Sailing Greece’s Cyclades Islands: Syros

2 01 2025
Hoisting a cold one at the marina cafe in Finikas harbor

With a stiff wind over our stern, we headed to Syros. Syros is a blend of the urban life of the city and quiet coastal villages. Its primary city, Ermoupoli, is the regional capital with a rich history, opera house, two cathedrals and port large enough for ship building and repairs. We spent two nights on Syros. I rented a car so we could get around. Since my insurance doesn’t cover overseas rentals, I had to opt for the insurance offered by the rental car company. We paid for it out of the group kitty.

Gina looking good!

Rather than dock in the city, George chose what was to become my favorite port of this trip, Finikas. Finikas is worthy of an Ernest Hemingway novel. The marina, with showers and a cafe, sits at one end of a 600-yard long semi circle harbor. From there, you can walk the boutique hotel and taverna lined waterfront to which the cutest brightly colored fishing boats are tied. As you stroll, occasional steps lead down to the the narrow beach and its free umbrellas. Sailboats swing at anchor. Being so late in the season, no tavernas were more than 25% filled at dinnertime. The atmosphere was peaceful bliss.

For supper, some chose to visit Ermoupoli, but I couldn’t resist the opportunity to check out the waterfront restaurants at Finikas Port! The attraction was too much. When the time came I set out wandering along the waterfront, passing fishermen mending their nets, a marine supplier, and checking out menus as I went.

I settled upon an open air spot with lots of open tables. The server was incredibly pleasant. I sipped a glass of red wine and awaited my meal. And then, my luck turned gold and just as I hoped, the magic happened!

A trio of local musician friends sat down right across from me and began practicing, whilst waiting for their own meal! THIS is what travel is all about. It is priceless moments like this!

The following day we did a little exploration of Ermoupoli. We strolled the steep streets, with their pastel painted Italian inspired buildings, checking out shops, and spending a little time at the Apollo Theatre, built in 1864. More music! A pianist was practicing!

Then it was time to explore Ermoupoli’s cathedrals. One of them was closed, but I found a cliffside restaurant with a commanding view just a short walk away! Terrific lunch spot.

Next, we drove to St. Nicholas Church, a cathedral built in 1870. A Greek-Australian wedding was taking place!

If I had to pick favorite stops on this voyage, I would choose Ano Koufonisi, and Finikas, on Syros! Love love love them!


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Sailing in Greece: Ancient Greek Ruins on Delos, and A Little Bite of Mykonos

29 12 2024

Our sailing journey would put us this day on the infamous party island of Mykonos, something I was set to endure, not enjoy, or so I thought. What actually transpired turned out to be one of the highlights of my Greek vacation! I love archaeology and ancient civilizations, and I was not expecting to see a lot of Ancient Greece on this sailing-oriented vacation. What I discovered on this day was that there is a very important Ancient Greek island city a 30-minute water taxi away from the hubub of Mykonos! It is the island of Delos.

After our snorkel and lunch break, we motor sailed on our way to Mykonos. Passing amongst some smaller islands, George pointed out some ruins on the shore. It was Delos! Cool!

As we sailed past, George gave us a briefing on Mykonos. One of the activities was to take a water taxi to Delos, and the price included a guided tour of the ruins! Kathryn and I were in. This would be a perfect way to avoid the Mykonos crowds and take in some Ancient Greece! It would complete my vacation! I was stoked!

Past Delos, we came into what I learned was the windiest passage in the Greek Islands – between Tinos and Mykonos. We took a long starboard tack north upwind before coming about and making a port tack east over to Mykonos. Some of the waves came over the bow! The hull actually pounded after going over some waves.

Eventually, the Mykonos waterfront came into view. What I read was true. It would be packed with tourists. There were three cruise ships – Royal Caribbean’s Odyssey of the Seas, a 1,138 ft monster with 5,510 guest capacity, Carnival Cruises’ 963 ft Carnival Legend, with 2,124 guest capacity, and another from a cruise ship line I could not recognize. Together, these three ships are capable of dumping about 10,000 people on the port. I didn’t want to be there.

We docked at the comparatively minuscule sailboat marina, and George educated us that Mykonos has an efficient water taxi system which can whisk us around the bay, with “bus stops” along the way. He let Kathryn and I know which stop to use for the Delos water taxi. We were on our way! We were dropped off at another water taxi station, where Delos tour operators sold all inclusive tickets to the island. While waiting to buy our tickets, we saw a hundred cruise ship guests waiting in line for prepaid “shore excursions,” and they just reminded me of cattle being herded around. I was glad for our freedom.

