The completely stress-free way to island hop in Greece – discovering its less-crowded beaches & towns
LAYING on a sunbed at the front of the yacht, the wind in my hair and sun warming my skin, I have no idea where we are going.
My holiday is entirely in the hands of Captain Sotiris, who we called Captain So, a native Greek who has been sailing the waters for 15 years.
All I had to do was lay back and enjoy the scenery while he navigated our vessel through the fresh blue waters for three days.
From one secluded beach to another, with white wine in hand, I figured this was great competition for the more all-inclusive-style stress-free getaways I am used to.
Island hopping in Greece — where to start? From the Cyclades (Santorini and Mykonos) to the Dodecanese (Rhodes, Symi and Kos), there’s plenty of choices to suit all tastes.
Helm is a company that connects guests to the best boat in Greece, Croatia, the Caribbean and more.
When you organise your getaway via the firm, a quiz asks you where you want to go, your desired activities, and whether you want a skippered or crewed boat, or to sail it yourself.
Set your budget, anywhere from £1,500 per week to the millions, and the experts at Helm do the hard work for you before you board.
We flew into Athens and took a short drive to the harbour where the catamaran Oneida was waiting.
There were also three crew on board who, by the end of the trip, felt like old friends.
Penelope, our deckhand, was there for every beck and call and Kristo, the chef, kept us “awing” and “ahhing” at each meal.
Captain So told me his favourite part of yachting is meeting people from all around the world.
With millionaires as standard customers, I asked Captain So what are the wildest requests he receives, and is anyone as awful as made out on reality TV show Below Deck?
He told me guests expecting to visit Santorini within a short timeframe can be tricky.
Mornings were lazy — book-reading and sipping coffee. Afternoons slipped away into Aperol spritz as the sun set behind another rugged mountain.
The hugely popular destination can be difficult to moor at, but many holidaymakers won’t take no for an answer and sail for two days or more to reach the location.
Charters are “plexible” — there is a plan, but it’s flexible, dependent on weather and mooring conditions.
But above all, guests are seeking complete relaxation which is in no short supply (in between the snorkelling, paddleboarding, jet-skiing and other exciting activities on offer).
Mornings were lazy — book-reading and sipping coffee.
Afternoons slipped away into Aperol spritz as the sun set behind another rugged mountain.
Captain So stuck to the Saronic Islands, blending breathtaking landscapes, preserved architecture and even some ancient ruins along the way.
We first stopped off at Epidaurus, a quiet town Captain So says hasn’t changed in 15 years, despite being just a two-hour drive from Athens.
It is home to one of the most important archaeological sites in Greece — a preserved 4th-century amphitheatre.
Nestled in the mountains, dozens of rows seat up to 14,000 people.
Russian dockyard
Incredibly, those watching from the highest tier can hear a pin drop from the small stage below.
There’s magic about this classical theatre — sound scientists have tried to replicate its acoustics but failed.
How did they do it?
Captain So told me: “There’s nothing the ancient Greeks did by accident.”
Today, the monument still hosts ancient dramas and music events.
That afternoon we sailed to Poros, admiring the view of white houses with terracotta roofs climbing the hillsides as we approached.
The island was the most “touristy” of the locations we visited but far from the likes of British favourites Kos, Crete and Rhodes.
Rather, it felt as if we were popping in to get a flavour of what life is like for the locals.
After anchoring, we meandered for a few minutes up the narrow cobbled streets to the town’s main landmark, a clock tower on a hilltop, where we watched the sunset on the harbour.
Then we browsed the restaurants.
I loved Poseidon, a romantic open dining space serving seafood and local dishes.
But it was hard to beat the food on board Onedia.
Kostas has 15 years of culinary experience but he doesn’t overcomplicate things, rather elevates familiar tastes.
Breakfast was fluffy eggs and crepes, lunch Greek salad and homemade pastries and dinner slow-cooked beef or fresh fish.
Near to Poros is Russian Bay, a quiet beach shaded with pine trees.
At its centre is a beautiful abandoned Russian dockyard.
It’s the first beach I’ve come across where you can get a bit of history with your cocktail.
Wildlife enthusiasts would enjoy Moni Island, which friendly deer and dozens of peacocks inhabit.
As night fell we become one of the many boats that twinkled on the harbour in a chorus of laughter or cheering “Yamas!”
I felt like an explorer discovering an island for the first time as I approached on the paddleboard (and there are more sunbeds and a bar to relish, too).
Each location offered something unique, I thought, as we approached the buzzing, more traditional town of Aegina.
It’s renowned for its pistachios which are sold in every form imaginable — from pestos, spreads and oils to cosmetics.
While we spent our last evening here, you could easily explore the historic landmarks, markets and streets of gift shops over two days.
After dinner, Kostas served us Karidopita, a walnut dessert that his pastry chef father used to win over his mother, when dating.
As night fell we become one of the many boats that twinkled on the harbour in a chorus of laughter or cheering “Yamas!”
GO: GREECE BY YACHT
SAILING THERE: Prices to charter the Oneida via Helm.yt start from £1,543pp, based on ten sharing the five-cabin catamaran with five bathrooms. Prices including crew, food and drink from £2,100pp.
MORE INFO: Helm.yt has yachts, catamarans and gulets sleeping six to 12 guests in locations including Greece, Croatia, France, Turkey, Italy, Balearic Islands, Caribbean, Bahamas and Thailand.
Three services are offered via Helm.yt.
- Bareboat – for experienced sailors with a licence who want to sail themselves, prices from £1,500.
- Skippered – with captain to do the sailing (and possibly add a hostess), prices from £5,000.
- Crewed – chef-cooked meals and top service, prices from £16,000.