Sailing The Dodecanese
Sailing the Dodecanese is an incredible experience, and if you have the chance to sail Greece then these cruising grounds should be top of your list.
With good weather most of the year, stunning white-washed towns, and beautiful secluded anchorages, sailing the Dodecanese was a real highlight from our trip to Greece and one that really stands out for a whole number of reasons.
We’ve been asked many times about the best place to go sailing in Greece, and depending on what people are looking for, this is usually our top answer.
For this reason, we’ve decided to put together a sailing the Dodecanese guide for anyone heading there!
Obviously, it’s almost impossible to plan out a sailing route for you as we have no idea what wind and weather conditions you’ll experience on your trip!
What we’ve done instead is pick out some key islands and anchorages that you’ll want to consider including in your itinerary, and made a rough itinerary based on that, which you can alter depending on different factors such as your confidence, your boat speed, the weather conditions, your preferred anchoring or mooring set up etc!
If you’re sailing during the summer months then the wind is predominantly from the north (see below).
We’ve designed our itineraries based on this scenario, as summer holidays are a popular time to go sailing.
In our opinion, the best thing to do is sail north into the wind for the beginning of the trip. Then if you get caught out in a strong Meltemi and need to get home, you can almost guarantee downwind sailing for your return trip.
Quick Guide To Sailing The Dodecanese
Sailing The Dodecanese: Itinerary 1
Sailing The Dodecanese: Itinerary 2
Sailing The Dodecanese: Weather
The Dodecanese is a great place for a sailing holiday in Greece as it’s blessed with great weather pretty late into the year. Compared to the Ionian, it’s likely you’ll get some windy days, but it’s usually on the edge of the Meltemi winds so when they do blow they tend to be less strong.
The Meltemi blows from June to September, though over the last few years we’ve noticed they can start earlier so be a little prepared!
The great thing about the Meltemi is that it’s almost always well forecast in advance and it always blows from the north, so you have plenty of warning to find somewhere safe to anchor up and protected bays are well mapped.
If you’re comfortable sailing in higher winds then you will almost certainly get some really good sailing days, compared to the Ionian where you’re much more likely to have the motor on!
During the shoulder seasons you’re more likely to have long stretches of calm seas and little wind, but keep an eye out for thunderstorms and violent southerlies.
Although less frequent, when they do hit they’re a little harder to prepare for and find decent anchorages as most listed are focused on escaping the more common northerlies!
Being right on the border with Turkey, the Dodecanese is HOT during the summer, and into the Autumn. The sea in protected anchorages can literally feel like a bath at times and stays warm quite late into the year.
I get cold easily and found that I started needing a wetsuit for long stints of snorkelling around mid-October. But we even swam with no wetsuit on Christmas day and once you were in it was bearable!
For hiking the Dodecanese is definitely preferable in the Spring and Autumn. It’s greener then too and even prettier!
On some days during the summer months, the heat felt almost too much, as we both love hot climates. On a stuffy boat during the summer you’ll want to plan for trips to restaurants with air con during the day, and it’s important to make sure your boat is fitted out with decent, working fans!
Sailing The Dodecanese Itinerary 1
If you’re sailing during shoulder season then you’ll be best off starting with this itinerary and then mixing in bits of 1 and 2 depending on what weather you’re blessed with.
Starting in Kos gives you the option to head north or south (or even west if you fancy!) so you can choose when you get here and have some more flexibility!
We’ve designed this itinerary for sailors who are looking to visit the quieter, less explored islands in Greece.
Along this route, you’ll find off-the-beaten-track anchorages, some hot spots that are hard to reach without a boat, and some potentially trickier anchorages (with the option of nights on town quays if you prefer!) This was our favourite cruising area in the Dodecanese.
Kos
Start your Dodecanese sailing holiday in Kos.
Kos has easy transport links as it’s a popular holiday destination for all, and there’s also a large range of charter fleets that operate from here so you’ll have a choice of companies to pick from to suit your needs.
There’s a lot to love about this island and it’s a popular holiday destination for a reason, but as it’s easy to explore from a land base we would recommend leaving ASAP and heading to some of Greece’s less-visited islands. This is part of the reason you’ve hired a boat after all!
If you want a few days here to relax before the adventure starts then there’s a huge range of accommodation on the island. Check out these top picks!