After disembarking at Delos, we were met by our English-speaking tour guide, also an on-site archaeologist. It was a 90-minute walkabout. The island isn’t big. It’s 5KM long and 1,300M wide. It isn’t favorable to agriculture, so food had to be imported.

For people of antiquity, Delos was a very important island city. It was said to be the birthplace of Apollo and Artemis. Situated at the center of a spoked wheel, if you will, Delos was a wealthy cosmopolitan trading center for all ancient civilizations, and a melting pot for religion and culture. At one point it had various neighborhoods housing Greeks, Romans, Egyptians and Syrians. Its earliest settlements began about 2,500 B.C. Its greatest importance grew from when it was declared a free port in 167 B.C. Wealthy merchants, bankers, ship builders, and traders from Persia, Rome, Egypt, Syria, Turkey and beyond set up businesses.

It became “Maximum emporium totius orbis terrarum,” the greatest commercial island in the known world. Its prosperity attracted organized looters, for it was sacked twice and eventually abandoned. Today, evidence of its role as a crossroads are everywhere on the island. There are sanctuaries for Greek, Syrian and Egyptian gods.

I really enjoyed the Naxian Lions, checking out the 6,000 person amphitheater, the fish monger / butcher areas, and admiring the mosaic tiles on the residential floors.

As it was late in the afternoon, the light was very striking. It was breezy and pleasant. Then it was time to head back to the water taxi, and Mykonos. Kathryn and I arrived about dinner time, and set out to find a unique and economically priced restaurant. George told us that the places on the Mykonos waterfront are not only overpriced but charge a reservation fee! So we prowled the back streets. It was there that we noticed a guy walking by with a to-go food box. We asked him where did he get that? It was a place called Sakis, around the corner, and he said it was great! We checked it out and scored big time! It is an “over the counter” style eating place with shared tables. Not a restaurant with servers. So, we ordered from the counter and found seats. It wasn’t long before we were joined by other guests, and then a street artist. We gladly shared our stories! This turned out to be pure joy. And my meal was only 9 Euros! Wow!

This was a lot of food. And so fresh. Over fed, completely stuffed and happy, we waddled back to the water taxi station out on the waterfront. There, we found Mario, Ingrid and Natalie too! So all in all, my Mykonos – Delos experience turned into one of the crown jewels of this Greek vacation.


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Sailing in Greece: Naxos – Ancient Ruins, Winding Streets and Castles

26 12 2024

From Ano Koufonisi, we navigated to our next destination, Naxos. Naxos is the largest of the Cyclades Islands. It boasts a working harbor with multiple ferries and fishing boats, a bustling waterfront with many restaurants, cafes and shops, a hill top castle with rooftop restaurant nearby, and some ancient Greek ruins to explore. As of 2024, the island’s population was just over 20,000.

Gliding towards our marina, we passed by some smaller naval ships and Running on Waves, a “boutique barquentine” for vacationers, one which we’d run into later in our cruise. It has a capacity of 42 passengers total. I bet it’s nice!

Once docked, George gave us ideas on things to check out. There is the Apollo’s Gate, the waterfront, an ancient Greek Dionysus temple, walking up to The Kastro Venetian Castle, and perhaps a group dinner with music and smashing plates at the Flamingo Restaurant.

I definitely wanted to see the temple and walk about town. But I declined the Flamingo option, sensing an expensive and awkward tourist trap situation.

We all headed over to the Portara of Naxos, or Apollo’s Gate, part of the Temple of Apollo, which is easily reached along the waterfront. It’s free and has a nice view of the town, hillside neighborhoods, and the waterfront. And we had such nice weather!

The Temple of Apollo, an unfinished temple founded in the 6th Century BC, is one of the most pretty spots on the island. According Ancient Greek folklore, this is where Minoan Princess Ariadne was abandoned after helping her fiance Theseus kill the Minotaur at Crete. She got over it. She was later to marry Dionysus. As for us, we took the opportunity to snap some lovely images with the temple!

Myself and Ellie
Gina, Ellie, Sian, Nicole

Next, we climbed the winding walking streets, past shops and cafes, up to the 13th Century Kastro Venetian Castle and its rooftop cafe. Along the route we passed bougainvilleas, as well as an art gallery and 16th Century Catholic Church.

