SEPTEMBER
MILE BUILDER TO THE DODECANESE ISLANDS.
Mile
Building Week – September 2025
Each year, our sailing school
organizes mile building weeks for students. These weeks allow students
to log valuable sea miles while also experiencing the realities of offshore
sailing. Passages are designed between islands that are
beyond the reach of typical charter routes, ranging from 70 to 120 nautical
miles. Crews learn to stand night watches, sail in stronger winds and seas, and
develop confidence in handling offshore passages.
For this September’s mile builder,
the plan was a round trip of more than 450 nautical miles: from our base on
Poros to the Dodecanese Islands and back.
Day
1 – A Delayed Start
September 13th arrived, but there
was no yacht at our dock. We had chartered a Cyclades 51.5, due to arrive from
Athens the previous day. Due to weather delays and earlier technical issues, it
never made it on time. Instead, one of our instructors had to sail her down
from Athens that morning.
This meant our planned departure was
postponed until the following day. In the meantime, the crew slowly assembled
on Poros and gathered at Perla Coffee Shop — a relaxed start that allowed
everyone to get acquainted.
The crew was an interesting mix:
- Tom, a
computer engineer
- Loren,
a farmer from Virginia
- Marc,
a microbrewer, also from Virginia, with his partner Christine, a
lawyer
- Adrianna,
another lawyer, from New York
- Laurel,
our Head Women’s Instructor
- Jonathan,
the yacht’s captain, a retired Royal Naval officer
By late afternoon the yacht finally
arrived at our dock. Once the crew stowed their gear, Jonathan conducted a
safety briefing and introduced everyone to the yacht’s systems. The outline for
the next day’s departure was discussed, and with preparations complete, the
crew had the evening free to explore Poros Island before the adventure began.
Day
2 – Poros to Naxos
The crew was up early as we
arrived with provisions. Everyone immediately pitched in, loading and stowing
supplies with impressive efficiency. In just an hour and a half we were ready
to leave the dock.
Our first passage was
ambitious — around 120 miles, with an expected arrival sometime early the next
morning. The crew would soon learn one of sailing’s golden rules: there is no such thing as an ETA at
sea.
By 10:30 a.m. we were under
sail, heading toward the island of St. George, roughly the halfway point
between the Saronic Gulf and the Cyclades. Conditions were favorable: a steady
15 knots on the beam, giving us easy reaching conditions. Forecasts, however,
warned of stiffer breezes ahead — 20–25 knots with seas of 2–3 meters once we
entered the Cyclades. Fortunately, the wind would be mostly on the beam or
slightly abaft, making for fast and manageable sailing.
The crew quickly settled
into rhythm, steering confidently and trimming sails as needed. Jonathan, our
captain, rotated helm duties among the crew, assessing their skills. All proved
competent, and with bigger seas ahead, it was clear they would improve rapidly.
By early afternoon we passed
St. George’s Island, where conditions began to change. At 13:00 we entered the
Cyclades, and the wind freshened immediately — gusts over 20 knots, seas
beginning to build. Time for the first reef and a smaller headsail. The crew
executed the sail change smoothly, and the yacht powered on, making 9 knots in
comfort.
By late afternoon, we
rounded the southern tip of Kythnos. Seasickness began to set in, first among
the women, then a few of the men. To their credit, no one complained — all
stood their watches, determined to push through.
With seas rising and
daylight waning, Jonathan challenged the crew to consider their options.
Sailing demands flexibility: the skipper must balance weather, crew condition,
and destination. It was 17:00, with about three hours of light left. The next
40–50 miles promised more of the same — high winds and heavy seas on a broad to
beam reach.
The crew discussed possible
harbors:
·
St.
Stephen’s Bay (Kythnos)
– 35 miles to windward, a tough beat.
·
Finiakas
(Siros) – 45
miles east, a close reach in cross seas.
·
Lividia
(Serifos) – 45
miles south, a night approach with following seas.
·
Paros – 45 miles south-southeast, beam to
broad reach, manageable seas, and a well-lit ferry harbor.
