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Sailing Vacation in Greece: Discover the Ionian Islands by Yacht
If you are dreaming about a sailing vacation in Greece, you probably imagine warm waters, quiet bays, and evenings in traditional tavernas on a beautiful Greek island.
The good news: that picture is real.
The even better news: you don’t need racing‑level sailing
skills or years of experience to enjoy it.
From our base in Lefkas Marina in the Ionian Islands, Oasis Sailing
has spent more than a decade helping guests set sail
on relaxed, skippered yacht charters and all‑inclusive sailing
holidays in Greece.
This guide will show you:
- What the best sailing itinerary looks like
- When to come
- What it costs
- Why the Ionian is one of the easiest places to start sailing the Greek islands
Why the Ionian Is Ideal for a Sailing Trip in Greece
Many people hear about the strong winds of the Aegean Sea and believe every sailing
trip around Greece is an intense experience. The Ionian, on the west side of the country, is different.
- Short sails between islands: Most days are a short sail of 1–3 hours.
- Sheltered bays and marinas: Tranquil anchorages for swimming and snorkel stops.
- Warm waters and light afternoon breeze: Comfortable even for first‑timers.
- Picturesque villages: Stone harbours, Greek tavernas, and laid‑back boat life.
If you want to sail around the islands of Greece without stress, the Ionian is one of the best sailing
destinations you can choose.
Skippered or All‑Inclusive: Choose Your Type of Charter
When you book your Greece yacht charter with Oasis Sailing
You can choose the type of charter that fits your group.
Skippered Greece Yacht Charter
A skippered yacht charter in Greece is perfect if you want the sailing
experience without worrying about navigation.
- A professional skipper takes care of the yacht, moorings, and safety.
- You can take the helm and learn, or simply relax on deck.
- Your skipper shares hidden bays, local Greek tavernas, and island hidden gems.
All‑Inclusive Sailing Holiday in Greece
For a more pampered sailing holiday in Greece, choose an all‑inclusive option:
- Skipper + hostess on board
- Breakfast and most lunches are prepared for you
- Help with provisioning and cleaning so you enjoy every moment
It feels like a private cruise around the Greek islands, but with the flexibility of your own private yacht.
Bareboat and Custom Sailing Tours
Experienced sailors can also book bareboat charters or join a custom sailing
tours.
We help you design your sailing itinerary around the Ionian islands and stay available by phone and WhatsApp throughout your sailing
trip.
Greek Island Sailing in the Ionian: Highlights of the Route
Leaving Lefkas Marina, you can head out to some of the most beautiful Greek sailing
spots in the Ionian.
Meganisi
A small green island full of quiet bays with crystal‑clear water.
Perfect for your first night at anchor on your sailing
adventure.
Kalamos & Kastos
Two small islands that feel a thousand miles away from the crowds.
- Stone harbours
- Friendly locals
- Quiet anchorages
They are ideal for a slow sail
around the Ionian.
Ithaca
Famous in Greek mythology, Ithaca offers colourful villages, hiking paths, and sheltered coves.
It is a very popular stop on many sailing holidays in Greece.
Northern Kefalonia
Dramatic cliffs, turquoise water, and postcard harbours.
A highlight for guests who want to experience Greece both from the sea and on land.
These islands give you the classic Greek island sailing experience—island hopping by yacht, swimming in clear bays, and evenings in traditional Greek tavernas—without long, tiring passages.
When Is the Best Time to Sail in Greece?
The Ionian sailing season runs roughly from April to October. Each part of the season has a slightly different feel:
- May–June: Warm but not too hot, fewer crowds, and often the best possible price.
- July–August: Peak season, ideal for school holidays and long days at the beach.
- September: Considered by many the best time to sail—warm sea, stable weather, and quieter marinas.
- October: Cooler evenings and a slower pace, ideal if you prefer a peaceful sailing trip.
If you are flexible, we commonly recommend June or September for your first sailing
vacation in Greece.
What Does a Greek Yacht Charter Cost?
Each Greek yacht charter is unique, but the basic elements remain the same:
- Yacht or catamaran charter: Base price for the week (size, year, and whether you choose a monohull or catamaran charter).
- Skipper and optional hostess: Fixed weekly fees.
- Fuel and marina fees: Typically, a small part of the total in the Ionian.
- Food and drink: Groceries on board and dinners in local tavernas serving excellent food and local specialties.
- Getting to Lefkas: Flights and transfers from airports such as Preveza or Corfu.
When several friends or a family share the yacht, a sailing trip in Greece can cost about the same as a quality hotel group trip—but with much more freedom and adventure.
7‑Day Sailing Itinerary: Ionian Islands from Lefkas Marina
Here is a sample sailing itinerary that many of our guests follow on their first sailing
vacation.
Day 1 – Lefkas Marina to Meganisi
Arrive at the marina, meet your skipper, and settle into your sailboat or catamaran.
After a short afternoon sail
, anchor in a quiet bay on Meganisi and enjoy your first swim.
Day 2 – Meganisi to Kalamos
Cruise along the coast, stop for a swim in crystal‑clear water, then moor in Kalamos harbour.
Enjoy dinner in a family‑run taverna with fresh fish and traditional Greek dishes.
Day 3 – Kalamos to Kastos
A gentle short sail to Kastos.
Explore the village, visit the windmill bar, and watch the sunset over the Ionian Sea.
Day 4 – Kastos to Ithaca
Sail to Ithaca and drop anchor in a secluded bay.
