems that pineapples, particularly when displayed in upside down fashion (unless in a cake) are indicative of “swingers,” and I’m not talking about one of my favorite 90s movies.]



A Lot to Learn

I learned a whole lot on these lengthy trips, but I still feel like an amateur compared to the regulars with dozens of itineraries and hundreds of nights under their loosened cruise ship belts.

What tips, tricks, or habits are your favorites when it comes to cruising? 


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7 thoughts on “47 Lessons from 47 Days on 3 Repositioning Cruises”

  1. Haha mate I would think twice about the pineapple club… just so you know, the pineapple is code for swinger on cruise ships. Next trip have a suss and see which people wear pineapple on their clothes or have a pineapple on their door 😅

    • What??? You learn something new every day.

      How about the Spinnaker Club? Or Barnacle Club? SOunds a bit like Pinnacle without inviting unwanted attention.


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  3. “I’m averaging 3.14 desserts a day, plus or minus a slice of pie. ”

    I see what you did there and it is good. Maybe not at good as the macadamia nut pie that I just had in Hawaii, but close.

    One day, we will go on a cruise together and amuse each other with silly jokes.

    Cruises are something I never thought I’d like because of the commercials I used to see as a kid (drunk people dancing). But then I went on one and found that it’s whatever you make of it. You certainly can stay drunk the whole time, do the belly flop contest**, and lay out on the deck all day until you look like a lobster. But you can also walk laps around the deck while looking out at the ocean, check out the library, and take tours where you see this ship’s mechanicals.

    *like a pecan pie, but with macadamias
    **there are no winners here

  4. Your review of 3 repositioning cruises is a lot to unpack (pun intended). I have many sea stories that I could share, but I’ve got a couple of financial tidbits to add.

    First, when you have identified a cruise which you would like to take, get prices from the cruise line and whatever other source you’d like–but don’t book the cruise, yet. Then, request quotes on that cruise at cruisecompete.com . It is free and as repeat World Cruisers, we have saved, literally, tens of thousands of dollars.

    Also, if you are a military veteran, complete the process BEFORE the cruise to be eligible for military OBC (onboard credit). On Princess or other of the many Carnival cruise lines, the amount of this credit is the same as the Shareholder Onboard Credit, discussed, above.

    • Thanks for the tips!

      I don’t qualify for any military discount, but I’ll be interested to see what cruisecompete is all about.



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