After weighing the options,
the crew reached a sound decision: sail
on to Paros, aiming for a 21:00–22:00 arrival. The harbor
offered shelter, good lighting, and easy entry, with ferries providing useful
navigation aids.
Jonathan approved. With
reefed sails and a clear plan, we pressed on into the night.
Night
Sailing and Arrival in Paros
Sailing at night requires a
different set of skills. The first is preserving your night vision. At the
helm, you steer more by feel than by sight — listening to the wind in
the rigging, the rush of water along the hull, and the rhythm of the waves.
Wind direction generally holds steady, so maintaining course is relatively
easy. The challenge comes from the darkness itself. Sailing into pitch
blackness can be intimidating, and helming at night demands confidence and
trust in your abilities.
Once land is in sight, navigation
becomes easier. Identifying shore lights allows you to steer toward fixed
bearings as you close on the port.
Marc took on the role of navigator
for our entry into Paros. He quickly picked out the lights on Portes,
two rocks that guard the harbor entrance, and then located the red and green
harbor entrance lights. His only small miscalculation was distance — the light
on Portes Rocks seemed forever distant, even though he had called it at eight
miles. At 9 knots, those miles pass more quickly than expected, but even so,
closing on a target in the dark can feel like it takes an eternity.
At 22:30, we finally dropped anchor
in Paros harbor. The crew celebrated with a hearty pasta dinner and meat sauce,
washed down with more than a few well-earned beers.
Day 3 –
Milos
Arriving at a port in the
dark means you never really grasp its beauty until the morning light. When the
crew awoke in Paros, coffee in hand, the view gave that first cup an entirely
new flavor.
The plan had been to go
stern-to on the quay, allowing time ashore before departure. But with rough
weather outside, the quay was already packed with catamarans and charter
yachts. Instead, the crew loaded into the dinghy and went ashore while Jonathan
remained onboard to tend to the yacht and review the next leg of the voyage.
Some maintenance was needed.
The batteries had to be charged, but the generator failed to start. The engine,
which had only been run for two and a half hours, had already lost an eighth of
its oil — a worrying sign and something to monitor closely. The generator would
have to wait for repairs at the next port.
Meanwhile, weather reports
painted a grim picture further east. Winds in the Dodecanese were expected to
rise above 40 knots, with seas building to 3–4 meters — conditions more suited
to survival sailing than training. Jonathan made the call: instead of pressing
east, we would head south and west toward Milos, about 50 miles away. The passage
meant crossing an exposed stretch of water where 25–30 knots of wind and
occasional 4-meter waves could be expected. But the angle — a broad reach at
around 120° — promised fast sailing.
When the crew returned from
town, Jonathan explained the decision. They welcomed it eagerly. A stop at the
pharmacy had armed them with seasickness medication, and far from being
discouraged by the previous day, they were excited to push on.
At noon we raised anchor and
slipped out of Paros. Along the coast, Christine and Adrianna shared the helm
in 20+ knots of breeze on the beam. With one reef in and 75% of the headsail
out, they drove the yacht confidently at 8–9 knots.
By the time we rounded the
southern tip of Paros, conditions sharpened. The waves grew larger, the wind
stronger. The men took over the helm as we bore away onto a broad reach. Now we
were running diagonally with the seas, catching surfs that pushed us into
double-digit speeds — 10 knots steadily, with bursts of 12 knots as the yacht
accelerated down the faces of the waves.
The transformation in the
crew was remarkable. Seasickness had vanished, replaced by excitement and
confidence. Sandwiches were being made below while others laughed at the helm,
thrilled by the ride. Jonathan, watching from the cockpit, noted with pride: this was not the same crew from
yesterday.
Approach
to Milos
The approach to Milos from
the east is never straightforward. Two smaller islands guard the entrance,
leaving two possible routes. One option is to sail around the islands — the longer path, but it
exposes the yacht to hours on a lee shore in heavy winds and steep beam seas.
The other is to slip between
the islands, through a gap barely 250 meters wide. In that passage the seas lie
flat, sheltered by the land, but strong gusts funnel off the hillsides, testing
both helm and sail trim.
