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      • All Greece
      • Ionian Islands
      • Cyclades
      • Dodecanese
      • Saronic Islands and Athens area
      • All Italy
      • Northern Sardinia
      • Aeolian Islands
      • Aegadian islands
      • Tuscany
      • Liguria
      • Pontine Islands
      • Amalfi Coast
      • All Spain
      • The Balearic Islands
      • Andalusia
      • Catalunya
      • Galicia
      • Valencia
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      • BVI - British Virgin Islands
      • Antigua and Barbuda
      • Cuba
      • Grenadines & Martinique
      • Guadeloupe
      • Bahamas
      • Belize
      • All Indian Ocean
      • Bali
      • The Maldives
      • Mauritius
      • Seychelles
      • Corsica
      • French Riviera and Porquerolles
      • Brittany and Normandy
      • Split Archipelago
      • Kornati Islands
      • Turkey
      • French Polynesia
      • Norway
      • Adventure
      • Courses & regatta
      • Day trips
      • Flotilla
      • Offshore
      • Sport & wellness
      • WWF Sailing Cruises
      • Whole boat with skipper
      • All inclusive
      • Crewed
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      • Gulet and sailing ship
      • Monohull
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      • Families
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      • Whale watching
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Gulet sailing holidays & luxury cruises

Gulet sailing holidays & luxury cruises

Enjoy the old-world charm of a gulet or sailing boat cruise. a gulet or sailing boat cruise. Choose your itinerary: the coast of Turkey, the home of the gulet, as well as Greece and the Aeolian Islands are waiting for you.

  • Sailing Holidays
  • Gulet and sailing ship

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • confirmed

    Discover the Ionian Islands from Zante on a beautiful Caicco - Breakfast and lunch included

    from 6 May - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    747€ Per person
  • confirmed

    Discovering the Aeolian Islands aboard a Gulet!

    from 6 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    1.129€ Per person
  • confirmed

    Discover the Ionian Islands from Corfu on a beautiful Caicco - Breakfast and lunch included

    from 13 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    747€ Per person
  • confirmed

    Discover the Ionian Islands from ZANTE on a beautiful Sailer Yacht - breakfast and lunch included!

    from 13 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    747€ Per person
  • confirmed

    Discovering the Aeolian Islands aboard a Gulet!

    from 13 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    1.129€ Per person
  • 3 reviews

    Cruise to the Aeolian Islands in a 24-meter luxury gulet

    from 20 May - 7 nights
    Aeolian Islands Italy
    3 people interested
    in this holiday
    848€ Per person
  • The Ionian Islands in 7 days

    from 20 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    954€ Per person
  • confirmed

    Discover the Ionian Islands from Corfu on a beautiful Caicco - Breakfast and lunch included

    from 20 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    835€ Per person
  • confirmed

    Discover the Ionian Islands from ZANTE on a beautiful Caicco - Breakfast and lunch included

    from 20 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    835€ Per person
  • confirmed

    Discovering the Aeolian Islands aboard a Gulet!

    from 20 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    1.129€ Per person
  • The Ionian Islands in 7 days

    from 27 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    900€ Per person
  • confirmed

    Discover the Ionian Islands from Corfu on a beautiful Caicco - Breakfast and lunch included

    from 27 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    835€ Per person
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Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Gulet sailing holidays & luxury cruises

107 reviews
20 / 10
Giorgio  M.

Giorgio M.

review about Cruise between Pontine and Flegree on a luxurious maxi sailing yacht of 22 meters August 2022

10 / 10
Great trip reliable and confident skipper. Friendly and welcoming hostess. Boat with large outdoor spaces for pleasant moments of conviviality. The kitchen is also excellent.
Francesca  L.

Francesca L.

review about Whale watching cruise with WWF researcher on an 18-meter schooner August 2022

10 / 10
Experience to live absolutely! It opens your heart and mind, it changes you inside.
BENEDETTA L.

BENEDETTA L.

review about The Aeolian Islands and their wonders August 2021

8 / 10
Saro is an experienced and kind skipper. We could almost never go sailing because of the little wind and it's a shame, the heat didn't help. The boat is nice, maybe a bit small for 7 people.
Giovanna F.

Giovanna F.

review about Aeolian Islands in Gulet September 2020

8 / 10
Nice and interesting trip . Gulet conducted with skill following according to the weather the best possibilities of navigation. Good and extremely helpful staff.
Renato M.

Renato M.

review about Weekend in Ponza and Palmarola, 2 nights. Half board included September 2020

10 / 10
I thank Nicola and Carlo for the wonderful holiday on the beautiful schooner. Pleasant punctual navigation. The spaces are large, sunbathing for everyone and the cabins are very comfortable. Nicola is an attentive and caring commander but also an excellent chef... what about paccheri... Yummy!!!! We will definitely come back on board but in the meantime I recommend everyone a cruise with them. Good wind Renato
Anne Cécile C.

