For Do-er’s & Don’t-er’s: The Best of Both Worlds.

Best. Cruise. Ever.

Okay, right. I say that literally every time I step off a cruise ship but, this time, I mean it. 

For those who haven’t been eye-rolling my never-ending posts of sunset photos, my husband and I recently returned from a 14-day dream of a vacation that included a ten-day cruise. A ten-day cruise? Are we ridiculously wealthy? No. It was, in fact, a repositioning cruise, a pseudo-secret cruise category. Or at least they were a pseudo-secret. Now that all 900 of my readers are in the know, the cat may be out of the bag. Cat? Okay, maybe just a paw.

A repositioning cruise offers a unique twist on the traditional cruise experience, blending elements of luxury travel with the adventure of a long journey. Unlike regular cruises, repositioning cruises happen when ships need to relocate to a different part of the world, often due to changing seasonal routes. A ship might travel from the Caribbean to the Mediterranean in the spring or from Alaska to Asia in the fall.

What makes repositioning cruises amazing?

The Accountant in Your Home Will Smile

Typically, each relationship has a spender and a saver who are forced to fight their way to compromise. This is especially common when it comes to big spends, such as vacations. In my home, I am the saver. My husband? He lives by the philosophy that our bank accounts are replenishable, always. This drives me bananas. I’d rather stay plenished and that often comes out on our vacations as I monitor each dime spent. 

Do I really need another ten-dollar mojito? (Me) Just get the damn mojito. (My husband).

Since repositioning cruises are more about moving a ship than catering to the high demand of a specific location, they are typically priced much lower than a traditional cruise. As in . . . a fraction of the usual cost per sailing day. This allows travelers to experience the amenities of a luxury ship while allowing the spender and the saver in each cabin to feel like winners. 

The Rhythm of the Ocean

If you love the rhythm of life on a cruise ship, repositioning cruises are a dream come true. These cruises often spend more days at sea than a standard cruise, providing ample time to enjoy all of the ship’s facilities at a leisurely pace. Relaxation is immersive as there is no need to keep a schedule or hop on and off the ship at the daily port stop. Pools and spas often remain less crowded as guests don’t feel a time crunch to use them. 

Disconnecting is all but guaranteed as the interwebs become more dodgy further from land. 

This does sound terrifying but, once the shakes go away, it is delightful. You will be shocked to find yourself without your phone and then be shocked to find that you don’t miss it. For those panicking, yes, there are ways to beef up your digital access, but I recommend ignoring those offers.

The Do’er and Don’t-er Will Thrive 

All that disconnection aside, repositioning cruises offer all kinds of onboard activities because, frankly, the ship’s staff enjoys keeping travelers busy (aka…out of their hair). There are endless classes (dancing, musical instruments, cooking), seminars (local history, ship tours), entertainment (musicals, comedians, bingo, trivia), and more. There are also numerous passenger-lead options (SeaDay 5k, Cabin Crawl, Pub Crawl, gift swaps, book clubs) found in each sailing’s Facebook group. 

Just like the spender and the saver, many relationships include a Do-er and a Don’t-er. In my home, I am the Do-er while my husband is the Don’t-er. He showed up for our vacation with a stack a books and plans to live on the verandah for two weeks. I showed up with a list of new friends to meet, tasks to complete, and classes to attend. Interestingly, I bailed on about three-quarters of my planned plans as I leaned into living on the verandah. It was bliss.

A repositioning cruise offers the perfect vacation for both the Do’er and the Don’t-er while on the same trip. 

The Road Water Less Traveled

While traditional cruises tend to stick to popular ports, repositioning cruises stop at more unique destinations. Imagine starting your trip in Miami, stopping at the Azores, then winding up in Barcelona or leaving Fort Lauderdale, stopping in Cartagena, Spain, and then making your way to Rome. On the Pacific side, ships depart Vancouver, CA before making their way to Asia while island hopping through Hawaii and Fiji. 

Travelers explore locations that are not found on typical cruise itineraries and that are often only visited by cruise ships once or twice per year. These locations are much less “touristy” than the usual ports as the area is less reliant on the income brought by visiting cruise ships. Shopping is less t-shirts or magnets and more artisan.

The Unhurried Pace

On a repositioning cruise, the pressure that can come with back-to-back-to-back port visits never forms. With days of open ocean, there is plenty of time to relax and enjoy the ship’s offerings. This offers the chance to savor time onboard and truly “get to know” the ship and all it has to offer. The experience really is more about the journey than the destination, a unique but often forgotten approach for those who find joy in slower-paced travel.

