The whitewashed houses line up like a game of Tetris against the blue sky, and the beaches, with their turquoise waters, shimmer in the sun. The Greek islands at their finest: Naxos, Ios, Mykonos, and Santorini – white alleys, blue domes, and beaches glowing in Aegean light. This gay island-hopping journey blends lazy swims, taverna lunches, panoramic sunsets, and a speedboat adventure to hidden coves. All with plenty of time to slow down, soak it in, and live the island rhythm.

With so many beautiful islands to choose from, where do you even start? This round trip brings you the very best of the Cyclades! Athens, Naxos, Ios – and of course Mykonos and Santorini, the classic Cycladic islands. Island hopping, lazy swims, beach picnics, taverna stops, and views that take your breath away – all with time to simply unwind. Beyond the relaxation, we’ll head out on a speedboat tour with snorkelling stops – and take in unforgettable sunsets with panoramic views of the islands.

These and many more highlights are waiting for you:

• Ten days of island hopping across the Aegean – Athens to Naxos, Ios, Mykonos, and Santorini

• Mykonos & Santorini: Greece at its boldest and most breathtaking

• Naxos: Wide beaches, rugged landscapes, and mountain villages with everyday island life

• Ios: Slow summer days, hidden coves, and sunsets that stop you in your tracks

Greek Islands Hopping Gay Tour Itinerary

Day 1
Welcome to Greece!
You’ll arrive in Athens in your own time. Head to the hotel - the metro is an easy and affordable way to get there.

If you’re here early, take a first walk through the city: narrow alleyways and tiny shops, old blends with new, and the Acropolis watching over it all.

In the evening, your guide will show you some of the best local spots - a relaxed introduction to Athens and the other guys. Rooftop views, neighbourhood favourites, and a taste of the city’s rhythm.

You’ll end the night in the Gazi district, the heart of Athens’ gay nightlife, and toast to the adventure ahead.

Accommodation: Arion Athens Hotel, Athens

Day 2
Call of the Cyclades
Rise and shine - today you’ll catch the first ferry from the Port of Piraeus. You’ll settle in on deck with a frappé from the bar and watch the first Cycladic islands appear on the horizon.

First stop Naxos, the largest of the Cyclades. Your luggage will be taken to the hotel, and you'll head straight into the bustle of the harbour: a stroll along the promenade into the narrow alleyways of the old town.

The higher you climb the castle hill, the quieter it becomes - and from time to time, the deep blue of the Aegean flashes between the whitewashed houses.

In the evening, you’ll sit down in a taverna for freshly grilled dishes, Greek salad and a glass of local wine.

Later, we’ll wander along the Paralia promenade to enjoy live music, a starry sky, and that unmistakable Greek zest for life. Island mood: activated!

Meals Included: Breakfast & Dinner
Accommodation: Annita's Village Hotel, Naxos

Day 3
Two Sisters of the Cyclades
Today your guide will take you island hopping to two very different “sisters” of the Cyclades - Delos and Mykonos.

One is uninhabited, sacred, and full of archaeological treasures; the other is a living postcard of whitewashed houses, boutique cafés, and Aegean glamour.

We’ll step ashore on Delos, once the spiritual centre of the ancient Aegean world. Ruins of temples, carved lions, and sun-bleached stones tell stories of gods, traders, and travellers who crossed these waters long before us.

Then it’s onward to Mykonos - bright, bold, and legendary. Here, narrow lanes open onto stylish squares, windmills crown the skyline, and the sea sparkles like stage lighting.

A day of contrast: ancient silence and island glamour - both framed by the endless blue of the Aegean.

Meals Included: Breakfast
Accommodation: Annita's Village Hotel, Naxos

Day 4
Road, ridge and sea
Rugged mountains, fertile valleys and white-sand beaches – today you’ll cross Naxos from the highlands to the sea. Winding road, panoramic view - and again. Hairpin bends and sweeping horizons carry you deep into the island.

You’ll stop in Apiranthos, a mountain village far from the beaches and seemingly untouched by time.

After a final short ride to Komiaki, you’ll shoulder your daypacks and begin your panoramic hike down toward the coast. For three hours, the path opens to the open sea, that endless Aegean blue pulling your gaze outward again and again.

You’ll cool off at the beach of Apollonas, where the water waits like a reward.

Before you return along the coastal road, you’ll stop at the Kouros of Apollonas - a 10-metre-long marble colossus, unfinished, resting in the hillside for 2,500 years. What stories could this ancient giant tell?