The crew weighed the choices
and voted for the more challenging but safer option — the narrow gap.
Tom took the helm first,
steering steadily into the passage. Once lined up, he handed over to Marc, who
guided the yacht through the flat but blustery channel with calm precision. The
decision and its execution proved sound: the yacht slipped safely into the lee
of Milos, the crew’s confidence growing with every mile.
Arrival in
Milos
Once through the narrow gap
between the islands, it was a straightforward reach toward the entrance of
Milos harbor. Loren took the helm, steering confidently despite the challenging
winds. Only later did we learn that he had sprained his wrist while steering
through the heavy seas — a testament to his determination.
The approach to Milos harbor
is long, leading into a wide bay with excellent marina facilities. By 18:30 we
were Med-moored securely. When we checked the log, we realized we had covered 62 miles in just six and a half hours
— an average speed of over 10 knots. Not bad at all for a crew on only their
third day of heavy-wind sailing.
Day 4 – Monevasia,
The Peloponnese
Our stop in Milos proved
especially meaningful for Loren, who is an avid student of Greek mythology. His
great hero is Homer, and when he learned that the poet is believed to be buried
on Milos, he was overjoyed. A visit to the site was a highlight of his trip.
With Monevasia — another ancient site steeped in history — next on our route,
he was eager for more.
The weather, however,
remained unsettled. The Meltemi was still blowing hard, with 25–30 knots of
wind and seas running 2–3 meters. Jonathan made the prudent call: rather than
pressing further east toward the Dodecanese, it was time to turn westward,
begin the homeward journey, and take a day’s rest at Monemvasia.
The passage was about 80
miles, due west from Milos. We departed at 08:00, heading out through the
straits. Conditions were much the same as the previous day — strong winds and
lively seas — but by now the crew was accustomed to it, rotating comfortably
with 45 minutes each at the helm. With one reef in and 75% of the headsail set,
the yacht charged along steadily at 8–9 knots.
By mid-afternoon, the gusts
began to ease. At 15:00 we were sailing under clear skies with a steady 20
knots of wind. We rolled out the rest of the headsail and held our speed,
enjoying some of the best sailing of the trip.
It wasn’t until the final 20
miles that conditions changed again. The wind dropped to 15 knots, though the
sea remained confused and lumpy. The yacht pounded into steep “pothole” waves —
sharp, two-meter crests with no backs, dropping the hull hard into the troughs
with a loud crash. With boat speed bleeding off, we eventually started the
engine for the last two hours.
At 18:30 we tied up safely
in Monevasia harbor. Despite the final motor, we had covered 83 miles in 10 hours
— impressive progress, and clear evidence of how far the crew had come in just
a few days at sea.
Day – 5
Today is a rest day and a
chance for the crew to explore the ancient city of Monevasia.
Founded in the sixth
century, and thus one of the oldest continually-inhabited fortified towns in
Europe, the town is the site of a once-powerful medieval
fortress, and was at one point one of the most important commercial
centres in the Eastern Mediterranean. The town's walls and many Byzantine churches remain as testaments to the town's history.
Day 6 –
From Monemvasia to Sampatiki
The crew woke abruptly to
the yacht dragging anchor in Monemvasia harbor. The holding there is
notoriously poor — soft sand and weed make it difficult for any anchor to bite
properly. The culprit, of course, was the return of the Meltemi. After a day
of calm sunshine, the wind had returned overnight. Sheltered inside the harbor,
we hadn’t felt it while asleep, but by dawn the breeze had built, and suddenly
our anchor was dragging.
We had two options: go back
out and relay the anchor, or run a spring line further up the dock to hold us
off. We chose the latter, giving us time for breakfast, planning, and preparing
the yacht for departure.
The day’s goal was Leonidion, birthplace
of King Leonidas of Sparta, hero of the stand at Thermopylae in 300 BC. The
challenge was the weather: the first 4–5 hours would be hard upwind sailing
until we reached the shelter of the northern Peloponnese. There, the winds
would ease and, hopefully, the seas as well.
