Symi Island, Dodecanese
Pserimos Sponges
Kos Yacht View

One Week Sailing the Dodecanese South from Kos

One week Kos South

Follow in the footsteps of ancient Greeks and Romans

This one week route (as the name gives away) heads south once you’ve picked your boat up from Kos. And with no shortage of islands to fit in you can get all the way down to Tilos in the south and Astypalaia in the west. Having all the typical Greek charms and no shortage of ancient ruins this area of Greece harks back to the old times. This far flung archipelago beckons modern day adventures to explore these timeless islands.

On this route you’ll be following in the footsteps of many time periods, from Greeks and Romans to crusading medieval knights and Ottoman potentates. If you want to take a walk and explore the views then Tilos is your best stop, while if you’re more into climbing then the limestone cliffs of Kalymnos are for you. If you want to explore from a different angle then go diving and explore the underwater caves and ancient wrecks, these islands are off the beaten track slightly and give you Greece from a different perspective.

What's the weather like?

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 in Greece 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

When you arrive at the marina you'll be met by the charter company staff who will handle your check-in. Once this is done they will show you to your boat and after a quick briefing it's over to you! Time to relax with a drink!

On your first evening there's plenty to explore in Kos. The town has a fantastic mixture of Turkish and Italian influences, particularly when it comes to the food! It also some has a great balance between peaceful mornings and fun-filled bars in the evenings.

  • Kos Old Town Wall Kos

Days 2 - 3, Nip north to Kalymnos

From Kos why not head north to the island of Kalymnos? Here you can choose from the bustling Pothia which is the main harbour on the island where you'll find mopeds whizzing around the narrow streets, or if you prefer a slightly quieter scene then head to Vathi Bay. We can only describe this place created by a fjord as a little slice of heaven.

From Kalymnos it's a short hop up to Leros Island. This town has a main port in Lakki, full of friendly marina staff and the town behind which has a slightly 1930's Art Deco feel to it.


  • Kalymnos Village Kalymnos
  • Leros Marina Leros
  • Quaint Taverna by the water in Little Vathi, Meganisi Vathi

Days 4 - 5, Sail South and island hop away

From Leros a great day's sailing is heading south to Astypalaia. This town is covered in rocky coasts and pebble beaches and is steeped in history. If you head to the main town of Chora you'll see the old castle at the top of the hill.

After you've had your history fill in Astypalaia sail east for around 20 miles to the island of Nisyros. This island is completely untoched by tourism and is one one of the most beautiful islands in the Dodecanese. It has plenty of tiny villages with tavernas serving fresh seafood and its main harbour Mandraki is a popular stop over. Its lovely winding streets that reveal hidden bars and tavernas all surrounded by the typically Greek white washed houses make this town perfectly picturesque. 

  • Gorgeous Greek Church overlooking bay Nisyros
  • Astypalaia, Dodecanese Astypalaia

Days 7 - 8, Top it all off in Tilos

Tilos from Nisyros is around 10 miles and is a lovely sail. This island is often overlooked but the main harbour of Livadhi is a quintessential Greek village which has some great restaurants lining the waterfront.

On your last day it's time to head back to Kos and nice last sail back up from Tilos. It's around 15 miles and most charter companies like you to be back in the marina between 4-6pm, giving you one last evening to enjoy what Kos has to offer.

  • Yacht anchored in Turkey with a mountain view Tilos
  • 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

  • Kalymnos

  • Leros

  • Vathi

  • Nisyros

  • Astypalaia

  • Tilos

  • Kos


Tell us about your holiday


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