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Explore the Ionian Islands on this unique walking and sailing holiday, combining guided coastal hikes with island-hopping by catamaran. Discover secluded bays, swim in crystal-clear waters and unwind in charming village harbours.

  • Discover islands by catamaran
  • See picturesque traditional villages
  • Hike breathtaking coastal trails
  • Swim in secluded bays & coves
  • Paddleboard, kayak & snorkel

Beginning in Lefkada, sail to Meganisi, Kalamos, Kastos and Ithaca, with each day revealing a new part of an island and walking route. Trails lead through olive groves, pine forests and traditional villages, with views across the Ionian’s turquoise waters. Along the way, explore historic landmarks, quiet harbours and hidden beaches, with time to swim, snorkel, kayak or paddleboard in secluded bays, creating a perfect balance of exploration and relaxation.

Days begin with breakfast on board, before the main part of the day is split up with a walk of around three hours, and time to enjoy the sea and a freshly prepared lunch on the catamaran. Evenings are spent ashore, where you can explore atmospheric villages and dine in local tavernas.

With comfortable accommodation onboard and a small group setting, this journey offers an intimate and varied way to experience the Ionian Islands, blending gentle activity, cultural discovery and the freedom of travelling by sea.

Typical Itinerary

  1. Day 1: Arrival in Lefkada

    Make your own way to Sivota harbour in Lefkada. Transfers can be arranged from the airport for a supplement.

    Tonight, there's free time to spend ashore in Sivota. The catamaran is docked in the harbour until setting sail towards Meganisi the following morning.

  2. Day 2: Meganisi Island

    After breakfast on board, there's time to swim, paddleboard, kayak or snorkel in a secluded bay before lunch and our first hike. 

    From the harbour, a trail leads us through Vathy towards the fishing village of Atheni. We continue to Elia Beach and Katomeri, where there are views across the neighbouring islands. We explore the vibrant, narrow streets adorned with stone houses in the village of Katomeri, before making our way back to the catamaran.

    There's free time in the evening to wander around and have dinner ashore.

    Walking distance: 9 km | Ascent: 65 m

  3. Day 3: Kalamos Island

    In the morning, we depart Meganisi and travel to Kalamos Island, with time to enjoy a secluded bay.

    On today's trek we explore the small mountainous island of Kalamos. From Episkopi we head north, passing the Venetian castle, Greek chapels and windmills, and the village of Kalamos. It's possible to extend the hike and have a swim at Agrapidia Beach.

    After the walk, head back to the catamaran to freshen up and relax before an evening spent exploring Kalamos village.

    Walking distance: 10 km | Ascent: 95 m

  4. Day 4: Kastos Island

    Today we head to the smallest of the islands we visit during this itinerary, Kastos.

    From the island port, our hike takes us along a coastal road to Agios Emilianos Beach and the Fokotrypa Cave. The views along the route are magical, with secluded beaches and blue waters. The trail continues until the town of Kastos and the old windmill, with views across the surrounding islands.

    After the walk, head back to the catamaran to freshen up and relax before having dinner in a local taverna.

    Walking distance: 10 km | Ascent: 50 m

  5. Day 5: Ithaca Island

    After breakfast, we depart Kastos Island and sail to Ithaca, located east of Kefalonia. Upon arrival, we set off on a walk from Filiatro Bay to Vathy. The route follows a quiet paved road, lined by pine and cypress trees, and breathtaking views of hidden coves, beaches and bays.

    As we reach Vathy, the road slopes down to the waterfront, where cafes and tavernas line the shore. After exploring Vathy, we return to Filiatro Bay for a refreshing swim in the crystal-clear waters before heading back to the catamaran.

    There's time to relax and freshen up on the catamaran, before dinner in a local taverna.

    Walking distance: 8 km | Ascent: 70 m

  6. Day 6: Ithaca archaeological sites

    After the catamaran arrives in the port of Frikes, we begin our hike by following a quiet road, with views of Frikes Bay and neighbouring islands. The trail continues until we reach the Palace of Odysseus. This archaeological site dates back to 1,300BC. There's time to explore the site and soak in the views, before we head back to Frikes, passing through Platrithias village.

    After the hike, we travel back to Meganisi Island, specifically Spilia Bay. Here, there's time to swim or enjoy some water sport activities before dinner ashore in the beach bar or a local taverna.

    Walking distance: 8 km | Ascent: 175 m

  7. Day 7: Meganisi villages

    Beginning after breakfast, our final walk is on Meganisi Island. From Spilila we walk to Spartochori, a village made up of narrow streets and whitewashed buildings. The village's hillside location makes it a prime spot for views. We continue along the trail to the Meganisi channel before heading back to the catamaran.

    For the last night onboard, we venture to a secluded bay to enjoy the crystal-clear waters before continuing to Sivota Bay in Lefkada. Upon arrival, the remainder of the evening is free to relax and explore the village before a final dinner.

    Walking distance: 10 km | Ascent: 140 m

  8. Day 8: End of our catamaran adventure

    Our walking and island-hopping adventure in Greece comes to an end after breakfast. Make your own way to the airport or your onward destination from Sivota Bay.

    Transfers can be arranged for a supplement. 

Please note: It's important to note that the itinerary remains flexible and may change depending on weather conditions and sea state. Sailing routes and timings can change to ensure safety and to make the most of favourable conditions. As a result, the exact order of islands or specific stops may vary, although the overall experience and mix of walking and island hopping remains the same.

Flights & extra nights: The closest airport is Preveza; direct flights are available from several UK airports and Athens. If you wish to have more time in Lefkada, this can be arranged - contact us.

Price and Other Information

  • Duration and price excluding international flights: 8 days from £1,039 per person
  • Duration and price including flights from/to UK: 8 days from £1,375 per person
  • Single room supplement: On request
  • Walking grade: Easy
  • Guiding: Guided Group Private-Guided
  • Max alt: Low
  • Group size: 2-10
  • When to go: View Dates & Prices
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  • Route map:
    Route map for Greek Island Sailing & Walking Adventure
  • What’s included
    • Catamaran x 7 nights
    • 7 x breakfasts & 6 x lunches
    • Guided hikes
    • Access to paddleboards, kayaks & snorkelling equipment

Next Steps

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Guided Group Dates and Prices
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All prices are per person. All our guided group trips can be taken as a private guided itinerary, tailored to dates within the holiday's ‘when to go’ range. Please contact us to discuss your plans.

* Available: this holiday is available to book. ** Guaranteed: this holiday is available to book and is guaranteed to run. *** Fully Booked: if your preferred holiday is full we may be able to offer you a private departure or tailor a holiday to suit your requirements, contact us for more details.
2026 24 May 31 May £1,039 Guaranteed** Book or Enquire
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2026 11 Oct 18 Oct £1,039 Guaranteed** Book or Enquire

If you can’t see the holiday or departure date that you are looking for please contact us. We may be in the process of finalising further departures and are often able to arrange a holiday for you according to your own requirements.