Anne Cécile C.

review about Sailing and Wellness (Il Veliero del Benessere) August 2019

10 / 10
Great family cruise, the description of the cruise corresponds quite to our daily life on Gianluca's boat, really a wellness cruise or Gianluca is at the top sceance of osteo on the boat really do not hesitate if you need. And do not forget the cook, Gianluca ?????? In the Michelin guide, the top. I really advise this service you will not regret it ????
Alessandra P.

Alessandra P.

review about Weekend on a traditional schooner among the crystalline waters of Isola del Giglio July 2019

10 / 10
The experience on a schooner was for all of us, unique, enthusiastically and exciting. A boat handmade by an ax master in Canada is a rarity... and Francesco a precious source of life experiences and great professionalism. The boat all in wood and totally eco-sustainable (plastic free) is very essential inside.
Stefano D.

Stefano D.

review about Cabin Charter Amalfi Coast July 2019

10 / 10
We found a crew attentive to all our needs. Really GOOD ????
Andrea M.

Andrea M.

review about Educational weekend sailing in Liguria March 2019

10 / 10
Alfonso is a commander attentive to everyone's needs. He constantly strives to ensure that the needs of all crew members are, within limits, met. With Alfonso you can deepen your sailing knowledge or simply enjoy the holiday, this makes him the ideal skipper who manages to shape the group inside and outside the boat. In this holiday, personally, I greatly appreciated the opportunity to put into practice concepts not entirely familiar to me under the expert guidance of Carlo (owner) and Alfonso (commander) Advised
Francesco D.

Francesco D.

review about GOKOVA GULF IN CAICCO! August 2018

10 / 10
A real holiday of comfort, relaxation and nature. The gulet is maintained very well and is very comfortable especially for those who are used to the traditional sailboat, thanks to the spacious cabins with private bathroom and the outdoor spaces. We shot in truly enchanting places, alternating bays with marinas, having the good fortune to meet twice the much coveted "caretta caretta"! The staff is professional and very kind, knows very well the areas visited and is very attentive to meet the needs of guests. Of note are the local dishes cooked by the chef Ege for lunches and dinners on board, really good! Until next time!
Michela C.

Michela C.

review about Discovering the Pontine Islands by sailing ship August 2018

10 / 10
I am very happy with the choice I made. I was welcomed with great affection and sympathy. The staff on board was very attentive to my needs and requests, also the island is wonderful and it would have been very difficult to experience it if I had not been on the boat, since you would not have been able to see and explore the coast. The boat is wonderful and very spacious, because according to the needs, there is the possibility to carve out moments in solitude and complete relaxation!
ROSSANA F.

ROSSANA F.

review about Share our experience of sailing around the beautiful Pontine islands aboard a unique classic schoone August 2018

10 / 10
Cruise to the sound of guitar and charcoal grapes, aboard a historic schooner built by a magician of Trieste boating. The chameleonic whimsy of the commander Alessio (true expert of the Italian sailing school) and the professionalism of the master of classic sails Antoine, made the holiday unforgettable, thank you!
Ignazio R.

Ignazio R.

review about Ionian Greece in Schooner June 2018

10 / 10
Hello everyone, we are back from an unforgettable week of vacation aboard the schooner! Claudio and Maura were a revelation for us, their passion for sailing can be seen from the first moment we got on board. On the schooner, we spent relaxing days and evenings in joy, and between a bath and the other we visited the most suggestive coves of Paxos, Antipaxos and surroundings. Claudio and Maura were always available, reliable, they took care of us transmitting great confidence even to those who, like my girlfriend, were at her first experience on a sailboat. I really advise you to set sail on board their boat, with a wonderful history and still fascinating today (it often happened that passers-by took a selfie with the schooner behind). Good wind!
Martina T.

Martina T.

review about South Sardinia in Caicco Very space and comfort to live the best August 2017

10 / 10
The gulet is extremely comfortable and spacious. We had a very relaxing holiday and would also highly recommend it to those travelling with children. The skipper is also an excellent cook who spoiled us with a very varied, good and well-kept cuisine. On board there are all the comforts and the staff is really kind and dedicated. I recommend it to anyone looking for a holiday of relaxation and company. If you love swollen sails, however, it is not for you.. the gulet travels by motor!
Francesca C.

Francesca C.

review about Sail to Elba island, and then... August 2016

10 / 10
Week of relaxation and joy on a very charming 70s boat with its wooden bunks, the two trees, but above all with a fantastic hammock to enjoy the sunsets and starry nights. Marco (the captain) and Giaime (his collaborator), made us sail between Elba, Corsica and Capraia, always trying to satisfy our requests and making us discover small corners of paradise. Until next time!
Martina C.

