June - October

7-Day Sailing Holiday Southern Dodecanese Islands, Greece

June - October

7-Day Sailing Holiday Southern Dodecanese Islands, Greece

Seven days, endless sunshine, and a sailing holiday in Greece that feels like a cheeky wink from the Aegean. This Southern Dodecanese sailing adventure is all about swapping busy harbours for secret coves, cruise crowds for chilled vibes, and hurried sightseeing for slow, salty days. You’ll glide from the candy-coloured charm of Symi to Tilos’s wild hills, drop anchor in Chalki’s colourful bay, and marvel at Nisyros’s volcanic drama—all classic Greek island magic, minus the selfie sticks. We’ll squeeze in a quick hop to Turkey for a legendary feast at Ogun’s (because, let’s face it, who says no to Turkish meze?), but the real story is sailing in Greece the SeaScape way: barefoot decks, local laughs, fresh sea breezes, and sunsets so good they should come with a soundtrack.

We love this one week South because it has lots of variety, and we also get to see a glimpse of Turkey when we sail into Datca. There’s an active Volcano on Nisyros, Simi is always popular and simply beautiful, famous for its main town encircling the harbour, with rows of beautifully coloured houses.

* Mentioned islands are indicative, as the routes we plan and the islands we visit always depend on sailing conditions dictated to us by the Greek gods Poseidon and Aeolus. As true SeaScapers we always make sure you’ll have the trip of a lifetime.

Greece sailing holidays for solo travelers & private groups

All Greece sailing holiday itineraries are available for everyone. Traveling solo, with your partner or a friend? Hop on board of one of the ‘share boat‘ weeks together with other fellow travellers. The other option is to book a private charter week for your own private group, which is available for up to 8 persons.

share boat - 7 days

For individuals, couples, or friends travelling together – join likeminded adventurers on one of our share boat weeks.

Based on sharing a bunk bed or double cabin (ensuite)*

€ 1395

low season

€ 1595

high season

private charter - 7 days

Already have your own group? Charter the whole boat with our skipper and hostess to have the time of your life with your partner, family or friends on a private sailing trip. Private charters are available from

€ 6500

low season

€ 7500

high season

Low Season – May and October
High Season – June, July, August and September

*Cabins for private use in Greece are available at a 50% extra fee

Best months to sail

For those who like a little adreline with their sailing, the midsummer months have the strongest winds: 25knots or so on average. It tends to be a little mellower in the early and late season. Even if you never sailed before, you could join any month really. There is no such thing as beginner months or intermediate / advanced months. From late May-Oct, it’s pretty much guaranteed sun, sun and more sun – once again, a perfect yachties’ playground!

Sample Itinerary

Kos to Nisyros

Embark 9:00 AM in Kos. After boat briefing, unpacking, and generally getting comfortable with the yacht, we’ll set sail for Nisyros – the volcano island. After noonwe will stop in a quiet bay for a delicious on-board lunch and a swim, before we continue our sail to Nisyros. The island is not on the main ferry routes, nor does it have an airport… which has happily kept it from any mass tourist influx. The traditional little harbour town is just gorgeous – a photographer’s dream of postcard material around every corner. The volcano is still officially active, though has not erupted since 1888. One can hike around the huge, lunar-like crater, the smell of sulphur still very much in the air. During the day we’ll arrange a car for you to hire so that you’re all prepared to head up to the volcano the next morning by the crack of dawn. After enjoying our first ‘anchor beer’ – our daily ritual after successfully docking the boat in port – we’ll go out for dinner in a small family taverna right next to the dock.

Miles: 22.5
Duration: 4.5 hours

Nisyros to Tilos

Tilos is a green, eco-conscious island with just the right amount of charm to make you want to linger. The island is famous for its medieval ghost village, Mikro Chorio, perched on the hillside, where abandoned houses echo with the past and goats act as unofficial tour guides. Bonus trivia: dwarf elephants once roamed here. Yes, you read that right. History, wildlife, and a perfect swimming bay make Tilos a quiet, restorative stop.

Miles: 18
Duration: 3.5 hours

Tilos to Chalki

Next up is Chalki, a tiny island that’s basically Greek island life distilled. Pastel neoclassical houses cluster around the harbor, fishermen mend nets at the water’s edge, and the pace is slow enough that you start to forget what day it is. We want to arrive in Chalki on time to find a space at their tiny town dock. Many of our passengers say that Chalki was one of their highlights, not only because of its picture-perfect pastel houses, but also for enjoying the little things in life… Wandering around without specific destination, enjoy a delicious freddo cappuccino and meze dinner until late, or swim in the beautiful blue bay around the corner.

