Bareboat Sailing the Greek Isles

Sailing Greek Islands

After months of research and endless group discussion, we had a plan, a one-way seven-day sailing trip starting near Athens and ending in the island of Ios, hitting lots of the best and prettiest islands of the Greek Cyclades including Kea, Syros, Mykonos, Paros, and Antiparos. At the end of sailing, we would be an easy half-hour ferry ride to Santorini, where we had post-sailing cliff-side hotel reservations. Provisioning orders were all set and food deliveries to the three catamarans were scheduled.

When you sail, you have to be prepared to change your plans on the fly. Stuff goes wrong, boats break, the weather can go bad, folks can have health issues. But we (and 11 other couples) were not prepared for what we were presented with upon our arrival in Athens.

“Sorry, but the catamarans you reserved for your 7-day sailing adventure are no longer available”.

The previous charter group had wrecked them in various ways (ran aground, engine problems, ripped sails) and all three of our reserved boats were now in dry dock on a distant Greek island far from Athens. Obviously, that left us and our vacation plans way up in the air. The charter company had a semi-palatable solution – they came up with 3 catamarans at a different marina. We could have them at a slightly reduced rate (they were lower quality) with the catch being that we would have to return them to the same marina – no one-way trip was possible. It was either that or cancel the sailing portion of our trip and figure out something else to do in Greece (which would not have been difficult). After some group discussion, we chose Option A, but we still did not have an itinerary. As a bonus for our troubles, the charter company threw in free ferry rides from Athens to Santorini (6 hours instead of a half hour) and a bus to get us to the ferry after sailing.

The morning of sailing was a frenzied, stressful, frequently comical ordeal for many reasons.

  • Our hotel was very near the original marina, but nowhere near the new one.
  • Our food order had to be cancelled. Instead we rented vans, shopped at a nearby market and schlepped it all back to the new marina.
  • This marina was not really equipped for group charters so the skippers had difficulty getting information about the boats and our itinerary options.
  • By the time we finally were underway, there were only a couple hours of daylight remaining, so our only real option was to go halfway across the Saronic Gulf to the island of Aegina.

Aegina in time for sunset

We got it all done, made it to Aegina for sunset, and rafted the sailboats together for a planning meeting and a much deserved “holy crap, we made it” party. We were tired, but happy we were still going to have a sailing vacation. We had several nice options for our modified itinerary and we went through them as a group. What we did NOT have was consensus. With two dozen folks to please, there were all kinds of opinions as to what was important. From our perspective, we wanted a fun, leisurely time with a variety of experiences. Some folks were very insistent that Mykonos was a non-negotiable piece of the puzzle (otherwise there might have been a mutiny or a splitting of the group). Mykonos was part of our original itinerary, but would be difficult to reach and still allow time for the return trip. Since we only had 6 days left, we mapped out a course that got us there in 3 days, allowed for 2 overnights in Mykonos, and a return trip of just 2 days. The distances between anchorages (daily sailing distances) were much longer than originally planned. The group generally likes the sailing to be no more than a half day so that there is more time to enjoy each destination upon arrival. Some of the sails would be close to 50 miles. But the skippers all agreed to be early risers so that we could pull it off.

The next challenge – little or no wind – great for sunning, not so great for sailing.

Fortunately, there is an easily solution for this – fire up the engines and motor away. We did get to sail occasionally during the week, but mostly we were under propeller power. Once we were under way with a plan, we got into relax and have fun mode quickly.

We never made it ashore during our first overnight in Aegina, so even though we had a very scenic anchorage, and it was calm enough to raft the boats together, we were anxious to get our new itinerary underway:

Kea and one of the top 10 beaches in the world. Not.

Next stop was the island of Kea where a guidebook had told us that one of the top 10 beaches in the world awaited us. We’re not sure who created this list, but I wouldn’t trust the other 9 picks. The beach was scenic and interesting to be sure – but top 10 in the world?? It was covered with fist sized rocks and very little sand – impossible for walking barefoot. The water was clear, but very cold – only a couple from our group took a dip. The highlight was a short hike to the remains of the Greek Temple of Athena. We did have the beach to ourselves, but there is a good reason for that. Since there was zero civilization where we anchored, it was dinner aboard that night.

Ermoupoli, Syros

In Syros we anchored in a pretty cove on the west side of the island and took taxis to the main town of Ermoupoli on the east side. Dinner was yummy and the setting along the bustling harbor was fun.


