Sailor Spotlight: Captain Kayleen VanderRee

In the heart of British Columbia, Captain Kayleen VanderRee embodies the very essence of adventure. Her story has been an inspiration to sailors like myself — it’s a testament to the allure of the ocean and encompasses the feeling of enchantment the sea brings.

In an exclusive interview with Dockwa, she generously shares insight into her captivating voyages and vibrant life on the water.

A lifelong love affair with the ocean 

Growing up on the ocean, Kayleen’s bond with the outdoors was woven into the fabric of her life from a young age. 

"Sailing and coastal cruising is something we’ve done as a family since I was little," she explains. "My grandparents raised my dad and his siblings cruising the British Columbia coast and American San Juan Islands. My Grandma actually wrote a cruising guidebook, one of the first for the British Columbia coast. It's safe to say that it's in my blood."

Among her most cherished memories are adventures on remote coves and islands, where her family would spend hours collecting eagle feathers and hunting for crabs. 

She reminisces: "We’ve had orcas swim under the boat, making eye contact with us as we peer over the edge. We’ve had hundreds of dolphins join us at our bow. Humpback whales breached all around us. I constantly refer to these moments as some of my favorites." 

Talk about core memories! Kayleen’s childhood was just the beginning of a life close to the sea.

The pull of the sea

Anyone who has experienced the true enchantment of sailing knows the irresistible pull toward the horizon. It’s an inexplicable — somewhat unexplainable — yearning to explore and challenge the open ocean. 

Kayleen says, "I find that the water brings a mixture of calmness and adventure. I feel very grounded around the ocean, but it also gives me a lot of challenges, forcing me to up my skills as a mariner. I appreciate that balance." 

It wasn’t long before Kayleen was leaving the remote islands of her childhood behind, and setting off on her own adventures in the deep blue.

Time to set sail: From snowy peaks to southern shores

In recent years, Kayleen has captained various boats, expanding her horizons along the way. Her love for the sea and the mountains inspired her to captain sail-to-ski expeditions in Canada. 

Drawing inspiration from similar expeditions in Norway — where crews voyage to snow-covered mountains, drop anchor, and then hit the remote slopes — Kayleen successfully assembled an all-female crew to combine the thrill of snowboarding with the serenity of sailing, all against the breathtaking backdrop of Canadian fjords. 

During this time sailing in Canada, Kayleen was always working towards her big dream: Cruising to Mexico. After six years of planning, sacrificing, and learning, Kayleen left the snowy mountains behind, and sailed from the Pacific Northwest to Mexico aboard her Tartan 42, Footloose. Kayleen shares the highs and lows of her sail south: 

“The journey was everything and nothing like I expected. It gave us the adventure I was hoping for, some moments of terror and wanting to quit, but also moments of pure bliss.” After a humbling offshore jump from Victoria to San Francisco, Kayleen and her partner, Tyler, experienced relatively smooth sailing down the coast. 

“Hopping down the California and Baja coast was amazing!” Kayleen said. “ We spearfished along the Channel Islands and surfed down the Baja. I dove, solo sailed and just enjoyed life in Mexico. It was incredible.” A dream-come-true for Kayleen.

On her return back to Canada this spring, Kayleen and her father set off on the Clipper Route, an infamous path known by seasoned sailors that arches offshore towards Hawaii before veering back to Canada. This nonstop 4,300 nautical mile journey took Footloose 44 days to complete. Undertaking a voyage like this demands not just a profound love for the sea but also an unwavering dedication to the sport. 

Kayleen reflects upon her successful voyage, “I think that sailing/cruising full-time is often very romanticized and not often acted on. It is easy to come up with excuses, so I’m most proud of executing this dream. It takes a lot of patience and determination.”

Kayleen and I move on to discuss the culture of the boating world, the tough parts, and why we just can't quit.

Community and camaraderie

Something that I personally have always valued as a boater, is the beauty of the boating community. It’s where I have gained inspiration, insight, confidence, and friendships. I ask Kayleen about her interactions with the boating community, and she emphasizes the impact camaraderie among fellow sailors has had on her own journeys. 

"The cruising community is what makes cruising so special!" she declares. "We’ve met some of the most amazing people, like Ben and Alie (Breaking Waves on Youtube) who have become lifelong friends.” Kayleen continues to share a story about sailors Greg and Lynn, who helped her fix her water maker. In exchange, Kayleen replaced their zincs. Despite age gaps and diverse backgrounds, the commonality of cruising brings people together. It’s truly something special.

Breaking boundaries: Being a woman captain

Navigating a traditionally male-dominated industry isn't all smooth sailing, but Kayleen is one of the sailors who is shattering stereotypes. 

"Being a woman captain in a male dominated world is a bit of a messy experience, and it is full of self-doubt and sexist comments. Equally there are encouraging friends, helpful strangers and moments where I know “I can do this! It’s a bit of a rollercoaster, but ultimately it’s changed from many years ago when most sailors were the salty bearded type and the women were in the galley." 

My guess would be that most women on the water can relate to this in some way. When Kayleen bought her boat it came with a book which was titled “A Woman's Guide to Sailing: Recipes and Cleaning Tips”. She has kept it for years to remind herself that even when it’s hard, she is pushing her own limits and helping push the limits for women in the cruising world. People like Kayleen are paving the way for the future, and serving as a tremendous source of inspiration, for me and for many other young women who share a passion for sailing. 

Embracing the great outdoors

Kayleen's adventurous spirit knows no bounds, and her story beautifully aligns with Dockwa’s belief that spending time outdoors, connected to nature and each other, enriches our lives. 

She shares, "Sailing and spending time on the water can bring a sense of understanding and connection to nature in a whole new way. Sailing has taken me to the most amazing places, whether it’s accessing remote mountains or scuba diving remote islands, it allows me to connect to the world in a slow, thoughtful way."

Kayleen VanderRee's voyages are a testament to the power of chasing dreams, breaking boundaries, and finding solace and adventure on the open waters. Her narrative reminds us that the cruising community is more than just boats; it's a shared passion for exploration and a deep connection to the natural world, beckoning all who dare to set sail to commit to the dream. 

To follow along with Kayleen’s adventures, be sure to check out her Instagram account, @FromSnowToSail!