Martina C.

review about Discovery the coast of Istria August 2015

10 / 10
Marco proved to be an excellent skipper: in addition to being technically very prepared, he has a sociable and balanced character able to unite the crew that sails with him.
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Why you should choose a skippered gulet cruise

  • Let yourself be captivated by the slow rhythms of the gulet and sail through landscapes of rare beauty.
  • Be a pirate on board a sailing ship: a cruise in a gulet, a charming wooden boat with two tall masts, will give you the feeling of an unforgettable adventure for adults, legendary for a family holiday with children.
  • When choosing a gulet holiday, you will be guided by a skipper, often assisted by a second crew member who will be responsible for preparing some meals on board. For the maximum of luxury, think about renting a whole gulet in Turkey, where the crew is fully booked and all you have to do is pamper yourself!
  • Enjoy some healthy lazing around, lulled by the waves: the gulet's spacious decks, cosy cabins and comfortable sundecks offer unparalleled comfort.
  • Discover the origins of these boats by sailing on the rocks of Turkey, the home of the gulet, but also among the Greek islands: Cyclades, Dodecanese and Ionian Islands await you! Maybe you don't know that you can also explore Italy by gulet: the Aeolian Islands are a must-see.
  • Don't worry if you're not a sea dog or if it's your first time on a boat: the wide and livable spaces of a gulet and the motorboat navigation along the coast will make your holiday relaxed and comfortable!

The best routes for sailing in a gulet

The best routes for a cruise on a gulet in Turkey with crew on board have as a starting point Bodrum, a tourist resort built on the ancient Halicarnassus, but also a peninsula in the south-west of the country overlooking the Aegean Sea and a privileged sailing area for gulet cruises.

Many cruises from Bodrum sail to the Datça Peninsula (or Datca), one of the most beautiful corners of Turkey, where the Aegean and Mediterranean meet: blue-green sea, quiet fishermen's taverns, archaeological sites and a myriad of small bays and sandy beaches. The peninsula is a 70km-long protected area and stretches from Marmaris to Knidos, which is the extreme point.

Another option is to sail along the coast from Bodrum towards the Gokova Gulf, discovering the famous little Seven Islands and the legendary Cleopatra's Beach.
You will be captivated by the clear, aqua-green sea framed by a landscape rich in pine forests and dotted with fishing villages.

Exclusive gulet charters in Turkey allow you to choose your own itinerary and enjoy a luxury holiday at affordable prices.

Bodrum is also an ideal starting point for gulet cruises between Turkey and Greece, towards the Dodecanese; of the 26 inhabited islands of this archipelago, the most popular are Rhodes and Kos, while Simi and Nisiros are among the closest to the Turkish coast.

Staying in Greece, you can choose a gulet cruise from Athens to the Cyclades Islands, which are characterised by typical blue-and-white houses and churches set in an arid landscape lashed by the Meltemi wind. Do you prefer the romantic Santorini with its scenic windmills overlooking the sea or Mikonos, a nightlife destination with beach parties and discos open until dawn? Each island is unique in its own way, with beautiful, lively, often perched villages, wide bays and dreamy coves, with sandy or pebble beaches.

A holiday on a boat in Greece can also take you to the Ionian (or Ionian) Islands, which are the closest in distance but also culturally to the Italian coast. There are seven islands belonging to the archipelago, of which Corfu is the largest and best known, directly accessible by ferry from Brindisi; Zante and Ithaca permeated with literary quotations, and then Kefalonia, Paxos with Anti Paxos, Cerigo and Lefkada, attached to the mainland by a mobile bridge.

Dulcis in fundo, why not also explore the coasts of Italy on board a gulet? A trip to the aeolian islands on a caique is an unforgettable experience, but we also offer unusual weekends in Calabria and schooner trips in the seas of Tuscany and Sardinia. The choice is yours!

Why choose a sailing holiday

  • Cruising on a sailing ship is a unique experience. The boat has a taste of yesteryear: it offers the comforts of a motorboat but with the spectacularity of its sails that dominate the wind.
  • Elegance, comfort, comfort and a sense of adventure.
  • Elegance, comfort and advanced navigation systems, guarantee a sailing holiday full of adventure, relaxation and the tradition of sailing, with a service of the highest quality.
  • Sailing on board is predominantly motor-assisted, which is why they are perfect for a quiet cruise and for a first sailing holiday and for families with children.
  • The cabins are spacious and comparable to real 5-star hotel rooms.
  • Luxurious styling and a high level of service that will make you feel cared for 24 hours a day.
  • A crew dedicated to the guests, from the captain to the performers of the evening shows, all work to the best of their ability to satisfy the guests on board.
  • The sailing ship is the perfect choice for those who want to experience the sea at all times of the day, but don't want to give up comfort and appreciate a luxury service on board.
  • The atmosphere on board is relaxed, pleasant and informal.

Gulet and sailing ship: best destinations

  • Greece (117)
  • Italy (51)
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Top Destinations

  • Italy
  • Greece
  • Tuscany
  • Aeolian Islands
  • Northern Sardinia
  • Ionian Islands
  • France
  • Caribbean
  • Pontine Islands
  • Lake Garda
  • Aegadian islands
  • Cyclades
  • Croatia
  • Liguria
  • Spain
  • The Balearic Islands
  • French Riviera and Porquerolles
  • Sicily
  • Gulf of Naples
  • Amalfi Coast
  • Split Archipelago
  • Grenadines & Martinique
  • French Polynesia
  • Dodecanese
  • Brittany and Normandy
  • The Maldives
  • Saronic Islands and Athens area
  • Guadeloupe
  • Corsica
  • Canary Islands

Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet and sailing ship
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
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