EER033: Sailing, Podcasting, Large Family Travel Planning

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Erik Hemingway, sailing, podcasting and family travel planning #EER033

If you’re interested in long-term large family travel planning and don’t know Erik Hemingway yet, then it is my honor to introduce him to you. As the creator of the Family Adventure Podcast, Erik has interviewed dozens and dozens of family travelers (86 episodes available on iTunes at the time of writing), and I credit his work as a huge influence on me and my desire to start a podcast of my own.

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Sailing, Podcasting, Large Family Travel Planning

Erik has a large family with six (SIX!) children, like the Denning Family, but that didn’t deter him from buying a boat and sailing the world for years — learning to sail as they went. Now based on the east coast of the US, Erik and his podcast inspire thousands of families to take the leap. Listen in as we discuss money, homeschooling, family travel planning and much, much more.


  • Names: Erik and Rachel Hemingway and their six children
  • Hold passports from: USA
  • Type of travel: 3 1/2 years sailing and overland travel
  • A few places they’ve been: Greece, Costa Rica, Senegal, Turkey and Israel

Find Them On: The Family Adventure Podcast | iTunes | Facebook | Twitter |  Google+ |  Pinterest


  • A job in Costa Rica led to a boat in Greece where they learned to sail with their (then) 5 kids. The plan was to sail for a year. Three and a half years and 26 countries later, they returned to the United States.


  • Communication
  • Learning to forgive — and ask for forgiveness
  • How to get teens involved in travel (details in the podcast)


  • Spent USD $1,300-1,400 a month on average. That includes insurance, boat repairs, fuel and food for a family of 8 (doesn’t include the boat purchase itself)
  • Sold some property for their main chunk of savings
  • Owns a mini-storage business that he ran remotely
  • Used a BBVA Compass credit card

Erik Hemingway, sailing, podcasting, large family travel planning #EER033EPIC ESSENTIALS


  • The Hemingways have homeschooled since the beginning, and then while traveling. They’re now in a large homeschooling community in Wilmington, North Carolina, with a similar outlook to unschoolers.


Erik Hemingway, sailing, podcasting, large family travel planning #EER033EPIC ADVICE

  • Foster a teamwork attitude
  • “See the Need” (details in the podcast)
  • Make a pros & cons list


  • Italy
  • Turkey
  • Malta
  • The Caribbean
  • USA National Parks and Highway 1 on the west coast

Sailing, Podcasting, Large family travel planning #EER033: Interview with Erik Hemingway

Disclosure: This post contains affiliate links. This means, at no extra cost to you,  we might receive a small commission if you make a purchase or book using those links. My opinions are my own and I only recommend places/services that I believe will genuinely help your travel.