Santorini Sailing Tour

The Santorini private sailing cruise is a good combination of crowded islands with some quite, small places at the Small Cyclades.

  • The cosmopolitan island of Santorini is in the higher priority in all of our guests mind. Everybody loves and for sure it’s worth, to visit this unique place with a private yacht.

  • For those who will chose this itinerary we have to mention that because the north winds are dominant in the area, you will have a very easy downwind sailing leg up to Santorini but on your way back you will have to motor a lot against the wind in order to get again at the protected area south of Naxos.

    Furthermore, especially from mid-June to mid-September, anchoring in Santorini is almost impossible due to lack of space in the marinas and due to congestion. Our opinion is that if you especially sail out of the high season its worth to try it. You are not going to find something similar on the whole planet.

  • Islands hopping: The following Cycladic islands, Paros – Ios – Santorini – Koufonisia –  Iraklia – Antiparos – Paros
  • Duration: 7 days
  • Suggested for: Couples ,  honeymoon
  • Dates for this trip: May, June, July, August, September, October
  • Max sailing time per day: 5-6 hours
  • Miles in total: 130 – 150
  • Sailboats you can pick:
  1. Beneteau40 sailboat(2 – 4 guests)
  2. Sun Odyssey 440 sailboat for rent (up to 6 guests)
  3. Lagoon39 Catamaran(up to 8 guests)

2022 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)




Sailing the Cyclades


Greek Water Yachts

Interactive Map for Your Sailing Vacations in Santorini sailing route


Route info

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

Day 1: Meet your skipper at Marina cafe at 11:00 and board the yacht. After the briefing set sail for our first island, Ios. The sailing time is going to be 4-5 hours depending on the weather conditions. 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 that you prefer to explore the beauty of the island.

Day 2: Today we will continue further south to the famous island of Santorini. We will enter the bay of Thira from the north and get ready to take as many pictures as you can of Oia, Fira town, and the volcano islands. We are going to sail around Nea Kameni(volcano) which is unbelievably unique and beautiful. Finally, we will head for the marina at Vlihada, very close to Perisa. The marina is on the south coast of Santorini and is the only place for yachts. It is about eight miles from Nea Kameni to reach the area, that means about one and a half hours more sailing. A rental is going to wait for you at the marina arranged by us in order not to waste your time and be on time in the town for your sunset photos.

Day 3: One day at Santorini is not enough. So we think it would be better to spend the whole day exploring the island with your rental. There are hundreds of beaches with black sand. Interesting wineries and archeological sites which worth to be visited. Watch the sunset from Oia and experience the nightlife at Fira town.

Day 4: Today we will start early this morning heading north for Koufonisi. It’s a long day trip but it’s worth it. A refreshing stop for swimming at Kato Koufonisi, before entering the marina in the afternoon. Rent a bicycle to visit the amazing sandy beaches.  On the island, you will find the best taverna of the Cyclades, Capitan Nicolas, excellent recommendations from all the tourist guides. Wander in the small streets of the tiny island and finish your day at the windmill bar for a drink, enjoying the view of the nearby islands.

Day 5: 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 Schinousa on our way from Koufonisi 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 6: Antiparos is the last island of our Cyclades sailing 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 local bars. Nightlife here, especially in high season is a must for everyone.

Day 7: 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.

Meet the islands

Paros in a few words: For most travelers at Cyclades, Paros is the most beautiful island of the area. Once you visit the island you fall in love with it and promise to come back again. Paros can satisfy the most demanding traveler. Gorgeous golden beaches all around the coast, traditional settlements, sports activities, nightlife for all interests are some of its characteristics.

Location:The location of the island in center of Cyclades and near Naxos, Ios, Sifnos, Mykonos, Santorini and Syros is ideal for sailing excursions at the nearby islands and the connection with the mainland.


  • Panagia Ekatontapiliani  in Parikia.
  • Naousa (Greek: Νάουσα) is a village in the north eastern corner of the island.
  •  Lefkes village is in the middle of the island with many nice tavernas, and beautiful alleys.


  • Visit as many beaches as you can, don’t stay in one every day.
  • take a very nice walk at the old stones of the Byzantine Route down to Prodromos.

Eat – Drink:

Select a place you like and taste: Gouna fish, Local cheese ,Kapari ,Souma ,Ntakos ,Octapus

Alternatively you can arrange with the crew of the boat a Greek dish with local products

Read More:

Find more information about Paros at wikipedia, wikitravel 

Ios in a few words: For some people, Ios is the home country of Homer and for some others, it is only the place where Homer died. Anyway, nowadays Ios is well known for the thousands of bars and for the all day and night parties at the famous beach of Milopotas.

