6-day Sailing Itinerary from Rhodes
There are tens of islands in the Dodecanese, of varying degrees of development: from thriving tourist spots like Kos and medieval towns like Rhodes, to secluded bays that you can only access by boat and which, if you didn't know better, you could imagine you are the first person ever to have visited. If you're only chartering for one week, then the natural itinerary from Rhodes are the islands immediately north of it, with Symi and Nisyros obvious destinations. If you had longer, or like longer days on a boat, it’s certainly possible to head out to Karpathos or Astipalea, or even right across to Crete.
The suggested itinerary below is a six day itinerary which covers 148 nautical miles. Although you'll charter for seven days, this itinerary is only for six days because you'll usually struggle to do any meaningful sailing on the first day – you might not be able to check in until after 4pm, and you'll be busy getting supplies on board for the week – or the last day (you have to return to the home base on Friday night, and won't be sailing at all on the Saturday you check-out).
That means you'll be sailing on average about 25 nM a day, and, with an average speed of at least five knots, should mean only four or five hours of making way (but shorter if you kick out more knots). The pace of your holiday should be quite leisurely, and you'll have time to get to know each of the places you visit, or spend time playing at sea, or throwing in extra stops, as the mood takes you – after all, this is your holiday. Enjoy.
Day 1. Rhodes to Halki – 33 nM 
Once you're certain you know which ropes are which, you've stowed all your kit, and you've checked that the crew are all on board, it's time to slip the lines and away. Gently bob your way out of the marina, point into the wind, and get the sails up! Then head North, taking the time to admire Rhodes from the sea – the medieval scene is a sight that has been like this for hundreds of years, so imagine leaving from here to go to war to fight for your religion!
Thankfully, we're not going to battle on this itinerary. After getting past Rhodes, we're heading South-west, following the northern coastline of Rhodes island (and past the airport) as we make our way to the small island of Halki. You'll likely be beating or close-hauled in the prevailing wind, so you should be seeing exactly what sort of crew you've assembled. But don't worry – you'll have a week to lick them into shape.
Halki is a tiny island with a population of fewer than 500 people at the last census, in one village. There used to be more people here, but the whole island was abandoned in the 1850s after people got so fed up of being ransacked by local pirates that they just left, with many emigrating to the USA. Of course, one of the things that made life difficult on the island is that there was no water source – until 2014, when they opened their first water desalination project, water had to be shipped in from nearby Rhodes. No, actually.
It's a sleepy island which is pretty much off the beaten track, and life moves at a different pace here. There are a number of tavernas or places to eat though, and you can be comfortable here. Outside of the village, there's still signs of derelict white-washed buildings ,and the beaches and nature are pretty much unspoilt.
Day 2. Halki to Tilos – 19 nM 
After a relaxing night in Halki, we’re heading north-west to the slightly bigger island of Tilos and the town of Lividia – it’s capital. From Halki, this could be reaching against a wind from the West or beating into a wind from the North-west, which are the two options for prevailing winds in summer in this part of the world. It’s only 19 nM, so there is even time to explore a few of the secluded bays on the South side of Tilos if you are inclined.
Tilos is about double the size of Halki, but given how small Halki is, that doesn't say too much! There are more facilities for tourists – including a hotel – but in general, this is a place which will feel a world away from all the passengers you shared an aeroplane with on the way to Greece.
This itinerary is honestly not just about abandoned former towns of Greece, but in Tilos there is the creepy ghost-town of Mikro Chorio, which was abandoned just after the second world war. The people left laden all their roofing tiles, but the stone walls are still standing and it’s a quirky place to wander around (and it’s only a short walk from the marina).
Tilos is also notable for being the first island in the world to run off green energy (wind and solar), and for the exceptional quality and privacy of its nudist beaches – so keep an eye out for those.
Day 3. Tilos to Kardamena – 26 nM 
From quiet beaches and tavernas, our next destination offers long and lustrous sandy beaches, as well as a lively night-life with strips of bars and even a few nightclubs. Kardamena, on the island of Kos, is a popular tourist destination in its own right, and people flock here to spend beautiful holidays on the beach here, and bathing in the crystal-clear waters.
If you're getting good speed or would prefer a longer sail, then you could head to the historic old town of Kos instead of Kardamena (check out our destination guide for Kos if you want to find out more about it), but we didn’t want too many long legs on this itinerary, and the change of pace at Kardamena shows the other side of holidays in Greece - it might be just what your crew need before we head back out to remote islands. Plus it gets us in a good position for heading to the volcanic island of Nisyros tomorrow, and giving us plenty of time to explore there.
