A month of island hopping in the Greek Isles on a sailing boat


Scattered like pearls around the shimmering Aegean and Dodecanese coasts, the dazzling colors, the charms, and the great food of the Greek islands have attracted many.

Don’t put on hold a vacation that will be in your memory for a lifelong. It will be for sure an amazing experience filled with all kinds of adventures.

Charter a private sailing boat or catamaran without the need to pack and repack and you can discover most of the Greek Islands (Cyclades and Dodecanese).

Peek into all the ancient ruins you can, swim from the boat in secluded coves, discover the stars, participate in sailing, 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 great sense of why Greece is beloved by so many travelers and much more.


Benefits for a month-long sailing trip in the Greek Islands?

  1. Really feel like you are on vacation
  2. Immerse yourself in the culture and feel like a resident
  3. Maximize your flight cost and flight time
  4. More time you can see, do and experience

At a glance

  • Islands hopping: Naxos – Kalanto – Koufonissi – Astypalaia – Nisyros – Tilos – Chalki – Simi – Kalymnos – Leros – Lipsoi – Arkioi – Agathonisi – Patmos – Levitha – Amorgos – Sxoinousa – Iraklia – Despotiko – Paros
  • Duration: 4 weeks
  • 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: 9 hours
  • Average sailing time per day: 4 hours
  • 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)

What are the total costs for a one-month vacation trip to the Greek Islands on a sailboat?

Except for the boat fees and skipper fees that can be found in the tables below, extra costs are estimated at around 20-30 euros per night in ports for docking. Of course, we can do a lot of moorings. The fuel is paid for by the customer locally as well (he picks it up full and delivers it fully, around 800€ for 4 weeks). Also, the final cleaning is 150 euros because we will change sheets 4 times.

In total extra costs for the boat are around 1100€ and 1500€ depending on the type of boat.

Now if you would like to calculate how much money you are going to spend during 4 weeks for food and drinks, we can assume that it is not more than 500€ per person if you have breakfast and lunch on board and dinner offshore. This is coming out from our experience in the Greek islands, but of course, it might vary and it totally depends on you.

What is the cancellation policy for  for a one-month vacation trip to the Greek Islands on a sailboat?

For a month sailing trip the cancellation policy is not the same as our general cancellation policy. Contact us for more info

Prices in €/4 weeks for skippered charter October May, June, July & September August
For 2 people 10700 12680 13760
For 3 or 4 people 12140 13760 14840
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
Prices in €/4 week for this skippered charter(boat + skipper included) before May 23 May 23 - June 20 June 20 - Aug 1 Aug 1 - Aug 15 Aug 15 - Aug 29 Aug 29 - Sep 26 after Sep 26
Up to 6 persons 14220 17000 18330 21050 18330 17000 14220
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.
Prices in €/week for skippered catamaran charter May & Oct June & Sep July Aug
Up to 6 guests 17540 21140 22940 24020
For 7 & 8 guests add 5% for each person
Check in / Check out Paros at 17:00 / Paros at 09:00
What is included catamaran Lagoon 39, skipper, insurance, VAT, taxes, bedding, linen & towels, motorised tender, AC current for charging your small devices, end cleaning.



…A feeling came over me that was like being caressed by a cosmic wind, reminding me of what travel at its best can do: I was set free…

Paul Theroux


leros sail;ing

Route info


Typically Astypalea belong s to the Dodecanese complex of islands but on the map and also on the character it belongs to the Cyclades. Astypalea has the same architectural style as the other islands in the Cyclades but it stands out for its beauty. Built on and around hills with mills and a castle on the top with an amazing view, certainly it worth the title of the most beautiful island in the area. It is also the island with the most sun and the clearest sea waters. The scheme of the island reminds butterfly and in fact, it is like a rare butterfly, unique, sensitive, and full of charm and summer.


Nisyros belongs to the Dodecanese complex of islands. It is an island marked by the presence of a volcano. The island has the characteristic volcanic earth morphology which offers a wild sense of beauty and a special vibe. Besides, the volcano can be visited. This visit to the lunar scenery along with an amazing view and the characteristic smell of brimstone will be a memorable experience. Visit also the traditional villages, dance in the local fests, and have a bath in the hot springs located in an impressive public building.


It is a very small island, one of the Dodecanese group of islands. As a tiny island is an unspoiled paradise, the first “green” island of the Mediterranean Sea. Tilos is known for its philosophy of life which is based on ecological and humanitarian values. As a result, Tilos has achieved to be self-sufficient in energy and it preserves by choice a low touristic attendance in order not to lose its authenticity. The society of Tilos has developed a high social consciousness and they have organized an excellent center for refugees and on the island took place the first homosexual wedding in Greece. Furthermore, the natural beauty and the simplicity of life are some spots of the islands that are ideal for a relaxed, sophisticated vacation.


Halki is a small island situated on the southeast of the Aegean Sea. The first look of the island when you arrive in the port is so eye-catching that will keep Halki in your heart forever. Halki is an ideal destination for a peaceful vacation on a traditional island full of hospitality, good food, a simple way of life, and the pleasure that gives a beautiful nature and magical beaches.


Symi is part of the Dodecanese complex of islands. It is well known for the exceptional architecture and atmosphere that comes from the mansion houses which are built amphitheatrically. The island is a cosmopolitan destination with a sense of luxury in every step. There are also a lot of sights and magnificent beaches.


It is the fourth largest island of the Dodecanese group of islands. It is called the island of the sponge divers because Kalymnos are produced and proceeded sponges since the 1940s. Kalymnos has a special geomorphologic that offers opportunities for climbing, hiking, speleology, and scuba diving. It is an excellent choice for an alternative, active vacation, and delicious local food (fish, cheese, ouzo).


Leros is an island of the Dodecanese complex of Islands. It is an island full of flora, a green island. Agia Marina the largest village on the island has been built by Italians, it is a sample of extraordinary architecture. The island offers all the touristic services along with a traditional atmosphere and fantastic beaches and beautiful small villages.


It is a gorgeous small island on the southeast side of the Aegean Sea. It is considered to be the island of Kalypso the goddess that prisoned Odysseus for seven years. The description of the island by Homer is not far from reality. Leipsoi is an exquisite island with crystal blue waters, very hospitable people, and a calm atmosphere.


A tiny island in the Dodecanese group of islands. A hidden paradise ready to be revealed by an alternative visitor. The islands have not been ruined by tourism. It is an island with small white houses, multicolored plants, and authentic people. It is an ideal choice for those who wish to spend some time in a peaceful and immaculate area.


Patmos is the “Holy Island” of the Aegean Sea, the place where John wrote the “Apocalypse”. If you look around the island you will ascertain that that choice wasn’t random. The volcanic ground, the inaccessible beaches, and the wild beauty of the island give a spiritual sense in the atmosphere. A unique sight of the island is the Holy Cave of the Apocalypse the cave where John heard the voice of God. Today this cave can be visited. The Monastery of John the Theologist is a significant monument. The island has a medieval settlement with a very interesting character. Also, the beaches of the islands are organized or remoted beaches.


Booking Form

Make your introductory reservation request to Greek Water Yachts for a 4-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 a skipper



greek island-hopping itinerary 28 days


Greek Water Yachts