A monsoon rainstorm in the middle of the South Pacific Ocean was not Karyn Blasi Hellar’s idea of a perfect getaway. It was there on a Windstar ship that Hellar led her first artist’s retreat with a group of 10 people focused on yoga, discussion and wellness. But when the weather pushed the activities indoors, a chance encounter led to an introduction with a Windstar executive on board, and the rest, as they say, is history.
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In the wake of the pandemic, Hellar, who had spent more than a decade in the women’s cancer support field, embraced wellness and creativity. She picked up “The Artist’s Way,” a book she credits with changing her life, and spent six months writing and exploring her passions. “I love ships. I love art. I love wellness. I love bringing people together,” she said. “All of these things just started happening.”
She took her first Windstar cruise in French Polynesia and was so impressed, she returned for a second cruise with her retreat guests. That’s when serendipity stepped in. Despite the monsoon, opportunities grew from there.
Meanwhile, Windstar was planning its Themed Voyages Collection of cruises with a variety of niche options from art to wellness to maritime history. “Masterpieces at Sea began with our partnership with Fountainhead, a Miami‑based organization that champions contemporary artists,” said Lieven Van Dael, director of Guest Experience at Windstar Cruises. “Fountainhead curates artists who create original murals onboard our ships. As each new mural was added, we expanded the concept into a fully art‑themed cruise by layering in additional programming.”
After a series of phone meetings, Hellar was invited to Miami to pitch her ideas to the team. That led to her inclusion in the collaboration as Windstar’s Global Host of Art Cruises.
“What I love about these new themed voyages is how they turn the whole ship into part of the adventure,” said Janet Bava, chief commercial officer of Windstar Cruises. “One cruise you’re learning to tie the perfect bowline or painting alongside a world-class artist, the next you’re dancing under the stars at a pirate party or deck BBQ.”
Masterpieces at Sea
The initial Masterpieces at Sea program consists of four sailings over the course of one year. Past sailings include the first cruise out of Málaga, which featured a mural painted live on board by a Fountainhead artist, sip-and-paint classes and art-themed lectures. The second centered around Mediterranean-themed daily painting classes, coffee chats and excursions, and an artist on board who completed a painting each day from start to finish.
Upcoming cruises include a return to the Mediterranean in August 2026 with a focus on mosaics, and the fourth cruise will explore the Leeward Islands out of Puerto Rico this fall and switch gears to drawing with Caribbean inspiration.
To connect the art classes with the ports of call, Windstar sources artists for each cruise and creates an experience tailored to each medium and location. During a port call in Nice, France, Windstar invited a local artist and a musical group to showcase their talents on board for an evening of local culture. On another day, guests were invited onshore for a sketching class with art expert Bruce Anderson, who was also selected by Van Dael to teach painting classes on the Rome to Barcelona sailing. “We look for artists who are not only talented, but also natural educators who enjoy engaging with guests,” Van Dael said. “Bruce is a great example — I attended his class in Barcelona and immediately saw how well his approach aligned with what we wanted to offer onboard.”
Small ship magic
Small ship sailing is in a league of its own. On the Star Legend, not only do guests become acquainted with the crew, but they also make friends with each other. Whether taking a few different art classes during the week or spending evenings in the lounge, the atmosphere is casual and friendly. Friendships are formed not just by proximity but by shared interests and curiosity.
And while Windstar’s vessels are smaller than traditional cruise ships, there is plenty of room to spread out and relax. The art classes are one activity, but there are also many dining options, the pool deck and the spa. The staterooms are generously sized with a queen-sized bed and a full sitting area, making it difficult to leave. A greeting by name from Hotel General Manager Wilhelm Steinbrunner will bring a smile to your face, and by the end of the week, dancing with strangers becomes dancing with friends.
As themed cruises continue to rise in popularity, cruise lines of all sizes are experimenting with different offerings. Travelers seeking more than just a destination can find an itinerary for nearly any interest. For Hellar, inspiration was just a monsoon away.
Andrea Updyke is a food and travel writer at Just is a Four Letter Word, where she shares easy recipes and family travel tips. When she isn’t traveling, Andrea loves spending time with her husband and two teenage sons in Raleigh, N.C.