We set two reefs in the main
and only 50% of the headsail. Outside the lee of Monemvasia, the Meltemi struck
in full force: 25–30 knots with big seas running. Our first tack wasn’t a
making tack — we had to hold off from falling too far below the rhumb line
before turning onto the better tack northward. After eight miles we had only
slipped half a mile down, so we tacked and settled onto the making tack.
It was hard steering.
Helmsmen had to thread the yacht between the waves, avoiding the biggest
crests. For three hours we held course, and by the time we tacked again, Monemvasia
was far astern. Gradually, the winds eased as we sailed out of the grip of the
Meltemi. The seas, however, remained large, slowing us down even as our boat
speed fell.
By late afternoon, with 20
miles still to run, we turned on the engine and motorsailed north at 7 knots.
Leonidion came into view, but the sight was discouraging — yachts in the harbor
were rocking and rolling violently in the surge. It was clearly not a place to
spend the night in comfort.
Jonathan, not satisfied,
suggested an alternative: Sampatiki,
a tiny harbor just 20 minutes further north. With only one tavern, one church,
and about 100 residents, it was as quiet as Leonidion was exposed. Thanks to a
generous EU harbor grant, it was also beautifully sheltered.
That evening turned into one
of the most memorable of the trip. The tavern served fresh snapper, grouper,
octopus, and more. The crew feasted for four hours, washed down with wine,
laughter, and stories. The bill for seven people came to just €190 — almost
unbelievable for such a banquet.
Day 7 –
Homeward Bound
The final day was meant to
be an easy hop — just 30 miles back to Poros. After what the crew had already
endured, it seemed straightforward. Instead, it turned out to be one of the
most challenging legs of the trip. What should have been 30 miles became 52 miles sailed, with
11 hours on the water.
We slipped out of Sampatiki
at 08:30 and set a course across to Spetsai Island on a close reach. Winds were
gusting 15–20 knots with a light sea running. It was only 12 miles, yet helming
suddenly became a struggle. Somehow, after six days of improving skills,
everyone seemed to forget the basics. Four hours later we were just approaching
Spetsai, with the wind freshening to 20–25 knots — now right on the nose.
Threading our way between
the islands made the beat even trickier. The crew continued rotating helmsmen
every 45 minutes, but what one gained on the helm, the next often gave away.
Tacking up Hydra Channel normally takes 2–3 tacks. For us, it took six. At last
we reached the Teslavina Cut, leaving only six miles to home.
As often happens, once
through the cut the wind began to die. The final stretch was motorsailed. But
just when it seemed the challenges were over, the mainsail halyard failed
— the cover stripped from the core, which slipped through the jammer and jammed
itself high inside the mast. After much effort, the crew had no choice but to
cut the halyard to get the mainsail down. It was not the ending we had hoped
for.
Finally, at 19:00, we
Med-moored back at our home port. A long, frustrating day, but one that left
plenty of stories to tell. Jonathan, ever the good captain, took the crew
ashore, placed two bottles of rum on the table, and declared: “These will go bad if not finished in
the next two hours.” Spirits rose quickly, and the trip ended on a fittingly
cheerful note.
Summary
This was, at its heart, a
true mile builder.
The goal was to give the crew experience of offshore sailing in all conditions:
strong winds, rough seas, night sailing, and harbor entries under pressure.
That goal was more than achieved.
What began as a group of
strangers — aged 35 to 67, from professions as diverse as farmer, computer
engineer, brewer, and lawyer — ended as a cohesive, capable crew. They
respected one another, looked after each other, and shared the hardships with
good humor. They obeyed safety rules, stood their watches, cooked and cared for
each other, passed around seasickness medicine, and learned to sail a big yacht
with skill.
By the end of the week, they
had sailed more than 450 miles, steered confidently in heavy weather, trimmed
sails for speed, navigated challenging passages, and gained both miles and
memories that will last a lifetime.
Our school runs Mile Builders twice a year,
in spring and fall. If you’re ready to challenge yourself, learn offshore
sailing in earnest, and be part of a great crew, we’d be delighted to welcome
you aboard for the next one