I can’t tell you the number of times we’ve left a cruise ship and discovered, later, what we had missed. Wait, there was a bowling alley? No, I never saw the chapel! Oh, I could never get into the spa. Because the bulk of a repositioning cruise is spent on board, there is ample time to explore, find a favorite spot, and still have plenty of time to enjoy it. We have also felt torn when picking port excursions because there are often several at each stop that interest us. Because stops are to those ports less traveled, excursion options are much more limited. At first, it felt weird. Then, it felt great not to have to weigh one against another and stress about if we’d picked the right tour. 

Yeah, yeah, but what didn’t you like?

I know. Can’t offer the pros without the cons, can I?

But It’s So Looooong. That’s What She Said. She Was Me.

Repositioning cruises are often longer than typical cruises, sometimes lasting over two weeks. For travelers who don’t have the luxury of time, this extended duration can be a major drawback. There are often options to depart mid-way through a repositioning cruise which some miss when researching. For example, the ship we were just on was sailing from Vancouver, BC to Sydney, Australia for a 28-day total trip. We opted to disembark in Honolulu, HI which brought our sailing down to 10 days.

Cabin Fever is Real

The extended time at sea and fewer stops can sometimes lead to feelings of restlessness, especially for those who are used to a more active, fast-paced vacation. With several days at sea in a row, some travelers may experience cabin fever. This is particularly true for individuals who thrive on regular shore excursions and new activities. For travelers who need constant stimulation, the slower pace of a repositioning cruise may feel like a drawback rather than a perk.

Tipsy Weather Equals a Tipsy Ship

Because repositioning cruises cross vast bodies of water and go through multiple climates, there’s a higher chance of encountering varied—and sometimes rough—weather. Long stretches at sea mean that if there is inclement weather, you’ll have fewer port stops where you can escape it. For travelers prone to seasickness, this can be quite intimidating and is absolutely something to plan ahead for. We had quite a few passengers affected by the tipsy waters of the Northern Pacific when we departed Vancouver (including my husband). The ship handled the ill like professionals and we found our fellow passengers happy to share their own remedies (while ours waited at home, forgotten). Within a few days, everyone on board was acclimated to the water and back to enjoying the long days. 

Limited Amenities? Sort of.

Depending on the cruise line and ship, repositioning cruises may occur in conjunction with the ship’s preparation for the next cruise season. As such, some amenities may be limited or undergoing maintenance. Not all restaurants, shows, or attractions may be fully operational as the crew readies for the ship’s next phase. Our ship included a brand new entertainment crew who were working out the kinks while we sailed. Still, the shows were fabulous! 

Because these sailings tend to have fewer passengers, the onboard “vibe” may be quieter than what seasoned sailor are used to. This can be a positive or a negative, I suppose. We loved it and made some fabulous friends because we were able to easily spend so much time together. 

While I would certainly not recommend a repositioning cruise to anyone who has never cruised before, I would absolutely recommend it to those who have. This cruise was not our original plan or even our second. Initially, we were to kick off our Empty-Nest Era by sailing the Baltic Sea with stops in Russia. The Russian-Ukrainian war caused a bit of a hiccup there and so we shifted our plans to an Alaskan cruise. Life struck again due to some family health issues and we opted to postpone the Alaskan cruise.

Admittedly, I was feeling pretty deflated by that point which is when this Vancouver to Honolulu sailing landed on my travel agent radar. When I showed it to my husband, he was an enthusiastic “YES!” while I was less enthusiastic because “but that’s a lot of days at sea…”. Still, we went for it, the Do-er and the Don’t-er. The accountant in me was pleased and we were off on a trip that, for the first time ever, would include an itinerary that was 100% new to both of us.

Now, I know I say this literally every time I step off a cruise ship but, this time, I mean it.

Best. Cruise. Ever.


Have I gotten your interest sparked? Sweet. That was my point. I’m only slightly ashamed to say that, upon returning to the real world, I spend a full two-days researching every repositioning cruise for the 2025 season. Did I totally nerd out and create a whole spreadsheet of options? Yes. Will these repositioning cruises also be offered in the following years? Yes, again. I’m ready. Let’s go. Want to see that list? Head here and check out the Highlighted Travel Opportunities section.

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