In the evening, your guide will prepare a beach picnic on Naxos - the perfect ending to a day of discovery on your gay island-hopping adventure.

Meals Included: Breakfast & Dinner
Accommodation: Annita's Village Hotel, Naxos

Day 5
The rhythm of Ios
You’ll board the ferry in the morning, and in just under an hour you’ll arrive in Ios.

You’ll be welcomed by the harbour, dotted with yachts, a sandy bay, and a whitewashed Orthodox church perched on the rocks.

During the day, Ios’s Chora shows its romantic, almost sleepy side. A seat in a taverna, a patch of shade, and a Greek coffee - that’s the rhythm here.

In the late afternoon, you’ll make your way up to Panagia Gremiotissa Church - the landmark of Ios and one of the island’s most beautiful sunset viewpoints. And then, the shift - as night falls, Ios changes tempo.

The rooftop bars, cafés and tavernas come alive, and the Chora becomes a small-world playground of music, laughter and open-hearted summer nights - one of the most welcoming party scenes in gay island travel.

Meals Included: Breakfast
Accommodation: Poseidon Hotel, Ios

Day 6
Hike, swim, repeat:
A long night in Chora? No problem - you won’t head out until around noon.

A quick stop at the village supermarket for picnic supplies, trekking shoes laced, daypacks stocked - and you’re ready.

First stop: Manganari Beach, where powder-soft sand and turquoise water make the midday heat disappear. You’ll cool off, stretch out, breathe, and reset.

Then you’ll hit the trail. The path winds steadily downhill to the Odysseas Elytis Amphitheatre, dramatically perched above the town, before continuing toward the harbour of Chora.

The two-hour hike is worth every step - the reward is a wide-open panorama: terraced hills, the Aegean, and the circle of Cycladic islands scattered around us. Sun, movement, the body in motion, and good company - this is gay island travel at its most natural.

Meals Included: Breakfast
Accommodation: Poseidon Hotel, Ios

Day 7
Santorini - the Icon
You’ll board the boat to Santorini this morning.

Even with a few cruise ships in the bay, the island still outshines every postcard cliché. White houses spilling down volcanic cliffs, the sea a deep ink-blue below - Santorini is pure drama in sunlight.

High on the caldera rim lies Fira, the island’s capital. You’ll take your time here: walk the narrow paths along the edge, feel the drop of the crater at your feet, and look out across the vast, open Aegean.

A coffee, a cold drink, a moment to just stand still and take it all in - this is Santorini’s real luxury.

Later in the afternoon, you’ll take the ferry back to Ios, watching the island fall behind you, the sky turning gold.

Meals Included: Breakfast
Accommodation: Poseidon Hotel, Ios

Day 8
On, above and below the sea
Today you’ll take it easy - sleep in, enjoy a slow breakfast, and let the island rhythm settle in after the last nights out in Ios.

In the afternoon, you’ll head out on a speedboat to explore the hidden coastline of the island. Caribbean-blue coves, secret sea caves and quiet beaches - places you can only reach from the water.

On board, the pace is simple: sun, salt, laughter, good company. You’ll snorkel in clear water, float, stretch out, doze, and daydream.

You’ll return to land as the afternoon light softens, and make your way to the Odysseas Elytis Amphitheatre, overlooking the island and the sea.

It’s one of the best places on Ios to watch the sunset - a wide horizon, warm stone beneath you, and the Aegean stretching out below. A drink in hand, good company around you, the sky turning gold - a perfect end to the day.

Meals Included: Breakfast
Accommodation: Poseidon Hotel, Ios

Day 9
Back to the city
In the morning, you’ll board the ferry back toward the mainland - the Aegean breeze on your skin one last time.

A few hours of sun, sea, and that familiar, easy island rhythm. Time to stretch out, daydream, and let the memories settle. After about seven hours, your ship will dock in Piraeus.

Back in Athens, your guide will say goodbye - but not before sharing one last insider tip for the evening: head up to Philopappos Hill. From here, Athens stretches out below and the Acropolis glows in the evening light. It’s a quiet, steady view - a moment to take in where you’ve been, what you’ve seen, and the days shared together.

Meals Included: Breakfast
Accommodation: Arion Athens Hotel, Athens

Day 10
Farewell to the Aegean
Your time in the Cyclades comes to a close today.

Make your way to the airport at your own pace for your individual journey home - or linger in Athens if the city calls you to stay a little longer. The end of one gay island adventure, and the beginning of whatever comes next.

Meals Included: Breakfast