Sailing Itinerary Around Kos Greece

When our friends arrived we sailed around the island of Kos visiting several locations. Use our trip as a sailing itinerary for the area around Kos Greece. The places we stopped included: Palionisou on the island of Kalymnos, Alindas – Leros, a bay in Leipsoi, Skala – Patmos, Xerokambos – Leros, Palionisou – Kalymnos, and Pserimos.

If you’re going to hire a charter boat and sail these waters or even if you have guests to visit you in Kos, here’s a handy itinerary you can use.
We were fortunate to have Steve, Becks, and Megan Stubbs (age 11) with us for some Greek island hopping in the Dodecanese region (map below). For them, it was a sailing vacation. For us, it was an opportunity to share our new lifestyle with loved ones.

The Stubbs family has been our first family aboard Britican for a sailing vacation.

And for them, it’s the first time they’ve spent longer than a couple of days aboard a boat. Previous vacations included camping, renting a French villa, or staying at a hotel for a fortnight. If it wasn’t for us going on our grand adventure, I’m not sure if they’d ever considered a sailing vacation?

So, now that their time with us is over, I wonder what they’re thoughts are?

Was it what they expected? Did they like it better than other vacations and is it something they’ll want to do again? What did they like the most and what did they dislike? Or did any of them discover that 10 days aboard our floating home wasn’t for them?

Carry on reading to find out what we did over the 10 days and also discover the Stubbs family thoughts…

Before I get started – some background on taking a sailing vacation.

Making the decision to enjoy a sailing holiday isn’t something that’s taken lightly. Several people worry about seasickness. Others worry about what is involved and how to go about planning a sailing excursion. And I’m sure several people happen onto sailing holidays simply because a friend or friends invite them to the experience like we have invited the Stubbs family.

There are several options for anyone or family interested in a sailing holiday. On one extreme, you can personally hire a boat and sail it to wherever you want to go. Often very little training is required – it depends on where in the world you want to go and your past experience. When we first chartered a boat my husband went on a weekend sailing course and that’s all that was needed for us to hire a 35’ sailboat in the Ionian Islands, Greece.

On the other hand, you can have a boat sailing for you by a professional or you can join other parties on larger boats.

And there are options in between! Perhaps you want to sail but are less confident when it comes to leaving and entering a mooring. If you join a flotilla there’s a crew, on land, helping to slip lines and then show you where to go and helping to get you tied down or your anchor set at your next destination.

Anyway, let me paint a picture for you as to what a sailing vacation can be like. I’ll walk you through the 10 days that the Stubbs family spent with us.

Day 1: Arriving in Kos, Greece

A few weeks before our friends booked flights, we told them to check the prices on two locations – Kos or Rhodes. The flights to Kos worked best, so they booked flights while we headed from Athens towards the Dodecanese islands. Having 3 weeks to get to Kos was plenty of time.

Two days before their arrival we entered Kos marina and spent our time cleaning the boat, doing laundry, and preparing for our friends. Not before long, it was hours before we’d be greeting them. After 4 months of not seeing our friends, we saw a taxi arrive at pontoon ‘B’ and I heard my husband, Simon, yell out, ‘I think they’re here!’

My daughter who stayed up late until 10:30 pm jumped off the boat and ran as fast as she could.

Stopping 2 feet away from Megan, Sienna looked at her best friend with absolute happiness. Simon said, ‘Sienna, it’s okay – give Megs a hug!’ The two girls hugged and then there were loads of hugs and smiles going around.

As the sun was setting behind the marina, we walked the Stubbs’s onto the boat leaving their luggage on the aft deck.

Sienna was so excited that she wanted to give everyone a tour. And there was a surprise in Megan’s room – Sienna put up streamers and a picture of her and Megs that was taken last summer.

Steve and Becks were shown their room and then we all sat in the cockpit enjoying some wine and beer chatting about all sorts. We couldn’t help but recount many of our sailing stories. Our desire to share our experiences with close friends was unstoppable.

The two girls went to bed and the adults stayed up until 1 am. Tomorrow our sailing adventures would start, so we helped Steve and Becks get their bags into their room and we said goodnight.

Day 2: Palionisou (harbor), Kalymnos (island), Greece (country)

We all woke around 8 am, ate some cereal, and leisurely prepared the boat to leave Kos. We stowed things away, tidied up, closed windows and hatches, readied the lines, and put the cushions in the cockpit.

