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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.



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The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Gulet sailing holidays & luxury cruises

126 reviews

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Whale watching cruise with WWF researcher on an 18-meter schooner


Francesca A.



Vacanza meravigliosa immersi nella natura alla ricerca dei cetacei. La nostra guida Laura è una professionista competente e appassionata che ha saputo coinvolgere tutti con il suo entusiasmo e la sua competenza. La Mahayana è una barca estremamente affascinante e il suo capitano estremamente disponibile e simpatico è un vero amante del mare. Sulla barca vige una politica zero sprechi, e regala ai partecipanti l'occasione di riflettere sull'impatto che abbiamo sul nostro pianeta. Inoltre tutti sono chiamati a contribuire sia alla ricerca degli animali, che alla cucina e alla gestione della barca, e questo a mio avviso crea un grande senso di comunità. Consiglio questa vacanza a chi vuole riconnettersi con la natura, incontrare persone belle e a chi non si stanca mai di guardare il mare!
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September 3-7 Pontine on a spacious 22-metre yacht with skipper


Tilde D.



Porto con me dei bellissimi ricordi di questa mia prima esperienza in barca a vela, esperienza condivisa con un'amica e con altre simpatiche persone conosciute a bordo della bella e comoda barca che ci ha ospitati. Lo skipper Luca mi ha trasmesso da subito sicurezza e fiducia grazie alle sua esperienza e capacità, comprensibili anche da una neofita come me, e ci ha anche deliziato con gustosi pasti consumati con vista sui meravigliosi panorami delle isole pontine. Esperienza da fare e ripetere.
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September 3-7 Pontine on a spacious 22-metre yacht with skipper


Raffaella A.



Vacanza davvero molto bella. La barca è  grande con ampi e comodi spazi esterni. Abbiamo navigato nell'arcipelago Pontino e ammirato e goduto di posti davvero meravigliosi, con acque limpide dai mille colori e panorami mozzafiato. Palmarola in particolare è un incanto. Luca è stato il valore aggiunto di questa crociera, abile e capace Skipper sempre padrone della situazione, che infonde sicurezza, gentile premuroso, paziente e magnifico cuoco. Abbiamo mangiato davvero benissimo. Pasti ottimi preparati con cura e prevalentemente di pesce. Ho fatto diverse crociere in cabin charter, 3 con Sailsquare,  senza nulla togliere agli altri questa è stata senz'altro la migliore. Un grazie di cuore a Luca e anche ai miei magnifici compagni di viaggio.
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Whale watching cruise with WWF researcher on an 18-meter schooner


Manu M.

È stata una bella esperienza. La passione e grandissima competenza della ricercatrice wwf che ci ha accompagnato, Joelle, ci ha permesso di conoscere di più sulle diverse specie che vivono in mare e sui rischi su cui ognuno di noi può nel quotidiano agire! A causa del maltempo siamo rimasti in porto due giorni e non abbiamo avvistato molto. Il gruppo di persone a bordo è stato semplicemente fantastico, ci siamo divertiti molto!

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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.

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