Sailing in Greece: 5 Hidden Gems to Add to Your Itinerary

Sailing blissfully through the plethora of Greek islands is a magical experience that sits high on the bucket lists of many.

As you drift through peaceful fishing villages and dock for the day in thriving ports, you’ll soon learn that no two islands are the same. That said, it’s important to separate those well-trodden islands worth side-stepping from the untouched gems crying out to be explored.

If you’re planning an island hopping trip amid the 6,000 island-strong Greece archipelago, here are five unique stops to add to your itinerary.

Porto Heli and The Peloponnese

Porto Heli

The Peloponnese region is one of the most sacred in all of Greece. Rustic, charming, and enriched by a landscape of beautiful simplicity, this is my go-to pit stop for a slice of history and culture.

Boasting over five sacred archaeological sites, you could easily spend a number of weeks here exploring the region’s diverse offerings, ranging from the birth site of the Olympics to Epidaurus, a 3rd Century BC theatre with superb acoustics.

Dock your boat at the colorful harborside resort of Porto Heli, where you can enjoy the cosmopolitan coffee-sipping vibe before sampling some of the locally caught fish in one of the many waterside restaurants.

The varied landscape affords some of the country’s most spectacular hiking and biking as it is formed of rocky mountains, verdant olive groves, and everything in between.



The trip east of Skiathos before docking at Skopelos for the day is a worthwhile journey for the views on arrival alone. There’s no airport here. Arrival by boat is the only way in or out, meaning you won’t be treading on the toes of snap-happy tourists during your trip.

As you sail towards the island, you’ll first notice the unforgivingly rocky coastline, before your attention is quickly diverted towards Skopelos Town’s port. Terracotta tiles crown white-walled homes that are nestled among the hillside. Look closely, and you’ll see chapels, monasteries, and even the ruins of a fortress, all strewn within the landscape.

You might be familiar with the box office smash, Mama Mia, which was filmed here, but that should just be a side note in your reasons to visit. Rolling hills beckon the explorer to call into one of the local tavernas located on their slopes for a taste of the local cuisine, accompanied by a fine view.

Skopelos will appeal to those of you who enjoy exploring on foot, before retiring to a charming traditional eatery later in the day.



This tiny island is located in the middle of the shimmering sea, off the coast of buzzing Corfu. The island itself is basically uninhabited, and there are certainly no flashy tourist hangouts awaiting here. This is rustic Greece at its best.

Many residents of neighboring Paxos make the 2km journey to the island daily to tend to their vineyards. If the notorious Antipaxos wine is one to tick off your list, be aware that you won’t find it in shops elsewhere and that you’ll need to make the journey to the source – the perfect excuse to dock for the day! Not only this but the beaches are said to be some of the best and most secluded in all of Greece, with crystal-clear shallow waters that are perfect for a day of relaxation away from it all.


Loutro, Crete

Located on the southwest coast of Crete, in an enclave of calm waters, accessing Loutro on foot via the winding foothills is no easy task, but it is the only way – unless you have a boat.

Situated in the foothills of a 600-meter-high mountain, the radiant whitewashed village has been a stopover for boats for hundreds of years. With no cars, hotels, busy restaurants, and beaches to be found, you are guaranteed to enjoy nothing but the sun, the sea, and serenity – now that’s luxury.

Visit during the cooler periods of Autumn or Spring if you are here for the hiking, or any other time for the water-gazing, tavern dwelling, pebbled beach lounging, ruin exploring side of affairs.


Amorgos Island

Shaped elegantly like a seahorse, Amorgos is undoubtedly one of the most beautiful islands to grace the Aegean Sea and should be at the top of the to-visit list for any sailing enthusiasts out there.

Many tourists frequent the island to explore the Monastery of Hozoviotissa, which is perched precariously on the steep hills and affording of grand sea vistas, however, the sheltered bays and coves are where you should dedicate your time. Katapola Bay and Aegiali Bay provide the perfect spots to enjoy a day of rest amid breathtaking natural beauty.

Due to the island’s jagged coastline, it has become a mecca for rock climbing as well as a popular dive site, with rich marine life in abundance. Visit the peaceful village of Arkensi on the southern tip of the island to discover the ancient remains of Kastri, a settlement occupied from the Mycenaean to Roman times.

For sweeping island views, hike to the summit of Mount Krikelos, the highest point on the island. The island isn’t swarming with tourists, but there are still a number of small 5* luxury hotels dotted around the cliffside overlooking the blue of the sea in Aegiali.

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