Greece Sailing Vacation: Routes, Costs & How to Book

There's island-hopping, and then there's sailing the Greek islands. Waking up anchored in a different cove each morning. Swimming off the back of the boat before breakfast. Watching sunset from a harbor where you picked your own mooring. It's a completely different experience from ferries and hotels — more freedom, more adventure, more connection with the sea.

A Greece sailing vacation was once exclusively for the wealthy or seriously experienced. Not anymore. Charter companies, flotilla options, and booking platforms have opened this world to anyone willing to try. You don't need to be rich. You don't necessarily need sailing experience. You just need to know what you're getting into.

This guide covers everything: boat types, charter options, the best sailing routes, realistic costs, and how to book your first Greek sailing adventure.

Sailing in Greece: The Basics

Why Sail Greece?

The geography is perfect. Over 6,000 islands scattered across the Aegean and Ionian seas, with distances between them measured in hours, not days. You can visit 5–10 islands in a week, anchoring in different bays each night.

The conditions are ideal. Reliable summer winds (the Meltemi in the Aegean, gentler breezes in the Ionian), calm seas most of the season, and countless protected harbors make Greece one of the world's great sailing destinations.

The infrastructure exists. Marinas, charter bases, provisioning, and support throughout the islands. You're never far from help or supplies.

When to Sail

Peak season: July–August

• Strongest winds (Meltemi can reach 25–35 knots in Cyclades)
• Hottest temperatures
• Most crowded anchorages
• Highest prices

Best for most sailors: June, September

• Moderate winds (10–20 knots typically)
• Warm weather, warm water
• Less crowded
• Better value

Shoulder season: May, October

• Variable conditions
• Occasional rain possible
• Fewer boats, empty anchorages
• Lowest prices
• Water still swimmable in October

Avoid: November–April

• Most charters closed
• Unpredictable weather
• Many island services closed

Boat Types: Catamaran vs. Sailboat

The first big decision: monohull (traditional sailboat) or catamaran.

Catamarans

Pros:

• More space (wider beam = bigger living areas)
• More stability (less heeling/tilting)
• Shallower draft (access to more anchorages)
• Better for families and mixed-experience groups
• More privacy (separate hull cabins)
• Easier to board and swim from

Cons:

• More expensive to charter (30–50% more than equivalent monohull)
• Less "authentic" sailing feel
• Harder to maneuver in tight spaces
• Marina berths can be limited

Best for: Families, groups prioritizing comfort, first-time charterers, anyone prone to seasickness.

Monohull Sailboats

Pros:

• Classic sailing experience
• More affordable
• Better upwind performance
• Easier to handle in some conditions
• More marina options

Cons:

• Less interior space
• Heeling in wind (not everyone's favorite)
• Deeper draft limits some anchorages
• Less stability at anchor

Best for: Experienced sailors, couples, those wanting authentic sailing feel, budget-conscious charterers.

Typical Boat Sizes

Charter Types: Bareboat vs. Crewed

Bareboat Charter

You're the captain. You (or someone in your group) skipper the boat. Full freedom, full responsibility.

Requirements:

• Sailing license (ICC, RYA Day Skipper, or equivalent)
• Demonstrated experience (charter companies will ask)
• VHF radio license (technically required, sometimes overlooked)
• Confidence in your abilities

Pros:

• Lower cost (no crew to pay)
• Complete privacy
• Flexible schedule
• True adventure

Cons:

• All responsibility is yours
• Navigation, anchoring, weather decisions
• Provisioning and cooking yourself
• Potential stress

Cost: 30–50% less than equivalent crewed charter

Skippered Charter

A professional captain sails the boat. You relax, swim, and enjoy. The skipper handles navigation, anchoring, and boat operations.

Requirements:

• None — the skipper is the professional
• You just need to book

Pros:

• No experience necessary
• Expert local knowledge
• Stress-free sailing
• Someone else handles the hard stuff

Cons:

• Less privacy (skipper aboard, usually sleeps in small cabin)
• Additional cost (€150–250/day typically)
• Less flexibility than sailing yourself

Best for: First-time charterers, groups without sailing experience, those wanting relaxation without responsibility.

Fully Crewed Charter

Captain plus additional crew (chef, stewardess, deckhand depending on boat size). A floating luxury hotel experience.

What's included:

• Professional captain and crew
• Gourmet meals prepared for you
• Cleaning and service
• Local expertise and recommendations

Pros:

• Pure luxury
• Exceptional food
• White-glove service
• No responsibilities whatsoever

Cons:

• Significantly more expensive
• Less privacy
• Crew accommodations reduce guest space

Cost: Premium boats with crew start around €15,000–25,000/week and go much higher.

