What it’s really like to sail the Greek islands

Every summer, Alimos Marina transforms into a self-contained, hyperactive universe: the hiss of cleaning hoses mixes with voices in different languages, sailboats moored side by side, and people coming and going with backpacks, or even supermarket trolleys loaded with supplies for their upcoming days at sea — forming a scene that goes completely unnoticed by most. You’d never imagine what’s happening right beneath Poseidonos Avenue unless you make that small detour to get here, ideally on a Saturday afternoon.

Saturday noon, hour zero

Just one Saturday stroll around Alimos Marina is enough to see how this little microcosm rebuilds itself from scratch every week. Boats empty out from the previous booking and get prepped for the new passengers checking in, eager to start their trip. Container offices from rental companies sit side by side, a small snack bar serves drinks, staff work nonstop cleaning boats, and supplies arrive at the dock and get unloaded onto the boats hand to hand.

Boat vacations are no longer a niche choice for the few – they’ve become a habit with their own rules, their own people, their own language. As Rabie Chalatsi, Executive Manager at boat rental company Crystal Sea Yachting, tells us: the trend gained particular momentum after the pandemic, as more people looked for a way to vacation safely and privately, just with their own group of friends or family, away from crowds. That habit stuck even afterward, since those who tried the logic and freedom of a boat rarely went back.

While waiting for check-in, you can spot a bit of weariness on people’s faces as they wait in the heat next to mountains of luggage. But the moment someone from the company approaches and announces the boat is ready, any anxiety turns into the feeling of an adventure about to begin.

At this time of year, most of the people waiting at Alimos Marina are foreigners. A group of young Dutch travelers waits casually, without knowing exactly which route they’ll take. A little further along, a group of Swedes in their sixties, with their own skipper friend in tow, run final checks before boarding their home for the next week. And what about the professionals? Even in late August, the summer season is still going strong, and the rental offices don’t stop moving for a minute.

Renting a Sailboat: My way of spending summer holidays

For the past few years, whenever people ask what I’m doing for my summer vacation, my answer is always the same: same crew, one catamaran, one week of island hopping. It’s become my standard by now, but every year with new islands, new hidden spots, new stories to keep me company until next summer.

And yet, the truth is it’s not a vacation with every comfort. Every year I come back either sleep-deprived, or sick, or with broken toes (yes, all of that has happened to me). You wake up early, help out with chores, adapt to the boat’s schedule instead of the other way around, that’s at least been my experience, since our group doesn’t pay for an outside skipper and instead relies on friends who hold a license. But don’t let that discourage you – most of the day is spent lounging in the sun out at sea, reading your book, exploring beaches and diving spots, playing around on the SUP, jumping in the water, chatting with the group with a glass of wine in hand as the light fades.

The Reward That Beats Every Hassle

The payoff is one of a kind. What other way lets you see so many different islands in one week, without ferries, without hotels or Airbnbs, without lugging suitcases from port to port? Crystal-clear waters and untouched beaches you can’t reach by car. Stargazing with your friends with zero light pollution. Waking up and jumping straight into the water without any hassle. Arriving right at sunset at a tiny harbor, ready to eat at the taverna you’d already noted down.

My friend Anna, the captain of our group, describes this magic well: it’s one of the few vacations where you truly disconnect and relax, because your mind is on completely different things than usual – the wind, the sea, where you’re headed and where you’ll anchor. New friendships form, you meet people, and you bond with those around you. And there’s no other kind of vacation that brings you as close to the sea.

But why does she choose to spend her vacations this way, when objectively, for the skipper, it’s neither easy nor restful, with the constant stress of responsibility? For her, that’s actually a big part of what draws her to sailing, the adrenaline, the adventure, and the fact that you never quite know how the day will unfold. Something will always happen, the weather will change, something won’t go as planned, you’ll have to change the plan, and every time you find a solution.