Snorkel and have lunch on board. In the evening, take a waterfront stroll and soak up the ancient Greece legends of this island.
Day 5 – Ithaca to Northern Kefalonia
Head to the northern harbours of Kefalonia.
Expect colourful houses, clear water, and relaxed evenings on your private yacht.
Day 6 – Kefalonia Back Towards Lefkada Area
Choose another favourite anchorage or harbour near Meganisi or Lefkada.
Swim, relax, and enjoy your last night of boat life.
Day 7 – Return to Lefkas Marina
Enjoy a final sail around the coast back to Lefkas Marina.
Take your last photos, pack, and say a relaxed farewell.
Any itinerary is subject to change. We tailor your sailing tour to the weather conditions, your group, and what you enjoy most—more time sailing, more beaches, or more villages.
Is a Sailing Vacation in Greece Right for You?
For many first‑time guests, the big question is whether a sailing holiday in Greece is too adventurous.
With a professional skipper, light conditions in the Ionian, and short legs between the islands, most people are surprised by how spacious, comfortable, and relaxed life on board feels.
- Families love safe swimming spots and beaches.
- Couples enjoy quiet anchorages and sunset dinners.
- Groups of friends share an adventure in the Greek islands without the rush of a big group tour.
You do not need to be an expert sailor—only ready to slow down, enjoy the sea, and explore some of the best Greek islands from a different perspective.
Plan Your Sailing Vacation in Greece with Oasis Sailing
Whether you imagine a simple sailing trip with a skipper or a fully all‑inclusive cruise on a private catamaran, we can help you design the right Greece sailing tour.
Tell us:
- Your dates and preferred sailing season
- Your group size and whether it is family, friends, or a couple
- Whether you prefer skippered, all‑inclusive, or more hands‑on sailing adventures
We will recommend the best yacht options, a customised sailing itinerary in the Ionian, and a clear price so you can decide with confidence.
Ready to set sail in Greece and discover the islands by yacht?
Contact us and let’s start planning your Greece sailing
holiday from Lefkas Marina.
Frequently Asked Questions About a Sailing Vacation in Greece
1. What is the best month to sail in Greece?
For the Ionian Sea, June and September are often considered the best months. You get warm water, steady but gentle winds, and fewer crowds in the marinas.
May and October are quieter and cooler, while July and August are hottest and busiest, ideal for school holidays.
2. Where is the best place to sail in Greece?
If you want calm seas and short distances, the Ionian Islands on the west coast are one of the best places to sail in Greece. From Lefkas Marina, you can easily reach Meganisi, Kalamos, Kastos, Ithaca, and Kefalonia with comfortable day sails and plenty of sheltered bays.
2. Where is the best place to sail in Greece?
If you want calm seas and short distances, the Ionian Islands on the west coast are one of the best places to sail in Greece. From Lefkas Marina, you can easily reach Meganisi, Kalamos, Kastos, Ithaca, and Kefalonia with comfortable day sails and plenty of sheltered bays.
3. Do I need sailing experience or a license?
No. For a skippered yacht charter, you do not need any license or previous sailing experience. Your professional skipper handles navigation, mooring, and safety. You can simply relax or learn the basics and take the helm when you feel comfortable.
4. Is a sailing holiday in Greece safe for children and beginners?
Yes, especially in the Ionian Sea. The waters are generally calm, the passages between islands are short, and we choose protected bays and marinas. We brief everyone on safety rules on board and can adapt the itinerary to the ages and needs of your group.
5. How much does it cost to rent a sailboat in Greece?
The price depends on the type of yacht, season, and services you choose. In general you pay for:
– The yacht or catamaran charter
– Skipper and optional hostess
– Fuel and marina fees
– Food, drinks, and airport transfers
When a family or group of friends shares the yacht, a sailing vacation in Greece can cost a similar amount to a quality hotel holiday, but with much more freedom.
6. What is included in an all‑inclusive sailing holiday in Greece?
An all‑inclusive option usually includes:
– Professional skipper and hostess
– The yacht, bed linen, and towels
– Breakfast and most lunches are prepared on board
– Help with provisioning and cleaning
You only need to cover dinners in tavernas, fuel, marina fees, and your travel to Lefkas.
7. What should I pack for a sailing trip in Greece?
Pack light, using soft bags instead of hard suitcases.
We recommend:
– Swimwear and light clothes
– Hat, sunglasses, and reef‑safe sunscreen
– Non‑slip shoes or sandals
– A light jacket or hoodie for evenings
– Personal medicines and toiletries
We provide bed linen, towels, and all essential safety equipment on the yacht.
8. How long should a sailing vacation in Greece be?
Most guests choose a 7‑day sailing trip, which is ideal for exploring the central Ionian from Lefkas Marina. If you have more time, 10–14 days allow you to visit more islands at a slower, very relaxed pace.
9. How accessible is Wi‑Fi and mobile signal during the sailing tour?
Most harbours and many anchorages in the Ionian have good mobile data coverage, so guests usually stay connected using their phones. Many marinas and tavernas also offer Wi‑Fi. If you need reliable internet, we can help you choose a local SIM card or data plan.
10. Can we change the suggested 7‑day itinerary?
Absolutely. The sample 7‑day Ionian itinerary is only a starting point. We tailor every route to the weather, your interests, and your group—whether you prefer more sailing, more beaches, or more time exploring villages and local tavernas.