Flotilla Sailing

Group sailing with other boats. A lead boat with professional crew guides a fleet of charter boats, providing daily briefings, assistance, and social events.

How it works:

• Morning briefing about the day's route and conditions
• Sail independently during the day
• Regroup at the evening destination
• Group dinners, social events (optional)
• Lead crew available for assistance

Best for: First-time charterers who want support, couples wanting social experience, those nervous about going fully independent.

Typical cost: Similar to bareboat plus 10–20%

Best Greece Sailing Routes

The Cyclades Loop

The iconic Aegean experience

Route example (7 days): Paros → Naxos → Amorgos → Koufonisia → Ios → Folegandros → Santorini → Paros

Character: Dramatic volcanic islands, whitewashed villages, famous destinations. Strong Meltemi winds in July–August.

Best for: Experienced sailors who can handle wind, those wanting iconic Greek island aesthetic.

Wind conditions: Meltemi can reach 25–35 knots July–August. June/September more moderate (15–25 knots).

Highlights: Santorini caldera anchorage, Koufonisia swimming, Folegandros clifftop town, Amorgos monastery.

Considerations: More challenging sailing than Ionian. Meltemi can pin you down or force route changes. Less protection than other areas.

Find Cyclades sailing charters

The Saronic Gulf

Athens doorstep cruising

Route example (7 days): Athens (Alimos Marina) → Aegina → Poros → Hydra → Spetses → Nafplio → Epidaurus → Athens

Character: Close to Athens, protected waters, beautiful islands plus Peloponnese coast. Calm conditions, easy sailing.

Best for: First-time charterers, shorter trips, combining sailing with Athens visit.

Wind conditions: Generally light to moderate (8–15 knots). Occasional stronger winds but well-protected.

Highlights: Hydra's car-free charm, Nafplio's romantic harbor, Epidaurus ancient theater, Poros's proximity.

Considerations: More developed/busier than other areas. Shorter distances between stops.

Find Saronic sailing charters

The Ionian Islands

The best for beginners

Route example (7 days): Lefkada → Meganisi → Ithaca → Kefalonia → Zakynthos → Kefalonia → Lefkada

Character: Green islands, calm waters, reliable gentle winds. Easier sailing than the Aegean.

Best for: First-time sailors, families, those preferring calmer conditions.

Wind conditions: Gentle thermal winds (10–18 knots typically). Rarely challenging. Light mornings, building afternoon.

Highlights: Zakynthos beaches, Kefalonia caves, Ithaca mythology, beautiful anchorages.

Considerations: Further from Athens (fly to Preveza for Lefkada base). Less "classic Cycladic" aesthetic.

Find Ionian sailing charters

The Dodecanese

Eastern exploration

Route example (7 days): Kos → Nisyros → Tilos → Symi → Rhodes → Chalki → Kos

Character: Eastern islands near Turkey, diverse character, less crowded. Mix of sailing conditions.

Best for: Those wanting fewer tourists, historical interest (Rhodes), variety.

Wind conditions: Variable, generally moderate. Meltemi influence but less intense than central Cyclades.

Highlights: Symi's colorful harbor, Rhodes medieval town, Nisyros volcano, remote anchorages.

Considerations: Longer distances between some islands. Turkish coast visible (not a problem, just context).

Find Dodecanese sailing charters

Greece Sailing Costs

Bareboat Charter Costs

Prices vary significantly by boat size, age, season, and location.

Additional Costs

Beyond the charter fee, budget for:

Total Trip Cost Examples

Budget (6 people, 38 ft monohull, bareboat, low season):

• Charter: €2,500
• Fuel: €150
• Provisioning: €1,500 (self-catered)
• Marinas: €200
• Cleaning: €150
• Total: ~€4,500 (~€750/person)

Mid-range (6 people, 40 ft catamaran, skippered, shoulder season):

• Charter: €5,500
• Skipper: €1,400 (7 days)
• Fuel: €200
• Provisioning: €2,100
• Marinas: €350
• Cleaning: €200
• Total: ~€9,750 (~€1,625/person)

Luxury (8 people, 50 ft catamaran, crewed, peak season):

• Charter + crew: €18,000
• Fuel: €300
• Marinas: €500
• Gratuity: €2,000
• Total: ~€20,800 (~€2,600/person, all-inclusive)

How to Book a Sailing Charter

Best Booking Platforms

SamBoat Peer-to-peer and professional listings. Wide selection, competitive prices. Good filters for boat type, crew options. User reviews helpful.

Click&Boat Similar to SamBoat — large inventory, professional and private owners. Good interface, secure payments.