Finally arrived in Mykonos early afternoon on day 4. It was definitely worth the effort to get here. We were ready for some couple time on our own, so we strolled the picture perfect streets together, stopped in lots of shops and churches, and drooled at the bakeries and restaurant menus. Mykonos streets are laid out like a maze. This was done deliberately to make it tough on marauders – all it did for us was get us lost (in a fun way) a few times, but not for too long.

The next day featured some welcome relaxation, more exploring, a fantastic sunset, and a very fun group dinner at a restaurant featuring authentic Greek traditional dancing. One of our sailing friends is Greek with contacts in the area, so he found out where they would be performing. We never would have found this restaurant on our own and oddly, this turned out to be the only time we were part of such local dancing.


The early morning of Day 6, it was time to start the journey back to Athens. In spite of the lack of wind, we were making great time and decided to bypass Syros and made it all the way to Kythnos. We found a beautiful little sheltered harbor with a nice quiet shaded beach, but not much else. That’s okay because it was leftovers night on the boat and plenty to choose from.

Our last full day featured a surprise visit by a pod of friendly dolphins swimming with us for several minutes. One sure way to get Sheila out of bed early is to start screaming about dolphins! Later we stopped for a fun hike up Poseidon’s Temple at the southern tip of the peninsula south of Athens, and finally back to the marina in Pireas. Since we had an early morning ferry scheduled to Santorini, our last night (after our farewell group dinner) was spent in the marina on the sailboat.

I think he’s coming too fast – he’s definitely coming too fast – I think he’s going to hit us!! Hold tight!! CRUNCH!!

This happened toward the end of our trip when another boat was attempting to maneuver through an anchorage. The collision was obviously not our fault. After all, we were at anchor. Another challenge: one of the boats suffered from an extreme water shortage of their own making. It seems the crew didn’t know that long luxurious showers are not practical on a sailboat and water tanks do run out. The other boats were able to give them enough water to get by, but it did get a little stinky over there toward the end.

What have you done to my boat?

When we got back to the marina at the end of the trip, the boat’s owner went berserk and started screaming at our skipper. Our skipper remained calm and kept stating that we were at anchor when the collision occurred. It was like getting blamed for being rear-ended while sitting at a stop light. Fortunately, the owner eventually calmed down. Good thing insurance covers such things. Our group insists we all pitch in for boat insurance and we highly recommend it.

She said: Speaking of stinky…we’ve adapted to the fact that when sailing it’s necessary to either use approved biodegradable TP or actually stash your TP in a ziplock and never flush it. We were a bit surprised to find that habit requested even in many nice establishments in Greece. Their plumbing just isn’t robust enough for TP.

Olives? Yech! Throughout our sailing, and also at our post sailing stops, the food was delicious with lots of variety, and relatively inexpensive. We also enjoyed the local wine. Service was always friendly, though not necessarily speedy (but we weren’t in a hurry anyway).  Olives are a staple in Greece and it’s one of the very few foods that Tom just doesn’t like (not even a little). He got some funny looks when his plate was wiped clean except for the olives. Sheila loved the food, esp. the platters of gyro meat and our friends drooled over the caprese salads.

Athens, Milos and Santorini

After the sailing part of this trip, we took a ferry to Santorini for 3 picturesque days, then on to Milos for 4 unexpectedly amazing days, and then back to Athens, before heading home. But those are additional stories…

Our overall impressions of bareboat sailing the Greek Islands were mixed.  We would sail there again, but now that we’ve been on five destination sailing trips (also BVI, Belize, French Polynesia and Thailand), we’ve decided we prefer to sail in tropical locales with warm water. In Greece, the water in June was just too cold for extensive swimming and there’s no snorkeling/diving to speak of, which is tough on a mermaid.  There were no mooring balls and anchoring was sometimes difficult. Conversely, provisioning options are everywhere and the food and wine are great!

We LOVE Greece and especially the Greek islands. The time spent with our sailing friends was wonderful and Greece has a magic about it. There are many islands we’d love to visit, including some that were on our original plan that got scrapped. Their ferry system makes it very easy to island hop, so next time we might spend more time exploring the various communities.

Trip Date: June 2011

?  What is your favorite Greek food?


  1. Mary Ann stevenson
    August 3, 2016 at 1:23 PM — Reply

    Hi Kids!

