Hiking the Urupukapuka Hillsides

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We left Roberton Island and headed 4nm to Urupukapuka Island.  Matt and I knew a lot of boats anchored in this area and had scheduled a hike and luncheon with everyone.

We had a lovely group of people on our 4nm hike. Beth and Dave (Warrior), Jim and Pam (Roam), and Joanne and Scott (Fundango).

There are loads of trails around Urupukapuka.  We decided to take the red track all around the island which is a medium grade track.

It was a perfect sunny day with cloud cover.  Not too hot and not too cold.

This is an absolutely stunning hike. 

Every turn offered a different gorgeous view.  Each time we were convinced the view could not get any better and yet it did!  

The colors in the sky against the rich browns and greens on the hillside were lovely.

The trail was easy to follow and well maintained.

And we encounter more amazing views. 

I kept picturing a beautiful house where we stood overlooking this view!

Joanne and Scott peeled off after the first hour to watch the NFL playoffs.  But the rest of us finished our loop with pride.

We stopped in at Otehei Bay Cafe for some cold beers and a snack before heading back to the boat.

Urupukapuka

Our neighbors, “Roam” were anchored next to us. 

I could not resist taking a photo of our two beautiful Catana Catamarans – sister ships.

Later that night we had everyone over for happy hour.

Below we have Charlie (Purr), Pam (Roam), Joanne (Fundango), Dee and John (Go Baby Go), me, Jason, Matt, Jim (Roam), and Dave (Fundango).  Such a great group of people. 

We hiked the hillsides of Urupukapuka toward the end of May 2026.

Our blog posts run 6-8 weeks behind actual live events.

Whangamumu and Roberton Island

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We arrived in Whangamumu harbor around 2:00am, dropped the hook, had a celebratory beer and crashed.  

Jason woke up to a glorious day showcasing the beauty of Whangamumu!

That is Jason sitting on the port helm seat as Matt takes his photo with the drone.

Last month we released a full blog post on Whangamumu and its rich history with whaling.  Be sure to read all about it here.

We took Jason ashore to explore the whaling station and waterfall.

It had not rained recently so the waterfall was not gushing down, but it was still very pretty.  We were able to hike up the falls about 25 meters and just soaked up the beauty.

Sugar Shack had the bay all to herself.  The water gently lapped against the hull, the sun was shining, and everything was so peaceful.

It would have been lovely to hang out here for a few days.

However, we only had a few more days with Jason so we decided to move on to our next stop.

Roberton Bay, Bay of Islands

As you round Cape Brett you pass by two must see spots.  The first is the “hole in the rock on Motukokako / Piercy Island.”  This is an iconic natural attraction.

The peak of the island stands nearly 148 meters high with the top of the archway standing nearly 16 meters high.

Experienced and a little crazy skippers will take their boats and jet skis through the center of the tunnel.

We are content to just pass by on this beautiful day.

We dropped the hook at Robert Island (Motuarohia Island) which is a stunning little island with two lagoons.  

Captain Cook anchored and landed here in 1769.  The Maori’s named this island Motuarohia which means “Island of Loveliness.”

Mother Nature gave us a gorgeous sunset with a full moon on display.  

The sky had so many beautiful colors that it took our breaths away.

Our blog posts run 6-8 weeks behind actual live events.

We visited Whangamumu for a 2nd time with Jason around the end of May 2026.

Crewless: They Come and They Go

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Many people offer to come on a passage but very few actually do.  There are so many moving parts, sliding schedules, and things to work around that it makes it difficult for “the working man” to make the trip.  We had two people interested in doing the New Caledonia (New Cal) passage.  So, how did we end up crewless?

Adam from New Zealand was our first “victim.”  I say that jokingly.  Adam lives here in New Zealand which made it appealing because he could easily be at the boat at the first weather window.  However, the weather did not cooperate and the departure date kept sliding. Eventually, Adam had to back out due to family circumstances.

Jason from Austin.  Matt worked with Jason 15 years ago.  We ran into him a few years ago and he mentioned he would be interested in doing a passage.  He had lots of charter and sailing experience – just no passage or overnight experience.

We did not think he would be able to get to NZ in time but reached out and asked him if he was interested.  He moved heaven and earth to get here.

The Waiting Continues

We had been working toward a departure date about 6 days after Jason’s arrival.  In the meantime he worked remotely from the boat.  After his work hours we took him around Whangarei.

Matt took him on a 7 mile hike.  They hiked up to the top of the mountains (by the antennae’s) and then around the park and back to town.

We also walked the Hatea Loop several times.  I made the boys partake in all the fun activities along the trail.

The Disappointment

Our proposed departure date was upon us and we had to make a decision.  Depart and get pummeled by the weather or wait for the next weather window. 

We went back and forth, had many discussions, talked with several weather routers, and finally decided not to take the risk.

It was really disappointing as that meant Jason would not be able to make the passage with us.  Why is that?  He had a flight out on the 9th of June which meant we had to leave NZ no later than the 2nd of June.  However, there were no weather windows between now and then.

So, Jason made the hard decision to stay for a week, change his flights and go home a week early. 

Despite being crewless for the passage we were determined to show our crew the best time during his stay.

Overnight Sail

We left our cozy marina dock after many sad goodbyes.  We decided to take Jason out to the Bay of Islands to show him a little more of New Zealand.

And since, Jason had never done an overnight, we decided to give him that experience too.

We left Whangarei late in the afternoon and headed 50nm to Whangamumu.

We had a beautiful sunset to send us offshore.

The moon was 3/4 full which shown brightly during most of the night.

Jason and Matt found the Southern Cross.

Jason did really well.  He got a little sick once he lost the horizon, but he managed to stay outside all night!  It may not seem like that big of a deal but it was 40F outside!  Freaking cold.  What a solider!

Our blog posts run 6 weeks behind actual live event.

Jason visited Sugar Shack toward the end of May 2026.

Stay tuned for more adventures with Jason in New Zealand.