Miles: 18
Duration: 3.5 hours

Chalki to Symi

From Rhodes we return to the delicate charm of Symi Town, a harbor that’s one of the prettiest in all of Greece. Pastel mansions climb the hills like an Aegean painting, their reflections shimmering in the water. While it has some similarities to the architecture you’ve seen in Chalki, Symi is more lively with all of its restaurants and bars around the horseshoe-shaped port. After we let all of you wander of in town, we reunite later for a dinner that will most certainly include Symi shrimp. Lively as Symi is, we won’t expect you to be back on the boat and in bed before midnight – this is the place to go out for some late night drinks if you’re up for it.

Miles: 31
Duration: 6 hours

Symi to Hayıtbükü, Turkey

Sail to Hayıtbükü – a lovely sandy beach; a little village and farmland as the backdrop. The key feature here is “Ogun’s Place” – an off-beat little establishment, right on the beachfront. It’s a restaurant, bar, hangout spot all rolled into one. We’re welcome to use their beach beds, wifi, showers and generally feel like visiting family (we pretty much are, after all these years). The main character is Ogun himself – the larger-than-life, exuberant proprietor. He bounces around from table to table with his characteristic Ogun laugh; smiles are always infectious, and Ogun’s Place reflects his contagiously positive energy. Ogun’s sister, Semra is responsible for the very unusual array of home-cooked food which they are also famous for. Married to a French guy, imagine the combo of French and Turkish cuisine… yum!!!

Miles: 18
Duration: 3.5 hours

Hayıtbükü to Kos

It is time to sail back to Kos. The luxury of land showers and a laundry, and perhaps a cold one at a bar. We will stop in a remote bay somewhere en route to enjoy our last lunch on board before continuing the journey back to Kos, where the loop began. After arriving back we’ll have an anchor beer, say YAMAS to this unforgettable time together, and possibly share favourite highlights with a sense of melancholy about this trip coming to an end. Our final dinner is usually at a gorgeous beachfront restaurant.

Miles: 27
Duration: 5.5 hours

Disembark the boat

Disembarkation is at 9:00 AM. For those wishing to stay longer in Kos, we can recommend some great little places to stay around the island. For onward travel, there are several daily flights to many European cities. You will definitely be heading home with a nice tan!

Sailing Schedule Greece 2026

June - October

Week	Dates	Destination	Type	Availability
20	May 15 – 21	Greece, Dodecanese	Private charter
21	May 22 – 28	Greece, Dodecanese	Private charter
22	May 29 – June 4	Greece, Dodecanese	Share boat
23	June 5 – 11	Greece, Dodecanese	Private charter	FULL
24	June 12 – 23	Greece, Dodecanese 12 days	Private charter	FULL
26	June 26 – July 2	Greece, Dodecanese	Private charter	FULL
27	July 3 – 9	Greece, Dodecanese	Private charter	FULL
28	July 10 – 16	Greece, Dodecanese	Private charter	FULL
29	July 17 – 23	Greece, Dodecanese	Private charter
30	July 24 – 30	Greece, Dodecanese	Private charter
31	July 31 – August 6	Greece, Dodecanese	Private charter
32	August 7 – 13	Greece, Dodecanese	Private charter
33	August 14 – 20	Greece, Dodecanese	Private charter	FULL
34	August 21 – 27	Greece, Dodecanese	Share boat
35	August 28 – September 3	Greece, Dodecanese	Private charter	FULL
36	September 4- 15	Greece, Cyclades 12 days	Share boat
38	September 18 – 24	Greece, Dodecanese	Private charter
39	September 25 – October 1	Greece, Dodecanese	Share boat
40	October 2 – 8	Greece, Dodecanese	Private charter
41	October 9 – 15	Greece, Dodecanese	Private charter
42	October 16 – 22	Greece, Dodecanese	Private charter	FULL

What's included with SeaScape Sailing

We don’t do ‘hidden extra fees’. Excluded are transportation from and to the boat, onshore dinners, and alcoholic drinks after the Happy Hour supply we provide you with (BYO!).

Artemis, our sailing yacht in Greece

Artemis is a modern-designed 55′ sloop, with a semi-pilothouse design which creates a very unusual – and huge! – split-level saloon. She has 4 ensuite cabins for 8 guests in total, 2 double cabins in the aft and 2 bunk bed cabins forward.

Ready to hop on board?