    Wow! You guys turned what could have been the granddaddy disaster of disasters into a glorious trip! That’s why we love you guys so much! I would have been the tramp queen again soaking the sun and letting everyone else battle it out! Lol!
    We’ve committed to the Greece trip and we’re very excited. We arrive on the 8th, set sail on the 10th of June 2017. We are so excited. We will be spending a week in Santorini that will end our trip. Thanks for all the advice. This was a very informative article. I will check back with questions when they come up. We are in the very early stages but G and I have booked our hotel near our marina for the start of our trip. We are still researching our accommodations for Santorini. We want these seven days to be perfect. Feel free to throw us some suggestions.

    • Avatar photo
      August 8, 2016 at 2:14 PM — Reply

      Hey Mary Ann! You and G will LOVE sailing in Greece! Can’t wait to hear about the whole itinerary! We’re still on the waiting list as unlikely since we get back from Fiji only the week before, but it sure is even more tempting knowing you two are on the trip!! Glad you’re spending extra time in Santorini! Get ready for astonishing sunsets. We loved it – stayed at a place called The Lithies on a cliff overlooking the caldera in the Firostefani area. Happy to answer any questions you have! Wish we were toasting “Opa!” together 🙂

  2. Doug Sample
    July 27, 2015 at 12:49 PM — Reply

    You asked the question, “What is your favorite Greek food?” Well, I just LOVE Greek food! Besides gyros, tzatziki and basically anything with feta cheese, here are a few of my favorite traditional Greek dishes I seek out whenever I have the opportunity … and now I’m hungry! ?

    1) Tiropita (a Greek layered pastry pie of a feta cheese filling).

    2) Moussaka (a casserole made of typically fried eggplant, potato, and spiced minced meat).

    3) Pastitsio (a baked pasta dish with a filling of ground, spiced minced meat and sauce topping).

    4) Souvlaki (anything grilled on a skewer — lamb, chicken, pork, swordfish, shrimp, etc. — typically marinated in oil, salt, pepper, oregano and lemon).

    5) Gigandes Plaki (giant baked beans with tomato sauce and various herbs, often made spicy with various peppers).

  3. Doug Sample
    July 27, 2015 at 12:19 PM — Reply

    Having vacationed in the Greek Islands many times in the 1990’s and having lived/worked in mainland Greece in 2004-2005, I enjoyed reading this story. My first thought was I agree with BOTH of you on your “He Said, She Said” comments. I, too, found the water a little colder than I prefer regardless of the time of year I vacationed in the Islands (late May, July, September were the months I always went). The food, however, make the trips all worthwhile though (I love Greek food)! For your blog readers who may be interested in visiting Greece, I’ll offer the same three pieces of advice here that I share with my friends:
    1) When you visit the islands, do not rent a vehicle. Instead, each person should rent their own scooter to easily scout the islands at your leisure. You’ll find many small dirt roads or paths littering the islands and hillsides to where you can see quaint little chapels, get some phenomenal panoramic photos, and perhaps even find your own private little beach area.
    2) If you’re planning a trip to Greece and you want to see both mainland Greece and the Islands, definitely go the mainland Greece first and get that sightseeing out of the way first because once you get to the islands and are relaxed and on “island time” so to speak, you won’t want to go directly from that to the hustle/bustle of Athens, etc. I have done it both ways in different years, and I will always tour mainland Greece first.
    3) While “island time” in Greece may not be as relaxed as it is in some of the Caribbean islands, it does exist so don’t be surprised if island ferries and seaplanes are not on time like you may be used to in your home country. My recommendation is to just relax (possibly don’t even wear a watch), go with the flow and enjoy whatever comes your way because you’re in a very unique place where many people never get to visit in their lifetime. As demonstrated in Tom and Sheila’s article, the best laid plans may not work out and the unexpected adventures are the ones that become the most memorable, possibly humorous, and the ones people want to listen to at social gatherings.

    • Avatar photo
      July 31, 2015 at 11:57 AM — Reply

      Hi Doug! Great suggestions and I especially agree with point #2. Seeing the highlights of Athens is important and certainly worth doing, but I find that my tolerance for all things “city” changes after time in the islands or the countryside or coastlines. Greece is truly special, even with the colder water and fragile plumbing 🙂 I’d go back again and visit a whole different set of islands!

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