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How to rove: Cruise your way to a new life

Watching a cruise liner @ Half Moon Cay, Bahamas
Watching a cruise liner @ Half Moon Cay, Bahamas

Last updated on April 7th, 2026 at 04:16 pm

Cruise Your Way to a New Life — <a href="https://rovertreks.com/stories" title="Top Seven Tips To Get Your Story On RoverTreks" class="pretty-link pretty-link-keyword prli-keyword" data-prli-link-id="298">RoverTreks</a>
Updated March 2026  |  Prices and routes reflect original 2017 research. Verify current fares directly with cruise lines.
Watching a cruise liner arrive at Half Moon Cay, Bahamas

How to Rove | Boating & Cruising

Cruise Your Way to a New Life

When you stop measuring travel by how fast you get there, the ship itself becomes the destination — and crossing an ocean by sea changes everything.

Watching a cruise liner arrive at Half Moon Cay, Bahamas. Photo: RoverTreks

“Once you remove ‘time' and ‘anchors' as travel constraints, the ship stops being transportation — and starts being the journey itself.”

There are many ways to rove the world. Most people fly — it's fairly cheap and fast. And most are single-destination travelers. They'll fly to and hang out in a city or town, or simply explore a geographic region. Time and money drive this behavior.

But let's face it: flying is a hassle. Many people wouldn't do it at all if time weren't a factor.

If you're a rover — especially a full-timer — time isn't always driving your travel train. You're always traveling. You've got all the time in the world. If you weren't where you are right now, you'd be somewhere else, to overstate the obvious.

Get Rid of Your Anchors to Set Sail for Freedom

Once you've shed your “anchors” — a house, kids, pets, or a job tethering you to one location — time becomes relevant only for staging travel from one area to another. It becomes a question of logistics: where do I need to be, and when, to catch my next ride to destination X?

When you start thinking this way, you open your mind to possibilities about modes of transportation over time, rather than treating destinations as the only goal. Stated differently, the mode of transportation becomes a destination worthy of exploration in its own right — on the way to somewhere else.

Once you eliminate “traveling quickly” as a constraint, cruising becomes a real option. And yet, like many of us, you've probably thought about it and talked yourself out of it — time, money, fear, health concerns, arrogance, or the occasional horror story on the evening news.

Arrogance and negative headlines were my excuses. Years ago, I lived and worked on aircraft carriers and various classes of naval vessels. My attitude was: how could a commercial cruise line possibly match the U.S. Navy? That bias, combined with well-publicized cruise ship incidents — pandemic illnesses and accidents at sea — reinforced my skepticism.

But I was wrong.

In 2015, my wife and I took our 26-year-old son and a friend on a two-week Mediterranean cruise aboard Norwegian Cruise Line (NCL). Since then, we've completed two trans-Atlantic crossings and a Panama Canal transit with Holland America. I'm now a genuine convert. When I think about reaching another continent, my first question is: is there a cruise that gets me there?

The Azores, Portugal

The Azores, Portugal — a mid-Atlantic archipelago most travelers never see because they fly over it. A trans-Atlantic repositioning cruise makes it a natural port of call. Photo: RoverTreks

Why Every Rover Should Consider Cruising

Cruising is one of the finest ways to see the world — and repositioning cruises are the best of the best for rovers. These are sailings in which a cruise line moves a ship from one region to another at the start or end of a season — and sells the passage at a steep discount to fill the cabins. They're an affordable, unhurried way to cross from one continent to another.

Consider what a cruise actually provides that a flight never can: a hotel room and three meals a day while you travel from point A to point B. Shore excursions — real stops in real places — along the way. Entertainment, exercise facilities, swimming pools, and the rare luxury of arriving somewhere fully rested. A cruise is a floating hotel on the move.

We've met full-time travelers who cruise by a simple rule of thumb: if a repositioning cruise costs $100 per person per day or less, they take it. Once you account for accommodation, meals, and entertainment bundled into that rate, it's genuinely hard to beat.

