Astypalaia, Dodecanese
Kos Yacht View
Kalymnos Yacht

Two Weeks Sailing The Dodecanese from Rhodes

Two week Rhodes

Soak in the history and culture

Much like our one week route out of Rhodes this option is perfect if you want to soak up all the history and culture the Dodecanese has to offer. With ruins and old forts by the bucket load all spread out across numerous islands, this route is ideal for the more adventurous sailors. Those who want slightly stronger winds and to explore this relatively undiscovered area.

What's the weather like?

Being closer to Turkey than the rest of Greece means this area stays 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 Rhodes

Once you arrive at the base you'll be met by the charter company who will handle your check-in. After your paperwork is complete you'll be shown to your boat and after a quick briefing it's over to you! Time to relax and start your holiday! There's plenty to do on your first evening here. The Old Town is particularly stunning to stroll through and see the old moat walls that used to be the town's defense.

From Rhodes a great first sail is around 10 miles over to Symi. This colourful town is a must visit with its neo classical look and there's also some great beaches, particularly Toli Bay. 

  • Rhodes yacht through peephole in fortress Rhodes
  • Symi Island, Dodecanese Symi

Days 3 - 6, Cruising past Kos

From Symi you could head west to the island of Nisyros. Under a 20 mile sail and in that time you can get to Mandraki, the main harbour on the island. There are plenty of pretty villages to discover and it's often called one of the most beautiful islands in the Dodecanese. Due to it's volcanic nature and the white washed houses made from this rock we can see why.

After Nisyros head north past Kos and up to Emporios on the island of Kalymnos. Emporios is a quiet seaside town with some traditional tavernas, cafes and seaside restaurants and if you fancy it venture to Kastri in the north of the island, where the old fort from the Hellenistic period still stands.

After you've explored Kalymnos Island continue north to Lakki on Leros Island. Lakki is the main port of the island and has a distinctly Art Deco feel to it which makes it stand out from the other islands. 

From Leros Island it's a short hop northwest to Patmos Island. This island is often compared more to the Cyclades than the Dodecanese with its barren rocky slopes and white wash houses. The monastery here is worth a wander around above Chora.

  • Kalymnos Village Kalymnos
  • Leros Marina Leros
  • Gorgeous Greek Church overlooking bay Nisyros
  • Patmos White washed Patmos

Days 7 - 10, Nip north to Samos and back

From Patmos it's a very short hop over to Arki Island. Around 5 miles east of Patmos this island is a great place to have some peace and quiet. The main harbour has some traditional tavernas next to the port and the nearby beaches are great for snorkelling. We highly recommend Tiganakia beach.

After Arki you can get as far north as you can up to Samos. This is around a 10-15 mile sail from Arki. Samos is great for any wine connoisseurs as it used to be famous for its vineyards and wine production. 

From Samos it's best to start heading back south, and a nice stop off is in Agathonisi on the island of Nera. This is a short sail over, less than 10 miles and once you get here it's peace and quiet you'll find. The main port is Agios Georgios which has some bars and tavernas and the beauty of this island is it's basically traffic free.

Once you've seen all that Agathonisi has to offer, contiune south for less than 10 miles back to the island of Leros. Except this time on the west of the island to the town of Pandeli. The houses here are covered in bougainvillea and fishing is the main income here so you'd be silly not to try some of the fresh fish caught that day in one of the local tavernas.

  • Leros Marina Leros
  • Agathonisi Agathonisi
  • Arki Island, Dodecanese Arki
  • Pythagorion, Samos, Dodecanese Samos

Days 11 - 13, Pop to Pserimos and beyond

From the island of Leros it's less than 10 miles south to Pserimos. A peaceful and sleepy island, with one main harbour, Ormos Pserimou that has tavernas and bars surrounding it.

Once you've soaked up all that Pserimos has to offer it's a very short hop over the vibrant island of Kos. This much larger island has plenty of bars for you night owls but it also has a unique mixture of restaurants due to its interesting turkish and italian influences, so there's a wide variety to choose from.

From the bustling Kos why not sail south to Tilos. It's around 15-20 miles and is often missed on the mass tourism radar. The little quay in Lavadhi is nice place to stop and there's a surprising number of restaurants for such a small village. 

  • Yacht anchored in Turkey with a mountain view Tilos
  • Kos Old Town Wall Kos
  • Pserimos Yachts Pserimos

Days 14 - 15, One last stop before heading back to base

From Tilos on your way back to Rhodes you could stop off in Chalki. Less than 10 miles from Tilos this is the smallest island in the Dodecanese. There's only one town on the island called Nimporio and along the promenade here you'll find many tavernas and cafes offering traditional greek delicacies. Also on Chalki are some stunning beaches, Giali and Potamos are our favourites.

Once you've had your fill of Chalki it's time to head back to base. The sail back to Rhodes from Chalki is a great last days sail, around 20 miles and it's good to note that the charter company usually like you to be back in the marina between 4-6pm. This gives you one last evening to soak up what Rhodes has to offer before heading home the next day.

  • Rhodes yacht through peephole in fortress Rhodes
  • Chalki Marina Chalki


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


  • Rhodes

  • Symi

  • Kalymnos

  • Leros

  • Nisyros

  • Patmos

  • Leros

  • Agathonisi

  • Arki

  • Samos

  • Tilos

  • Kos

  • Pserimos

  • Rhodes

  • Chalki


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