Kalymnos
If the winds are favourable, head to Kalymnos for your first sail. Depending on which anchorage takes your fancy, you can make this sail a short one to get to know the boat, shake out your sea legs and leave plenty of time for a well-deserved drink at the other end!
Kalymnos is a stunning island, famous in the climbing community for its excellent rock climbing. The mountains make for incredible backdrops and if you can, try and hike up high for spectacular views.
One of the best things to do on this island is to go walking as the views are incredible, so make the most of the shoulder season here when the weather is cooler.
If you don’t fancy anchoring out then head to the Port of Kálimnos on the south side of the island. It’s relatively cheap to moor here and is very well protected, especially from the northerlies.
You’ll find all the amenities you would expect from a town, with a large range of restaurants, but it’s quieter with a more traditional feel to the touristy island of Kos.
You’ll find several museums and historic monuments here, and a visit to Chrysocheria Castle is worth while if you have the time.
If you’re feeling brave then head to stunning Vathys anchorage. It’s a tricky place to anchor in as it’s a busy, tight spot, but it’s pretty beautiful once you’re in there! If you get there and decide it’s a little too hectic then there are several good anchorages just round the corner.
If you decide to head a little further away to the West of the island then we loved Emborios bay, which was quiet and remote with a nice relaxing walk into the small village. If you’re there overnight then head over the top of the hill for sunset which is pretty spectacular!
Sailing In The Dodecanese: Leros
The next island up from Kalymnos is Leros. We found this island a bit of a mixed bag! On the East of the island, we loved Agia Marina with its pretty little town and winding path up the hilltop castle and row of windmills.
The town also has a great restaurant that serves fake meat for any veggies out there who want to try gyros!
We weren’t so keen on Lakki on the Western side of the island, but for history lovers, it’s well worth a visit.
You can find out all about it in our post on the best things to do in Leros. It’s very well sheltered from the northerlies and there’s a handy water-making machine in the small fishing boat harbour next to the main marina.
You’ll also find the best fruit and vegetable store in Leros in the town centre (possibly the best in the whole of Greece!) It’s got so much fresh produce that lasts forever and is super cheap. Just head up to the main roundabout and it’s behind the butchers there.
If you make it up to the North of Leros then Partheni has a great hurricane hole type anchorage. Good holding in mud and very well protected.
It’s not the prettiest and the water is murky, but it’s a good place to head to in bad weather. If you’re not here on charter then there are also two great boatyards here. We stayed in Artemis over the winter and can speak highly of the facilities and friendly staff.
For anchoring in the North of Leros head to Archangelos island. It’s well protected from the prevailing winds and is perfect for a swim or three.
Head to the small restaurant (the only inhabitants of the island live there) for an evening meal and to watch the sunset. But only if you like cats!
Lipsi
Lipsi was one of our favourite islands in the Dodecanese. It’s the perfect place to head to if you want to escape it all as it’s quiet and peaceful here.
If you’re heading here from the south then make sure you stop off at the small island of Makronisi. It’s a tricky place to get the hook down but the search for a shallow enough sandy patch will be worth it if you like to snorkel!
There’s a swim through here that leads to a fully enclosed sea lake, which is quite magical. The coordinates are listed on Navionics, so just follow the directions to find it.
We didn’t have the directions but managed to find it by following the light shining through the tunnel, but you’re best off being sure!
This isn’t a great place to stay overnight or in any bad weather, as the holding isn’t fantastic, so you can make a short jump to the nearby anchorage of Papantria Cove which is nice and enclosed.
Climb up to the viewpoint above the anchorage to get a pretty view of the bay below, and if you’re feeling more energetic you can follow the road into the main town.
Follow any of the roads and you’ll get some great hikes, almost all of which will lead to secluded beaches and coves. Pack a picnic and your kindle and pick a direction, then relax and swim in the crystal clear waters.
There are some great farms and local stores dotted along the roads so if you spot one make sure to pop in and purchase some local Greek goods. The honey is delicious!
For a day trip/lunch spot head northeast to a small collection of rocks just off the main island.
This place is a paradise for anyone who likes to simply relax. Put up the hammock and enjoy the turquoise waters from your boat or head to the white pebble beach and cool off with your feet in the water.
Patmos: Sailing The Dodecanese
According to the tradition, Saint John the Divine was inspired to write the Book of the Apocalypse inside a cave in Patmos. Thousands of pilgrims come to Patmos island every year to visit this important religious island.
