Sailing Greece 2 Week

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Sailing Adventure Vacation In Greece

This is an example of a popular sailing vacation itinerary on our 2wk Greek trips. However, no two trips are ever exactly the same; one of the greatest things about being on a sailboat is the flexibility to change our minds and our route to suit personal preferences, prevailing wind conditions, etc. The start and finish points are fixed, of course, but all else is changeable according to the whims of the wind gods and those on board !

A typical two week vacation itinerary

Day One
Your yacht will be awaiting you at 11am in Evros Marina in Lakki (the main town/harbour of Leros). We'll have drinks, boat chat, show you're the ropes—and then head off for our first destination of Vathi, on the island of Kalymnos; a relaxing downwind sail to ease those landlubberly legs into shape slowly! About 3 ½ hrs sail time.

Vathi is a dramatic little spot; a well-hidden and very narrow fjord-like entrance, opening up into a tiny fishing village at the head of the bay. It boasts one main street and a collection of houses scattered into the valley; an unexpected patch of lush vegetation on an otherwise very dry and arid-looking island. Vathi is the only place on the entire island that is lucky enough to have it's own spring water supply, and they use it carefully to cultivate citrus fruits, figs, grapes and anything else that can be persuaded to grow.

It's also the home of "Poppy's"—one of our "adopted families", where momma makes the best homemade dolmades (stuffed grapeleaves) you'll ever taste in your life, and the swordfish steaks are out of this world!

Day Two
After breakfast and morning swims, we'll sail to Pandeli Bay on the east coast of Leros. This can be one of the longer sailing legs of the trip - if the winds are right, it's a perfect time to get a feel for the boat, especially for those who want to learn to sail. Great tacking practice! Time varies from 3-5hrs, wind dependent.

Pandeli Bay is one of the prettiest anchorages to sail into on this planet. The traditional blue-and-white houses scattered down the hillside; the little horseshoe-shaped bay, the beach tavernas conveniently just a 2 min swim from where we anchor the boat; it's a real picture-postcard scene. For those with plenty of night-owl energy, there is the infamous Savana Bar - a very idiosyncratic little local hangout, where we often end up dancing the night away!

Day Three
A leisurely morning in Pandeli; time to hike up to the fortress and get some stunning panoramic shots from the island's highest vantage point. Or perhaps just a cooling swim from boat to taverna, to recover from that dangerous Savana Bar place! Around midday, we'll set sail for Lipsos - island of the 42 blue-domed churches.

Lipsos is a quiet, very untouristy island; the harbour surrounded with an unruly array of whitewashed buildings - and those blue-domed churches everywhere! The vivid streaks of traditional blue trim and the blazing bougainvillea pinks & purples make it a real photographers' dream.

To cool off, there is a lovely little sandy beach, 5mins walk over the hill from where we moor the boats, and a great hike out to the headland with spectacular views out to sea.

Day Four
Here's hoping it's a calm morning so we can do our breakfast/swim stop at Macro Nisi ! It's a secluded little anchorage with sheer-sided cliffs, which have been known to entice the braver (or more foolhardy) amongst us to throw caution to the wind and leap off them ! For those more inclined to be adventurous in the water, there's a very cool, semi-submerged tunnel through the cliffs through which one can snorkel, emerging in little cave on the other side of the island.  

Then we're off to Patmos - the famous Monastery Island, where St John was inspired by visions to write the Book of Revelations. The 10th century monastery (built by Crusader Knights) reigns over the island, still an active and influential part of daily life here. The village that lies at the foot of the monastery is everyone's romantic image of a Greek village; narrow winding alleyways scarcely wide enough for a skinny donkey! - cats sunning themselves on whitewashed streets, old ladies in black collecting fresh bread from the bakery in the morning. It's well worth an early rise to get up there in the dawn hours; the old ladies will look at you in faint amazement that a foreigner should find their way up there at such a time; if you can remember enough of our Greek lessons to say "kalimera!" (good morning), they'll give you a huge smile and a "kalimera-sas" back (good morning to you too) ! (Note: that's "kali-MER-a", not "calamari" :> ).

Day Five
If you could paint a picture of the perfect, tiny Greek island retreat - Marathi would be it. A horseshoe-shaped sandy bay, no regular ferry connections with other islands; you need your own boat to get here. Our adopted family here are so wonderful and hospitable too - and the food is incredible!! This tiny spot has hit top of the Favourite Spot list with our groups for several years now - so much so that it's been hard to persuade people that, really, we should leave, there are other islands to visit !