The prevailing wind beyond Tilos is likely to be North-westerly, which means you’ll likely be beating up the wind as you work your way to Kardamena. Close-hauled is actually the fastest of all sail trims, and it’s not impossible that you’ll be able to make the distance in a single tack if the wind is blowing from the right angle of the North-west. Enjoy the sunshine, the beach, and your evening of being a land-lubbing tourist.
Day 4. Kardamena to Nisyros – 10 nM 
It's an easy sail from Kardamena to the volcano island of Nisyros, and it the shortest leg on this tinerary. That means you can spend more time on the beach in Kardamena, or, better, more time on land in Nisyros, where you probably have time to explore the youngest volcano in Greece, on one of the newest islands in the world (Nisyros is only 150,000 years old). It's possible to walk around in the 3km-wide caldera or crater of the volcano, or, if that’s not your idea of fun, to bathe in the naturally warmed 60 degree thermal waters.
The sail is pretty much due South, so you’ll likely be broad-reaching to run with the wind, but bonus points are available (and bonus street cred for the skipper) if you throw in a Goose-wing on your way down.
In Nisyros, you can choose to moor up in the picturesque village of Mandraki, which is the largest village on the island, and which has a brilliant monastery overlooking the village, or to berth at nearby Pali, which is even smaller, though there is still a bakery and a taverna there, and it’s only a few kilometres down the coast. If you opt for Mandraki, you might be surprised to find out it has its very own bar area – head to ‘Little Venice’ beneath the monastery, where you’ll find four or five lively bars. Oh, and you’ll need to buy a piece of local pumice for good luck when sailing away from the island.
Day 5. Nisyros to Symi – 35 nM .jpg "Symi")
And now for something completely different. Whatever you're expecting from a sailing holiday in the Med, it’s almost certain that Symi will surprise you. It's stunning, and impossible to put into words, but I'll try: it's a picture-postcard town made up of a mass of bright and colourful elegant neo-classical buildings which surround the port, and which cover the surrounding hillsides. By day it's incredible, and by night, it's phenomenal (and the port is the best place to be to see it). Wow!
The town has a good mix of shops (leather goods are the local product), and there’s plenty of tavernas and restaurants to sit and enjoy the evening with. You could also join the locals with a stroll along the promenade in the town. Aside from the beautiful town, Symi is a haven for wildlife, and everywhere on the island you’ll find tranquillity and unspoilt beauty. You can hike around the walking trails in the countryside and really feel like you are on another planet to your desk or computer.
Sailing-wise, you’re heading due East, so you should be reaching or broad reaching against the prevailing North-westerly wind, as you make your way below the Turkish coastline, and across to Symi. You’ll spot a few idyllic beaches on the Turkish coast - technically you’ll need to get the right paperwork in place before you’re allowed to visit – before nosing between Symi and the island of Nimos and heading South to the well-protected bay and Symi.
Day 6. Symi to Rhodes – 25 nM 
Oh no! How is it already time for the final leg of the voyage? This trip has gone so quickly, but it’s already time to head back to Rhodes, I’m afraid. From Symi, it’s a case of going North out of the bay, then following the coastline of Symi South. If you have time to pop back up and round the other side of Symi, the monastery of Panormitis is a very grand and impressive building which seems out of place with the small bay and remote island it occupies.
Heading further South (and in this direction, you should be running or broad reaching with the prevailing winds) the island on the nose of your boat will be Rhodes, so set your sails for the furthest land you can see on the port side, as Rhodes town is just around that headland. Arriving back to your marina in Rhodes, head to the fuel berth to fill up on diesel, before returning to the vague area you picked up the yacht or catamaran from. Someone will be along to inspect the boat tonight, but you'll still be able to sleep on her, before checking out in the morning.
Hopefully you've had a brilliant week of sailing, and have enjoyed island-hopping. The views are tremendous, the Greek weather makes it super-relaxing, and I'm sure everyone onboard has had a big smile on their face. If you haven't already got one, don't forget to get a team photo of the crew on deck! If you haven't had chance to visit Rhodes, then now is a great time to see what it is all about, and it should be lively in town tonight (particularly near the marina) as all the sailors return from a week at sea and exchange all their tales and blow off steam!
.jpg "Must See if you're Sailing from Rhodes")
Rhodes has beautiful weather practically all year round, with temperatures very rarely getting down to single digits. From March onwards, the weather is above 15 degrees, which is t-shirt weather, and from May to September, it's usually above 20 degrees. It peaks in July and August with average temperatures in the high 20s, but there will almost certainly be days where the mercury pushes past 30 degrees – which is hot enough to get you sweating in the shade!
