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.



  • the highlight of the cruise is the less known islands you will discover. Most of them can only be visited by private boat

  • the early arrivals at the islands give you the opportunity to walk or drive around in order to explore the unique scenery.


  • 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, honeymoonnaturists 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:
  1. Beneteau40 sailboat(2 – 4 guests)
  2. Sun Odyssey 440 sailboat (up to 6 guests)
  3. Lagoon39 Catamaran(up to 8 guests)
  • 2023 Prices:

Discount up to 300€ for week charters on certain dates. Contact us

Prices in €/week for skippered charter October May, June, July & September August
For 2 people 3230 3870 4190
For 3 or 4 people 3480 4180 4520
Departure / Arrival Paros/Paros
What the package includes VAT 24%, the sailing yacht with all her equipment, skipper’s fee, taxes, insurance, credit card commission, wifi
What is not included Τhe diesel, the marina’s fees at the islands that you are going to visit and the end cleaning.This amount is 280€ in total. food & drinks are not included
Prices in €/week for this skippered charter(boat + skipper included) May June and Sep July August
Up to 6 persons 4820 5730 6200 6920
Departure / Arrival Paros only Saturdays 17:00 Check outs Paros only Saturdays 09:00 (return to Paros Friday afternoon)
What is included yacht, skipper, 24% VAT, insurance, taxes, bedding, linen & towels, cooking fuel, AC current for charging your small devices, CD & MP3 sound system.
What is not included 1. food & drinks for you and the skipper
2.the diesel(depends on the consumption), the marina’s fees at the islands that you are going to visit.From our experience for one week charter this amount is about 150€ in total.
3. end cleaning & outboard 150€ fixed at the beginning
4. refundable security deposit

Discount up to 500€ for week charters on certain dates. Contact us!

Prices in €/week for skippered catamaran charter May & Oct June & Sep July Aug
3 cabins for up to 6 guests 5420 6570 7190 7490
4 cabins for up to 8 guests 5830 7090 7770 8100
Check in / Check out Paros at 17:00 / Paros at 09:00
What is included catamaran Lagoon 39, skipper fee, insurance, VAT 24%, taxes, credit card commision, wifi, bedding, linen & towels, motorised tender, AC current for charging your small devices
What is not included 1. your food as well as your skipper's is at your charge.
2. end cleaning and fuel-water-port taxes (in total approximately 450 - 600 € per week depending on the fuel consumption at current diesel prices)



…We found ourselves naked upon the pumice stones, watching the rising islands, watching the red islands sinking into their sleep, in our sleep…

Giorgos Seferis


Map for a Greek island-hopping itinerary for 14 days

Route info

The check-in at 11:00 and check out at 17:00 is for the Beneteau40 and Beneteau50 and Lagoon39. The second Lagoon39 check-in is at 17:00 and the check out at 09:00

Day 1: Meet your skipper at the Marina cafe at 11:00 and board the sailboat. After the briefing concerning your trip, set sail around Paros for our first destination, Naxos. Depending on the weather conditions it’s going to take us 3-4 hours sailing trip. Naxos is one of the biggest islands of the Cyclades with great interest and many sightseeing. Don’t miss the sunset at the ancient temple of Apollo, just a few meters away from the marina. Grilled octopus with “ouzo” is a “must” here.

Day 2: Today we are going to sail south following the west coast of  Naxos ending up at the most south of the island, at Kalando bay. In the midway, your sailboat will stop at a nice anchorage, Roga, for swimming and lunch. Kalando is a special place. There is a safe port for the yacht but not a village. It’s an isolated area with a long sandy beach and many kilometers of trails by the seaside, ideal for hiking in the pure nature. For dinner, a primitive kiosk operated by a local shepherd offers BBQ only with local products. Don’t expect luxuries here. For sure it’s going to be your favorite place at the end.

Day 3: Set sail from Kalando heading for Koufonisi. Cruising between rocky coves with impossibly clear water. A shortstop before our final destination, at a wonderful spot, called Rina, where you can swim inside a sea cave. Amazing colors everywhere. Koufonisi is further the most beautiful of the small Cyclades islands with many sandy beaches all around. Rent a bicycle and visit all of them. Dinner at “Captain Nicolas” place is out of any kind of negotiation as well as a frozen mojito at the windmill bar just above the marina.

Day 4: If we have strong wind today we recommend to stay in the area visiting with the sailing yacht the nearby island of Kato Koufonisi and swim in crystal clear waters, snorkeling or go hiking around. The area is very protected from big waves because the huge island of Naxos to the north blocks the wind in order to make our life on board more comfortable. In the afternoon we will return to the same marina at Pano Koufonisi. An alternative in case the weather permits us, we will continue our sailing trip to Amorgos, the island of the “Big blue” movie. Rent a car or a bike here to explore the wild beauty of this heaven. Visit the famous monastery with the breathtaking view from its balcony and try “rakomelo”, the local alcoholic drink. Dinner at “Xilokeratidi” is going to be a memorable romantic event by the seaside.

