Experienced sailor or a total novice, Greece offers an unforgettable way to explore the Med. A chance to soak up the sun, where you can hop from island to island, swim in turquoise coves, and end your day sipping wine in a seaside taverna – tempted?
Greece is consistently one of the most popular holiday destinations for British travellers, attracting over 4 million UK visitors annually. With thousands of islands, ancient ruins, warm hospitality, and reliably sunny weather, it’s no surprise that many are now discovering its magic from the deck of a yacht.
A sailing trip offers the perfect balance of adventure and leisure. You can explore hidden beaches only reachable by boat, challenge yourself with navigating changing wind conditions, or drop anchor in a peaceful bay for a sunset swim. With direct flights from the UK, an abundance of charter options, and conditions to suit all skill levels, a Greek sailing holiday might just be your next great adventure.
In this guide, we’ll take you through everything you need to know to plan your Greek sailing adventure: the best regions to explore, how to get there, types of sailing holidays, insider tips, and more.
Why choose Greece for a sailing holiday?
There are plenty of reasons why Greece is a sailor’s paradise:
- Reliable weather: Sunshine is pretty much guaranteed from May to October, and the summer winds (like the Meltemi in the Aegean) make for exhilarating sailing.
- Stunning variety: Greece has over 6,000 islands and islets, so you’re spoilt for choice.
- Great value: Compared to Italy or France, Greece offers excellent value, especially for boat charters and eating out.
- Welcoming marinas: Most ports are well-equipped, and English is widely spoken.
- Food & culture: Think fresh seafood, friendly locals, and ancient ruins on your doorstep.
Best sailing regions in Greece
Each region has its own charm, and your choice may depend on your sailing experience, preferences, and how easy it is to get there.
Ionian Islands
Best for: Beginners, families, relaxed sailing
The Ionian Sea lies to the west of mainland Greece and is known for its calm, predictable conditions and lush, verdant landscapes. It’s the ideal region for first-time sailors or those looking for a gentle, leisurely experience. The terrain here is noticeably greener than the Aegean, thanks to more rainfall in the winter months.
Expect olive groves, pine-covered hills, and sheltered bays that are perfect for anchoring. Highlights include the charming harbour towns of Fiskardo (Kefalonia), Gaios (Paxos), and Nidri (Lefkada), as well as stunning beaches like Porto Katsiki and Myrtos.
- Wind: Light north-westerlies (Maistros), typically gentle and consistent.
- Points of interest: Corfu Old Town, Papanikolis Sea Cave (Meganisi), Skorpios Island (once owned by Onassis), and Ithaca (mythical home of Odysseus).
- Nearest airport: Preveza (Aktion), Corfu
Cyclades
Best for: Experienced sailors, classic Greek island vibes
The Cyclades are what most people imagine when they think of Greece: rugged, sun-drenched islands with whitewashed villages, domed churches, and bougainvillaea spilling over stone walls. The sailing here is more challenging due to the Meltemi winds – strong northerlies that blow in the summer, especially in July and August.
The terrain is more arid and dramatic, with steep cliffs and open anchorages. But the rewards are immense: iconic islands like Mykonos and Santorini, the charming authenticity of Sifnos or Paros, and secluded bays accessible only by boat.
- Wind: The Meltemi (northerly) can be strong and gusty; best for confident sailors.
- Points of interest: Delos (ancient sacred island), Little Venice in Mykonos, volcanic caldera in Santorini, Naoussa harbour (Paros).
- Nearest airport: Athens, Mykonos, Santorini
Saronic Gulf
Best for: Short breaks, easy access from Athens
Just a short sail from Athens, the Saronic Gulf is perfect for those with limited time or looking for a balance between city life and island tranquillity. The sailing is straightforward, with shorter hops between islands and mostly sheltered waters.
The terrain is gentler than the Cyclades, with pine-forested hills and small, welcoming harbours. It’s a great introduction to Greek sailing and a popular choice for long weekends or first-time flotilla holidays.
- Wind: Moderate southerly winds in spring and autumn, Meltemi influence in summer but less intense.
- Points of interest: The car-free island of Hydra, ancient theatre at Epidaurus, Aegina’s pistachio orchards, Poros town waterfront.
- Nearest airport: Athens
Dodecanese
Best for: Culture, off-the-beaten-path escapes
Located in the southeast Aegean near the Turkish coast, the Dodecanese Islands offer a unique blend of Greek and Eastern influences. The area boasts a longer sailing season thanks to its warmer climate and offers excellent variety – from lively medieval cities to sleepy fishing villages.
The terrain is diverse: mountainous in places, flat in others, with volcanic landscapes, rugged coastlines, and serene bays. It’s ideal for those looking to combine sailing with history and culture.
- Wind: North-westerlies and Meltemi in summer; generally manageable but can be gusty.
- Points of interest: Rhodes Old Town, Castle of the Knights, volcanic island of Nisyros, windmills of Leros, Turkish coastline nearby.
- Nearest airport: Rhodes, Kos
Sporades
Best for: Nature lovers, fewer crowds
Situated in the northwest Aegean, the Sporades offer a more tranquil, less touristy sailing experience. The islands are densely wooded and surrounded by clear, sheltered waters, making them perfect for swimming, snorkelling, and relaxing.
