Sail the Greek Islands

A 7-Day Adventure Through the Cyclades

Mykonos • Paros • Naxos • Ios • Santorini • Small Cyclades

Whitewashed villages clinging to hillsides. Brilliant blue-domed churches. Hidden beaches. Ancient ruins. Waterfront tavernas. And some of the most spectacular sunsets anywhere in the world.

Welcome to the Cyclades.

Here, sailing isn't simply a way to get from one Greek island to another.

The sailing is part of the adventure.

Wake up anchored beneath a hillside village. Have coffee on deck overlooking the Aegean. Spend the morning under sail. Drop anchor in a secluded bay for lunch and a swim. Then step ashore that evening and wander through a maze of whitewashed streets looking for the perfect little taverna.

With STL Skippers, the boat isn't simply where you sleep.

It's how you experience Greece.

Here's a taste of what seven days sailing through the Cyclades could look like.

DAY 1

Mykonos → Paros

Welcome to the Aegean

Step aboard, unpack your bags and settle into island life.

After getting everyone comfortable with the catamaran, we'll leave Mykonos behind and begin our first sail across the brilliant blue waters of the Aegean.

Our destination is Paros, one of the most beautiful islands in the Cyclades.

Along the way, we'll find somewhere to drop anchor for our first swim in Greece.

Later we'll head ashore and spend the evening exploring Naoussa, a picturesque fishing village filled with narrow stone streets, waterfront restaurants and traditional tavernas.

Find a table overlooking the harbor.

Order a few plates for everyone to share.

Raise a glass of Greek wine.

We're officially on island time.

Experience: First Sail • Swimming • Naoussa • Waterfront Tavernas • Greek Wine • Aegean Sunset

DAY 2

Paros → Naxos

Beaches, Villages & Greek Food

Coffee on deck.

Breakfast aboard.

Then we'll raise the sails and head toward Naxos.

The largest island in the Cyclades, Naxos gives us a little bit of everything—beautiful beaches, mountain villages, ancient ruins and some incredible local food.

After finding our spot for the night, we'll head ashore and explore.

Walk through the winding streets of Naxos Town.

Visit the massive marble Portara, the ancient gateway overlooking the harbor.

Find a local taverna.

Order more food than we probably need.

And watch the sun disappear over the Aegean.

Experience: Sailing • Swimming • Naxos Town • Portara • Greek Cuisine • Sunset

DAY 3

Naxos → Small Cyclades

Find the Quiet Greece

Today we're leaving some of the crowds behind.

South of Naxos lies the Small Cyclades, a collection of tiny islands surrounded by unbelievably clear water.

This is the Greece you can only truly appreciate from a boat.

We'll look for a protected bay, drop anchor and spend the afternoon exactly where we want to be.

Swim.

Snorkel.

Paddleboard.

Explore the shoreline by dinghy.

Have lunch aboard.

Or stretch out on deck and do absolutely nothing.

Later we'll head ashore to one of the small island villages for dinner at a family-run taverna.

Fresh fish.

Grilled octopus.

Greek salad.

Cold wine.

No hurry.

Experience: Secluded Anchorages • Swimming • Snorkeling • Paddleboarding • Small Villages • Local Tavernas

DAY 4

Small Cyclades → Ios

The Other Side of Ios

Today we'll sail toward Ios.

The island may be famous for nightlife, but there is much more to it than that.

We'll spend the afternoon enjoying the water before heading ashore to explore Chora, the beautiful whitewashed village climbing the hillside above the harbor.

Lose yourself in narrow pedestrian streets.

Climb past blue-domed churches.

Find a rooftop bar.

Stay for dinner.

And if everyone is feeling adventurous, Ios certainly knows how to keep the night going.

Experience: Aegean Sailing • Swimming • Chora • Blue-Domed Churches • Rooftop Drinks • Greek Nightlife

DAY 5

Ios → Santorini

Sail Into the Caldera

This is the day everyone has been waiting for.

Santorini.

We'll leave Ios behind and point the bow south toward one of the most recognizable islands in the world.

But arriving aboard a sailboat gives you a completely different perspective.

The massive cliffs of Santorini rise dramatically from the sea as we approach the island's volcanic caldera.

We'll sail beneath villages perched hundreds of feet above the water and experience a landscape created by one of history's enormous volcanic eruptions.

Depending on conditions and our plans for the evening, we'll find our spot and head ashore to explore.

Then it's time for one of the world's most famous sunsets.

Find a terrace.

Order a drink.

And watch the sky change over the Aegean.

Experience: Open-Water Sailing • Santorini Caldera • Volcanic Landscape • Oia • Greek Wine • Famous Sunset

DAY 6

Santorini

Explore the Volcano

We're not rushing away from Santorini.

Today we'll experience the island from both land and sea.

We might sail across the caldera toward the volcanic islands.

Swim near the thermal springs.

Explore Santorini's dramatic coastline.

Visit a winery.

Walk through the whitewashed streets of Oia or Fira.

Or simply spend the afternoon aboard the catamaran surrounded by one of the most incredible landscapes in the Mediterranean.

This is exactly why we're here.

Tonight we'll find one more great Greek meal and enjoy our final full evening in the islands.

Experience: Caldera Sailing • Volcano • Swimming • Santorini Villages • Wine Tasting • Greek Cuisine

DAY 7

Santorini → Final Island Stop

One Last Sail

Nobody is ready to leave.

So we'll make the most of our final day.

Coffee on deck.

Breakfast overlooking the Aegean.

One more swim.

One more sail.

And probably one more lunch that lasts much longer than planned.

Depending on our charter schedule and final marina, we'll begin working our way toward our departure point or finish the adventure with another island stop.

Because in Greece, sometimes the best part of the trip is the island you didn't expect to find.

Eventually, the sails have to come down.

But by then we'll have hundreds of pictures, a few new favorite Greek dishes and stories we'll probably be telling for years.

And somewhere during that last sail, somebody will inevitably ask:

“So…which islands are we doing next?”

This Isn't a Cruise.

There are no giant ships unloading thousands of people beside us.

No excursion buses waiting at the dock.

No buffet lines.

And nobody telling you that you have exactly two hours to experience an island.

This is your week.

Want more sailing?

We'll sail.

Want ancient ruins and Greek history?

Let's explore.

Want secluded anchorages and quiet beaches?

We'll find them.

Want to spend three hours eating lunch at a waterfront taverna?

That's Greece.

And if everyone decides they'd rather stay anchored in a beautiful bay for another afternoon?

Then we stay.

Weather, sea conditions and the famous Meltemi winds ultimately determine where we can safely go. That's especially important in the Cyclades, where conditions can change our plans.

But that's part of sailing.

We don't simply follow an itinerary.

We follow the adventure.

Come Sail Greece With Us.

Seven days. Incredible islands. One catamaran.

Swim in the Aegean.

Explore ancient villages.

Eat incredible Greek food.

Sail beneath the cliffs of Santorini.

Watch the sun disappear behind a blue-domed church.

And experience Greece the way it was meant to be experienced.

From the water.

STL Skippers

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