Previous to our friend’s arrival we were experiencing the Meltemi, a weather pattern in the Med that blows very windy from the north and northeast. Thankfully, the Meltemi was over and calmer winds were on the cards.

Upon leaving the docks at Kos Greece, attendants helped us remove our lines.

We then exited the marina, coiled our warps (ropes), put our fenders away, and then turned into the wind to pull the mainsail up. I took Steve up to the mast with me and explained how to raise the mainsail – I pointed out the main halyard, hooked it to a winch, and then started raising it. I indicated what I was watching out for – the sail needs to go up between two sets of guiding ropes and all the reefing lines needed to go up without getting tangled.

It wasn’t long before we pulled out the forward sail – the genoa. After a few minutes of work, the engine was turned off and we were sailing to our first destination. On the way we chatted, enjoyed some fresh-cut cucumber and carrot sticks, and took in the sites. I was so happy to have my bestie (and her hubby) with me! And of course, Sienna was thrilled to have her bestie too!

By 11 am, we were on our way to Palionisou on the island of Kalymnos.

The winds were mild and the sail was easy going – a great way for our visitors to start off.

Our sail was so calm and peaceful so I decided to serve lunch as we slowly made our way forward. We enjoyed a Greek Salad, Fresh Bread, Taziki, Hummus, and lunchmeats. Everyone enjoyed the light lunch over the more wonderful conversation.

After a few hours, we furled in the genoa, dropped the mainsail, and entered the harbor of Palionisou.

Our first mooring away from Kos Greece was ‘easy’ as there were several mooring buoys available to tie onto. Rather than having to back into a tight space along a quayside, we simply needed to run a warp from the bow of the boat to the buoy and then back to the boat. Mooring buoys are floating balls that are attached to cement blocks on the oceans floor that act as anchors.

Steve and I used the thing I call, ‘the pokey stick’ to reach down off the bow, pull the buoy upright and thread one of our warps through a metal hoop at the top. We then took the warp back onto the same side of the boat and repeated with another warp on the other side of the bow.

By having two warps you can rest assured that if one rope fails another is holding the boat fastened.

Fastening ourselves took ten minutes or so and then we had a few jobs to do before jumping into the beautiful blue water. We put the sail cover on, tidied all the ropes, and cleaned up the cockpit.

It didn’t take long for Steve, Becks, Megan, and Sienna to jump off the back of the boat! With 10 meters below us, you could see the ocean floor as the water was crystal clear. Steve and Megan put goggles on and went exploring. I took the time to tidy up the saloon but it wasn’t long before I was jumping into the sea to reduce my core temperature!

That evening, we took our tender to Taverna Ilias and were greeted very kindly by a Greek husband and wife duo.

When I heard that everything was home-cooked and they had mousaka (traditional beef mince based dish), stuffed peppers and tomatoes and dolmades (mince and rice mixture wrapped with vine leaves) on the menu I had a difficult decision to make! Becks and I decided on mousaka and we were both very happy about our decision.

So we all sat on a balcony overlooking a beautiful bay dotted with about 10 yachts. Everyone was full of smiles and eager to carry on with the trip.

Day 3: Alindas, Leros, Greece

The next morning, we took our time enjoying the morning. Steve did some exercises on the boat. Becks sat up in the cockpit enjoying a bit of reading and I made some bacon and eggs for everyone.

There’s nothing like bacon and eggs on a boat! They seem to taste more amazing than they do at home.

After dawdling around for a while, Steve and I pulled off our mooring lines from the buoy and we headed back out into the Sea. Our next destination was an island called Leros.

During our sail, we chatted, read our books, took naps, and simply enjoyed the passing scenery. There’s very little to do while sailing but to take in the views surrounding you.

When we made it to Alindas on the island of Leros we looked for a space to tie a rope unto the rock face.

The set-up was to anchor your boat, back up towards the rock face and then tie a rope from the stern of the boat to a fastener on the rocks. By doing so it prevents the boat from swinging and more boats can anchor in the same area.

After a quick look around we couldn’t find any places where we felt comfortable so we simply dropped our anchor a bit further out in the bay. The views were lovely. Along the side of us, we had a variety of sail and motorboats tied to the rock face. Above the rocks, we discovered a little village dotted with tavernas, windmills and Greek homes. And at the very top of the mountain was a castle and several windmills.

