Sailing WhitSunday With Captain And Tennille

This is a mistake … a terrible terrible mistake.

I’d just checked into my hostel in Airlie Beach and was shocked to find a bar blaring loud music IN the hostel. During my travels I’ve been like a pendulum swinging between cheap shitty hostels to way-over-my-budget but dammit I need to pamper myself accommodations. Tonight I managed to find the shittiest hostel in Airlie Beach filled with drunk young backpackers.

Since I was only staying the night in Airlie Beach, I figured whats the harm in booking the cheapest room I could find on

Turns out the answer is:  A LOT.

I go upstairs and open the door to the 10 person dorm room I’d booked. Walking in I’m immediately reminded of what it’s like to share space with teenagers.  It  …  was  …  F@&KING disgusting.

There was dirty laundry and other personal items strewn across beds and the floor. The bunk beds that lined the room looked cheap, the mattresses were flimsy and I refuse to discuss the bathroom situation. It’s been erased from my memory.

I was so disgusted I slept on the covers with my regular clothes on. That night I got no sleep. I was constantly woken by drunk roommates stumbling into the room. It was the longest 12 hours of my life.  The next morning I got up early, self checked out and ran out of the worst place I’ve ever stayed at.

I made my way to the marina eager to put the hostel experience behind me and set sail on the “Waltzing Matilda”, to explore the wondrous WhitSunday Islands. Arriving at the docks, the weather suddenly turned sour. Grey skies rolled in and it started to rain.


Not a promising start to the day. Now I’m worried the trip will be ruined by bad weather. All I can do is cross my fingers and hope this is only a morning shower.

Walking up to the boat, first impressions were positive. Matilda (a 60 foot fiberglass ketch vessel) is a smaller boat, fitting 14 guests and 2 crew members. This was going to be an intimate affair.

Waltzing Matilda
Waltzing Matilda is a 60 foot fiberglass ketch

I happily got on board and looked around at my fellow passengers. As I was introducing myself to person next to me, our conversation was cut short. We overheard a discussion between the Captain and two couples who just boarded the boat. Turns out there was a mix up in their reservations. Both had booked the master room and the double booking was just discovered.

Not good.

Normally I don’t like to eavesdrop on other peoples conversation, but this is a small boat and nothing is private. Plus it’s free entertainment, one of the couples was gonna have to downgrade their accommodations. If I was in that situation I would’ve gone bat shit crazy and created an epic scene. In this case, no shouting and histrionics went down. Both couples were reserved and the losing couple accepted the change in accommodations and a refund for the value of the downgrade.

The captain was genuinely apologetic and tried his best to smooth things over. I was impressed with how he handled the situation. It was a problem not of his making, but he did his best to make things right.

Even though the trip was off to a rocky start, I still had a positive feeling about it. After setting sail, the crew gathers everyone for the introductions. The captain (Damien) is a tall wiry Aussie. As he shared the boat safety instruction he displayed a sharp and witty personality, easily mixing comic quips with the boat’s rules. The second mate is a young lady called Noel. She too displayed an affable and quirky sense of humor. Finally there was Tennille, an unexpected guest from the sales team joining the cruise.

Thankfully, as we made our way to our first destination (Tongue Bay) the weather started to improve. The rain and the choppy waves eased and by the time we’d anchored the ship the dark skies had pretty much passed. As we walked into Tongue Bay I could feel the excitement building inside of me. This is the entry point into Whitehaven Beach. The most famous beach in Australia and the Pacific region. After a small hike through a wooded area, the path opened up to reveal a spectacular beach.

Seeing it in person was epic. The white silica sand glistened in the sunlight and the sea shimmered with a beautiful green blue color. From the “Hill Inlet Lookout” we got the full panoramic view of the beach. I won’t bother describing it. Below is a picture.

Amazing WhiteHaven Beach
Amazing WhiteHaven Beach

As we left Whithaven, I laid out on the deck, happily sunbathing under the warm sun. In the background I could hear Damien sharing stories with group and making everyone laugh. Aussies have a quirky sense of humor. It’s a good natured humor that stretches and bends the truth, to see how far they can take things before getting found out.

It’s the humor that invented the “Drop Bear”, a dangerous meat eating Koala that drops from trees to attack its victims. These stories work on tourists because we imagine Australia having the craziest and most dangerous animals in the world.

We believe it because …. well  ….  it’s Australia!  Everything wants to kill you.

Which is why we dressed up as ninjas before jumping into the sea to snorkel. It’s stinger season and, as a precaution against jellyfish, we had to wear these stylish suits. The main fear was of the Irukandji and Box jellyfish whose stings could kill. After that wonderful warning, we were invited to jump into the waters 🙂

The WhitSundays is part of the Great Barrier Reef, so there’s plenty of reefs with colorful fish to see. Unfortunately, due to the poor morning weather the visibility was not that great. But it was good enough to enjoy.

Stinger Season means dressing up as ninjas to avoid jellyfish stings
Stinger Season means dressing up as ninjas to avoid jellyfish stings

As we cruised to our next destination, Butterfly Bay, the sun started to set in the horizon. Nothing in this world is more beautiful than sailing on a boat and watching a sunset against an island backdrop. It moved us into silence. I enjoyed the moment, taking in the stunning views of the orange sun setting behind the island’s hilltops. In the background, Tennille (the bubbly sales agent) had an incredible playlist playing that perfectly fit the mood.

By the time we reached Butterfly Bay, the sun had set and the night sky was dotted with a sea of stars. I’d never seen a night sky with so many stars that clear in my life. A couple of the passengers had apps with them that helped identify what each star was. I knew nothing about Astronomy, but that night I was part of a masterclass on constellations and happily soaked it all in.

The evening was capped off with seeing my first moon rise. Normally when day gives way to night, the moon just appears in the sky. That night we watched as the moon slowly came up from the horizon, and as it came up, the light from the moon dimmed the stars. It was magical.

Map showing route and stops on our trip
Map showing route and stops on our trip

The second day we continued our tour of the islands and did some more snorkeling. It was another incredible day that passed way too quickly. Before I knew it our time in the WhitSundays was over and we were docked at Airlie Beach. Standing at the pier looking at the boat for the last time, it felt like a dream.  Why is it when you’re enjoying something it has to end so quickly?

If you ever visit the WhitSunday you must explore it by sail. It’s guaranteed to be a once in a lifetime experience.

Below is a video of my trip on the Waltzing Matlida. Enjoy.


Also, I enjoyed Tennille’s playlist so much, I recreated it on spotify (check it out below).

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