Sunsail Professional charter company with own fleet. Flotilla options. More standardized experience, reliable boats.

The Moorings Premium charter company. Well-maintained boats, professional support. Higher prices but quality assured.

Navigare Yachting Mid-range professional fleet. Good Cyclades coverage.

Booking Tips

Book early for peak season. July–August charters book 6–12 months ahead, especially for popular boats and routes.

Read reviews carefully. Boat condition and owner responsiveness matter. Recent reviews are most relevant.

Understand what's included. Cleaning, linens, dinghy, outboard motor, WiFi, SUP — ask specifically.

Check the deposit. Security deposits of €1,500–5,000 are normal. Some can be reduced with insurance add-ons.

Verify licensing requirements. Charter companies will ask about your experience and certifications.

Consider travel insurance. Specifically for sailing — standard travel insurance may exclude yacht activities.

What to Expect: First-Time Sailor Tips

Before You Go

• Take a sailing course if you're planning bareboat with limited experience
• Read about your route — understand distances, conditions, highlights
• Provision planning — create meal plans, shopping lists
• Download offline maps — phone signal isn't guaranteed
• Check weather apps — Windy, PredictWind

Packing for a Sailing Trip

Do bring:

• Soft duffel bags (no hard suitcases — storage is tight)
• Non-marking shoes (deck shoes, sailing shoes)
• Swimwear (multiple)
• Sunscreen (high SPF, reef-safe)
• Sunglasses with strap
• Hat
• Light layers for evening
• Seasickness remedies
• Dry bag for electronics
• Headlamp (useful on boats)

Don't bring:

• High heels or hard-soled shoes
• Excessive luggage
• Large toiletry bottles (space is limited)
• White towels you care about (they'll get dirty)

Daily Rhythm

Typical day:

• 7–8am: Wake up, swim, breakfast
• 9–10am: Depart anchorage
• 10am–2pm: Sail to next destination
• 2–4pm: Anchor, swim, lunch
• 4–6pm: Explore (dinghy to beach, walk to village)
• 6–8pm: Sundowners, prepare for dinner
• 8pm+: Dinner (cook aboard or eat ashore)

Anchoring vs. marinas:

• Anchoring is free and often more beautiful
• Marinas have water, power, showers, restaurants nearby
• Mix of both is typical
• Popular anchorages fill up — arrive by 3–4pm in peak season

Sailing Experience Needed?

For Bareboat Charter

Minimum typically required:

• ICC (International Certificate of Competence) or equivalent
• Demonstrated sailing experience (1,000+ miles, or significant coastal cruising)
• Ability to handle the specific boat size
• Knowledge of local conditions (charter companies will brief you)

How to get qualified:

• RYA Day Skipper or Yachtmaster courses (UK system, internationally recognized)
• ASA certifications (American Sailing Association)
• National sailing licenses from your country

No Experience? Options Include:

• Skippered charter — hire a captain, you're a guest
• Flotilla sailing — support boat guides you, you sail your boat
• Crewed charter — full service, zero responsibility
• Learn-to-sail charter — some companies offer instructional weeks

FAQ

How much does a Greece sailing vacation cost?

A budget bareboat charter for 6 people costs approximately €3,500–5,000/week (€580–830/person) in shoulder season, plus provisioning and fuel. A mid-range skippered catamaran runs €7,000–12,000/week (€1,200–2,000/person) including skipper but not food. Luxury crewed charters start around €15,000–25,000/week all-inclusive. Peak season (July–August) adds 30–50% to these prices. The Ionian Islands are generally 10–20% cheaper than the Cyclades. Booking early and traveling in May/June or September significantly reduces costs.

Do I need sailing experience to charter in Greece?

It depends on charter type. For bareboat charters (you sail the boat), you need a valid sailing certification (ICC, RYA Day Skipper, or equivalent) plus demonstrated experience — charter companies will verify this. For skippered charters, you need zero experience — a professional captain handles everything while you relax. Flotilla sailing offers a middle ground: you sail your own boat with support from a lead vessel and daily briefings. First-time sailors should start with skippered or flotilla options, or take sailing courses before attempting bareboat.

What is the best sailing area in Greece for beginners?

The Ionian Islands are the best sailing area for beginners and first-time charterers. Conditions are gentler than the Aegean — reliable thermal winds of 10–18 knots, rarely challenging, with light mornings building to pleasant afternoon breezes. Waters are well-protected, distances between islands are manageable, and navigation is straightforward. The Saronic Gulf (near Athens) is also beginner-friendly with calm conditions and short passages. The Cyclades are beautiful but more challenging due to the Meltemi winds, which can reach 25–35 knots in July–August — best left for experienced sailors or skippered charters.