Races on the Aegean islands: an island-by-island guide

The map: Cyclades, Dodecanese and North Aegean

The Cyclades are a cluster of about 220 islands in the South Aegean, covering 2,572 km2 with a population of 119,549 at the 2005 census, per Wikipedia; Ermoupoli on Syros is the administrative centre. The Dodecanese are a group of 15 larger and 150 smaller islands in the southeastern Aegean, with a population of 200,452 (2005) and Rhodes as the area's dominant island "since antiquity". The North Aegean region comprises Lesbos, Chios, Psara, Oinousses, Ikaria, Fournoi Korseon, Lemnos, Agios Efstratios and Samos, with Mytilene as its capital and a population of 194,943 at the 2021 census.

In the bib2bib catalog, the 18 verified events in these three regions cover 12 islands: nine in the Cyclades (Kea, Serifos, Syros, Folegandros, Donousa, Santorini, Mykonos, Milos, Andros), two in the Dodecanese (Patmos, Rhodes) and one in the North Aegean (Lesvos).

• Cyclades: 9 islands, 14 entries
• Dodecanese: 2 islands, 2 entries
• North Aegean: 1 island, 2 entries

Cyclades: from Kea and Serifos to Andros

The Cyclades hold most of this guide's entries, with races from April through to June of the following year.

• GO KEA Open Water — 25 April 2026, Gyaliskari beach, Kea — 1.5 / 3.0 km swim
• 12th Serifos Sunset Race — 12–13 September 2026, Serifos — 5 / 10 km run (Saturday, Livadi) and 0.75 / 1.5 / 3 km swim (Sunday, Avlomonas beach), with parallel kids' running and swimming races
• Syros Trail Challenge — 12–13 September 2026, Ermoupoli, Syros — 3 / 10 km over steps and cobbled lanes on Saturday, plus a new +UP/-DOWN 2.5 km race on Sunday
• Folegandros Challenge Run — 26 September 2026, Folegandros — half marathon 21.1 km / 10 km / 5 km, three staggered starts the same evening
• 8th "On the Paths of Donousa" Trail Race — 10 October 2026, Stavros, Donousa — 9 km (+430 m) / 20 km (+1,200 m)
• Santorini Experience 2026 — 17–18 October 2026, Santorini — 2.4 km open-water swim (Volcano–Old Port of Fira), Ancient Thera 5.01 km road run (Kamari) and 5 / 10 / 15 km trail (Oia)
• Swim Grand Prix Mykonos — 29–30 May 2027, Mykonos — 10 / 5 / 2 km, plus a 400m youth and 200m kids' category
• UltraSwim 33.3 Milos — 3–6 June 2027, Pollonia, Milos — 33.3 km over four days
• Andros Challenge & Festival — 11–13 June 2027, Andros — trail 35 / 15 / 6 / 1 km, road running 10 / 5 km through the historic town centre, swimming 3 / 1.7 / 1 km, and a non-competitive 1.6 km "Drink & Run"

Dodecanese: Patmos and Rhodes

The Dodecanese hold two running events in the catalog, at very different scales: a local event on Patmos and the longest race by distance in this entire guide, on Rhodes.

• Patmos ChoRun 2026 — 13 September 2026, Patmos — half marathon 21 km (starting from Panagia Geranou), 5 km around Chora, 1 km kids'/family run
• 12th TUI Rhodes International Marathon — 18 April 2027, Rhodes — marathon 42.195 km, half marathon 21.097 km, 10 km, a competitive 5 km plus a separate 5 km walking route, and a 600m kids' race

North Aegean: Lesvos

Lesvos is the only North Aegean island in the catalog, with two very different September events: a relay around the whole island and a mountain trail race on Lepetymnos.

• Lesvos relay race — 5–6 September 2026, around the island — 320 km over 36 stages, organised by the Lesvos Runners Club with the North Aegean Region
• Lesvos Trail — 20 September 2026, Lepetymnos, Lesvos — 15 km (Lesvos Trail) and 6 km (Lepetymnos Run), organised by the Molyvos Tourism Association

Trail on the islands: where the climbs are

Six of the 18 entries are trail events, on six different islands: Syros, Folegandros, Donousa, Santorini, Lesvos and Andros. The longest single-distance mountain course is the 35 km Gerakones Challenge at the Andros Challenge & Festival, while Donousa offers the largest elevation gain among the events that publish elevation figures (+1,200 m over 20 km — no elevation figure is published for the Andros trail).

The Sitia Geopark Trail, the Sfakia Sky Marathon and the Minoan Athlos in Crete are not part of this guide — they are covered in bib2bib's separate guide to endurance races in Crete.

Open-water swimming and multisport festivals

Six of the 18 entries include an open-water swimming leg: GO Kea, the swim leg of the Serifos Sunset Race, Santorini Experience, Swim Grand Prix Mykonos, UltraSwim 33.3 Milos, and the swim leg of the Andros Challenge & Festival. Kea, Serifos, Mykonos and Milos are covered in more depth — distances, month-by-month sea temperature, wetsuit and tow-buoy rules — in bib2bib's separate guide, "Open-Water Swimming in the Greek Islands".

There is currently no dedicated triathlon (swim–bike–run) race in the Cyclades, Dodecanese or North Aegean in the catalog. The closest multisport format is the Andros Challenge & Festival, which combines trail, road and swimming as separate races across the same event week rather than as a single continuous three-sport race.

Practical notes: getting to these islands, in general terms

bib2bib does not cover ferry timetables, fares or frequencies — these change often and should be checked with a ferry agent or the race organiser. In general terms, Piraeus serves, as Wikipedia puts it, "almost every island in the eastern portion of Greece...the Cyclades, the Dodecanese, and much of the northern and the eastern Aegean Sea" — making it the main gateway for all three regions in this guide, Rhodes and Lesvos included. Rafina, per the same source, serves "most of the Cyclades" and is usually the shorter option for islands such as Syros, Andros or Mykonos. Kea is the exception: its only ferry link is from Lavrio, not Piraeus or Rafina.

This guide's races are spread across almost the whole year, but the majority (September–October) fall during or just after the meltemi season — the etesian winds that blow across the Aegean "periodically from about mid-May to mid-September" and can reach force 7–8 on the Beaufort scale, per Wikipedia — a factor that affects ferry crossings more directly than the races themselves.

When the races happen: the year at a glance

September is by far the busiest month in this guide, with six events on five islands (Lesvos ×2, Serifos, Syros, Patmos, Folegandros). October follows with two events on two islands (Donousa, Santorini). The remaining five entries are spread across April 2026 (Kea), April 2027 (Rhodes), May 2027 (Mykonos) and June 2027 (Milos, Andros) — outside the height of summer heat.