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Join this flotilla from Kos to explore some of the smaller and lesser known islands of the Dodecanese - an irresistible flotilla choice for more experienced sailors.

This sailing area in the south-east Aegean stretches along the coast of Turkey and is a wonderful sailing destination for flotilla sailing holidays. It suits sailors looking for stronger winds and longer passages between unspoilt islands.

Once you set sail you will discover islands which have completely escaped tourism - Leros, Kalymnos, Niseros, Simi and Tilos. Here you'll find traditional fishing ports and quiet waterfront restaurants. The swimming and snorkelling is superb in many locations and Kalymnos, once the centre of sea sponge fishing in the Med, has many interesting dive sites.

Winds are variable ranging from moderate to fresh Force 4–6, with stronger winds during the meltemi season from late July through to late August, so this flotilla is recommended for more experienced sailors.

This flotilla is run in conjunction with Seafarer Holidays.

Dodecanese Flotilla

  • Overview


    shutterstock_Leros 720x480


    shutterstock_Pserimos 720x480


    shutterstock_TilosAbandonedVillage 720x480

    Tilos abandoned village




    Kefalos ruins

    Dodecanese flotilla sailing holidays

    • Two 1 week itineraries - Symi route and Kalymnos route
    • Perfect for more experienced sailors
    • Visit stunning islands untouched by mainstream tourism
    • Includes end cleaning, 1 tank of fuel, bed linen & shower towels
    • Minimal mooring fees (approx. €10-€20/week)
    • Runs May to October. Operates Saturday- Saturday
    • Supermarket is located within the marina
  • Symi Route

    Symi Route on the Dodecanese Flotilla

    2023 dates : 13, 27 May | 10, 24 June | 8, 22 July | 5, 19 Aug | 2, 16, 30 Sep | 14 Oct

    Day 1 (Saturday) : Kos Marina

    Embark at Kos Marina.

    Day 2 (Sunday) : Kardamena, Kos (18 nm)

    A protected port, sheltered from the northerly winds. A lively port perfect for the punch party and first group meal.

    Day 3 (Monday) : Nysiros (10 nm)

    A short sail south today to the island of Nysiros, leaving the afternoon free to explore the active volcano if you wish. A visit to the monastery is also recommended followed by dinner at one of the superb seafood tavernas.

    Day 4 (Tuesday) : Tilos (20 nm)

    The epitome of a traditional Greek Island with nice beaches and a friendly ‘far from the madding crowd’ feel.

    Day 6 (Thursday) : Symi (24nm)

    The stunning harbour of Symi is a great place to sail into. The amphitheatre town retains its' traditional character and charm having been much renovated over recent years. Be sure to climb the steps to the church for a superb panoramic view.

    Day 6 (Thursday) : Free Sailing Day

    Your lead crew will be happy to make suggestions for you.

    Day 7 (Friday) : Kos

    Two-weekers continue with independent sailing. One-weekers end their week in Kos with a farewell evening ashore in lively Kos town.

    Day 8 (Saturday) : Kos Marina

    Disembark at Kos Marina.

    Routes and places may vary during the season due to weather conditions & other factors.

    Dodecanese Symi Route 1 week flotilla sailing holiday itinerary

  • Kalymnos Route

    Kalymnos Route on the Dodecanese Flotilla

    2023 dates : 20 May | 3, 17 June | 1, 15, 29 July | 12, 26 Aug | 9, 23 Sep | 7, 21 Oct

    Day 1 (Saturday) : Kos Marina

    Embark at Kos Marina and get settled onboard your yacht. Kos is a lively town with many bars and restaurants to enjoy.

    Day 2 (Sunday) : Pothia, Kalymnos (17 nm)

    Known as the island of the sponge divers. The bustling harbour town boasts several museums, and a lively neoclassical sea front.

    Day 3 (Monday) : Lipsi (30 nm)

    The largest of a small group of islands to the south of Patmos, explore the local market for thyme honey and other local specialities.

    Day 4 (Tuesday) : Patmos/Arki (12 nm)

    Weather dependent, we will either head to Patmos where you can visit the monastery of St John, an UNESCO World Heritage Site, or alternatively the smaller island of Arki and the quiet village of Port Augusta, a sleepy little spot with just two tavernas ashore.

    Day 5 (Wednesday) : Leros (21 nm)

    We moor in the marina in Lakki, on the south west side of the island. Lakki has an Italian influence that can easily be seen when walking around the town. It has a good range of facilities ashore.

    Day 6 (Thursday) : Free Sailing Day

    Explore the area at your leisure, there are an abundance of beautiful spots to choose from. The lead crew will be happy to make suggestions for you.

    Day 7 (Friday) : Kos

    Continued independent sailing for the two-weekers. One-weekers end their week in Kos for a farewell evening ashore.

    Day 8 (Saturday) : Kos

    Disembark at Kos Marina.

    Routes and places may vary during the season due to weather conditions & other factors.

    Dodecanese Kalymnos Route 1 week flotilla sailing holiday itinerary

  • What's Included

    Included on the Dodecanese flotilla

    • Assistance of the flotilla lead crew throughout your holiday
    • End cleaning
    • Bed linen
    • Shower towels
    • Dinghy with outboard engine
    • Welcome punch party
    • One full tank of fuel, full water tank and cooking gas
    • Starter pack of provisions and cleaning products

    Mooring fees are not included. These are approximately €/week. One tank of fuel is included, any extra fuel must be paid for.