There’s a lovely anchorage on the East of the island, Grikos, which is near Petra beach with its giant rock feature rising from the sea. You can climb it for impressive views but be careful of your footing!
Skala town itself is pretty and full of the usual delicious Greek tavernas and a decent supermarket for provisions.
We anchored here and took the dinghy in as the town quay itself looked a little hectic! You can get to the so-called “Cave of the Apocalypse” which is one of the island’s main attractions. There’s also a large monastery dedicated to Saint John above Chora.
There are some other great anchorages around the island, all with lovely walking trails nearby or great water and snorkelling.
One of our favourite little bays was Livadi Geranou where we found some good snorkelling and had some really peaceful nights at anchor and incredible sunrises! Just be careful on the entrance, but the hidden rocks are marked clearly on the charts.
Fournoi
When we visited Fourni in October we saw one other boat on the whole island – the one we’re anchored next to in the picture above! It’s a lovely, laid-back island with a really traditional feel. Plus, look at the colour of that water!
In terms of anchorages, we really struggled here. There are a few that would be well protected from northerlies but we had a horrible swell coming in and eventually found a tiny anchorage tucked away that isn’t listed on Navily. We’ve added a link to it on No Foreign Land.
The town here is tiny but has a few small restaurants and shops. You can moor in the harbour but just watch out for the big shipping boats that come and go.
The trekking on this island is fantastic and we stumbled across some great walking routes with good views. Though it might be best to save the long walks for the shoulder seasons to save you walking long distances up hills in the heat!
If You Have Time: Samos
Technically not part of the Dodecanese chain of islands but if you’ve ventured up this far north then we’d be remiss not to mention it.
Samos is just a short hop from Fourni and well worth a visit if you have the time and weather.
We fell head over heels in love with this island. It has a certain charm that’s very individual and we haven’t seen another island quite like it in all of Greece.
If you are lucky enough to get calm weather or southerlies then try to make it to Kokkari in the north of Samos.
This little town has a relaxed, laid-back vibe and has the stunning backdrop of some beautiful mountains. The harbour here is relatively protected from all but northerlies.
You should also make time to visit Pythagorion, with its mathematical history and art-filled streets. There’s the option to come onto the town quay here or anchor out in the harbour.
Visit the church here for some great sea views and pretty architecture. There are some decent supermarkets to get provisions and lots of options to eat out along the main drag.
Walk along the harbour towards the rocks to find some cute cafes and bars that aren’t as crowded as the main options!
There is also a decent marina/boatyard in Samos but we found prices to be a lot more expensive compared to Leros. Rates change all the time so if you’d rather winter here then make sure to enquire!
Sailing The Dodecanese Itinerary 2
Rhodes
There are some lovely anchorages between Lindos and Rhodes town but they were small and very busy. If you fancy a few nights away from a town then we’d suggest getting there late and leaving early. That way you’ll probably have them to yourself!
You can moor up in Rhodes town but we read negative things about the protection in there and anchored put instead. There’s an anchorage south of the town that’s just close enough to walk in (though it can feel a bit of a trek in the summer heat!)
The old town is just stunning. We planned a day here and extended our stay so we could wander the little ally ways and the fort for longer. It’s a tourist hot spot for a reason!
Sailing The Dodecanese: Symi
We loved it here but (for us at least) it wasn’t the easiest place to anchor! There are some really beautiful anchorages that are super deep, so be prepared to get in shallow and drop a lot of chain!
St George’s anchorage is just stunning but we dragged here when the catabatics kicked in so be a bit careful!
Our favourite anchorage was in the little village of Pedi. You can anchor in reasonable depths or tie up for free on the town quay (and we hear they’re building a proper marina here – if you have any news of this we’d love to hear from you in the comments section below)
There’s a little store here that sells most things and some lovely restaurants along the waterfront.
Take your dinghy around the corner to the lagoon-like bay where there’s a little island with a chapel on, and a huge stretch of shallow, sandy water to relax in!
The other great thing about Pedi is that it’s a nice walk into Symi town itself. It’s a bit hilly so set off early or late, but stop halfway up the hill at Secret Garden restaurant, that’s covered with plants like a tropical garden! Walk all the way to the church at the top of the hill for incredible sunset views.
Symi town itself is the perfect place to just wander. If you come on the town quay here then make sure to walk up high and get the view down on the town! It was busy on the town quay when we visited but there were lots of people around to help with lines and a nice buzz in the air.
