Getaway : Sail from Athens to Santorini


A few years ago, ’round this time of year, I was planning the TRIP OF A LIFETIME. Surprises ensued but alas, utopia found us after all. HERE’S MY RECOLLECTION OF THIS AMAZING ADVENTURE FOR THOSE WHO DARE TO CATAMARAN FROM ATHENS TO SANTORINI…

Did that prep you well enough for a crazy story? Cause this trip’s about to get real…
Skip to the bottom to cut straight to my recommendations for Santorini.
Greece was a country I’d dreamed of since covering Greek & Roman mythology for my Art History dissertation in college. I naturally fell in love with a culture that centered all passion around nature, art, luxury, & wine [go figure]. While in the midst of a frigid Colorado winter, I caught up with a group of friends in London. They wanted to sail the Mediterranean to celebrate big birthdays within the crew, mine included! So it was on. We booked a 42 foot catamaran with the namesake “Second Wind,” & figured we’d sleep on the boat, letting everything else fall into place. That’s when the universe threw us a few flip sides of paradise. Things didn’t just fall into place, they barreled in like a bull …


To start the trip off on the right note, our plane was held over for 6 hours in Amsterdam before we could make it to Athens. Amsterdam was SUCH a cool town. Full of deeply rich culture, laid back people, and lots of street cart vendors with the best french fries I’ve ever had. Getting around town was mostly by boat or bike, how fun is that? The architecture was stunning, – even the 1800’s pubs were a work of architectural artistry! We only had 6 hours, but we made the most of it. While in Amsterdam, we (what I like to call) “wine-hopped” a few bars, grabbed a bite to eat, took a canal tour, &…caught food poisoning. It didn’t hit me until we arrived at the airport, but it was a hilarious ailment to have while racing {literally, full-sprint} through a foreign terminal to catch a flight to Athens. We made it just in time – and I’m not joking there either, they were calling our names over the intercom to threaten us with the final chance to board as we were rounding the corner to the homestretch. But we made it! We arrived to Athens late, the cab dropped us off too early, & by the time we finally reached the boat we’d walked about a mile and a half with our luggage. It was a comedy of errors! Athens – freshly compared to Amsterdam – was insane. It felt a little like Los Angeles traffic, mixed with New York’s road rage. When we finally settled in – I became terribly, terribly sick. All through the night, & of course into the morning, when we set sail for Kea. I was so happy to be on the water, but couldn’t hold down my Dromamine, so sea sickness set in on top of food poisoning. IT WAS THE WORST. Regardless, I was so ecstatic to be in Greece! I just kept right on with all the smiling [this is where all the reading about enlightenment really came in handy]. I couldn’t get enough of the rugged shores, the temps, & the smell of the ocean air. We soon arrived at our first island, perfectly on time. The wonderful thing about Kea, was that it was an easy place to get to know. My friends were sweet enough to meet the locals & found a nice couple who agreed to let me sleep in their rental apartment for $30 a night. It was my first experience on a Greek island. I was so thankful to feel land, my feet on land, a bed on land – so grateful for these hospitable Greeks. I slept, & slept, & slept, until it was time to set sail for Santorini in the morning.
1. Watch what you eat in Amsterdam.
2. Arrive super-early to the airport when flying in a foreign country.
3. Genuinely befriend the locals.
4. Take Dromamine hours before open seas.
5. Plan on a backup hospital & hotel plan on every island in case someone falls ill.


