Ready for the ultimate island-hopping experience? The Cyclades Expedition is the perfect combination of active sailing and pure relaxation. But be warned: this isn’t just a trip, it’s an expedition.
We leave the Dodecanese behind and cross over to the world-famous Cyclades. This means more serious sailing days (sometimes 30+ miles), the chance of rougher weather, and magical nights at anchor in middle-of-nowhere bays, where we’ll take the dinghy to shore.
Sailing experience itself is absolutely not required – the skipper and crew are happy to teach you the ropes! What is important is that you understand our ‘camping on the water’ vibe. We recommend this trip if you love a healthy dose of adventure and understand that life on board is a bit more basic and cozier than in a hotel.
Is this your trip? Then this is what awaits you: real sailing, hiking to iconic spots, discovering remote bays, and toasting in the liveliest Greek villages in the evening.
We are sailing the 12-day West Route from June 11th to 23rd, 2026
All our routes are indicative and depend on weather and wind conditions.
Below is an example of our West Route:
Day 1 (Thursday): Kick-off on Kos! Welcome aboard! From 6:00 PM, you can check into your floating home for the next 12 days. We kick off the trip with drinks, you’ll meet the rest of the crew, and we’ll go over the need-to-knows. Once everyone has arrived, we’ll all dive into a cozy Greek taverna. The perfect start!
Day 2 (Friday): Off to climbing island Kalymnos Cast off! Today we set course for the famous (climbing) island of Kalymnos. Along the way, we’ll drop anchor at Pserimos for the first perfect lunch and swim stop. We’ll spend the night in the breathtaking bay of Vathi, a kind of mini-fjord. In the evening, we’ll eat at a family restaurant with a killer view over the bay.
Day 3 (Saturday): The castles of Leros After breakfast (with the best view ever), we hoist the sails. Today we’re tackling a beautiful trip north: Leros. This island is a mix of everything: green hills, clear blue water, and serious history. Time to explore and check out those medieval castles.
Day 4 (Sunday): Off-the-grid on Levitha (BBQ night!) Today is for the sailing enthusiasts! We have 20 NM ahead of us towards Levitha. A perfect day to actively take the helm yourself and learn all about sail trim. Levitha itself is next level: a mini-island, virtually uninhabited, rugged, and with water so clear you can see the bottom. We drop anchor, dive in, and in the evening… it’s time for an epic BBQ on board. This is ‘camping on the water’ 2.0.
Day 5 (Monday): Cyclades vibe on Amorgos Waking up in total silence. After breakfast, we sail further west, into the Cyclades! Our stop: Egiali on Amorgos. This is the Greece from the postcards. A stunning bay, traditional white houses, and relaxed taverns right on the beach. Grab a drink, explore the picturesque streets, and soak up the atmosphere.
Day 6 (Tuesday): Hike & Scooter Time on Amorgos Short sailing trip, maximum adventure. We move to Katapola, the other port of Amorgos. This is the ultimate base to conquer the island. Rent a scooter or car and must-see: the iconic monastery of Hozoviotissa, spectacularly plastered against a cliff. Amorgos is perfect for hiking, discovering remote beaches, and being amazed by the rugged cliffs.
Day 7 (Wednesday): Full sails to Ios! Brace yourself for a serious sailing day! We’re blasting 30 NM westward to the notorious Ios. After days at sea and in quiet bays, it’s time for some action. We moor up and head into the lively Chora. Ios is the perfect mix: beautiful beaches and ancient ruins by day (they say Homer is buried here), and a buzzing nightlife by night. Time for a cocktail!
Day 8 (Thursday): The highlight: Santorini! Today is the day. We sail 20 NM (often downwind) and then it appears: the world-famous Santorini. Arriving by sailboat in this volcanic crater (caldera) is an unforgettable experience. We find a spot and admire the iconic sunset, the whitewashed villages, and the blue domes. In the evening, we find a taverna with the most insane sea view. Bucket list: checked.
Day 9 (Friday): Anafi & Franky’s Famous Curry After the bustle of Santorini, we turn the bow eastward. On to Anafi, 20 NM away. This is the complete opposite: a small, untouched island with a super relaxed atmosphere, rugged nature, and crystal-clear water. We spend the night in a bay, and the evening becomes legendary: time for Franky’s famous curry on board!
Day 10 (Saturday): The ‘Butterfly’ Astypalaia Ready for the longest sailing trip of the journey? We get up early and set course for Astypalaia, about 35 NM away. A full day of sailing, steering, and trimming. Astypalaia, also called ‘the butterfly’ because of its shape, is a gem. It combines the Dodecanese with the Cyclades vibe. We’ll climb the Venetian castle and get lost in the narrow streets of the beautiful Chora.
Day 11 (Sunday): Back to Kalymnos We begin the return journey. Another beautiful, long sailing day brings us back to Kalymnos, where this time we’ll anchor in the bay of Vlichadia. Time for a final relaxed evening: we’ll have a cozy dinner in a local taverna or cook together on board one last time.
Day 12 (Monday): Last sailing day & Kos by Night The circle is almost complete. We sail the last stretch back to our home port. But not before we drop anchor one last time for lunch and a final swim in a beautiful bay. Around 5:00 PM, we moor up in Kos Marina. In the evening, we go out with a bang: one last Greek dinner with the whole crew, and then (optionally) we dive into the nightlife of Kos!
Day 13 (Tuesday): Until next time! It’s a wrap. Time to check out. With (most likely) a healthy tan and a backpack full of new memories and friends. Until next time!
The Crew: Minimum 5, maximum 8 adventurers.
Please note: This is real sailing! The route is a plan, but the wind and weather have the final say. Our skipper will always choose the best and safest route based on the conditions. Flexibility is key – that’s what makes it an adventure!