  • Getting There

    Flights to Kos and Rhodes

    Bonded for your financial protection under ATOL 3016EasyJet, Thomson and British Airways all have flights to Kos on Saturdays. Transfer time from the airport to the marina is around 30 minutes.

    Yacht charter rates are shown WITHOUT flights giving you the flexibility to book your own flights. If you would prefer a flight-inclusive holiday Nautilus Yachting is a fully bonded ATOL tour operator and can book flights from the UK to fit your sailing holiday. All flight-inclusive holidays are fully bonded for your financial protection under our ATOL 3016.


    Transfers are not included on this flotilla but can be added at an additional cost. Return airport transfers cost from £40/person.

"We chartered Icarus to celebrate a big birthday and could not have made a better selection. A beautiful boat with excellent skipper and hostess who will make you feel at home within minutes and you will wish for nothing. Robert is an expert skipper and teacher if you want to get involved, as well as having tremendous knowledge and experience of the area. The yacht is spotless, cabins are spacious and well equipped, the deck is spacious and sunbeds are laid out to sunbathe in comfort. Thank you for a fantastic holiday!!"

Crewed Yacht Icarus 2016 - B.M.

Dodecanese Flotilla prices

2023 GB£ per yacht on flotillaDufour 382 - 2016Dufour 390 - 2021Bavaria 41 - 2014
Departure Dates3 cabins / 1 WC max 6 people3 cabins / 2 WC max 6 people3 cabins / 2 WC max 6 people
13 May233724692579
20 May233724692634
27 May, 03, 10, 17 Jun283729803145
24 Jun, 01, 08 Jul326634803645
15 Jul368038374002
22,29 Jul, 05, 12 Aug419444094574
19 Aug419438374002
26 Aug, 02 Sep368038374002
09, 16 Sep326634803645
23 Sep283729803145
30 Sep, 07, 14, 21 Oct233724692634
13 May432145794744
20 May479650645229
27 May 03, 10 Jun529655755740
17 Jun570460506215
24 Jun, 01 Jul613265506715
8 Jul652668897054
15 Jul742977897954
22, 29 Jul, 05 Aug794383618526
12 Aug794378187983
19 Aug745472467411
26 Aug694072467411
02 Sep654669077072
09 Sep613265506715
16 Sep572560756240
23 Sep482150905255
30 Sep, 07,14 Oct432145794744
2023 GB£ per yacht on flotillaOceanis 45 - 2015Sun Odyssey 519 - 2019Lagoon 42 - 2020
Departure Dates4 cabins / 2 WC max 8 people5 cabins / 3 WC max 10 people4 cabins / 4 WC max 08 people
13 May391152506379
20, 27 May 03, 10 Jun483467507976
17, 24 Jun517170308561
01, 08, 15 Jul528172508781
22 Jul576274709001
29 Jul, 05, 12 Aug587283509826
19, 26 Aug, 02, 09 Sep528172508781
16 Sep483467507976
23 Sep472465307756
30 Sep, 07, 14, 21 Oct367452505967
13 May80341117013463
20, 27 May 03 Jun89571267015060
10 Jun92771293615617
17 Jun96141321616202
24 Jun97191342516411
01,08 Jul98291364516631
15 Jul102861385416840
22 Jul108721491017843
29 Jul, 05 Aug109821579018668
12 Aug104201474517676
19, 26 Aug 02 Sep98291364516631
09 Sep94041317015866
16 Sep88521246114851
23 Sep77451102512932
30 Sep, 07,14 Oct6695974511143
Includes: Welcome pack, welcome punch party, service of flotilla staff, end cleaning, 1 tank of fuel.
Extras payable on embarkation:


  • Refundable deposit €2000 - €3000
  • Inflatable SUP (stand up paddle board) £150 per week
  • Child safety netting (upon request) – from £200 per charter
  • Skipper – from £190 per day (+ compulsory non-refundable damage waiver of £350 per week)
  • Hostess – from 3170 per day
  • Wi-Fi (2GB) – £70

Sailing Qualifications

To skipper a bareboat charter or flotilla yacht, you need to hold a practical sailing certificate equivalent to RYA Day Skipper Practical qualification or RYA International Certificate of Competence (ICC). For charters in Greece, you must now have the ICC certificate. You must also be assisted by at least one competent crew member over the age of 18.

For charters in Croatia, Malta and the Canaries, at least one member of the crew or the skipper will also need a VHF licence.

RYA qualifications can be obtained by RYA sailing schools in the UK or alternatively choose from one of our overseas centres in Gibraltar, Greece or Turkey.

For Caribbean and Tropical charters, formal qualifications are not compulsory, however, you should be Day Skipper standard and be assisted by at least one competent crew. A brief sailing resume should be provided to outline your experience.

If you don't hold the relevant qualifications then why not add a skipper?

Sailing Levels

Level 1

Winds force 2-3 (4-11 Knots)combined with generally shorter distances. Good for beginner or intermediate sailors. Line-of-sight navigation but basic knowledge of charts and ability to plot your position required.

Level 2

Winds force 3-5 (7-21 Knots) with approximately 15-20nm per day. Intermediate experience required. Predominately line of sight navigation but an understanding of how to sail in open water.

Level 3

Winds force 4-6 (11-27 Knots) with mileage of approximately 20nm+ per day. Ideal for experienced skippers looking to venture out to new destinations. Day skipper standard but with experienced crew would be recommended.