It’s worth coming for a couple of days at least. We ended up here for two weeks and loved it. If you don’t fancy sailing here then the ferry is super easy and quick to catch from Rhodes so you could take a day trip to sightsee instead of actually sailing here.
Tilos
Tilos has very few listed anchorages for a biggish island, probably because the depths here can be pretty substantial. We found it hard to find shallow enough spots to anchor in a few places so that’s something to bear in mind if you head here.
The main harbour can be a little chaotic and busy during the summer months so we stayed well away!
There’s also a huge ferry that comes and goes frequently kicking up quite a wash, so if you’re anchored anywhere near the entrance to the town be on the lookout for that!
The town is nice with a range of restaurants and cafes. We were interested to read that the local authorities have turned the island of Tilos into a fully self-sustained island by using renewable sources, have performed the first same-sex marriages in Greece in 2008, and have in place an excellent program for refugee integration.
This warmed us to the place!
It’s quite a wild, mountainous place once you get away from the main town, with some good trekking routes and nice rugged scenery. Just be sure the hook is in as the catabatics can be quite strong!
Nisyros Sailing The Dodecanese
We didn’t actually stop at Nisyros island but we really wish we had! We heard great things from other cruisers so it will certainly be top on our list for when we return.
Anchoring here is tricky so you’ll want to come onto one of the two town quays and hire a car to explore the volcano island properly.
Chalki
Head to Chalki for the charm of Symi without the crowds. With little to do here except relax, eat delicious seafood, or head off on a hike, this is a great overnight stop.
It’s a small island with basic facilities but there are a few nice anchorages where you can either enjoy a stroll around the town or head further out to take a swim in crystal clear waters.
Another good option for anchorages close by is to head to the neighbouring island of Alimia, which is even smaller but perhaps even more naturally beautiful!
Sailing The Dodecanese: Lindos
Lindos, back on the island of Rhodes, is a fantastic anchorage to spend a few nights and is especially good to keep in mind for unsettled weather.
It’s super protected with good holding, and it’s not too shabby looking either! It’s a great place to come full circle on a sailing tour of the south Dodecanese, and from here it’s an easy sail back to Rhodes to drop off the boat.
It does get a little busy with powerboats so it’s not the ideal place to swim, and the wake is a little much at times, but hopefully, you’ll be busy exploring the town most of the time anyway!
There’s a huge range of restaurants (we ate Indian for the first time in two years!) And the hilltop ruins are well worth a visit.
Climb up there at night too for a view of all the town lights. There are some small grocery stores but think postcards and fridge magnets rather than useful boaty provisions. Get lost in the backstreets and head in early for some quiet.
Check out the best things to do in Lindos for some great beaches and for more details on some of the best things to do in this charming tourist town.
Alternative Sailing Destination: Astypalea
This butterfly-shaped island is a little out of the way, and might be better suited to a sailing holiday in the Cyclades, but as it’s a Dodecanese island we thought it deserved a mention here!
Astypalea is simply beautiful. Untouched by tourism with so much to love. The only problem with it is getting here, and leaving!
Astypalea is bang smack in the middle of the worst of the Meltemi’s path and it can blow strongly here and for weeks at a time (we spent 3 weeks trying to leave and even when forecast 10knts we got hit by over 30 every time).
It’s a great problem to have, being stuck in paradise, as long as you don’t have somewhere to be! So think it through before you come here!
We’ve written up the best things to do in Astypalea. If you’re looking for anchorages, I think we visited every single one except the town quay (which looked pretty quiet in June)!
The highlights were Ormos Livadhia, a big wide bay with great holding when you found a sand patch and good protection from the winds. From there it’s a hike up to the old town.
We also loved the tranquil Agrilidi and the nearby island of Koutsomiti for a lunch swim stop. To the north of Astypalea Vathy provides excellent all-around protection.
Hopefully, this has inspired you to visit this incredible area of Greece. Sailing in the Dodecanese is a really special experience and we would absolutely love to hear from you if you’re planning a trip or have more we could add to this guide!
You can leave a comment below or send us an email at twogetlost at gmail dot com! And please do join us on social media to see what we’re up to now and get regular updates on our newest posts.
About Us!
Hi there! We’re Emily, Adam and Tiny Cat, liveaboard sailors travelling the world on our 38ft sailboat and writing about it as we go. We hope we can inspire you to live the life you’ve always dreamed, whether that’s exploring the world or living a more simple way of life in a tiny home.