She also has a favorite moment she never tires of, no matter how many times she experiences it: dawn at anchor. Absolute silence, the sea calm, the light slowly shifting around you. It’s one of those moments that, no matter how many times you live it, you never get used to. Every year, she makes sure to wake up early at least one of the days, just for that reason.

A Bond that no photo can capture

There’s something else that isn’t obvious at first: you learn to function as a team with people you may never have lived alongside like this before. No personal space, maybe no signal, no easy escape. But that closeness creates a special bond, with stories you remember and retell again and again. The Swedish woman I met at the marina described the same thing. What she likes most, she told me, is the social side of it – how it puts you in a rhythm where you have no choice but to be truly present with the people around you. Her group was so large, in fact, that they needed two boats to fit everyone.

Starting to get tempted?

Essential tips for your first sailboat trip

Pack light. Space is very limited, and trust me, you won’t wear everything you packed. Focus on clothes you’d wear at sea all day on the boat, plus 3-4 slightly dressier outfits for the evenings you go out to eat or for a drink – it won’t be every night.

Prepare for provisions. Supplies can be pre-ordered through the company – send your list at least a week in advance and it’ll be delivered to your boat on check-in day. You’ll need to restock at the islands along the way too, but don’t overdo it from the start. Don’t forget cleaning supplies and a mini first-aid kit – you won’t find a pharmacy in every cove.

Choose your crew wisely. It sounds a bit harsh, but it’s true, especially when you’re not paying for staff and everyone has a role on board. You’ll spend a week with 7-9 other people in a few square meters – it takes patience, being useful, and not taking everything personally. At the end of the day, we all want the same thing: to have a vacation, not drama.

The schedule can change, and that’s okay. As mentioned, something might go wrong and you might not end up seeing what you originally set out to see. But that’s no reason for stress, nor a reason to avoid trying it in the first place. The best moments usually come when you least expect them. And at the end of the day, remember: the captain is always right.

How much does a sailing vacation cost?

The price varies a lot depending on boat type, capacity, and season. As a rough guide, a four-cabin catamaran (up to 12 people) costs from about €7,000 a week in low season up to €12,000+ in high season. For a smaller group, there’s also the option of a monohull for 6-8 people, with prices starting around €4,000 a week without a skipper – a more budget-friendly option if you don’t need the space and capacity of a catamaran. Prices don’t include fuel, water, provisions, transfers to/from the boat, or port fees.

According to Crystal Sea Yachting, September pricing sits closer to August than to October, so if you’re after something more affordable, October is the safer bet. In fact, plenty of good deals come up for October. There are also discounts for early booking, as well as for two- or three-week rentals.

If you want a skipper, the cost is a fixed weekly rate (budget around €1,400, though this varies too). If you go bareboat (no skipper), at least one crew member needs an official boating license recognized in their home country, plus a second person with some experience (a declaration is filled out at boarding). If you pay for a skipper, you don’t need a license yourself. Payment is usually made in two installments: 50% at booking and the remaining 50% about a month before departure. Check-in is usually Saturdays at 4:00 PM, though many companies offer, for a fee, early check-in at 2:00 PM. It’s good practice to return the boat a little before the end of your booking, to allow time for inspection before it’s handed over to the next customer.

The route mostly depends on how much time you have. For a few days, the Saronic Gulf is the most convenient choice, with nearby islands and short crossings. For a full week, the Cyclades or the Ionian offer a richer experience, with more time for island hopping without rushing from port to port.

Organize your group first, decide on a budget and destination, and start your search early. If you’re thinking of going right in the heart of summer, I’d suggest booking by March or April. And if you can avoid August altogether, even better, since the meltemi winds are completely unpredictable during that period.

At some point, summer ends, the boats return to Alimos Marina and the other marinas of the Riviera, and the traffic gradually dies down. But something remains that doesn’t fit in any suitcase. A list of places you’d never seen before, a group of friends who bonded a little more, and the same thought that will find you again in a few months: where should we sail this year?