It’s a long one… so get comfortable.

Be sure to reach the end of the post to see another one of David’s epic videos

We had so much fun last year on our sailing trip along the Dalmatian Coast of Croatia that we booked another one week sailing holiday.  This time, we went with Off the Beaten Tack in the Cyclades, island hopping in paradise.

On Saturday afternoon we met our trusty skipper, Jimmy, and the rest of our crew: our hostess, Carla, a couple from New Zealand, two women from Edmonton (of all places!), a woman from England and another from Australia.  After a meet-and-greet and short briefing, we got acquainted with our home for the next 7 nights, the 50ft sailing yacht, Ikaros.

We spent the first night on-board in the harbour after a group dinner at a local taverna and a fabulous sunset.

Nudists in a secret bay

Before breakfast, we sailed to the middle of the caldera to enjoy our yogurt and muesli with a view of the hill top towns of Santorini and Oia and everything in between. As we sailed away, continuing our journey, the towns disappeared into the horizon, looking a lot like snow-capped mountains before going out of sight.

Jimmy took us to the impeccable clear turquoise waters of Maganari Beach on the island of Ios.  I couldn’t believe how beautiful the water is there. It looked like one giant salty swimming pool.

After some swimming and some lunch, we sailed to a secret bay with a firepit Jimmy recently discovered, only to find it wasn’t so secret and used by a group of nudists.  On a side note binoculars are fun!

After uncomfortably waiting around until they finished their naked sun tanning and snorkeling, we took over the fire pit and began cooking up our lavish dinner of chicken, beef and vegetable kebobs, corn on the cob and mussels in white wine sauce. Pretty snazzy for a meal cooked over an open fire.

Lunch at a sunken ship

The next day started like most others would… sun tanning, swimming and sailing. By lunch, we pulled up to the half-sunked ship, Olympia, on the island of Amorgos.

The story of how Olympia met its fate goes like this (according to our captain, wannabe pirate): a band of pirates were transporting drugs from Turkey to Greece aboard Olympia when the coast guard caught wind of it and chased them down. They sailed into the bay to hide but meltemi winds caught them off guard and drove them right into a rock. They battled the coast guard, took over their boat and got away. Now the ship lies there holding the secrets of the sea where we can marvel at the passage of time and the power of the sea.

That evening we pulled into the port town of Katapola on the island of Amorgos. After two days of salty skin and ratty hair, I needed a shower. Badly.

Once I felt human again and was all cleaned up, we strolled around the small town stocking up on snacks and drinks and had a wonderful meal at Akrogiali Restaurant. Our group shared the largest grilled fish I’ve ever seen. Weighing in at 3.5kg, it easily fed 10 people.

Sweet liquor at a monastery

Going for a run the next morning was a real treat. We had been averaging about 15,000 steps a day before starting our sailing trip and quickly went down to 1000 steps. Plus, I hadn’t quite gotten my sea legs and was close to going green a few times, so it was really nice to spend the morning and afternoon on land.

Our group rented ATVs and scooters to explore the island and visit the monastery of Panagia Hozoviotissa. Clinging to the cliff the white washed stone of the 1000+ year old bricks glistened at the top an incredibly long, windy and steep stone path. Those not suitably dressed sorted through a pile of donated clothes and played dress up to gain access inside. Even in +30 C heat, men have to wear pants and women must wear long skirts (not pants) with their shoulders covered.

Once inside, young volunteers asked the male visitors to carry up large water bottles (the kind you’d find in an office water cooler). That was a small price to pay to help the kind, generous monks who served us their deliciously sweet local raki, unlimited loukoumi and must-needed cold water. It was all worth it for the spectacular views of the Aegean some 300m below.

We continued our day with a drive to the town of Chora. We loved this quaint little town with perfectly white buildings sporting impeccably painted accents around the doors and windows. The variety in colours made it all the more charming: pink, teal, blue, red and yellows of all shades.

A dolphin leads us

After lunch, we returned to the boat and made our way to Ana Koufanisis. Along the way, a lone dolphin joined us, a highlight in an already perfect day. He playfully swam along the boat, switching between starboard to port, cresting the surface, showing off his fin and then taking the lead, just inches from the bow.

