Sailing Charter in Greece – Part 1: The Planning

This is the first of several posts I’ll write about our trip to Greece last summer. Julie and I (mostly Julie) put in a lot of time planning this trip so we thought others might benefit from our experience.

Choosing the Charter and Itinerary

Our original plan was to visit Greece, specifically the Peloponnesian peninsula, during spring break in 2011. When Julie and I learned that the weather would be similar to Oregon weather during that season we opted for another trip instead. Julie had visions of sunny beaches and sea swimming that just weren’t compatible with a spring visit.

We considered a few different travel options – a driving tour of the Peloponnese, a cruise, island hopping via ferry or airplanes. Given that there would be eight of us, it seemed like we should be able to find economic efficiencies better than the usual hotel or cruise options. We also weren’t thrilled with the idea of changing rooms every day or two – packing, repacking, uncertainty about how nice the next room would be, etc. this led us down the path of chartering a sailboat that could be our home for an extended island-hopping adventure.

Chartering a sailboat isn’t something most(any?) Greece guidebooks cover. So Julie and I ran off to the interwebs to see what we could learn. These sorts of research projects can be daunting. There are so many variables to consider. Many websites out there are simply pushing their own advertising agenda. Pricing can vary greatly based on what’s included. We found a few helpful sites along the way:

  • SailingIssues — a site maintained by a German national with sailing experience in the Mediterranean. It is ad-free and was a nice source of general information and potential itineraries. There’s also a great narrative of a bareboat vacation (i.e. they did not need to hire a skipper) that is worth a read.
  • Archipel Club — this is a sailing charter site but has solid general information
  • TripAdvisor — we use TripAdvisor any time we are headed overseas. The site isn’t perfect but has such a critical mass of active users that you can get a decent picture of suggestions and potential pitfalls.
  • Aegean Cruises — another charter site with good information
  • Seafarer Cruises — had to include them as this is who we went with for our charter

So we had choices to make. To name a few:
* What part of the Aegean do we want to visit? Cyclades, Ionian, Saronic, …
* What type of sailboat should we charter, a dual hull catamaran or a monohull?
* Where should we sail from? If we want to spend a lot of time in the southern Cyclades islands (think Santorini) maybe it would be best to fly from Athens to an island port then sail from there.
* How long should we and can we sail for? A week seems too short for the islands we likely want to hit. Can everyone in our group go for two full weeks plus travel time?

Julie and I started planning in earnest in January. Here’s part of an email she sent me in January:

Ok – so there are a lot of boats out there. From all these quotes it seems like the Lagoon 440 (up to the 470) is going to be a good, reasonable fit for us. We should dig through these and talk Sunday night. I even have a few more I haven’t sent you! Perhaps we can narrow down to a boat type (and list of amenities), launch point, etc. and then choose a couple companies to really dig into the details.

In short order we settled on a catamaran after weighing quite a few factors. We felt it would be more stable and have more sleeping and living space than a comparably priced monohull. More on this in a later post as this all turned out to be true but there were other surprising factors that may have led us back to a monohull. Specifically we booked a Lagoon 400 with Seafarer, with a 50% down payment wire transfer that we sent over at the end of January.

Julie did a great job summarizing what the trip would be like in an email she sent to our extended party, so I’m going to include that verbatim here:


  • We will fly in and out of Athens, and will will join/leave our yacht at the Alimos port (outside Athens).
  • We will be living on the yacht the entire time – no hotels. We looked into other options, but this is the least hassle (no other flights, ferries, hotel changes, etc.) and allows us to see the most islands.
  • We will hire a professional skipper. That’s a wild card – no idea who it will be! It will just be us and the skipper on the yacht, so we will help with docking, sailing, etc.
  • We will sail a loop in the southern Cyclades, stopping at islands of our choice. We will definitely go to Santorini. Here is a possible route, although we’ll have less than 2 weeks sailing, so would need to cut a couple islands.
  • We are sailing, so plans may be changed due to wind conditions.
  • On a typical day, I believe we will start to sail around 9am, and sail for 2-4 hours to our next stop. We will likely stop somewhere along the way to drop anchor, swim, have lunch on the boat, or take the dinghy in to shore at an island along the way. On our destination island, we will have the afternoon to explore, hike, see archaeological sites, etc. We will spend each night on our yacht in port.
  • We will buy groceries to provision the boat and will have breakfast and lunch on board. Dinner will be in town each evening.
  • We will see some of Athens on our arrival day (Saturday) – we need to fill time until we can get on the boat at 5pm. If we want to see more of Athens, we can choose to come back to Alimos port at the end a day or two early. The yacht would still be our home.

