What is a sailing holiday?
A sailing holiday is a week (or more) spent aboard a sailing yacht or catamaran, cruising between islands, harbours, and anchorages under sail. Unlike a cruise, you set the route, the pace, and the stops. You wake up in a new bay each morning, swim off the stern, and sail to the next destination after breakfast.
Sailing holidays range from budget bareboat trips where you skipper the boat yourself, to fully crewed luxury charters with a private chef, water toys, and five-star service on the water.
Best sailing holiday destinations
| Destination | Best months | Highlights | Experience level |
|---|---|---|---|
| Greece — Ionian | May–October | Sheltered waters, green hills, family-friendly | Beginner |
| Greece — Cyclades | May–June, Sept–Oct | Mykonos, Santorini, dramatic scenery | Intermediate |
| Croatia | May–October | Medieval ports, Hvar, 1,200+ islands | Beginner |
| Caribbean (BVIs) | November–April | Trade winds, warm water, short hops | Beginner |
| Sardinia | June–September | Crystal water, Costa Smeralda, Italian cuisine | Intermediate |
| Thailand | November–April | Phang Nga Bay, Similan Islands, exotic | Intermediate |
Types of sailing holiday
Bareboat — for experienced sailors
You charter the yacht and skipper it yourself. You need RYA Day Skipper or equivalent, plus a recent sailing CV. This is the most affordable option and gives you complete freedom over your itinerary. Typical cost: £1,500–£5,000 per week depending on yacht size and destination.
Skippered — for intermediates
A professional skipper joins you on board. You can participate in sailing as much or as little as you like, while the skipper handles navigation, mooring, and safety. Adds £150–£250 per day to the charter cost. Ideal for groups with mixed experience or anyone who wants to learn.
Crewed — for luxury
A full crew handles everything: sailing, cooking, cleaning, and itinerary planning. On larger yachts, you get a captain, chef, and stewardess. No experience needed — just step aboard and enjoy. Crewed sailing holidays start from around £5,000 per week and go up to £25,000+ for premium catamarans with all-inclusive packages.
Sailing holiday costs
| Type | Weekly cost (Greece) | Weekly cost (Caribbean) | Guests |
|---|---|---|---|
| Bareboat sailboat (36ft) | £1,500–£3,000 | £2,500–£4,500 | 4–6 |
| Bareboat catamaran (40ft) | £3,000–£6,000 | £5,000–£9,000 | 6–10 |
| Skippered catamaran (42ft) | £4,000–£8,000 | £6,000–£11,000 | 6–8 |
| Crewed catamaran (50ft+) | £5,000–£15,000 | £8,000–£20,000 | 6–10 |
Prices are per week. Add 20–30% for provisioning, fuel, marina fees, and tips on bareboat charters. Crewed charters are often all-inclusive. Peak season (July–August) adds 30–50% to these rates.
Sailing holidays in Greece — a closer look
Greece dominates the sailing holiday market for good reason: over 6,000 islands, reliable summer winds, warm water, affordable prices, and extraordinary food. The country has two distinct sailing regions.
Ionian Islands (west coast)
Corfu, Paxos, Lefkada, Ithaca, Kefalonia, Zakynthos. Sheltered by the mainland with light, predictable winds. Short sailing distances (2–4 hours between stops). Green, wooded islands with quiet anchorages and traditional tavernas. The best choice for first-time charterers and families.
Cyclades (Aegean)
Mykonos, Santorini, Paros, Naxos, Milos, Ios. Dramatic volcanic landscapes, whitewashed villages, and vibrant nightlife. The Meltemi wind blows strongly in July–August (Force 5–7), making this better suited to experienced sailors or those with a skipper. Shoulder season (May–June, September) offers calmer conditions.
How Stirling Access helps
Tell us your dates, group size, experience level, and budget. Our AI concierge searches charter fleets across Greece, Croatia, the Caribbean, and beyond — returning a curated shortlist in minutes. We handle the booking, provisioning preferences, and flights.
For the ultimate experience, we combine private aviation with your sailing charter. Fly private to Athens, Preveza, or Split, transfer to the marina, and step aboard. No airports, no queues, no connections.