Where to Sail in Greece? 3 Proven Ionian Sea Itineraries

When planning a sailing holiday in Greece, the most important question is simple: where should you sail to enjoy a smooth and pleasant week at sea?

The Ionian Sea is known for its milder winds, shorter distances between islands, and routes that allow you to explore without rushing. It is a region that works well for a first sailing experience, but also for those looking for relaxed holidays on the water.

In this guide, you’ll find three proven Ionian Sea itineraries to help you decide easily.

Why the Ionian Sea?

If your priority is a calm and comfortable week at sea, the Ionian Sea is often the first choice. The islands are located close to each other, so there are no long passages required. You can sail shorter distances and spend more time swimming, anchoring in quiet bays, or enjoying evenings in small harbours.

Winds are generally gentler, conditions are easier to predict, and routes can be adjusted depending on weather or mood. It’s a region where both beginners and experienced sailors feel comfortable.

Lefkada – Meganisi – Kalamos – Kastos

The Calmest Route for a First Sailing Holiday

If this is your first sailing holiday in Greece, this itinerary is often the best place to start. The route runs between smaller islands located close to each other, making passages short and easy to plan.

Starting from Lefkada — one of the most convenient bases in the Ionian Sea — you can reach Meganisi with its peaceful bays, then continue to Kalamos and Kastos, where the pace slows down, crowds are smaller, and the atmosphere feels more authentic.

This is a route where there is no need to rush. You can sail just a few hours per day and spend the rest of the time swimming or enjoying quiet evenings in harbour.

Lefkada – Atokos – Ithaca – Kefalonia

More Space and Varied Scenery

If you are looking for slightly longer distances and more open water, this itinerary offers a stronger sense of real sailing. From Lefkada, you sail toward Atokos — a more remote island with clear-water anchorages — then continue to Ithaca, known for its peaceful harbours and green landscapes.

The route can extend to Kefalonia — a larger and more mountainous island with impressive bays and livelier towns. Here, you gain more variety, but also slightly longer passages.

This is a good option for those who feel confident at sea or want a bit more dynamic sailing.

Lefkada – Kefalonia – Zakynthos

The Most Scenic Ionian Route

This southern route brings more dramatic landscapes, higher cliffs, and wider stretches of open water.

From Lefkada, you sail south toward Kefalonia, known for its mountainous coastline and wide anchorages. Continuing to Zakynthos, you’ll find turquoise waters and striking white cliffs.

Passages are longer here, offering a stronger sailing experience. The pace is more active, but the reward is some of the most impressive coastal scenery in the Ionian Sea.

This route suits those who want more space, more horizon, and more contrast.

How to Choose Your Route?

If this is your first sailing holiday, choose shorter passages around Lefkada and nearby islands. It allows you to experience sailing without pressure.

If you have sailed before and want more variety, consider extending to Ithaca or Kefalonia for longer open-water sections.

If impressive scenery and dramatic coastlines are your priority, the southern Ionian route toward Zakynthos offers greater contrast.

The most important factor is not how many islands you visit, but whether the chosen pace suits your holiday.

Which Boat Is Best for the Ionian Sea?

The Ionian Sea is generally considered a calmer sailing region, suitable for both first-time sailors and experienced crews. When choosing a boat, the key question is what kind of holiday you want.

Catamaran

More stable and spacious. Comfortable for families or larger groups. Less movement and more deck space.

Monohull Sailing Yacht

A classic sailing experience. You feel the wind and sailing dynamics more directly. Often chosen by smaller groups or more experienced sailors.

With a Skipper

Ideal if you want to fully relax and not worry about navigation. A skipper helps choose safe anchorages and adapt to conditions.

Bareboat

Suitable if you have the required license and experience. Many Ionian routes, especially in the northern area, are well suited for this option.

When Is the Best Time to Sail in the Ionian Sea?

The Ionian sailing season usually runs from May to October. Conditions are generally stable, but each month has a slightly different atmosphere.

May–June
Quieter, fewer crowds, more space in marinas and bays.

July–August
High season. Stable weather, warm sea, livelier towns.

September
Warm water and fewer tourists than peak summer. Many sailors consider it one of the most pleasant months.