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.