We took an elevator up to the rooftop cafe, and enjoyed a leisurely lunch. When done, several of us wanted to take a taxi to see the Temple of Dionysus. The taxi dropped us off about a block from the entrance, because there was a construction truck blocking the road. When we got there, the temple was deserted and closed. Turned out it closed early as it was shoulder season! We called the taxi back, and tails between our legs, returned to the marina. It was late afternoon.

My evening turned out to be a fruitful solo exploration. I left the others to dine at the Flamingo, where plate smashing is part of the menu. Instead, I struck out on my own, wandering back pathways in search of a unique experience, which from my personal observation, is hard to find as a group. As I wound my way through the labyrinth of walkways, I checked a number of menus as I passed. Then one cafe struck my fancy. Reasonably priced, family owned, and with a back deck overlooking the waterfront beyond! I secured a small table by the edge, and was promptly offered a menu by a most agreeable server. I had a roast chicken breast with potato and vegetable, accompanies by a couple glasses of red wine. All for 12 Euros!

Naxos waterfront from the deck of Big Blue.

Afterward, I strolled the length of the waterfront, then retired to relax on the foredeck of our sailboat, Big Blue. From there, I could hear the Flamingo. A loud lute player, smashing plates, plus a cacophony of laughter. From the boat it sounded fine. Out on our boat, I was all set. I had a full moon and gentle breeze blowing through the rigging of docked sailboats. Later I was to find out from those who went to the Flamingo that it was hard to talk with the lute so loud! It got mixed reviews. Some liked it and others said they spent too much.

Our next destination was the infamous island of Mykonos. Its reputation as a hedonistic hard partying late night scene had me dreading the place! I was set to get hold of myself and endure. Little did I know how an alternative activity would completely change my time there and become a highlight of the trip!


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Sailing the Greek Cyclades: Amorgos

20 12 2024

Departing Ios, we motor-sailed to Katapola Harbor on the Island of Amorgos. Whilst heading in, I noticed other sailboats just like us, all arriving to spend the night here. Cruise ships cannot dock here as it’s too small. But ferries pay brief visits to drop off and pick up passengers and vehicles.

The harbor village is pretty compact – it only goes a street or two up the hill behind the marina. But there are enough restaurants, shops, cafes and markets for us. The island’s total population in 2021 was 1,961. Once docked, George told us about highlights and arranged for us to meet for dinner at one of the restaurants. It’s busy for such small village, with sailboats from New Zealand, Belgium, Poland, Holland, and France.

Amorgos is long and skinny with high hills running its spine. Two highlights are the mountain top Hora (village) with its famous windmills, and the cliff-hanging seaside Panagia Hozoviotissa Greek Orthodox monastery. George explained that while there is a bus system on Amorgos, the most time-efficient way to see everything and get back for dinner would be to rent cars. So we rented. I volunteered to drive – and surprises awaited! I had 4 in my car and the thing was as stubborn as a mule. The Amorgos roads consist of steep switchbacks climbing up and down all over the place. And upon every tight uphill turn, this car would just about stall in protest, then all of the sudden catch up with itself and zoom forward! After a few such turns I started yelling, “Go Donkey GO!” And I palm spanked the center column like a horseman urging his beast of burden forward. Everybody squealed with giggles and laughter.

The monastery, built in 1066, clings to the cliffside 800 feet above the Aegean. An impressive sight! Accessing it requires 25 minutes climbing a very well maintained hand chiseled and steep staircase. I was thankful for the sea breeze! We all made it up there.

The inside of the monastery was, well, steep, short and tight all at once. In other words, cramped. The stairs, wide enough for one, climbed quickly and the low ceiling required ducking to enter rooms. I wasn’t truly impressed. The worship enclave was stuffed with hastily arranged and abandoned artifacts. I was anxious to leave. The view was incredible! The cliffs plunged all the way to the sea.

Our next stop was the Hora. Gina, Ellie and I took a stroll around, then had some refreshments at a cafe overlooking the windmills. Then it was time to get back to port. We had a harborside table, outside, and it was very comfortable as dusk gave way to the evening! It was a leisurely paced meal. I chose a wonderful starter – Greek seasoned mussels. The main was a spicy spaghetti, slightly cheesy, creamy, with lots of veggies and red peppers, which I was quite fond of.

Here at the Katapola waterfront I captured some images of our boat! Inside and out. It has a beautiful blue hull and the galley was very nice!

