I wish I could remember where we got the idea to go on a sailing adventure in the Greek islands. What I do know, from saved Hangouts and emails, is that I started looking seriously at a sailing trip with Intrepid in August of 2015. My original plan was to be on a boat in the Mediterranean in August 2016 when I turned 30. I tossed around the idea with friends, trying to get a contingent to go with Josh and me, but the timing just didn’t work for anyone else.

Then, in October 2016, we started getting serious about booking for early Summer 2017. Our best friends (Hannah since middle school and Andrew since college) were on board, and we floated the idea with everyone we knew who liked to travel adventurously. Two local (DC) friends, Eli and Parthena, were interested and had the time off from work, and just like that our group was set.

In November 2016 we put our deposits down for a late May/early June sailing trip from Santorini to Mykonos with Intrepid Travel and started the obsessive planning in earnest. You might think I’m exaggerating about “excessive” planning, but those who know me know that is 100% how I operate. See below for a snippet of our itinerary.

Now here we are almost two years later, and I can honestly say that this trip changed our lives. It wasn’t just the best vacation I’ve ever been on–it started an obsession with sailing that has led to more sailing vacations, sailing classes to get my certification, and a new long-term plan for Josh and I to live on a boat full time.

We put together a lot of the video footage and photos we took and posted two videos (so far) to our brand new YouTube channel: I’d Rather Be Sailing. Check out the Sailing Greece playlist here and be sure to like and subscribe!