Cruising Home: My Repositioning Adventure on HAL’s Nieuw Amsterdam

A Reverse City Trip: Why I Took the Long Way Home

Jun 13, 2025

Let’s be honest: a cruise is a vacation—not necessarily travel. Yes, it takes you places, but often in an odd mix of hand sanitizer, buffet lines and Broadway-style shows. It’s an acquired taste.

Some cruises do offer genuine moments of discovery, especially if you choose your itinerary wisely. This spring, I boarded Holland America’s Nieuw Amsterdam for a repositioning cruise from San Diego back home to Vancouver. It wasn’t packed with ports or exotic stops, but as a unique one-way sailing, it gave me a different kind of travel experience—and a new appreciation for how to end a journey.

I dislike feeling at home when I am abroad. ~ George Bernard Shaw

Why Repositioning Cruises Are Worth It

Repositioning cruises happen when cruise lines move ships between seasonal home ports—like from the Caribbean to Alaska, or all the way from Europe to North America. In my case, Nieuw Amsterdam was returning to Vancouver for the summer Alaska runs, and I joined for the final stretch. These cruises can offer great value, fewer crowds, and special routes that aren’t available year-round.

I flew one way to San Diego, spent a few days soaking in the California sun, and then cruised back to Canada. It’s a fun way to turn a repositioning into a reverse city trip—start in the city, relax at sea, and arrive back home recharged.

San Diego: A Port City Worth Staying In

Unlike some chaotic cruise terminals1, San Diego made a great first impression. It’s compact, well-organized, and just minutes from the airport. If San Diego is a stop on your cruise, you can literally walk from the terminal to Little Italy or the Gaslamp Quarter.

If your cruise starts or ends in San Diego, I recommend adding a few days pre- or post-cruise. For a different vibe, I opted to stay in Coronado—technically “the middle of nowhere” but beautifully peaceful and just a short ferry ride from downtown. Forget about having to stay in the city centre. Sometimes the best experiences are slightly off the beaten path.2

Cruising with a Margarita Problem

Now, a quick confession. I had a bit of leftover birthday margarita in my suitcase. Not a full bottle, just about 25% of it. As a cheap Dutch guy, I hated the idea of wasting it. Turns out, that decision sent my luggage on a little side quest through ship security.

At one point, my AirTag even showed the bag moving away from the ship. Not ideal. Eventually, a kind room attendant helped track it down and security released it once they confirmed the bottle was nearly empty. Lesson learned: drink all the margaritas before boarding next time.

Life Onboard: Food, Friends, and... Questionable Comedy

Once the luggage panic subsided and I got settled in, I found out this cruise was actually the final leg of a much longer sailing—some guests had joined weeks earlier in Central or South America. It reminded me of my Panama Canal adventure years ago. If only I had booked the full itinerary!

Onboard, I definitely skewed the average age downward. Holland America is somewhat known for this, but my Koningsdam cruise the age gap was a lot less than on Nieuw Amsterdam. Most passengers were considerably older than me—but with age came wisdom. Some of my fellow cruisers were living proof that you’re never too old to explore the world. I genuinely loved hearing their stories.

Food on Nieuw Amsterdam was excellent throughout the trip. Drink service? Flawless. Entertainment, however, was hit and miss. The live music venues were consistently great—just like what I enjoyed on the Koningsdam. The comedy act, on the other hand... let’s just say it didn’t quite land. (To be fair, I’m not a big comedy guy. I tend to overthink jokes. And everything else in life.)

Travel Tips for Smarter Cruising

If you’re thinking about taking a cruise—repositioning or otherwise—here are a few tips based on this trip:

Look for deals that include drink packages or specialty dining if you’re into those things. Buying them separately can easily double your fare, especially on longer trips.
Check directly with cruise lines for repositioning routes—they don’t always appear on third-party sites or through travel agents. My travel agent was unable to book this specific itinerary at the rate I found myself online, and he phoned me back with the recommendation to “book it now”.
Filter your options based on what you truly want to see and when. The sheer volume of cruise itineraries can be overwhelming. It doesn’t hurt to be picky.

And if you're flying into a cruise departure city like San Diego, consider staying outside of the downtown core. It’s cheaper, quieter, and gives you the chance to explore local neighbourhoods you might otherwise miss.

Get Into Action

My short cruise was a mellow, meaningful way to come home. While it didn’t offer the thrill of daily new destinations, it gave me something else: time to unwind, reflect, and share stories with travellers who’ve been around the world and back—literally. That, to me, is a different kind of travel experience. And one I wouldn’t trade for anything... except maybe that bottle of margarita.

As a special thank you to my readers, I'm excited to offer a limited-time $50 travel credit for your next adventure! Simply click here to claim this exclusive offer. Don't miss out on this opportunity to save on your next vacation and have a drink (or two) on me next time you set sail.

Holland America Line $50 Credit