Pserimos Yachts
Patmos White washed
Astypalaia, Dodecanese

Two Weeks Sailing The Dodecanese from Kos

Two week Kos

Island hop until your hearts content

Much like our other two week route this option is perfect if you want to really venture further afield and see what the Dodecanese has to offer. With history everywhere you look you can island hop until your hearts content reaching all the way up to Fourni in the north and Astypalaia in the west.

What's the weather like?

Being closer to Turkey than the rest of Greece, the Dodecanese tends to stay warmer for longer. A windy destination for experienced sailors, the Meltimi blows through the islands reaching its peak in July and August with an average wind speed of force 4 – 6, with occasional gusts up to a force 7. It pays to pay attention to weather forecasts in the local area. At the beginning and end of the season, May and October, you will find an average wind speed of force 3 – 5.

The beauty of sailing here is that you will often find there are no mooring fees when staying on a town quay. If the local port authorities do come along, and ask you to pay, then you can expect no more than €10 for a 38ft yacht; note this is very very rare.

Typical Itinerary & Highlights

Days 1 - 2, Arriving in Kos

Once you arrive at the base you will be met by the charter company who will handle your check-in. Once you've completed the paperwork you will be shown to your boat, and after a quick briefing it's over to you, time to relax!

On your first day a nice warm up sail could be over to the island of Pserimos. This quiet and peaceful island has only one main town, Ormos Pserimou where there's a nice harbour with some great tavernas and a sandy beach.

  • Kos Old Town Wall Kos
  • Pserimos Yachts Pserimos

Days 3 - 7, Fast-track to Fourni

From the peaceful island of Pserimos you can island hop for days all the way up to Fourni.

Start with Kalymos Island, another short hop from Pserimos. And here you can choose from a few places to stop over, the main harbour of Pothia has a lively atmosphere or if you're looking for something a bit quieter than choose from Emporios or Vathi Bay.

From Kalymos continue north to the island of Leros. This island is less than 10 miles from Kalymnos, here you can choose again from Lakki, which has a 1930's Art Deco feel and is very quiet or head to Pandeli, a more lively town and harbour.

Once you've seen all that Leros has to offer keep heading north to the island of Arki. This is a great place to get away from it all, the tiny town next to the harbour has a few traditional tavernas and some great beaches, Tiganakia is our favourite.

After the short hop from Leros to Arki the next day is a longer sail up to Fourni, perhaps the furthest north you'll reach in a two week charter from Kos. Fourni is famous for its laid back atmosphere and has some great hikes and walk.

  • Kalymnos Village Kalymnos
  • Leros Marina Leros
  • Arki Island, Dodecanese Arki
  • Fourni, Kos, Dodecanese Fourni

Days 8 - 13, Sail South past Kos and beyond

From Fourni you can only really sail south and there's plenty of islands to stop off on. 

Fourni to Levitha island is a good 20 miles sail and once you get there you'll meet the only family who live on the island and run the great restaurant there. 

Another good sail is from Levitha on to Astypalaia, just under 20 miles. This beautiful island is steeped in history and has two stunning beaches, Kaminakia and Vatses.

From Astypalaia head east to the island of Nisyros. A slightly longer sail around 25 miles but well worth it. This volcanic island is known as one the prettiest in the Dodecanese and its main harbour Mandraki is a great place to stop over. There's plenty of bars and tavernas to visit whilst wandering the pebbled streets.

Once you've explored Nisyros it's a relaxed 10 mile sail to the island of Tilos. This island is often overlooked by tourists so is a great stop away from the hustle and bustle of peak season. The small village of Livadhi has a nice harbour with a surprising number of restaurants considering how little it is.

  • Yacht anchored in Turkey with a mountain view Tilos
  • Chalki Marina Chalki
  • Gorgeous Greek Church overlooking bay Nisyros
  • Astypalaia, Dodecanese Astypalaia
  • Levitha, Kos, Dodecanese Levitha

Days 14 - 15, Row over to Rhodes before heading back to base

From Chalki head to Rhodes (we don't actually suggest you row there!) but it's a nice sail over from Chalki and the Old Town is charming with all it's piazzas and the old moat walls that surround it.