As we were preparing for our departure, wind was raging around the shore of Kea, but we were all hoping it would fade once we hit open water. I was finally able to hold down some sort of Greek motion sickness medicine, so I was happily able to sit above deck and soak in the bountiful sunshine. It was all – “Oooooh, I’m in Greeeeeece, this is so magical….” But about an hour en route; SNAP!! Our main sail ripped wide-open from the wind, rendering it useless. We had to switch to the prop motor, but due to the distance out we were, the gas/power we had, & the proximity of the closest island that could bear a new sail for us, we had to go under 15 miles an hour. The hilarity of that, was that we were engulfed (soaking, sloppy wet) by 15 foot waves, in what had picked up to be 50+ mph winds. The waves just kept coming, punching us in the face – & the water was the coldest cold I’ve ever felt. It was insane, y’all. INSANE. Sifnos was a beautiful little island, very established compared to Kea. Once dry, we frequented a little bar a few blocks into town & killed some pastries from the local bakery. Other than that – it was  a whole bunch of waiting for our sail to arrive.
1. Pack an extra main sail if you can. Ha!
2. When sailing, regardless of the weather reports, prepare for the worst. Bring head to toe heavy duty rain gear.
3. Pack tons of hand & feet warmers.


So two days later, our boat “Second Wind” – oh, the irony – was suited up with a brand new shiny main sail & we were off again, this time on very calm seas to get as close to Santorini as we could come before nightfall. Ios was as far as we could make it, so we docked at this concrete slab & started to discover a quaint fisherman’s village. Very chill, we surmised this town consisted of a tiny church, grocery store, long dirt road, & a little hole in the wall diner right on the shore where we’d settle in for dinner. The people there were so fabulous. They prepared an absolute feast for us – it was almost like we were long lost friends surprising them from out of town. I stuck to the delish pita and hummus for the most part, as I was still recovering, but there were all kinds of minced meat, squid, cheese balls, chick pea balls, Tzatziki, & Mousaka passing around. By the end of dinner I’d eaten the first full meal since Amsterdam, absolutely elated. Then our sweet waitress brought out some sort of greek Tiramisu with a tall bright candle in the middle, & everyone started singing! It was my 25th birthday, how could I have forgotten?! What an amazing way to start my 2nd quarter of life. There, dry, safe, & warm with my friends laughing & drinking/mingling with the locals, the stars crazy bright and the waves lazily sailing onto the shore….It was absolutely perfect. I learned later that the waitress went across the street to the church to get the candle – & instantly I fell in LOVE with greek hospitality.


The next day, we finally made it to Fira! Hurray!! Get this, we docked first in Thira (seriously) & later made it to Santorini. We could’ve hopped up onto this sweet donkey to take us up the iconic mountain side entrance, but I love a good workout, so we stuck to it and trekked up the classic white cobblestone path. It was splendid. Views for miles & miles of the Mediterranean Sea.


So if you’re still with me, here’s my little guide to Santorini, now that we’ve finally made it there. We were on the island during the off-season (end of April) so many places were closed, but it was kind of like having the whole island to ourselves! Here are my faves :

Catching Santorini’s absolutely mystical sunset on a waterfront deck, glass of wine in hand.
Rolling seas greeting jagged coastlines.
The sweetest people I’ve ever met while traveling.
The free-range lovable dogs all over the island.
Endless amounts of joyous sunshine.

The gyros from a place called Lucky’s: all the fillings you want, including the french fries & some special sauce all wrapped up in a warm pita… ahhh-mazzzing!
For a snack try the delicious oranges from Crete!
Grab a scooter! We got off the grid with ours and went all over the island.
Greek white wine – delectable!

Sigalas Winery – we got a winery tour, + a tasting of 6 exquisite wines they vint on the island.
Any of the black pebble beaches – bring your sandals – they get scorching hot!
The volcano tour. How could you miss that one?

The Aressana in Fira (Best hotel experience I’ve ever had! The staff members were fabulous.)  Since we were there during the off season our luxurious room was only $150 a night! I would’ve paid anything to have that experience after barely surviving on a catamaran for 5 days.

Ahhhhh, Greeeece. I miss you.
Cheers & happy travels, Court

One thought on “Getaway : Sail from Athens to Santorini

  1. Pingback: Moving & Shaking – The Wearing of Too Many Hats | design wine sunshine

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