Windstar: 180 Degrees from Ordinary

For those who know me well, it’s no secret that my approach to photography is deeply personal—an autobiographical journey where each image, in addition to creating art, serves to expand and enrich my life’s story. Click.

More so, over the past decade, with the iPhone camera being at stage center, I see myself as an artist and a poet, rather than just a technician and mechanic. My goal has never changed: to live a photographic life, crafting art through light, color, and design.
Cruise photography holds a special place in my heart. Back in the ’90s, Shannon and I sailed around the world with Renaissance Cruises, a now-defunct line of small, boutique-style vessels. These ships offered an intimate atmosphere, with a higher crew-to-passenger ratio that ensured attentive service and a touch of luxury. It was an experience that shaped me, both as a photographer and as a person.

It’s funny how life travels in circles.

Fast forward to this past summer, when I took seven different cruises on two, similarly small, Windstar yachts—the Windstar Legend and Windstar Pride. Windstar operates a fleet of small ships that offer a truly unique experience. Their motto, “180 degrees from ordinary,” couldn’t be more fitting.

On the Wind Class ships, the romance and adventure of sailing are palpable, while the Star Plus Class ships focus on luxury and comfort, with all-suite accommodations. My time aboard these vessels was exactly that—180 degrees from ordinary.

There’s something profoundly romantic and intimate about being on the sea. In my humble opinion, small-yacht cruising is the ultimate way to see the world and the destinations it unfolds.

What made these recent Windstar trips even more special was the opportunity to share my passion with others. My job on each itinerary was to teach guests how to elevate their travel and cruise photography using their iPhones. The response? Pure enthusiasm and delight at every turn. Seriously.

These Windstar vessels are sleek, sexy, and just plain fun. I’m currently in talks with Windstar about organizing a themed cruise in 2025 focused on iPhone/mobile photography. Imagine that—an entire journey dedicated to capturing the world in the most creative ways possible.

How fun would that be? Wanna join me?

This mini gallery features a handful of my favorite photos from both the Windstar Legend and Windstar Pride.

Click.

Jack

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Jack Hollingsworth
Photographer