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Sample Itineraries · Hand-Tested Routes

Greek island-hopping, planned by the people who actually sail it.

Every itinerary below is a real plan our Athens team has walked, ferried, and slept through — a working preview of what lands in your inbox 1.7 days after you ask for one.

View of a Cycladic hillside village from above
From the archive Cyclades in 10 Days — Day 4, Sifnos
  • 11,400+ Nautical Miles Tested
  • 22 Athens-Based Planners
  • 1.7-Day Average Quote Turnaround

The Archive

Five more hand-tested routes — pick the shape that matches your trip.

Each plan is built by a regional specialist who lives there. None are templates; each route below was assembled from a working brief our team turned around, end-to-end, for a real traveller.

A wooden caique in a quiet Ionian bay

Ionian Slow Sail · 8 Days

A Bareboat Week Without the Bareboat Bill.

Lefkada → Meganisi → Kefalonia (Assos) → Zakynthos (north coast only) → Ithaca → back. Ferries and small water taxis stitched together so you island-hop at a sailing pace, with the same Adriatic-blue anchorages but none of the skipper licensing.

  • Crossings5 ferries · 2 water taxis
  • Pacing2 nights per island, no exceptions
  • SpecialistDaphne · Zakynthos-based
Request the Ionian plan →
Dawn light on Symi's neoclassical harbour

Crete & the Dodecanese · 14 Days

Two-Week Cross-Border Loop From Heraklion to Rhodes.

A longer shape. Heraklion to Sitia overland (we'll arrange the car), ferry east to Kasos, then Karpathos, then slow Rhodes for three nights before the Dodecanese direct back to Athens. Built for travellers who want Crete's archaeology without the package-tour chassis.

  • Crossings3 ferries · 1 regional flight
  • Pacing3 nights Crete · 2 Kasos · 2 Karpathos · 3 Rhodes · 2 Athens
  • SpecialistMichalis · Heraklion-based
Request the Dodecanese plan →
A pine-fringed Sporades cove

The Sporades · 7 Days

A Northern Greek Week Most Travellers Miss.

Volos to Skiathos to Skopelos to Alonnisos, with one night anchored at the marine park. Cooler water, denser pine, fewer queues — the route we walk for travellers who'd rather swim in a turquoise cove than queue for a Santorini sunset.

  • Crossings3 short ferries
  • Pacing2 nights per island
  • SpecialistEleni · Volos-based
Request the Sporades plan →
A quiet Hydra street in late afternoon

Saronic Weekend · 4 Days

Athens-to-Hydra, Done Before the Saturday Ferry Queue Forms.

Friday-evening Flying Dolphin from Piraeus, Hydra two nights, Spetses one, back Sunday evening. The plan we hand to anyone with four days, a carry-on, and no interest in meeting their fellow tourists. Optional: Aegina day-stop swap for travelling with kids.

  • Crossings3 fast ferries · no cars on Hydra or Spetses
  • PacingShort and deliberate
  • SpecialistKostas · Piraeus-based
Request the Saronic plan →
Plan My Greek Trip

Or ask for something off-archive. Most of the plans we deliver aren't on this page — they're built from a 30-minute call.

From your inbox to your island

How a custom itinerary actually gets built.

It is less automated than it sounds, and faster than most agencies promise. Here is the working order for a typical request — from the first message to a delivered PDF.

  1. 01

    A 30-minute consultation call.

    With whichever of our 22 planners covers your region. They ask about pace, ferry-tolerance, kids or pets, budget shape, dietary notes, and which sunset you actually want to be standing in. We share screen, take notes, send a written brief back the same day.

  2. 02

    One planner owns the build — end to end.

    No triage team. The person on the call designs the route, picks the ferries from our live Blue Star / Hellenic Seaways / SeaJets / Anek-Superfast integrations, walks every stop against their own notebook of personally-tested guesthouses. They keep the route until it's delivered.

  3. 03

    A 1.7-day turnaround, in plain prose.

    You receive a 14–22 page PDF: day-by-day plan with named ferries (times, durations, booking links), named stays, walking notes, restaurant shortlist, weather-aware alternatives, and our in-ground coordinator's mobile number for the duration of your trip.

  4. 04

    In-trip support from Athens & Naxos.

    Ferries shift seasonally. If yours does, your planner knows before you do and reroutes from the Athens office. Confirmed for July–August 2024 at a 98.4% booking rate — the toughest stretch of the Greek calendar — and we're quietly proud of that number.

By The Numbers

An archive is only as honest as the field-testing behind it.

11,400+
Nautical miles personally sailed by staff since 2009.
98.4%
Ferry-and-hotel confirmation rate, July–August 2024.
22
Athens-based planners, each covering a region they call home.
1.7days
Average quote turnaround for a custom island-hop.

Rated 4.92 / 5 across 3,400+ verified Trustpilot reviews — the highest score among Greece-specialist operators.

From the founders

“An island isn't a pin on a map. It's the second ferry you almost missed, the auntie who insists on sending a second carafe, the same cove you've seen forty-two times and still look forward to. Our itineraries are slow because the country is slow, and we think that's the point.”

Elena Papadakis Co-founder & Lead Writer · Athens, since 2009