Kos-tume Optional: Sail Dodecanese (October 2-9, 2027)

Price and booking details coming soon!  If you are interested in this trip, please contact us.

Dodecanese sailing for people who’d rather leave the swimwear at home. Seven days of island-hopping from Kos, with secluded coves, sponge-capital puns, Calypso’s island and swim stops where the dress code is entirely your call.

Curious about what’s included in this trip?  Scroll down to the bottom of the page for details.

To confirm your reservation, a 50% non-refundable deposit is required. Remaining balance is due & non-refundable 60 days before departure. View Booking Policy and T&Cs for full details.

This product is currently out of stock and unavailable.

Last Date to Book: 02/10/2027

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Description

Starting Port City: Kos (Greece)

Ending Port City: Kos (Greece)

Travel advice: 

  • Fly into Kos International Airport “Hippocrates” (KGS). It is the closest airport to the marina, and Kos Marina is in Kos Town. Most guests will connect via Athens or fly a seasonal direct service.
  • By sea: ferries run to Kos from Piraeus, Rhodes and Bodrum (Turkey). Ferry schedules are seasonal and thinner in October, so check them before booking, and bring your passport if you come from Turkey.
  • Airport to Kos Marina: taxi about 24 km and 30 minutes, KTEL bus about 1 h (check the seasonal timetable).

Planned Itinerary

(subject to change, for example due to weather)

Day 1: Saturday – Kos

Embarkation: After 18:00 at Kos Marina.

  • Welcome cocktails and a briefing, where the crew explain the boat, the safety rules and the route.
  • Early arrivals can visit Hippocrates’ plane tree in Kos Town. He gave the world medicine, and we’re prescribing full-body sun exposure.
  • Dinner in Kos Town, then the first night aboard in the marina.

Day 2: Sunday – Kos to Pserimos

  • A short first sail to a tiny island of about 150 residents, which means very few witnesses.
  • Swim at Vathys cove and see how long the swimwear lasts.
  • Sunset drinks on deck at anchor.

Day 3: Monday – Pserimos to Kalymnos

  • Kalymnos is the sponge-harvesting capital, so expect the most thorough scrub of your life and plenty of loofah jokes.
  • Swim in the island’s clear coves beneath the climbing cliffs (a good place to watch the fit climbers).
  • Local food tasting aboard.

Day 4: Tuesday – Kalymnos to Leros

  • Leros is Artemis’s island in Greek mythology, and its pine forests hide plenty of bays.
  • Anchor in a secluded bay and spend the afternoon swimming, with no towel in sight.
  • A quiet night in Leros, with drinks on deck.

Day 5: Wednesday – Leros to Patmos

  • A proper sail to Patmos, with its lace-like coastline and sheer volcanic cliffs.
  • Beach-hop between Psili Ammos, Vaya and Lampi and pick your favourite spot for peeling off the layers.
  • Evening drinks at anchor.

Day 6: Thursday – Patmos to Lipsi

  • Calypso famously kept Odysseus on her island for years, and we promise only a week.
  • Beaches of Katsadia and Chochlakoura, plus the tiny islets around Lipsi to explore.
  • Optional swim stop at the Arkoi islets on the way.

Day 7: Friday – Lipsi to Kos

  • Sail back to Kos with a last skinny-dip stop on the way.
  • Last swim, last tan-line check, last chance to swap numbers.
  • Farewell dinner in Kos Town to celebrate the week.

Day 8: Saturday – Kos

Disembarkation: By 09:00 at Kos Marina.

  • Exchange contact info with your new besties.
  • Head out to explore the town, or head to the airport for your return journey home with a ton of new memories and connections.

What’s Included?

IncludedNot Included
  • A fantastic sailboat charter for your entire trip
  • All mooring/marina fees at embarkation and disembarkation ports (first and last nights)
  • An incredibly fun and welcoming atmosphere!
  • Dinghy/tender with outboard motor (where available)
  • Expert, qualified skipper(s)
  • Fresh bedding, pillows, and towels
  • Fuel for both sailboat and dinghy/tender
  • Professional cleaning service after your journey
  • Your cabin with selected occupancy
  • Entry visas or travel immunizations
  • Meals and drinks (provisioned & catered by the passengers via a “kitty” system)
  • Mooring/marina fees at ports of call
  • Pre/post-trip accommodation
  • Shore excursions or entertainment (unless specified as “ticket included” in your trip details)
  • Travel to/from the marina (airfare, transfers, ground transportation)
  • Trip cancellation and international medical insurance (we strongly recommend getting these through a third party) – read more here

Additional information

Onboard Activities

Daily Meditation

Occupancy

Private Cabin (per person), Shared Cabin (per person)

Trip Duration

8 days

Comfort Controls

Adjustable hatches for fresh air

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