Day Six

Sail to Samos—a total contrast! Samos is quite the upmarket, cosmopolitan island; the little harbour of Pythagorion is lined with dozens of tavernas along the waterfront. Pythagorion is the birthplace and home of the famous mathematician who gave his name to the theorum. He also had a most ingenious way of making sure his students did not drink too much wine at his lectures - check out the "Pythagoras Cup" ! It's a pretty, lively little port, with a very fun nightlife in the midsummer months.

Day Seven

The major attraction of the island, however, is once one gets out of the port. Samos is beautifully green—mountains covered with pine forests, streams, stunning cliffs and beaches—a real contrast to most of the other Dodecanese islands, which aren't exactly what you'd call lush. We often do a fun "jeep safari" , spending the day exploring all over the island.

Or, there's also a chance to take a day trip to Turkey and visit Kusadasi and Ephesus - great bargain-hunting in Kusadasi's maze of bazaars, and immensely impressive ruins of the ancient city at Ephesus (the Acropolis has nothing on this !).

Day 7 is the mid-point for those leaving us after one week, and the rendezvous point for those meeting us to join for the 2nd week's sail.

Day Eight 

Sail to Agathonissi - approx 3-4hrs. A small, traditional island with just one fishing port and two tiny villages perched on top of the hillside; a population of just 150 people. On arrival, we'll no doubt be greeted by our host Giorgos - a.k.a. Unofficial Harbour Master and Ouzo King of Agathonissi ! A colourful evening at George's is usually on the menu; he loves to see our yachts sailing in - it's a great excuse for a party on an otherwise quiet and isolated island.

Day Nine
Sail for Arki. If the weather is sufficiently calm, we may be able to visit Tiganakia also en route; also known as "Caribbean Cove" for it's translucent turquoise waters!
Another tiny, traditional island, Arki boasts a permanent population of just 27 - not counting the goats! There is just one little port, a few houses scattered around the hillside - and most of all, Manoli's place ! Mr Cool Dude Manoli runs a wonderful little oasis of a taverna; cushions scattered around the shady patio, speakers hidden away in the trees. A short hike up the hill is a little church and the most amazing sunset views over the island.

Day Ten
A return visit to Patmos - timed to coincide with a great local dancing event! Up in the old village, there is often a traditional dance evening, with the most energetic and entertaining Greek dancing display we've ever seen ! It's a full-on costume event, with specialty dances from each of the Dodecanese islands - the first part of the evening, the locals show us how to do it - the latter part, it's our turn!

The next morning, there is still lots more to explore - we we could spend a week and still not be bored. Rent a little 50cc scooter or 4 wheel buggy and explore lots of little villages, bays, and our favourite "Quiche Beach" with their terribly decadent milkshakes! For the more energetic, there's a 45min hike to a really cool, sandy "clothing-optional" beach, often with a little surf rolling in on windy days.

Day Eleven 

A leisurely midmorning departure for a lunch stop at the little uninhabited island of Archangelos, with it's amazingly bright turquoise waters and deserted little coves. Plenty of time to swim, snorkel and just generally hang out, before sailing onwards for Emborios, on NE Kalimnos. A wide, sweeping bay surrounded by towering limestone cliffs; a great spot to chill out and relax after dancing the night away in Patmos!  

Day Twelve
Sail to Paleonissos - a little-known secret of Kalymnos. Another dramatic and mountainous bay, tucked well away in the north of the island; anchorages like this are what make landlubbers fall totally in love with the cruising lifestyle ! There is little here apart from herds of goats; at dusk and dawn, the sound of their bells echoes around the hillside. With no distracting light around, the night sky is a dramatic sight; many an hour has been spent sitting on deck / on the beach simply star-gazing. Our unlikely-seeming dinner spot is a hike-and-scramble 5mins inland, through bushes of sweet-smelling sage - to the backyard of our local buddy Nicolas. Nick is a very eccentric character who delights in telling stories of the old Kalymnian sponge divers, and sometimes invites his music-loving companions from nearby villages to serenade us - bouzouki, guitar or even a goat-bladder (yes, really!)

Day Thirteen
A very leisurely morning - swimming, snorkelling, and just generally chilling out. Or for the athletic, a little goat-track offers a challenging scramble up the steep, rocky hillside, to a superb view over the valley & boats.

A last chance to perfect those tacking skills, the final afternoon's sail being mostly into the wind. We'll arrive late afternoon into our home base of Lakki on the western side of Leros.

Farewell vacation dinner at Vromolithos - a beautiful beachfront taverna with the most amazing views over the bay - and for grand finale night - live Greek music !

Day Fourteen
Disembark 9am in Lakki where your singles sailing vacation ends.