FareHarbor celebrates World Pride Month: A conversation with Sundog Sailing

Listen to the episode: Celebrating World Pride Month: A conversation with Sundog Sailing

Host: Rebekah Costley
Guests: Captain Jen and Captain Janet, Co-Owners of Sundog Sailing

Episode overview

In this joyful and powerful Pride Month bonus episode of Growth Powered by FareHarbor, host Rebekah Costley talks with Captain Jen and Captain Janet — life partners, co-owners, and literal co-captains of Sundog Sailing in Charleston, South Carolina. 

Together, they share how they’ve built a women-owned, queer-operated sailing company that is as bold and welcoming as they are. From unexpected career pivots to breaking barriers in yacht clubs, they reflect on the journey of building a business rooted in visibility, pride, and strength — all while keeping joy at the center.

This conversation is a celebration of queer entrepreneurship, community on the water, and the kind of joy that ripples outward.

Key takeaways

Visibility creates a ripple effect

Captain Jen and Captain Janet emphasize how their presence as queer, married, women captains changes the dynamic the moment someone steps on their boat. Guests double-take — in awe, not disbelief — when they see two women communicating with bridge tenders, navigating a 50-foot sailboat, and creating a relaxed, inclusive atmosphere. 

For some, it’s the first time they’ve seen openly LGBTQIA+ leaders in tourism. For others, it’s the first time they’ve truly felt welcomed. Their visibility helps normalize queerness in a space that’s often closed off — and that alone makes guests feel safer to be themselves.

Hospitality is leadership, not just service

There’s something deeply transformative about the Sundog experience. As Captain Janet describes, guests often board the boat feeling anxious or guarded, but within minutes, they’re laughing, loosening up, and letting their walls fall. 

The sailing trip becomes more than a tour — it becomes a shared space for connection and healing. This level of comfort isn’t accidental. It’s a reflection of how Captain Jen and Captain Janet lead: through calm confidence, attention to emotion, and a commitment to making every person feel seen.

Their business is unapologetically personal

Sundog Sailing wasn’t designed to look like other tour companies — it was created to reflect who Captain Jen and Captain Janet are. Their values show up in everything from the crew they hire to the energy they bring to each trip. 

That authenticity makes a difference. 

It’s why parents feel comfortable enough to ask for advice about supporting their queer kids. It’s why women sailors are reaching out, saying “I didn’t know this was possible — how can I join you?” Their personal story is the brand, and it’s inspiring a new wave of confidence and possibility.

Sailing became a platform for queer strength and joy

For Captain Jen and Captain Janet, the water is more than a workplace — it’s a spiritual space. Sailing gives them strength, freedom, and perspective. They talk about sailing through storms, leading charters with banana superstitions and laughter, and creating an “island” where they and their guests can be fully themselves. 

Whether they’re welcoming a nervous solo traveler or a queer couple looking for a safe space, they see each sail as a chance to celebrate pride — not just in identity, but in being alive and together.

Representation in tourism still matters — deeply

Despite progress, there are still yacht clubs in Charleston that don’t allow women. There are businesses that won’t hire female captains. Captain Jen and Captain Janet aren’t just sailing through those barriers — they’re shattering them. 

They’re hiring queer crew, mentoring young women, and using their business as a vehicle to create access. They make one thing clear: when you choose to support queer-owned businesses, you’re not just booking a great experience — you’re helping open doors that were previously closed.

Links mentioned in the episode

Captain Jen and Captain Janet encourage donations to the following organizations:

• PFLAG – supporting LGBTQIA+ people and their families
• The Trevor Project – suicide prevention and crisis support for LGBTQIA+ youth
• We Are Team Jake – mental health advocacy and anti-suicide support in Charleston

You can also learn more about their business at Sundog Sailing.

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