I’ve always been a water baby. I’ve spent a good chunk of my life surfing and travelling to coastal places, but sailing had somehow escaped me. So, the idea of spending five days on a boat in Greece's Cyclades Islands filled me up with equal measures of excitement... and concern.
As someone who can barely sit still through a full day at work, I wondered whether being confined to a boat would end up feeling like a big mistake.
Much Better Adventures
Three weeks after clicking ‘Book Now’, I was stepping aboard Bianca, a 15.8 metre (52ft) monohull, alongside seven strangers and our skipper, Dimi. The group was exactly what you’d expect from a Much Better Adventures trip: people from all corners of the world, in their 20s through to their 50s. Friends escaping work for a few days, a couple celebrating their 25th anniversary, a solo traveller fresh from a Hyrox race, and me, also travelling solo.
Turns out, my worries were severely misplaced. Somewhere between watching seabirds glide over the water, taking the helm of the boat, helping to hoist the sails, reading on deck, chatting with the group and patiently waiting for dolphins to make an appearance, my concerns about boredom completely vanished.
Here are five things I wish I’d known before sailing the Greek Islands.
1. It's a proper live-aboard adventure
This isn't one of those sailing trips where you spend all day on the water before checking into a nice hotel each evening. You're living on the boat for four nights.
It never felt like chores; it made us feel like a little floating household.
You'll likely share a cabin (unless you've booked your own) and you'll quickly learn where everything lives below deck, and that everyone chips in. Breakfasts, drinks, light cleaning, tidying up after meals – it all becomes part of the rhythm of life onboard. It never felt like chores; it made us feel like a little floating household.
2. You won't get cabin fever
This was my biggest surprise. Most evenings you'll dock in a different harbour, so there's plenty of time to stretch your legs. Morning runs, sunset hikes, wandering through tiny villages, finding a beach, grabbing a gelato, or popping into the local market to top up on snacks - there's always something to do.
A little tip from me: if you stop in Kythnos, go for a run and explore some of the nearby coves. And if you make it to Serifos, the hike from Livadi up to Chora is well worth the hour or so climb. Your legs might disagree halfway through, but the views definitely won't.
So no, I never once felt trapped on the boat. Quite the opposite.
3. Fresh water suddenly becomes precious
Let's talk showers. Water is limited onboard, so you become surprisingly aware of every litre. Some ports have shower facilities, which I'd highly recommend making the most of, but showering on the boat isn't exactly a five-star hotel experience. Unless, of course, you embrace it.
It felt like discovering a quieter side of Greece I didn't know still existed in the middle of summer.
One of my favourite little rituals became showering on deck at sunset after a swim, surrounded by nothing but sea. If you've got long hair like me, there might be the odd evening where you go to bed feeling a little saltier than usual – but honestly, that's all part of the experience.
Also, a little public service announcement to save you five minutes of confusion: the shower head actually pulls off the tap. You're welcome.
4. You can still find quiet Greece… even in summer
I was fully prepared for crowds. We travelled in late June. Schools were breaking up across Europe, and I'd just spent a couple of days in Athens weaving my way through tourists. I assumed the islands would be similar, but I was wrong.
One of the biggest luxuries of travelling by sailboat is that, for hours at a time, it's just you and the Aegean. And when we stopped for swims? Maybe another boat or two. That's it. That deep blue becomes your only companion.
Much Better Adventures
By the time we reached each harbour, the villages felt alive without ever feeling overwhelmed. Local life carried on around us, tavernas buzzed, people gathered in the squares – but there were no giant cruise ships, packed beaches or streets overflowing with holidaymakers. It felt like discovering a quieter side of Greece I didn't know still existed in the middle of summer.
5. It'll make you want your own boat
Yes, really. By the end of the trip, our conversations had somehow evolved into marina fees, boat repairs, shared ownership and browsing boats for sale online. I even caught myself checking whether my credit limit could somehow stretch to buying one (spoiler alert: it can't).
Learning enough about sailing to feel like I was genuinely part of the crew rather than just a passenger, I left wondering how soon I could do it all again.
I don't even know how to start the engine properly yet, but somehow that didn't seem to matter. Sailing has a funny way of getting under your skin.
And that's probably the biggest thing I wish I'd known before booking. I thought I'd be counting down the hours until we got back to land. Instead, I found myself wishing the crossings were longer.
Much Better AdventuresLooking back, it wasn't just the islands – although they were incredible. It was watching the sunrise from the deck, the Greek salads, lying under impossibly starry skies, cutting through the water under full sail with the boat leaning over at 20 knots, laughing through bouts of seasickness together, and learning enough about sailing to feel like I was genuinely part of the crew rather than just a passenger.
And of course, there was our skipper, Dimi. An incredibly experienced sailor, endlessly patient, calm through rougher seas, always happy to answer questions, teach us the basics, recommend the best local tavernas, and somehow make the whole week feel effortless. I boarded wondering whether I'd enjoy four days on a sailboat. I left wondering how soon I could do it all again.
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