The terrain is lush and hilly, and the distances between islands are short, which suits laid-back itineraries. It’s a great destination for wildlife enthusiasts – the region is home to the endangered Mediterranean monk seal and several marine parks.
- Wind: Generally mild northerlies; less impact from the Meltemi than the central Aegean.
- Points of interest: Skiathos Town nightlife, Skopelos beaches (Mamma Mia filming locations), Alonissos Marine Park, Blue Cave near Peristera.
- Nearest airport: Skiathos
Types of sailing holidays in Greece
There’s something for every level of experience and comfort:
Activity resorts with sailing
These are land-based resorts that offer sailing as part of a broader holiday package. Ideal for families and beginners, they combine lessons, boat access, and lots of other activities like windsurfing, tennis, or paddleboarding.
- Best for: Families, beginners, sporty couples
- Experience needed: None
- Budget: From £800 per person per week, including accommodation, meals, and activities
Bareboat charter
You rent a yacht and sail it yourself. This gives you total freedom and privacy, but you’ll need a recognised qualification (such as an RYA Day Skipper or ICC).
- Best for: Experienced sailors, confident groups, adventurous couples
- Experience needed: Skipper must be certified; a second competent crew member is usually required
- Budget: From £1,500 to £4,000+ per week depending on boat size and season
Skippered charter
A professional skipper joins your crew, handling all the sailing. It’s a great way to enjoy the experience without the responsibility of navigating or mooring.
- Best for: Couples, small groups, first-timers
- Experience needed: None
- Budget: Boat rental (£1,500–£4,000) + skipper fee (£100–£150/day) + food & fuel
Crewed charter
This is the luxury option: you get a full crew (typically a skipper and a chef) who look after everything. Expect high-end service, gourmet meals, and complete relaxation.
- Best for: Luxury seekers, honeymooners, corporate retreats, special occasions
- Experience needed: None
- Budget: From £6,000 to £20,000+ per week depending on yacht and crew size
Flotilla sailing
Join a group of boats led by a lead yacht and skipper. You sail your own boat but get support with route planning, mooring, and social events along the way. It’s sociable and reassuring for first-timers.
- Best for: Families, sociable couples, beginner skippers
- Experience needed: At least one qualified skipper per boat
- Budget: From £2,000/week (including support and route planning)
Cabin charter
Book a cabin on a shared yacht. No need to hire the whole boat – just turn up and enjoy. You’ll usually have a skipper and host onboard, with shared meals and a ready-made group of travel companions.
- Best for: Solo travellers, couples, budget-conscious holidaymakers
- Experience needed: None
- Budget: From £800–£1,500 per person/week including skipper and some meals
Planning tips for UK travellers
Best time to go: May to October. July and August are hottest and busiest.
Licences: Bareboat charters require proof of competence (e.g. ICC or RYA Day Skipper).
Packing: Bring soft bags (not hard suitcases), light clothes, swimwear, and deck shoes.
Money: Greece uses the Euro. Cards are widely accepted but bring cash for small ports.
Insurance: Specialist sailing travel insurance is essential – check your travel insurance covers the sailing activities you have planned.
Costs & budgeting
Prices vary, but here are some rough ideas:
- Bareboat charter: From £1,500 per week (off-season) to £3,500+ in peak summer.
- Skipper: £100–£150/day extra.
- Fuel, mooring fees: Budget £200–£500 for the week.
- Food & drink: Tavernas are generally good value. A meal with wine might cost £15–£20/person.
Life on board
- Days usually start with breakfast on deck, a morning sail, lunch at anchor, and an afternoon exploring.
- You can cook onboard or eat out every night.
- Cabins are cosy, but you’ll spend most of your time outside.
- Many boats offer extras like paddleboards or snorkelling gear.
Tips for first timers
- Choose flotilla or skippered charters if you’re new.
- Bring seasickness tablets just in case.
- Don’t overpack. Storage is limited.
- Be flexible – weather may change your plans.
Sailing in Greece offers a unique blend of adventure and relaxation. Whether you want to island-hop with friends, enjoy a romantic escape, or explore hidden beaches with the kids, there’s a perfect route and boat for you.
So why wait? Grab your sunnies, pack your swimmers, and set sail for a holiday you won’t forget.
Get specialist Sailing Travel Insurance from SportsCover Direct
Another essential thing to consider before a sailing trip to Greece, is insurance cover. Sailing can be an exhilarating adventure, but it isn’t without its risks; furthermore, if you need rescue or medical help, being abroad can make things much more complicated and expensive.
SportsCover Direct is a leading provider of specialist sailing insurance for sailing trips, both in the UK and abroad. Our cover means that if you get ill, get injured, require rescue assistance, suffer transport disruption, or your luggage is lost, we can give you support that means you won’t be left out of pocket.
Included with our policies is cover for any private medical bills you might incur this is a vital consideration, as the European and Global Health Insurance Cards only extend to a limited level of healthcare.
Learn more about our sailing policies here.
This blog has been created as general information and should not be taken as advice. Make sure you have the correct level of insurance for your requirements and always review policy documentation.