Day 5: Schinoussa is an island enjoyable by the visitor in every way. You can enjoy the beautiful sea by swimming on one of its 18 beautiful beaches in the crystal clear waters. Hike, have an unforgettable evening at one of the cultural events, taste the delicious local food, taste fresh fish and have fun at the island’s festivals.

Day 6: Iraklia is another island of the “Small Cyclades” which is worth to be visited especially for those who want to experience tiny, quiet, cute and isolated places, representative of the Greek spirit. So after a short stop for swimming at Antikeros on our way from Amorgos to Iraklia, we will end up at the picturesque port of the island. Here you can swim to the nearby beach, diving from the yacht and hiking around enjoying the pure nature. Dinner at Iraklia means fresh fishes and the local tavernas more hospitable than anywhere else are ready to fulfill your expectations.

Day 7: Ios is the party island for all the young Europeans but don’t be afraid if you don’t belong to this category. The parties are taking place in the town of Ios 2 km away from the place we are going. The area offers some nice restaurants, a wonderful beach to swim and rentals in case you prefer to explore the beauty of the island.

Day 8: Thirasia is one of the five islands created from the explosion of the Strongili volcano in 1.600 BC. It is a rough island ideal for travelers who love discoveries and simple joys in life. As the size of the island is small, the most suitable way of transport is on foot. Also, make sure you bring cash with you as there is only on cash machine on the island.

Hiking in an active volcano is undoubtedly an experience of a lifetime! On Theresia’s eastern side, one will be able to see white lava volumes among the wild sceneries. One of Santorini’s most impressive volcanic veins is located on Theresia’s southern end. In fact, it is a vertical lava intrusion flowing into the earlier veins. The area is even more impressive due to the erosion of the surrounding materials and it stands out as a small wall. While Santorini is legendary for the sunsets, Thirassia is renowned for its beautiful sunrise! Visit the monastery of Panagia on the southernmost side of the island to catch the rising sun!

Day 9: Folegandros. Looking for a quiet Greek Island where you can get away from package tours and holiday-makers? Folegandros may be just the place but you better hurry. The cat is out of the bag. Walk through Hóra’s narrow streets and admire the traditional Cycladic architecture. Wait until the sunset reaches the eternal blue of the Aegean and join the locals on the squares of the village. Taste the local delicacies, such as “matsáta” (handmade noodles with rooster or rabbit), sourotó (white goat cheese), and drink “rakómelo” (raki with honey) the famous spirit of the island.

Day 10: Kimolos means chalk and you will enjoy a special white view of all the chalk mines all around and also a special formation of the rocks, like “the elephant”. At the port, you can find charming taverns but we strongly recommend to walk up to the village 2km away which is really beautiful. Try local dishes and ask for “ladenia” something like pizza but cooked in their own way.

Day 11:  Milos. We are going to stop for swimming in a lovely place called Ellinika with underwater antiquities. In this area, they have found the famous statue of Afrodite of Milos in the sea. At Adamas the main port of Milos you can find anything you are looking for, taverns restaurants bars supermarkets and so on. We recommend you to rent a car bike or take the bus and visit a wonderful spot called Sarakiniko. A unique place with white rocks that can have amazing shapes often compared to a moonscape. Finish your day at the capital of Milos Plaka enjoying a wonderful sunset drinking a mojito.

Day 12: Polyaigos – Sifnos. Today we are going to stay on the anchor for the night. Polyaigos is an uninhabited island full of goats. Here you can experience all the variations of blue and green in the sea, peaceful night and white rocks in amazing formations. Be prepared with food on board because there is no tavern. As an alternative, we may visit Sifnos. Platis Gialos has a wonderful long sandy beach nearby with nice taverns and charming coffee shops on the seafront. You can visit the local pottery shops and see live how they make the pots, dishes, and other articles made of earthenware or baked clay. Also, you can rent a car-bike or take the bus and visit the capital of the island, Apollonia. Try the local goat meat from the nearby island Kitriani cooked in clay pots.

Day 13: Antiparos is the last island of our cruise. After a 4-5 hours sailing trip and of course after the oblate stop for lunch and swimming, we will end up at Antiparos late in the afternoon. Wandering around the small streets of the beautiful village, have dinner in one of the hundreds of restaurants and continue with a drink at one of the locals’ bars. Nightlife here, especially in high season is a must for everyone.

Day 14: We strongly recommend you before setting sail for our final destination, to visit the cave of Antiparos. Buses are operating just 100 meters away from the yacht. On your return on board, we will leave immediately for a nice anchorage on a small island north of Antiparos with crystal clear water. The afternoon has already come as well as the farewell time at Paros port.

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.


Check out our questions and answers section about common questions concerning your private yachting vacation in Greece with skipper



greek island hopping itinerary 14 days


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