We then arrived at a popular cliff jumping spot with rocky ledges at different heights. David tackled the small and medium heights but upon my pleading (and let’s be honest, a bit of fear), he didn’t dare plunge from the tallest ledge, some 12 metres high. A few weeks earlier, Carla attempted the jump and broke her tail bone. Ouch!

A few people were at the top, staring down, contemplating the long, hard drop. Meanwhile, the scaredy-cats in the boats below egged them on to jump. As they did, I cringed, anxiously waiting for them to resurface, either in silence or screaming in excruciating pain. All those we saw survived and received loud cheers from the crowd.

One brave little 10-year-old girl happened to make the two jumps just after David and without hesitation.  Her brother then jumped off the tallest ledge and she was heading that way when her father, treading water below, yelled at her to stop. She wasn’t allowed to do it. To our amusement, she sulked and had a little tantrum 12 meters above before grumpily moving back to the lower ledge and jumping off.

Sailing at night under the Perseid meteor shower

After yet another delicious Greek meal and a beautiful sunset in Heraklia, we geared up for a sail to Naxos…by night. The Perseid meteor shower would peak that night and Jimmy took us to the middle of the Aegean to enjoy it in pure darkness.

Sailing off in to the dark is a little unsettling at first, but we soon got over that once we lied down on the deck looking up toward the sky. We counted about 30 meteorites before our heavy eyes gave way to sleep.

At one point, a large, bright meteor flashed across the sky. It lasted long enough to say, “I see one! Look there!” We were amazed when after a few seconds it exploded in a large flash and disappeared. I had never seen anything like it before. What a magical memory from the trip.

I wish we had it on camera, but alas, it’ll have to stay just a memory since astro photography doesn’t work on a moving boat.

We arrived in Naxos at 2:30am and the busy port was still full of action, music and lights. Tempted to make the most of the night and go for a drink, our old bones decided sleep was better.

Since it was peak season on the island, we couldn’t rent a scooter the next morning. So we took a local bus to explore the “must-see” town of Halki in the centre. Even though it was nice to see getaway from hectic Naxos port, the Lonely Planet oversold this small village and it wasn’t worth the 45 min bus right there and back. Sure, the town was cute and we visited the old distillery that still makes the local lemon liqueur and the notable ceramics gallery. But 2 hours was more than enough time to walk the same streets… some 6 times over.

Another beach BBQ

Our trip was already coming to an end after a few days of good laughs, good food, relaxing in a hammock on board and lots of sun tanning, swimming and sailing. We anchored in another secluded bay, just meters from a small rocky beach were we cooked up another feast over the fire. This time we had chicken, sausage, fresh fish, veggies and potatoes. We ate very well. Also drank very well. And then we had some fun with fire before settling into another dark night watching the stars. This time David captured some beautiful night shots of the Milky Way, including one with a shooting star.

Overcast skies and some drizzling rain greeted us the next morning. A local fisherman told Jimmy that he had never seen clouds and rain in August in Greece in his 70 years of life. So it was a rare sight but it was the perfect weather to explore the archaeological island of Delos.

We happily perused the ancient site for about 2 hours, protected from the hot sun and heat we experienced all the days earlier.   It was a good dose of history and culture. Visiting Athens has never appealed to me, but after Delos, I can understand why people flock there.  Walking among the ruins of an ancient civilization makes my 32 years on the earth seems so insignificant.

We finished our last leg of sailing once we anchored in the new port of Mykonos. We’d still have one night on board before parting ways with our new friends but I’ll save Mykonos for another time.

Sailing is by far the best way to see the islands.

Every time we saw a ferry or cruise ship dock at one of the ports, we saw travelers schlepping their baggage to their accommodations in the scorching heat.  We were glad we weren’t one of them.  We thought of all the beautiful bays they missed, the spots in the middle of nowhere they didn’t swim at, the beach BBQs they couldn’t eat and the luxury of not packing up a suitcase every two or three days.

Yeahhhh, you wouldn’t get this kind of holiday ferrying around the islands on your own…

Thanks for making it to the end of this post… it is a long one and only skimmed the surface of all the fun and happy times we had with Off the Beaten Tack aboard Ikaros.

Now, time for another epic video.  If this doesn’t convince… what will?!?

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About Author

My name is Emilia - I love versatile trips! You might find me at a trendy new restaurant one night, but the next day you're just as likely to find me at a local market sampling exotic foods. I'm open to just about anything when I travel and I want to encourage you to be open too!