Sailing vacations in Greece travel guide

First off, you don’t need to know your bow from your bowline to go sailing. Plenty of sailing vacations come with a fully crewed boat. Normally, boats are small enough to be sailed by just one or two crew, a skipper (often a local, who might also double as your tour leader) and maybe a mate, and accommodate between two and 11 passengers. Having few crew keeps the cost of your vacation down, but might also mean that you’ll be part of the cooking rota, preparing meals for your group, and you might need to contribute to a small group kitty to buy groceries. But you’re on vacation: you won’t be slaving away in the galley every night as there are plenty of local restaurants to try, too.

If you’re sailing in a larger gulet you may have up to 20 guests on board and more crew. On most crewed boats you don’t need to lift a finger on deck, but if you say you’d like to help, you might get roped into taking in fenders, coiling warps (lines), and keeping watch. If you want to get really stuck in to the business of sailing, opt for a 'learn to sail' vacation, or sail on flotilla. If you’ve already got a qualified skipper (captain) in your party, you can flotilla and bareboat on your own. Unless specified, most cruises are round trips. The boat will have a permanent berth in a marina which it returns to after the week – this is true of flotilla, bareboat and crewed vacations.

Sailing can be as participatory or as sedentary as you want. At its most relaxed you could take a luxury gulet cruise in the Aegean and lie under the awning on a huge shady aft deck. If you’re craving recreation, combine sailing with cycling, or wildlife on a sailing and conservation vacation in the Cyclades, where you might spot monk seals on Polyegos and follow dolphins to Despotiko (an uninhabited island – the kids will no doubt put that to the music of Despacito!). If you were to pair sailing with yoga, you could try out a unique ‘water massage’: get pulled behind the boat whilst it’s under sail. You can’t do that on your average yoga vacation.

If you’re traveling as a family, a flotilla vacation (skippered or not) is a great way to go, as you’ll get your own boat, but you’ll be able to socialise with the families on the other boats in your group in the evenings.

Main sailing season starts in May in Greece, and runs through to October. The best time to see dolphins is between March and October, particularly in the Ionian Sea. May is one of the best months to go sailing in Greece as a novice – there’s less traffic, so you don’t have to keep such an exhausting watch if you’re learning to sail on flotilla, and there’s less likelihood of strong winds. Plus: it’s cooler and cheaper, and islands such as the Cyclades will be covered in wildflowers. The only downside is that the water will still be a little chilly for swimming. If you’re planning on scuba diving and sailing, the water is getting nice and warm by June. Summer vacations start in Greece this month. Greek school children get three months off, so expect a bustling, happy vacation atmosphere on the islands. In July and August, offshore Greece isn’t as meltingly hot as you’d expect – thanks to the meltemi. This strong wind comes from the north over the land and wraps your boat in a dry, cool air, getting stronger throughout the day. Expert sailors will go straight out to sea to dance. Novices might want to stay close to the coast. It’s thanks to the meltemi wind that the Aegean Regatta runs in August, from the island of Skyros. September is cooler and the sea is a lovely swimming temperature. In Santorini, look out for fireworks above the island at Ifestia Festival; you might be able to see them from your boat. Some sailing vacations in the Cyclades only depart in September and October to avoid summer crowds. Most sailing operators in Greece end their dates by early October but some continue to run until the end of the month.