You may have noticed a key point in the above list – we didn’t have our skipper yet. This would come later and we ended up with a great assignment: Vassillis Spiliotopoulos. More on him later as we dive into the sailing adventure.

By chartering the boat from Athens for a full two weeks we greatly simplified our planning. No hotels to worry about and we could keep our food costs down by being able to eat some meals on board even while moored at Alimos in Athens. This turned out to be a great move. Note that most charters will only go for full week increments.

Site seeing

Julie did a ton of legwork preparing for our site seeing in Athens and out on the islands. She prepared a very handy site seeing guide that may be useful to others. My main contribution was chatting with some fellow board gaming geeks from Greece and identifying a potential private tour guide for our time in Athens. We messaged a few and settled on Demetra Potsika.

What to Bring

Fortunately I saved a lengthy email I sent to my niece and her new husband! This was almost like a backpacking trip for us in terms of the types of clothing and accessories we brought. We always travel overseas with travel backpacks that we carry on the plane. Here are the notes I shared:


  • You will carry on your luggage. No checky your baggage. We have to get on a boat the day we arrive, and the last thing you want to deal with is lost luggage. Keep everything with you at all times.
  • Don’t bring stuff you might need or will only use once. If you have a very nice camera, bring it. If you have a cheapass point and shoot, stick to your phone. “Good enough” snapshots are going to be just fine.
  • For clothing you will want to favor synthetic underwear. We like Ex-officio but there are probably other options. On a two week trip you can likely get by with 4 changes of underwear and some periodic washing.
  • Did I say washing? Yes – you can do laundry while you travel, and without a laundromat (though we may luck into one)! We may bring a few packets of Woolite, but even hand soap or shampoo can work fine.
  • You only need one pair of pants (or maybe a summer dress). If it gets too dirty we’ll have Jacob throw you off the boat to rinse and scrub off.
  • For warmth think “layers”. Consider a long-sleeve athletic synthetic sport shirt plus a sweater or fleece layer plus a wind or rain shell. You only need one of each of these.
  • T-shirts / golf shirts are where you might consider multiples. Synthetic is helpful as it will dry quickly after you clean it, but cotton isn’t the end of the world here. We will be in a dry, sunny climate and I suspect even cotton will dry pretty quickly.
  • Two pairs of shoes: one for water-type stuff, one for aggressive walking and exploring. This could be water shoes or Tevas plus light-weight hikers or running shoes.
  • Bring a baseball or bucket cap to protect your melon from the sun. CHEAP sunglasses too. I’m leaving my Ray-Bans at home.
  • Learn how to configure your phone to ensure that it doesn’t start doing data roaming abroad. This is different for each phone / provider. We may run into WIFI from time to time so you can check email, etc.
  • Also consider bringing a lightweight backpack for our day trips. We can check in late April to see where you stand on this.
  • As shitty as Greece’s economy is, it is very likely we can find whatever we forget when we get to Athens (and even some of the islands). So don’t stress too much about making sure you bring everything. Some of the adventure is making do without the comforts you are accustomed to.

I wouldn’t change much if anything in this guidance after going on the trip. One mistake I made was bringing both my extensive Canon 7D camera kit and my more portable Sony NEX 5N kit. The Sony was more than adequate for the landscape and portrait shots I took on this trip. I only need the long 200mm and 300mm lenses for wildlife and sports so the Canon gear mostly sat unused in my cabin.

Final Preparation

We coordinated our flights (originating from Portland, Oklahoma City, and Orlando) to convene at JFK so we could all be on the same flight into Athens. Julie shared details on arrival logistics – Athens is much easier to get around today than it was my last time there in 1990. Our plan was to take the light rail from the airport into the city center where we knew of a hostel with lockers for us to store our luggage. From there we would do some site seeing before heading to Alimos to check out our boat in the early evening. That was the plan anyway – I will share more on what really happened in my next post.