When I saw the view, I thought, ‘well, you don’t see that every day.’

After a swim, we ate a lovely fresh lunch: Greek salad, potato salad and a pasta salad in addition to some meats and cheeses. Of course, we also enjoyed some fresh bread.

Simon and Steve took the girls into the village by boat and Becks and I lazed about in the cockpit reading, chatting, and even taking a bit of a nap. Normally, I would get off the boat and go for a walk around the village but I didn’t feel like doing much of anything and so I didn’t!

The great thing about sailing is that you can do as little or as much as you want.

There are days when we don’t feel like going anywhere, so we don’t. On other days, we not only want to go somewhere, but we want to get off on land and go exploring, so we do.

Later that afternoon Simon and Steve had a little backflip competition off the side of the boat and everyone did some snorkel. There were several shells found – all added to the collection building up in a big white bowl.

Aside from swimming, the girls enjoyed doing crafts in the saloon and ended the day with a movie and cookies.

No matter how hard we tried to slow down the days, they were over in a blink of an eye. Soon we’d be back in Kos Greece dropping them off.

Holding tight on the anchor, we all went to bed and enjoyed a lovely night’s sleep.

The morning was so amazingly peaceful. I was awake before the sun came up and anticipated a beautiful ball of fire rising in the east – I wasn’t disappointed. To my delight, I noticed that Steve and Becks were also up. They too woke up to enjoy the delights of a morning sunrise.

And not before long, we off to yet another destination. Megan helped me get the anchor up and off went to the island of Leipsoi.

Day 4: Lera Leipsoi, Leipsoi, Greece

After a quick 3-hour sail we arrived in a cute little bay off the coast of Leipsoi. With quite a bit of wind blowing, we found a patch of sand to lay our anchor into. The wind was blowing hard so we quickly discovered whether our anchor was set or not – it was! We moored up next to a Turkish Gullet and enjoyed the view of several other boaters.

In the distance, we could see a tiny harbor behind a rock wall and it looked as if there was at least one taverna. There wasn’t much on land. Perhaps a few homes and one restaurant? The rest was rocky land.

With the wind blowing so much, none of us wanted to go swimming. We all chilled out doing our own things for a while. Some of us laying in the sun. Others playing games. We ate some snacks, enjoyed some quiet time, and really soaked up the experience.

I was so happy to have my friend Becks with me.

It’s a funny thing with good friends – you can go months and even years without seeing them, but when you do, you automatically feel as if you’ve never been separated. Becks and I would chat about serious things and then we’d giggle about silly stuff. It was wonderful to have the time to just sit next to each other and not talk at all!

During the day, Simon and Steve took the girls ashore to explore. Once again, Becks and I opted on staying on the boat. We just didn’t feel like doing much! When the crew came back, I noticed a beautiful necklace made of volcanic stone around Megan’s neck. ‘Where did you get that beautiful piece,’ I asked?

Simon and Steve stopped off at a beautiful café bar/restaurant that had an adjoining jewelry shop. The guys were so impressed with the venue that they said we must go to dinner there in the evening.

It wasn’t long before all six of us were showered and boarding the dingy to enjoy a meal off the boat.

The guys were right about the restaurant – it was definitely impressive. It wasn’t very Greek. In fact, I would have thought I was in the Caribbean if I didn’t know any better. It wasn’t like anything in Kos Greece.

There were the white and blues common to Greece, but then there were thousands of colored pieces of fabric hanging from the open-air ceiling. And there were also thousands of dried bamboo handing too – the light clatter was sweet music! Additionally, there were beautiful colors in the bushes and flowers.

It was a little paradise tucked away in a quiet area of Leipsoi.

While at the restaurant we ordered salads for starters and then a variety of meals. I asked the friendly waiter what he recommended and ended up getting a fresh warm tuna salad with greens and herbs from the garden surrounding the estate. I wish I could explain what was in the salad is it was so tasty, but I honestly couldn’t make out anything other than Tuna! It was gorgeous.

We all enjoyed our meals, allowed the girls to play on the beach, and then headed back to the boat to retire for the evening.

It was another perfect day.

Day 5: Skala, Patmos, Greece

Needing provisions, or groceries, we had to find a location with a supermarket. The closest big town was Patmos, so we enjoyed a lovely sail to the harbor of Skala. We put our anchor down and reversed into the town quay.

