Tour overview

This 15-day island hop travels from Athens through the Cyclades to Crete. A local leader travels with the group, which numbers no more than twelve, by ferry, boat and local bus. You stay fourteen nights in hotels and guesthouses, with breakfast on most days and a few shared meals.

From Piraeus you sail to Syros for a loukoumi workshop and a dinner in a remote village, then to Mykonos with a half-day trip to Delos. On Santorini you walk the caldera rim to Oia and have a free day before taking the ferry to Heraklion.

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On Crete you visit Knossos, Europe's oldest city, and taste local wine, then hike the Agia Irini Gorge to the south coast at Sougia, where a boat trip brings swimming stops and a family lunch. You finish in Chania with a guided tour of its Venetian old town and a free day.

The physical rating is medium. This trip suits island lovers who want variety and some walking.

Trip highlights

  • A village dinner on Syros (Day 3)
  • Delos (Day 5)
  • The caldera hike to Oia (Day 7)
  • Knossos (Day 10)
  • The Agia Irini Gorge (Day 11)
  • Chania old town (Day 13)

Your route

13 stops from Athens to Chania

15-day route: Athens – Syros – Mykonos – Santorini – Heraklion – Sougia – Chania
  1. Athens Day 1
  2. Syros Days 2–3
  3. Ano Syros Day 3
  4. Mykonos Days 4–5
  5. Delos Day 5
  6. Santorini Days 6–7
  7. Heraklion Days 8–9
  8. Knossos Day 10
  9. Omalos Day 10
  10. Agia Irini Gorge Day 11
  11. Sougia Days 11–12
  12. Chania Days 13–14
  13. Chania Day 15

Why choose this tour

Four islands in two weeks. Hikes, boat trips and local food.

Best suited to

  • Island hoppers
  • Active travellers
  • Solo travellers
  • Food lovers
A windmill on Mykonos

Day-by-day itinerary

15 days from Athens, Greece to Chania, Greece

  1. Day 1 · Athens Athens

    Welcome to Greece.

    Hotel
    Hotel
  2. Day 2 · Piraeus, Syros Syros

    By ferry.

    Hotel
    Hotel
    Meals
    Lunch
  3. Day 3 · Ano Syros Syros

    A village dinner.

    Hotel
    Hotel
    Meals
    Dinner
  4. Day 4 · Mykonos Mykonos

    To Mykonos.

    Hotel
    Hotel
  5. Day 5 · Delos Delos

    A sacred island.

    Hotel
    Hotel
    Meals
    Breakfast
  6. Day 6 · Santorini Santorini

    To Santorini.

    Hotel
    Hotel
    Meals
    Breakfast
  7. Day 7 · Fira, Oia Santorini

    The caldera hike.

    Hotel
    Hotel
    Meals
    Breakfast
  8. Day 8 · Santorini, Heraklion Heraklion

    Ferry to Crete.

    Hotel
    Hotel
    Meals
    Breakfast
  9. Day 9 · Heraklion Heraklion

    A free day.

    Hotel
    Hotel
    Meals
    Breakfast
  10. Day 10 · Knossos Knossos

    Europe's oldest city.

    Hotel
    Guesthouse
    Meals
    Breakfast, Dinner
  11. Day 11 · Agia Irini Gorge, Sougia Agia Irini Gorge

    A gorge hike.

    Hotel
    Guesthouse
    Meals
    Breakfast
  12. Day 12 · Sougia Sougia

    A boat trip.

    Hotel
    Guesthouse
    Meals
    Breakfast, Lunch
  13. Day 13 · Chania Chania

    A Venetian harbour.

    Hotel
    Hotel
    Meals
    Breakfast
  14. Day 14 · Chania Chania

    A free day.

    Hotel
    Hotel
    Meals
    Breakfast
  15. Day 15 · Chania Chania

    The trip ends.

    Meals
    Breakfast
Pastel houses on the Syros waterfront

Where you stay

  • Athens (1 night) Hotel
  • Syros (2 nights) Hotel
  • Mykonos (2 nights) Hotel
  • Santorini (2 nights) Hotel
  • Heraklion (2 nights) Hotel
  • Southwest Crete (3 nights) Guesthouse
  • Chania (2 nights) Hotel

Hotel names are indicative and may be replaced with a property of similar standard and location.

What's included

Included

  • Accommodation 14 nights in hotels and guesthouses
  • Meals 11 breakfasts, 2 lunches and 2 dinners
  • Ferries, boats and local buses
  • Delos and Knossos guided visits
  • Caldera rim hike and Agia Irini Gorge hike
  • Wine tasting and coastal boat ride
  • Local leader throughout

Not included

  • Flights
  • Meals not included 3 breakfasts, 11 lunches and 12 dinners
  • Optional activities
  • Travel insurance and personal spending
The red columns and frescoes of the Palace of Knossos

This trip might not be for you if…

Honest disclaimer — please read

  • You want luxury hotels
  • You want most meals included
  • You dislike ferries
  • You want flights included — they are not

Good to know

Meals by day Breakfast: Days 5–15 · Lunch: Days 2 and 12 · Dinner: Days 3 and 10
White houses and windmills in Oia, Santorini

In pictures

Departures & prices

From £3,665 per person, twin share, tour only. 27 upcoming departures.

Frequently asked questions

How do I book this tour?

Tap any "Enquire" button on the page and one of our travel specialists will be in touch within 24 hours (often same day). We'll confirm availability on your preferred date, run through anything you need to know, and only ask for the deposit once you've decided.

What financial protection do I get?

Every Travelisto booking is 100% financially protected. Your money is held in a ring-fenced Trust account until you return from your trip, and we are members of the Protected Trust Services scheme (PTS 6035). Most tours also include ATOL protection where flights are part of the package.

Do I need a visa for Greece?

No, UK citizens can visit Greece visa-free for short stays, though the EU Entry/Exit System applies at the border.

How do you travel between islands?

By public ferry, with tickets arranged.

How hard is the gorge hike?

A moderate downhill walk of a few hours on a rocky path.

Is there free time?

Yes, on Santorini, in Heraklion and in Chania.

Can I have my own room?

A single supplement is available on request.

How many people travel together?

No more than twelve travellers, with a local leader.

Can you tailor the trip?

Yes — every escorted tour can be modified into a private tailor-made version with your own dates, adjusted pace, upgraded hotels and add-on extensions. Tell us what you'd like changed when you enquire and we'll quote it both ways so you can compare.

What if my flight is delayed or cancelled?

If your international flight is part of your booking through us, we re-book at no cost. If you've booked flights separately, the tour's local team holds your transfer slot until you arrive. We strongly recommend a comprehensive travel insurance policy that includes delay and cancellation cover.

ATOL protected 100% financially protected in a Trust bank account PTS 6035 4.7 on Trustpilot
Tailor-made option

Not quite the right fit? Make it tailor-made.

If this group tour doesn't match your ideal trip, our specialists will turn it into a private tailor-made journey — your own dates, your own pace, upgraded hotels where you want them, and the parts you don't love swapped out. Same destinations, just rebuilt around you.

Contact us for a tailor-made version of this itinerary
From £3,665
See dates & prices