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!





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.





Sailing the Greek Cyclades: Ano Koufonisi

21 12 2024

Leaving Amorgos behind, we set sail for the “Small Cyclades” islands, specifically, Ano Koufonisi. These out-of-the-way islands offer a magical mix of quiet beaches, turquoise waters, delicious food, cultural authenticity, and completely laid-back vibe. None have more than 500 residents. OK back to sailing! With more wind, we could travel under sail only. George showed us a few things about skippering the boat, and Katherine, assisted by Sian, winched out the genoa.

George gives us a “how to” on some of the boat controls.

Grind Katherine! Grind!

It was a gentle breeze, very pleasant. It would bring us to a lunch spot / snorkeling cove. This particular one had totally clear turquoise / sapphire colored water! It was completely perfect for swimming and snorkeling.

It wasn’t long before we decided it was time to play some music. Ellie turned out to be a dancing queen! There wasn’t anything she turned down. We played B-52s, Trampled by Turtles, Shakira, oldies from Nu Shooz and Rod Stewart, Culture Club and more.

Once underwater, I was amazed how far I could see. The bottom was completely soft white sand.

There were a number of what at first looked like caterpiller tractor tracks in the sand. It wasn’t long before I realized each led to an anchor. So these “tracks” were left by the anchor chain moving back and forth across the sand! Changing my view from down to forward, I was rewarded by a school of 40+ fish lazily swimming by. Each was I guessed 8 inches long.

It was a warm day. When we reached our Koufonisi marina, I looked around and didn’t see much shade. Time for sun screen! The harbor and town are beautiful. The island only has about 450 residents.

George told about highlights. One suggestion was to walk the shoreline. Along the way there are secluded coves, beaches and a couple of cafes for a drink. Koufonisi is a very small island. No cars. Very laid back. One can walk around it in a day. I took my backpack and my book and headed out. Everywhere, purely clear waters. I passed by several isolated coves. And then, I spied something perfect! A tree shading a single beach chair by the pathway. So I sat down, relaxed, and read for a while. People strolled by, boats plied the waters. Some folks paused to test the waters. If you walk far enough, you may not have to share your beach with anyone! It was so beautiful!

ss

We all loved Ano Koufonisi. Toward the evening, we found a hillside restaurant with a harbor view, where we sat down and ate dinner as the sun set. Walking back, the moon had risen, bathing the village in silvery light.

I chose to visit Greece in late September, which turns out to be a terrific choice. The blistering summer heat is gone. So too are the throngs or tourists. Some of the hotels and restaurants are already closed for the off season, while others are uncrowded. It’s very nice.

It was hard to leave. Another day on this island would be great. But we had an agenda – Naxos was our next island. Here is myself, all morning grizzled pre-shave, as we depart the next morning! We’re gliding along a Mediterranean blue waters. Life on a sailboat is tough…





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!

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.

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!