Travel Journal: Sailing the Greek Islands with Bearing True South


Why Greece?
Stun­ning coast­lines, sun-bleached ancient ruins, incred­i­ble food, and warm hos­pi­tal­i­ty drew me to explore the Greek Islands. Pri­or to the trip, I had nev­er spent an after­noon on a sailboat–let alone an entire week–but that was­n’t about to stop me from sail­ing to five dif­fer­ent islands in the Cyclades archipelago.

Pack­ing Essentials
The tem­per­a­ture fluc­tu­at­ed quite a bit while sail­ing, so it helped to dress in lay­ers. A bat­tery pack also came in handy to charge cam­era bat­ter­ies and oth­er elec­tron­ics at times when we were not docked at a port.

Tell us about Bear­ing True South
From the moment I arrived in Athens, Bear­ing True South greet­ed me with open arms. This trip felt less like a tour and more like a sail­ing trip with friends. Our fear­less cap­tain, Andreas, and guide Stravos, showed us their favorite places on the islands and served up an authen­tic, once-in-a-life­time experience.

Some High­lights?
I quick­ly set­tled into the dai­ly rou­tine of fred­do cap­puc­ci­nos and savory pas­tries dur­ing our morn­ing sail. After­noons were spent swim­ming in the translu­cent, turquoise waters of the Aegean and explor­ing new towns and islands. Get­ting off the tourist cir­cuit, dis­cov­er­ing the less­er-known islands in the area, and con­nect­ing with the local peo­ple made this trip real­ly special.

Where do you want to go next?
I still have my sights set on sum­mit­ing Kil­i­man­jaro one day, but I might opt for hik­ing the John Muir trail this sum­mer and snow­board­ing in Japan next winter.


For more infor­ma­tion on book­ing a sail­ing trip with Bear­ing True South, check out our Clymb Adven­tures page here.