Rover Rule of Thumb

When evaluating a repositioning cruise, divide the total fare by the number of days. If you land at or under $100 per person per day, you're likely getting an excellent deal — once meals, lodging, and entertainment are factored in.

Beyond the economics, cruising solves one of the most persistent stresses of full-time travel: where will I sleep tonight? A cruise provides a stable, full-service, temporary home — your cabin, your routine, your dinner table. Many seniors have discovered this and turned cruising into a permanent way of life.

And then there's the geography. Water covers approximately 71 percent of Earth's surface. Many of the world's most remarkable places are accessible, in practical terms, only by boat. When you start moving between continents by sea, entirely new possibilities open up.

The Rover Playbook

Two Repositioning Routes That Will Change How You Think About Getting There

Eiders on Vigur Island, Iceland

Trans-Pacific Route

Vancouver to Yokohama — Through the Northern Pacific

Instead of enduring a 22-hour trans-Pacific flight, consider catching a Holland America repositioning cruise from the West Coast to Japan in September. Stops include Ketchikan, Juneau, Glacier Bay, Dutch Harbor, Kushiro, and Hakodate before arriving in Yokohama-Tokyo. From there, a short flight reaches anywhere in Southeast Asia. The return repositioning cruise departs the Far East in April — bookending an entire winter on the other side of the world.

~15 days Crossing time
~$1,600 pp Inside stateroom (2017 rate — verify current)
6 ports Stops en route
M.S. Rotterdam at Ísafjörður, Iceland

Trans-Atlantic Route

Fort Lauderdale to Copenhagen — A Europe Doorstep Delivery

Holland America's 18-day April sailing from Fort Lauderdale deposits you in Copenhagen having passed through the Azores, Spain, France, Belgium, the Netherlands, and Denmark — never setting foot in a terminal. Arrive relaxed and drive the continent, island-hop to Greece, or catch the Baltic cruise immediately. Stay two months and ride the return repositioning cruise from Rotterdam to the U.S. — a complete loop, zero flights required.

18 days Crossing time
No jet lag Arrive refreshed
7 countries Ports of call

Rover Assessment

How Repositioning Cruises Rate for Full-Time Travelers

9.5
Cost Value

Room, board, entertainment & transport bundled. Hard to match at $100/day or less.

10.0
Comfort

Arrive rested. No security theater, no middle seats, no jet lag after a 15-day crossing.

10.0
Freedom

Structured schedule, but multiple ports of call let you scout destinations at your own pace.

10.0
Accessibility

Seasonal departure windows require planning. But once you're on, the world opens up.

The Rover Verdict

Stop Flying Past the World. Start Sailing Through It.

The hardest part of becoming a cruise convert is unlearning the instinct to get somewhere fast. Once you do, a repositioning cruise stops being a novelty and becomes your default intercontinental strategy. You arrive at the next chapter of your life relaxed, unhurried, and full of stories from the crossing itself — not just the destination. That's what roving is supposed to feel like.

Plan Your Repositioning Cruise

Best Search Tool
VacationsToGo.com — filters repositioning sailings by region, date, and price per day
Specialist Resource
RepositioningCruises.com — dedicated listings updated each season
Cruise Lines to Watch
Holland America, Norwegian Cruise Line (NCL), Princess Cruises, Cunard
Best Booking Window
6–12 months ahead for the best inside stateroom rates; last-minute deals also appear 30–60 days out
Shoulder Season Tip
April–May and September–October repositioning sailings typically offer the lowest per-day rates as ships move between summer regions
Price Benchmark
Target $100 per person per day or less for exceptional rover value — all-in for cabin, meals, and entertainment

Pricing note: All fare figures in this article reflect 2017 research by the author. Current repositioning cruise rates vary significantly by season, cruise line, cabin category, and booking timing. Always verify directly with the cruise line or a travel specialist before planning.

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