Charter sailing represents one of travel’s most liberating experiences, offering adventurers the opportunity to explore coastal destinations with unparalleled freedom and authenticity. In our latest podcast episode of “Travels with Jim and Rita,” we were fortunate to speak with June Russell-Chamberlain, a seasoned travel writer and photographer who has discovered the joys of exploring the world’s most beautiful coastlines through chartered sailboats.
June’s journey to becoming a sailing enthusiast wasn’t predetermined by her upbringing. Growing up in Oregon with a family that loved road trips and explorations of small towns and wilderness areas, she first developed a passion for discovery and adventure on land rather than sea. Her early aquatic experiences were limited to paddling around in a rubber raft with her sister—a far cry from the sailing adventures that would later define her travel experiences. It wasn’t until her husband Mike suddenly announced his desire to learn sailing that June found herself reluctantly introduced to the world of sailing through what she described as “the fastest, tippiest, craziest little boat” her husband could find—hardly an ideal vessel for a beginner.
Despite this challenging introduction, June gradually developed her sailing skills and appreciation for larger, more stable vessels. The transition from local lake sailing to international charter adventures came after about a decade of experience, with June and Mike obtaining the necessary certifications through organizations like American Sailing or US Sailing. These credentials allowed them to charter boats around the world, essentially renting a floating home that gives them access to places most tourists never see.
What makes charter sailing so appealing to June is the remarkable freedom it provides. Unlike conventional travel with fixed itineraries and hotel bookings, sailing allows travelers to discover a place, fall in love with it, and simply decide to stay longer. There’s a flexibility that’s hard to match with other forms of travel. If a particular cove, island, or fishing village captures your heart, you can linger as long as you wish. This adaptability extends to the style of travel as well—you might anchor in a secluded bay one night, swimming directly from your boat in crystal-clear waters, then dock at a charming village the next day to enjoy local bakeries, restaurants, and cultural experiences.
Perhaps the most compelling aspect of charter sailing that June shared is the authentic cultural immersion it facilitates. When you sail into a small Mediterranean fishing village that isn’t on the main tourist routes, you experience a place that hasn’t been fundamentally altered by mass tourism. You dine at local tavernas alongside residents rather than other tourists, engage in genuine conversations with locals who are as curious about you as you are about them, and witness everyday life unfolding naturally. These encounters provide a richer, more nuanced understanding of a place and its people than conventional tourism typically allows.
Of course, charter sailing isn’t without its challenges and considerations. As June candidly shared, equipment failures can occur (like the time their anchor windlass stopped working as darkness approached), seasickness can be an issue (June recommends patches placed behind the ear), and living in close quarters with limited fresh water requires adjustment and cooperation among crew members. Weather considerations are also crucial, particularly wind conditions that affect sailing capacity and comfort.
For those intrigued by the possibility of charter sailing but lacking experience, June assured us that there are plenty of entry points. Charter companies worldwide offer vessels with captains who can both navigate and teach beginners the fundamentals of sailing. Alternatively, sailing schools provide week-long living-aboard courses that combine instruction with the experience of boat life, helping newcomers determine if this style of travel suits them before making a larger commitment.
As we concluded our conversation with June, her enthusiasm for charter sailing as a vehicle for authentic travel experiences was unmistakable. “It’s an adventure,” she explained, highlighting the unpredictable nature of sailing that keeps the journey exciting. But most importantly, sailing allows travelers to experience destinations with greater depth—to see “more layers and more history and culture” than conventional tourism permits. For travelers seeking freedom, authenticity, and meaningful connection with the places they visit, charter sailing offers a compelling alternative to more mainstream travel options.
Instagram @junerussellchamberlin
Website http://www.junerussellchamberlin.com
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