Hearing the loud scooters, trucks and beach go-ers pass by was a stark difference to the tranquil bays we’ve previously been mooring in. We tied off to the quayside, pulled out our passerelle, or gangplank, and put our sail cover on.

I was impressed to see that Becks offered to climb up on the boom and pack the sail in!

How brave was she? When all was sorted, we headed to the beach. With a very quick walk, we were on a small little beach lined with a few café bars.

Simon stayed back on the boat to exercise our stopcocks – a monthly maintenance task, while my daughter and I joined our friends on the beach. After enjoying a cold Coke and a chat we all took turns to swim and/or watch the girls enjoy themselves in the water or pouring sand all over themselves.

At one point, Steve looked at me and said, ‘I don’t like it here.’

Instantly, I knew what he was talking about. Skala is loud, dusty, and filled with locals and tourists crowding the streets. It’s a nice place if you haven’t grown accustomed to quiet, natural harbors.

That being said, the village is super cute, there are several boutique shops and towering above the town is the monastery where St Paul wrote Revelations. Furthermore, within 5 km there are some spectacular beaches. We’ve previously been to Patmos and enjoyed the sites. It’s well worth a visit.

In the evening, we enjoyed a lovely meal on board and made plans to get up early, buy our groceries, and then head to Xerokambos.

We received a text from sailing friends that they were in the area near Kos Greece.

A few weeks back, we met a lovely South African couple and their two children, Sienna (9) and Tanna (11). The girls played with our Sienna and had a great time. They also had two guests with them – their friends Paul and Dale. When we first met we had a great time chatting. And it was so nice to see the girls run around having fun with each other.

Day 6: Xerokambos, Leros, Greece

So in the morning, we did our shopping – got bread, meat, veggies and lots of snacks. We then prepared the boat, slipped our lines, and headed for Xerokambos. It was a new bay for us so I was excited to see what we’d find.

Our sail was quite turbulent! The sea was rough and there was too much wind to allow our full sails out. We had to put a reef in and furl the front sail in. Nevertheless, Simon and Steve found someone they could race and the whole boat went flying ahead.

My little ‘to-do’ journey book blew overboard but luckily Becks saved my book. We all sat up on deck holding on tight.

Soon, we were in Xerokambos where the bay protected us from the winds.

We found several mooring buoys and Steve and I tied us on. We noticed our friends aboard ‘Why Knot’ quickly and were waving ‘hello’.

My daughter was excited to introduce Megan to her friends. Within a few minutes, the girls Tanna and Sienna were aboard our boat, and to break the ice I invited them all to make crafts. Becks brought out some colored paper and a craft pack filled with feathers, charms, popsicle sticks, and foam shapes.

The girls spent hours creating all sorts of pictures.

Thereafter there was swimming and Simon rigged up the tube on the back of our tender. All the girls had a go. You could hear laughter throughout the bay! In the end, all of us eventually ended up on ‘Why Knot’s’ beautiful Catamaran for dinner.

So the four adults from our boat got together with the four adults from ‘Why Knot’ to enjoy an evening of food, discussion, and laughter.

And the four kids played until they dropped – they went swimming, played in the canoe, played hide and seek and eventually became too tired to move anymore.

In the end, the girls all cuddled together to watch a DVD on a laptop.

The evening was precious! How often do you find yourself in a foreign country mixing with people from other nations while swinging around a mooring buoy in a quiet little bay? Everyone in the sailing community is so kind and making new friends – even if you have friends with you – is something that happens easily.

That evening, Megan slept over on ‘Why Knot’s’ boat with ‘Big Sienna’, and Tanna came over to sleep on our boat with ‘Little Sienna’.

In such a short amount of time, we all felt like family.

Having such a lovely time with the crew on ‘Why Knot,’ we made plans to all meet up in the next bay together. We recommended the bay with a fantastic Taverna Ilias – the one we enjoyed on our first day out.

Day 7: Palionisou, Kalymnos (Near Kos Greece)

After a day of sailing, we picked up a mooring buoy and settled into the familiar bay. There were more crafts, swimming, tubing, snorkeling, shell-finding, and back-flipping fun.

For dinner, we all met up at Taverna Ilias – all 12 of us! The girls all sat at one end of the table and the crew of Britican and ‘Why Knot’ mixed in with each other. Within a few minutes of taking our seats, the ‘Why Knot’ crew fell to the floor shouting ‘Dead Ant’ while kicking their arms and legs.

