What Could Go Right?

If you’ve ever felt like sailing wasn’t for you because of the drinking culture—or if you’re simply curious about how alcohol-free adventures can go deeper—this episode is for you. You won't get judged for enjoying a glass of wine at sunset. You will find out what makes Navigator Sailing Trips different—how we built “dry” sailing adventures focused on connection, learning, and presence.

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Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

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Steve and Donna run a high-volume, precision manufacturing company. If you have ever been grateful for airbags in your car, some of their 300+ employees make those parts for your car. Do you want to know how they stay married, stay in love, stay in business and build a legacy? (That's quite an adventure!)  From factory floors to family dinners, Steve and Donna share applicable wisdom on teamwork, emotional intelligence, and the underrated life lessons found in everyday experiences. If you’ve ever wondered how to lead with purpose at home and at work, this conversation will leave you inspired to focus on what could go right.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

🎉 It’s our 100th episode — and we’re celebrating with honesty. If you're navigating a season of change—where joy and sadness sit side by side—this episode is for you. Erik and Emily Orton gently guide you through the tender terrain of transition, offering companionship and insight as you face the bittersweet beauty of letting go. Whether you're saying goodbye to a chapter, a role, or a rhythm that once defined you, you're not alone. In this heartfelt conversation, you're invited to be the hero of your own unfolding story, while Erik and Emily walk alongside you as thoughtful, hopeful guides—reminding you that every ending carries the quiet promise of something new.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

If there’s one thing sailing has taught us, it’s this: the wind doesn’t always do what you expect. And honestly? That’s where the good stuff lives. In this episode, Erik and I talk about the role of flexibility—not just on the water, but in life. We share stories of plans that went sideways and how those moments became some of our most meaningful memories. Whether you’re dreaming about a sailing trip or just trying to navigate your everyday, we hope this conversation leaves you feeling encouraged, open to discovery, and ready to ask, what could go right?

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

If Italy’s been calling you, this might be your last chance to answer. In this personal episode, Erik and Emily share the soul behind their upcoming sailing trip from Naples to Sorrento, Salerno, and Capri –woven with real stories of lost keys, missed flights, buttery sunsets, barefoot afternoons, and the compelling magic of the Blue Grotto. It's not just a vacation–it's a reset. It’s not just a vacation—it’s a reset. And, full transparency: this will likely be our last commercial sailing trip to Italy, as we focus on new adventures ahead. If you’ve been curious… this is the one to listen to.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

Real confidence—the kind that sticks—isn’t handed out like a participation ribbon. It’s earned through doing hard things. Stretching past what’s comfortable, and realizing, Whoa. I just did that. What else can I do? For example, there's something you take for granted now that you couldn't even do in the past. In this episode Erik and Emily discuss the relationships between competence, community, and growing confidence. Enjoy!

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Do you want an experience where you become the kind of person who trusts yourself more—because you did something that proved you could? Come test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

Ever feel like you need a reset button for your life? As the seasons shift, so can we. In this episode, Erik and Emily Orton dive into the magic of a spring reset—a chance to clear out mental clutter, shift your perspective, and realign with what truly matters. Whether you're feeling stuck, craving clarity, or just ready for a fresh start, this episode is your invitation to reset and set sail toward something amazing.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook

Do you know when sailboat racing was invented? When the second boat was built. Today we'll share stories about getting there first, getting there last, and what really matters.

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook 

People can change. This is one of the great superpowers of life. Are you changing from good to better? Shifting to something different? Or just parting your hair on the other side? Erik went from a Broadway guy, managing tours of Les Misérables, to a boat guy, teaching people to sail all over the world. He recently revisited his theatrical past taking our son, Eli,  to see the Broadway tour of Les Misérables. In this episode, explore the cathartic, redemptive, beautiful message of change in Les Misérables and pour it on your own life. However you are changing, it's healthy to stay open, flexible and pliable at every age.

What do you want to keep the same?

What do you want to change?  

⭐⭐⭐⭐⭐ Rate. Review. Subscribe.  

Resources:

Try Sailing for a Week: 

Perfect for rookies who want to test drive the live-aboard dream. Yes, we let you drive the boat. Relax, explore, and get as much/little sailing experience as you want with stunning 360-views. Sail with us.

Erik + Emily Memoirs:

Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat 

Knock: The Spiritual Journey of a Door-to-Door Salesman

Connect with Erik + Emily:

Email Subscribe to Encouragement

Youtube Like, Comment, Subscribe

Instagram 

Facebook