Location: Between Naxos and Sikinos


  • The tomb of Homer in Plakoto.
  • The imposing church of Panagia Gremniotissa.


  • Swim in the fabulous beaches of the island such as Magganari beach, Mylopotas, Koumbara beach and Psathi and discover the small bays all around the island.
  • Watersport almost in any beach.
  • Hiking via small paths in order to meet the nature of the island.
  • Have fun in the numberless bars where the mood is always up.

Eat – Drink:

Many kinds of local cheese.
Taste caper and fava and local recipes with handmade pasta.

Read More:

Find more information about Ios Island at Wikipedia, Wikitravel.

Santorini in a few words : A unique landscape due a volcanic eruption back at 1950, discrete black sand beaches and amazing night life, compose Santorini’s puzzle. Remember if you visit Santorini with a sailing boat one day is not enough. Plan to spend at least two nights.

Location: At the south of Aegean sea.


  • The island offers a breathtaking view from caldera, natural beaches surrounded by black or red sand.
  • The archaeological and prehistorical museum in Fira, very interesting, it contains exhibits from the geometric , archaic and Hellenistic period.
  • A visit to the Minoan city in Akrotiri.
  • Visit the Minerals and Fossils Museum in Perissa, where you can see a mineral collection and rare tree fossils.
  • Visit at the south east of the island the ruins of ancient Thira.
  • Visit the venetian castle in Imerovigli village.
  • Enjoy the unique sun set from Oia village.


  • Swim in the beaches of Perissa, Kamari, black, white and red beach.
  • An excursion by boat in the center of caldera – Nea and Palea Kameni- in order to bath into the hot springs of the area.
  • A lot of possibilities to relax and have fun in any kind of clubs, bars, restaurants in every village of the island.
  • Every Friday from May to October, Volcan Wines organize parties on their property.
  • A day trip to the Thirassia island.
  • Horseback riding in the paths of the island.
  • Water sports.

Eat – drink :

  • Taste the local wine which its famous.
  • Taste the great local product : fava
  • Tomato keftedes.

Read More:

Find more information about Santorini island at wikipedia, wikitravel

Koufonisia In a few words : Koufonissia are actually two islands one close to the other, which are made the group of islands that called Small East Cyclades.

Location: They are located at the southeast of Naxos and at west of the Amorgos island. In the same group belongs and the island Keros.
See :

  • If we translate exactly the word Koufonissi in English we get ”the deaf island. As soon as you take your first steps on the island you will sense that you are in a different dimension or that paradise really is here.
  • You might also walk to Profitis Ilias, which affords an exquisite view to half the island and the surrounding islands.Keros was one of the center of the Cycladic culture (3000 -2000 b.c.), where excavations on the western end yielded priceless finds, including 100 marble figurines.

Do :

  • swim at the excellent beaches with sparkling aquamarine waters .
  • Visit the cave of  “To Mati Tou Diavolou” (Devils Eye), Gala, and the sea caves at Xylobatis.
  • Walk all around the islands, it’s the best way to explore the place via small footpaths. It’s also your only opportunity to forget your car and your watch…

Eat – drink : Captain Nicolas is the best taverna in the Cyclades and with our recommendations you are going to experience the best hospitality.

Read More:

Find more information about  Koufonisi at wikipedia, wikitravel 

Iraklia In a few words : Iraklia is another tiny island with almost 100 islanders on it. Iraklia is part 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.

Location: Just opposite Schinoussa and south of Naxos
See : Very interesting is a cave at the south west side of the island, the cave of Agios Georgios, but you have to walk for more than two hours from the port to visit it. The bay of Alimia at the south west coast has a lovely beach and also a sunken battle plane from the second world war , visible from the surface.

Do : Here you can swim to the nearby beach, diving from the yacht and hiking around enjoying the pure nature.

Eat – drink : Dinner at Iraklia means fresh fishes

Read More:

Find more information about Iraklia at wikipedia, wikitravel 

Antiparos in a few words: A very small and beautiful island which has direct relation with the big sister, Paros.

Location: Very close to the west coast of Paros.


  • The Antiparos cave where you can go by bus from the port.
  • Despotiko island where there are a lot of archaeological see sights.


  • swim at the wonderful beaches all around the island, especially in Agios Georgios beach.
  • Visit the local festivals during summer.
  • Many bars, cafe and clubs for nights that never be forgotten

Eat – Drink: Taste traditional specialties in any type of restaurant you wish.

Read More: Find more information about Antiparos at wikipediawikitravel

Booking form

Make your introductory Cyclades sailing yacht rental request 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 sailing trip to Greek islands.