All Episodes
Episodes
Ep 128 - We Talked to 1,000 People: Most Frequently Asked Questions about sailing with us
We’ve spoken with over 1,000 people about our sailing trips, and we’ve gathered the questions you ask most. In this episode, we’re answering the updated FAQ based on what we’ve learned from more trips, more locations,...
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Ep 127 - Courage to Begin
Trying something new always sounds simple… until it’s your turn. Those first steps—whether it’s pressing “send,” showing up, or saying yes—can feel monumental. Because they are. In this episode, we talk about the...
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Ep 126 - Best of the British Virgin Islands
Our most requested sailing destination is the British Virgin Islands. Today, we’ll share what makes it so special — from secluded snorkeling spots where the fish are the only crowds to playful granite caves — and why...
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Ep 125 - Life is Short. Legacy is Long.
Life is short—no matter how long you live—and facing that reality can actually help you live with more clarity, love, and purpose. This month, we’ve been confronted with death more than usual—funerals for friends, the...
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Ep 124 - Compass vs. Map: Navigating Life Without Perfect Plans
You know that feeling when you’re trying to follow a map, but it keeps changing and you’re not sure if you’re going the right way? That’s where values come in—they’re your compass, steady and always guiding you, while...
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Ep 123 - Anchoring: Stable vs Stuck
Are your anchors keeping you grounded… or holding you back? In this episode, we explore the difference between being anchored in stability or stuck in fear. You'll get life lessons from our own sailing adventures so...
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Ep 122 - Adventure Right Where You Are
You don’t have to cross an ocean to live with more adventure. In this episode, we share simple, creative ways to break out of your daily routine and spark wonder right where you live. From flipping a coin at every...
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Ep 121 - Planning Your Private Sailing Trip
esign your dream sailing trip: your people, your destination, your adventure. What if you could choose the destination, curate the guest list, and create a week of laughter and connection at sea? In this episode, we...
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Ep 120 - 2026 Sailing Schedule
What if 2026 could be the year you stop saying “someday” and finally give yourself the gift of adventure? In this episode, we unveil our new sailing season—spanning the British Virgin Islands, the Abacos and Exumas in...
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Ep 119 - First Trip To Croatia
Sometimes travel shows us the world is bigger, richer, and more layered than our daily lives let us remember. Croatia did that for us—through pebble beaches, ancient ruins, local cuisine, and connection. This episode...
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Ep 118 - Adventure for Everyone with Paul and Val Osborne
What does adventure really mean — and how do you make it possible for every member of your family? Paul and Valerie Osborne share how sailing 37,000+ nautical miles with their kids, including their son with Down...
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Ep 117 - Travelpreneur Christina McEvoy on Adventure and Growth
Ever wonder if you could turn your love of travel into something bigger? In this episode of What Could Go Right?, travelpreneur Christina McEvoy shares how adventure, recovery, and clarity can transform not just your...
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