Two weeks island hopping cruise
Here you will meet the real Cyclades and some islands off the beaten path!
If you look at how travel can change lives and You are the lucky one to have 2 weeks time to spend in the Greek Isles, then this tour may be for you.
Without the need to pack and repack you can discover most of the Cyclades Islands on a private charter sailing boat or catamaran charter.
Peek into all the ancient ruins you can, swim from the boat in secluded coves, discover the stars, looking out over the water, discover touristic or more isolated isles, and visit a different restaurant each night(if there is one!).
You’ll get a good sense of why Greece is beloved by so many travelers and much more.
It is a combination of some busy islands, like Naxos, with some tiny, quiet places like Polyaigos and Thirasia.
- Islands hopping: Naxos – Kalanto – Koufonissi- Amorgos – Sxoinousa – Iraklia – Ios – Thirasia – Folegandros – Kimolos – Milos – Polyaigos – Sifnos – Antiparos – Paros
- Duration: 14days
- Suggested for: Couples and friends sailing, Family Sailing adventure, honeymoon, naturists sailing
- Dates you can do this trip: May, June, July, August, September, October
- Min sailing time per day: 1 hour
- Max sailing time per day: 4 -5 hours
- Average sailing time per day: 3 hours
- Miles in total: 250 miles
- Sailboats you can pick:
- Beneteau40 sailboat(2 – 4 guests)
- Lagoon39 Catamaran(up to 8 guests)
- 2026 Prices:
up to 10% discount on the boat fee on a 2 week trip in August
…We found ourselves naked upon the pumice stones, watching the rising islands, watching the red islands sinking into their sleep, in our sleep…
Map for a Greek island-hopping itinerary for 14 days
Gallery
Route info
Check‑in & Check‑out Information
- Beneteau 40, Check‑in: 10:00 Check‑out: 17:00
- Lagoon 39 (second boat) Check‑in: 17:00 Check‑out: 09:00
🌊 14‑Day Cyclades Sailing Itinerary
A complete day‑by‑day guide for your Greek island‑hopping adventure
Day 1 — Paros to Naxos: Start Your Cyclades Sailing Adventure
Meet your skipper at the marina café at 11:00 and board your yacht. After a short safety and route briefing, we set sail for Naxos, a 3–4 hour trip depending on weather conditions. Naxos is one of the largest Cycladic islands, known for its history, beaches, and vibrant town. Don’t miss the sunset at the Temple of Apollo, located just a few meters from the marina. Local tip: Try grilled octopus with ouzo, a Naxos classic.
Day 2 — Sailing Along Naxos’ West Coast to Kalando Bay
We sail south along the west coast of Naxos, stopping at Roga for swimming and lunch. Our final destination is Kalando Bay, a remote and untouched area with a safe port but no village. Expect a long sandy beach, peaceful nature, and excellent hiking trails. Dinner is served at a simple shepherd’s kiosk offering local BBQ dishes. No luxuries — just authentic island life.
Day 3 — Kalando to Koufonisi: Sea Caves & Sandy Beaches
We depart Kalando and head toward Koufonisi, passing dramatic rocky coves and crystal‑clear waters. A highlight is a stop at Rina, where you can swim inside a sea cave with stunning colors. Koufonisi is the most beautiful of the Small Cyclades, famous for its sandy beaches. Rent a bicycle and explore them all. Dinner at Captain Nicolas is essential, followed by a frozen mojito at the windmill bar overlooking the marina.
Day 4 — Explore Koufonisi or Sail to Amorgos (Weather‑Dependent)
If winds are strong, we stay in the protected waters around Kato Koufonisi for swimming, snorkeling, and hiking. The area is calm thanks to Naxos blocking the northern winds. If weather allows, we continue to Amorgos, the island featured in the movie The Big Blue. Rent a car or bike to explore its wild landscapes, visit the famous cliffside monastery, and try the local drink rakomelo. Dinner at Xilokeratidi offers a romantic seaside experience.
Day 5 — Discover Schinoussa: Beaches, Culture & Local Cuisine
Schinoussa offers 18 beautiful beaches with crystal‑clear waters, scenic hiking paths, cultural events, and excellent local food. Enjoy fresh fish, traditional dishes, and the island’s relaxed, authentic atmosphere.
Day 6 — Iraklia: A Quiet Gem of the Small Cyclades
After a swim stop at Antikeros, we reach the peaceful island of Iraklia. Swim from the yacht, dive into turquoise waters, or hike through untouched nature. Dinner means fresh fish and warm hospitality at the local tavernas — some of the friendliest in the Cyclades.
Day 7 — Ios: Beaches, Food & Optional Nightlife
Ios is known for its nightlife, but the party scene is 2 km away from our quiet mooring spot. Enjoy great restaurants, a beautiful beach, and rental options if you want to explore the island’s highlights.
Day 8 — Thirasia: Volcanic Landscapes & Sunrise Views
Thirasia is one of the five islands created by the volcanic explosion of 1600 BC. It’s ideal for travelers who enjoy simplicity, hiking, and geological wonders. Bring cash — there is only one ATM on the island. Explore volcanic formations, lava veins, and dramatic cliffs. Thirasia is famous for its sunrise, best viewed from the monastery of Panagia.
Day 9 — Folegandros: Authentic Cycladic Beauty
Folegandros is perfect for travelers seeking a quiet, authentic Greek island. Stroll through the narrow streets of Hóra, admire Cycladic architecture, and enjoy the sunset over the Aegean. Try local dishes such as matsáta, sourotó, and rakomelo.
Day 10 — Kimolos: Chalk Landscapes & Local Flavors
Kimolos, named after the Greek word for chalk, features white rock formations and old chalk mines. Visit the charming port tavernas or walk 2 km to the beautiful village. Try ladenia, a local specialty similar to pizza but uniquely Kimolian.
Day 11 — Milos: Underwater Antiquities & Lunar Landscapes
We stop at Ellinika for swimming above underwater antiquities — the area where the Venus de Milo was discovered. At Adamas, the main port, you’ll find everything you need. Rent a car or take the bus to Sarakiniko, famous for its white volcanic rocks and moon‑like scenery. End the day in Plaka with a sunset and a refreshing mojito.
Day 12 — Polyaigos or Sifnos: Anchor Under the Stars
We anchor overnight at Polyaigos, an uninhabited island known for its turquoise waters and dramatic white rocks. Bring food — there are no tavernas. Alternatively, we may visit Sifnos (Platis Gialos), known for its long sandy beach, pottery workshops, and excellent tavernas. Try goat cooked in clay pots, a local specialty from nearby Kitriani.
Day 13 — Antiparos: Charming Village & Lively Nights
After a 4–5 hour sail and a swim stop, we arrive in Antiparos. Wander through the picturesque village, enjoy dinner at one of many restaurants, and experience the lively nightlife — especially in high season.
Day 14 — Antiparos to Paros: Final Swim & Farewell
Before departing, we recommend visiting the Cave of Antiparos (buses depart 100 m from the yacht). After returning on board, we sail to a beautiful anchorage north of Antiparos for one last swim in crystal‑clear waters. In the afternoon, we return to Paros port for farewells.
Booking Form
Make your introductory reservation request to Greek Water Yachts for a 2-week boat trip through the Greek Islands by filling out the contact – booking form. We will respond within 24-48 hours.
Faqs
Check out our questions and answers section about common questions concerning your private yachting vacation in Greece with skipper
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