Tomorrow we set sail for one of the “Small Cyclades” islands, the very very small and jewel-like Ano Koufonisi!


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Sailing Greek’s Cyclades Islands: Ios

14 12 2024
A ferry arrives in our cozy harbor at sunset. From the Volcano Bar.

In September 2024 I undertook a 10-day sailboat adventure with Intrepid Travel in the Greek Cyclades Islands. I’ve been a sailor since I was six-years old. I’ve cruised and raced on everything from dinghys to 12-Meters. But I always dreamed of cruising overseas, and one of my top bucket list destinations is Greece. Experiencing the islands by sailboat allows explorations of intimate places and cultural experiences the big cruise ships due to size and sheer numbers of guests cannot offer.

This experience is not for everyone, but 100% perfect for me. There are no casinos, water parks or black tie dinners. On this trip we had a 55-ft sloop with George, our captain. We were 8 women and two men. Some were single, others were married without spouse, and there was a mother and daughter. We were a mix of American, Australian, Australian England resident, and Iranian now Australian. We were complete strangers all excited to become a team. We had shared cabins each with its own bath. We shopped for breakfast and lunch food and made it on board. We all took a hand at sailing. Our days typically began with breakfast, shoving off about 8 or 9, stopping in a cove for snorkeling and lunch, and then arriving at our island destination about 3 p.m. Then explore, with a dinner out at a local restaurant. Each island offered its own highlights. All had beaches with lovely “Horas,” or main villages. Others had ancient Greek ruins, cliffside monasteries, lively downtowns, and marina districts which varied from cozy Hemingway novel waterfronts to bustling with cruise ships like Mykonos.

We first met on the waterfront on Santorini, then took a fast ferry to Ios, where Big Blue, our sailboat, awaited. The waterfront had maybe two dozen boats like ours, hailing from many countries. Sweden, Poland, Belgium, New Zealand, Singapore, Germany and many more. One was from Marblehead, Massachusetts! I lived there and raced there! Big Blue had two wheels and a generous cockpit.

Big Blue had many modern features which made it easy to sail. It had a remote controlled anchor system. It had a self-steering GPS guided navigation system. The toilets flushed with a push button. And the mainsail furled into the mast. The galley was well equipped and generously sized.

Once settled into our cabins, George held an orientation session. Here, he explained life aboard. As with all sailboats, they heel, so cabinet doors and drawers had special closures. Windows/hatches must be closed when sailing. Loose items must be off tables. There were 3 coolers/refrigerators, a radio, stove, oven, kitchen sink. When conditions get rough, always hold on to something when moving about.

One of the most important items to get settled right away is the group Kitty. On most Intrepid Travel trips, guests contribute to a group kitty, and the guide uses this to pay admission fees, certain transportation, tips for local guides and bus drivers, and such. On this trip, the kitty is used to pay for groceries and rental cars and such.

Once orientation was complete, George told us about activities on Ios. Strolling the waterfront. Grocery shopping and provisioning. Later, enjoy a sunset cocktail at the spectacular hillside Volcano Bar, and then dinner in the Hora at a restaurant called Lord Byron. It was a bit more than my budget to do all, but I went ahead and WOW it was worth all of it.

The sunset view at the Volcano Bar. You can take in the whole Aegean Sea with an infinity pool right in front. And 100% perfect weather!

The Infinity Pool
Mario, Nicole, Natalie, Sian, Katherine
Ellie, Rod, Gina
So surreal at sunset!

Next, we took a bus down to the Hora, strolled the streets. Like all the Cyclades, the Chora is a village with white buildings up on a hill, with small, steep streets and walkways. And very neat and clean.

As dusk drew close, we headed to Lord Byron. Decorated in an eclectic cluttered style, each turn revealed something to feast my eyes. We ate with windows open and a moonlit view.

HUGE portions!

Completely over stuffed with full bellies, we waddled to the bus stop. The local bus takes about 10 minutes down the hill right to the marina where Big Blue was tied up. It wasn’t long before we were in our cabins fast asleep.

I awoke early and stepped out. Ios port had several cafes open early, and I checked out out.

It was chock full of fresh baked goods, and an espresso bar. I picked out a bakery item and was good to go!

We pulled out of the dock and were on our way to Amorgos, the next island. It was a beautiful morning with a light wind. We used the motor to make time.

Here’s a sailing video!

We stopped for lunch and a snorkel in a warm, windswept cove before arriving in Amorgos!


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