We just looked at them like they were nuts.

After they picked themselves off the floor, I asked, ‘what the heck was that for?’

Garth, ‘Why Knots’ captain explained that ‘Dead Ant’ is a game. Whoever is last to drop to the floor and do the ‘Dead Ant’ motion is ‘on’ meaning that they have to be the person that calls ‘Dead Ant’ next. When you’re ‘on’ you need to find the most inopportune time to make the call and everyone needs to drop down, yelling ‘Dead Ant’ while flailing around on the floor.

What a great game!

We all laughed and the restaurant owner had a sigh of relief after she realized that it wasn’t her restaurant that freaked everyone out. We ordered beers, wine, and homemade Greek meals like mousaka, dolmades, pork in the oven, and stuffed tomatoes.

We shared stories about all sorts. Paul, a ‘Why Knot’ crewmember told a funny story about a skit done over the VHF radio. It was all about saying ‘over’ over and over again. Normally, you say your message and then end with ‘over’ to allow the other person to respond. Paul was retelling the skit saying things like, ‘I just fell over, over.’ And then the response was ‘did you fall over, over, over?’ We laughed into the evening and finally made it home only to crash on our beds.

Day 8: Pserimos, Pserimos

We spent the morning watching a crazy boat leaving their mooring buoy, almost hit us, run aground, and then back into Tavern Ilias dock. Watching the incompetence of other boaters usually has high entertainment value. As long as we don’t get hit in the process, there’s always something to keep you entertained.

We sailed to the next bay – one recommended by ‘Why Knot’ and anchored outside the quayside. After 4 pm when all the day boats had come and gone we would be allowed to dock.

While waiting to moor on the dock we watched three of the day boats pull up other boat anchors.

It became quite stressful as boats started to come into the harbor wanting to moor on the quayside. There were only 4 spaces and already 3 boats were lining up to back in.

Imagine all these day boats trying to leave and getting stuck and then all these sailboats vying for a spot on the dock. After an hour, all the day boats were gone and the sailboats were safely secured. ‘Why Knot’ came in and got a space after the ferry left.

Wanting to return the favor for ‘Why Knot’ having us over for dinner, I invited the crew onto our boat for a range of salads and snacks. It would be the last night that Steve, Becks, and Megan would see ‘Why Knot’ so we enjoyed our time together. Megan slept on ‘Why Knots’ boat and Tanna slept on ours. It was great to see the kids have so much fun together.

Day 9: Kos, Kos Greece

That morning, we all gathered on the quayside and said our ‘good bye’s’. We took a group shot and then hugs and kisses went around to everyone.

Our plan was to head back to Kos Greece to spend the rest of the time exploring the island before the Stubbs’s had to fly home to England.

After leaving Pserimos we hit a bay not far for a swim and a spot of lunch.

While everyone was swimming, I made a potato salad with bacon, pasta ribbons with pesto, and a fruit salad. The food was greatly appreciated after so much swimming.

Sadly, we arrived back in Kos Marina where we moored the boat until the Stubbs family left us. We had time to walk around Kos Town, grab an ice cream, and find Hippocrates 2000-year-old tree. It was nice walking around for a while but I found the area to be very crowded. None of us used to seeing so many people!

Day 10: Kos, Kos Greece

For the Stubbs family last day, we all went to the see the Castle and walk around the many ruins – click on the pictures to see an enlarged image. We went for a swim in the sea and enjoyed food from the bakery. It was nice to see the sights but knowing that our time was coming to an end I couldn’t help but feel teary-eyed.

The 10 days that the Stubbs family spent with us were precious. We had time to enjoy each other’s company, time to appreciate simple things – good food, good friends, good swimming.

I will hold onto the memories of our time together forever. And hopefully, we can do it all again next year. Same people, same boat – different location!

But what did the Stubbs family think about their holiday? Good question… Read below to see comments left by Becks.

And hopefully, this sailing holiday example gives you an indication of how incredibly awesome sailing can be. Are you ready to book a sailing vacation now?!

Check Out Some Areas other than around Kos Greece & The Mediterranian

If you’d like a breakdown of all the places we’ve visited while sailing the Mediterranean please read our destination overview: Sailing The Mediterranean. Otherwise, check out more posts about our time spent in Greece.

• The Greek Ionian Islands
• Corinth Canal
• Delphi
• Poros Greece
• Kos Marina
• Symi