After Rhodes it's best to make your way back towards Kos, but a stop off in Symi wouldn't hurt. This island has a calm atmosphere and its colourful charming buildings will surely draw you in.

Sadly it's the last day and time to head back to Kos, this is a nice last days sail from Symi but just remember most charter companies like you to be back in the marina between 4-6pm that day. This gives you one last evening to enjoy what Kos has to offer before heading home the following day.

  • Rhodes yacht through peephole in fortress Rhodes
  • Symi Island, Dodecanese Symi
  • Kos Old Town Wall Kos


What's Included

    • Return flights
    • Transfers
    • Diesel
    • Linen & Towels
    • Dinghy
    • Harbour Guide
    • Starter Pack
    • Full Financial Protection

What's not Included

- Yacht Security Waiver (£80-£270)
- Mooring Fees (£40-£120)
- Food & Drink
- Personal Holiday Insurance
- Child Discount -£65 for one week 
- Child Discount -£115 for two weeks
- Infants travel for just £50

One & Two Week Optional Extras - South Ionian Highlights, Paxos, Whole and South Ionian Flotillas

  • Manchester Flights £25
  • Brimingham Flights £25
  • Stansted Flights £25
  • SUP (paddleboard):
  • One Week £95
  • - Two Weeks £155
  • Dinghy Outboard:
  • - One Week £70
  • - Two Weeks £95
  • Cruising Chute



One & Two Week Optional Extras - Corfu, Paxos & North Ionian

  • Manchester Flights £25
  • Birmingham Flights £25
  • SUP (paddleboard):
  • One Week £95
  • - Two Weeks £155
  • Dinghy Outboard:
  • - One Week £70
  • - Two Weeks £95
  • Cruising Chute


Two Week Optional Extras - Saronic Islands & Sporades Flotillas

  • SUP (paddleboard) £155
  • Dinghy Outboard £95
  • Cruising Chute

Quick Yacht Price Search - For prices simply select party size and date

Below is an indication of the yachts that will sail on this flotilla. Please call us on 020 8459 8787 to check live availability.

Our Shore to Sail holidays are a combination of a one or two week flotilla sailing holiday with another relaxing week or two ashore.

These holidays will appeal to those who enjoy sailing but have family or friends who are not quite so enthusiastic about sailing - a compromise can now be made!

Most people opt for a week of sailing followed by a week of winding down on shore. However it is entirely up to you to do what you want to do (and when!)

Iris Hotel and Apartments

The Iris Hotel has been a popular choice for flotilla sailors for many years. This accommodation option will fit in with any of our flotillas starting and finishing on Lefkas Island. The hotel itself is a small family run hotel located close to Nidri Town. It has a combination of studio rooms for two or three people and apartments that can sleep up to 4.

Salvator Spa Hotel & Villas

The Salvator Spa Hotel is perched in the hills above Parga town and is a slightly more luxurious offering. The rooms on offer range from the Deluxe Room for two people, up to the Superior 2 Room Villa for up to 6 people. The hotel itself has an excellent restaurant, pool and spa facilities and all villas come with their own private pool.


Villa MeandrosDJI 0202 copy

Our brand new villa in Sivota on Lefkas is exclusive to Sailing Holidays Ltd. Built with families and groups in mind, the 3 double bedrooms all feature en-suite bathrooms. Built into the hill the ground floor level comprises of the master bedroom, a large kitchen and living space. On the same level you will find a huge outdoor seating area and a private pool. 

Images from Flotilla


  • Kos

  • Pserimos

  • Kalymnos

  • Leros

  • Arki

  • Fourni

  • Tilos

  • Chalki

  • Nisyros

  • Astypalaia

  • Levitha

  • Rhodes

  • Symi

  • Kos


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