A Family Sailing Adventure around the Ionian Seas

 

For a family sailing adventure with plenty to do ashore, I’d look at the central Ionian — starting from Lefkada and exploring Meganisi, Kastos, Kalamos, Ithaca and Kefalonia. It gives you a lovely balance of sailing, swimming, beaches, villages, walking and a little adventure, without spending every day making long passages. Recent 2026 sailing guides also identify this area as particularly suitable for families because of the relatively short hops and sheltered anchorages

Day 1 — Lefkada → Meganisi

Sail: ~8–12 nautical miles

Start gently. Pick up the yacht in Lefkada and head across to Meganisi, perhaps anchoring in beautiful Vathy Bay.

Family adventure:

Swimming and snorkelling straight off the boat

Paddleboards/kayaks around the bay

Walk into Vathy for ice cream and dinner

Explore the little lanes and waterfront

Meganisi is particularly good for a first day because there are lots of sheltered bays and short sailing distances.

Day 2 — Meganisi → Kastos

Sail: ~15 nautical miles

This is where the holiday starts feeling like a real adventure. Kastos is tiny and wonderfully unspoilt.

Onshore:

Hire bicycles or walk around the island

Swim from the little beaches

Snorkelling expedition from the yacht

Explore the small village

Sunset dinner overlooking the harbour

I'd make this a slow day rather than trying to pack in too much.

Day 3 — Kastos → Kalamos

A short sail north brings you to Kalamos, another beautifully green island.

Family activities:

Morning swim from the yacht

Kayaking around the coastline

Walk through the pine forest

Find a traditional taverna for lunch

Evening swim and paddleboarding

The children can have a genuine feeling of exploring an island rather than simply visiting a resort.

Day 4 — Kalamos → Ithaca

Now head for Ithaca, the legendary home of Odysseus.

I'd aim for Vathy, the main harbour.

Onshore adventure:

Explore Vathy

Visit the archaeological/museum sites

Hire a car or scooters for an afternoon island exploration

Walk to one of the viewpoints

Have a proper Greek family dinner ashore

Ithaca adds something different to the trip: you're no longer just moving between beautiful swimming spots, but getting a sense of Greek mythology and island history. Discover Greece specifically highlights following in Odysseus' footsteps as an experience on Ithaca.

Day 5 — Ithaca → Kefalonia

Sail: approximately 10–15 nautical miles depending on your chosen stop.

Head across to Fiskardo, one of the prettiest harbours in the Ionian.

This is a good place for a shore-based adventure day.

You could:

Explore Fiskardo

Hire a car

Visit Melissani Cave

Visit Drogarati Cave

Go to a beach for the afternoon

Find a traditional Kefalonian restaurant

There are also established boat-excursion operators around Fiskardo if you want to add an activity without taking the sailing yacht. For example, Crystal Clear Cruising Sailing Trips operates from the harbour, while Ionian Discoveries is based in Fiskardo.

Day 6 — Kefalonia → a deserted bay

I'd deliberately make this your "no plans" day.

Find a beautiful secluded anchorage and spend the day:

🏊 swimming

🤿 snorkelling

🛶 kayaking

🏄 paddleboarding

🎣 fishing

🚤 exploring in the dinghy

📚 reading in the shade

For a family sailing holiday, these unstructured days can end up being the most memorable.

Day 7 — Kefalonia → Meganisi

Start heading back towards Lefkada, stopping somewhere such as Meganisi.

Make this your family challenge day:

Morning sailing competition

Children navigate using a chart

Anchor in a new bay

Snorkelling treasure hunt

Paddleboard race

Cook dinner together on board

Sunset swim

It turns the children from passengers into part of the crew.

Day 8 — Meganisi → Lefkada

A relaxed final sail back to Lefkada.

I'd allow plenty of time so you can stop for a final swim before returning the yacht.

🌴 The really nice thing about this route

You get five different types of holiday in one trip:

Experience Where

🏖️ Beautiful beaches Meganisi & Kefalonia

⛵ Proper sailing Between the islands

🏝️ Deserted-island adventure Kastos & Kalamos

🏛️ History & mythology Ithaca

🍋 Greek villages & tavernas Everywhere!

🤿 Snorkelling & watersports Almost every anchorage

🕳️ Caves & exploration Kefalonia

🚲 Walking/cycling Kastos, Kalamos & Meganisi

The Ionian is particularly attractive for this style of family trip because the islands are relatively close together and the sailing tends to involve manageable daytime passages rather than long open-water crossings.

🛥️ What boat would I choose?

For a family, I'd seriously consider a 4-cabin catamaran rather than a monohull.

You get:

Much more living space

Two hulls/greater privacy

Large cockpit

Easy access to the water

Plenty of room for children

More stable platform at anchor

Excellent space for paddleboards, snorkelling gear and the dinghy

If you have 6–8 people, a 4-cabin catamaran would be particularly attractive.

⭐ One variation I'd consider

If you have 10–14 days rather than just a week, I'd extend the trip substantially rather than sailing faster.

You could do:

Lefkada → Meganisi → Kastos → Kalamos → Ithaca → Kefalonia → Zakynthos → Kefalonia → Ithaca → Meganisi → Lefkada

This starts to feel like a proper family expedition through the Ionian, with sailing interspersed with beaches, caves, hiking, kayaking and Greek villages.

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