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Monohull yacht sailing holidays & skippered tours

Monohull yacht sailing holidays & skippered tours

Monohull

  • Sailing Holidays
  • Monohull

FLEXIBLE CANCELLATION.

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

  • Bridge of San Pietro e Paolo to the Pontine islands!

    from 29 June - 4 nights
    Pontine Islands Italy
    Join in on this experience!
    530€ Per person
  • 1 review
    confirmed

    Dubrovnik and Mljet: history and nature under sail

    from 1 July - 8 nights
    Split Archipelago Croatia
    4 people
    are onboard
    636€ Per person
  • confirmed
    whole boat only

    From the Pontine to the Flegree

    from 1 July - 7 nights
    Pontine Islands Italy
    Reserve this boat!
    (6 spots available)
    774€ Per person
  • 8 reviews
    almost
    confirmed

    Long weekend on Lake Maggiore

    from 1 July - 2 nights
    Lake Maggiore Italy
    1 person interested
    in this holiday
    200 189€ Per person
  • 29 reviews

    Weekend on the French Riviera, from Menton to Cap Ferrat

    from 1 July - 2 nights
    French Riviera and Porquerolles France
    1 person interested
    in this holiday
    255€ Per person
  • 9 reviews

    100% CAPRI

    from 1 July - One day
    Gulf of Naples Italy
    Join in on this experience!
    133€ Per person
  • 12 reviews
    confirmed

    Weekend sailing and relaxation between Elba Island and Giglio Island and Giannutri

    from 1 July - 3 nights
    Tuscany Italy
    5 people
    are onboard
    338€ Per person
  • 41 reviews
    confirmed

    Sailing and yoga in Capraia and Corsica

    from 1 July - 6 nights
    Tuscany Italy
    5 people
    are onboard
    870€ Per person
  • confirmed

    Gulf of Genoa and west

    from 1 July - 2 nights
    Liguria Italy
    3 people
    are onboard
    276€ Per person
  • 4 discounted
    spots

    Let's live this fantastic experience together!

    from 1 July - 2 nights
    Pontine Islands Italy
    1 person interested
    in this holiday
    382 360€ Per person
  • 58 reviews
    confirmed

    Weekend at Pontine

    from 1 July - 2 nights
    Pontine Islands Italy
    2 people
    are onboard
    414€ Per person
  • 2 reviews

    Weekend on the island of Capraia

    from 1 July - 2 nights
    Tuscany Italy
    2 people interested
    in this holiday
    414€ Per person
  • 1
  • 2
  • 3
  • 4
  • 5

Why you should book a holiday with Sailsquare?

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25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

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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 - Monohull yacht sailing holidays & skippered tours

11540 reviews
20 / 10
Federica P.

Federica P.

review about Amazing Pontine! June 2022

10 / 10
Amazing holiday, Enrico and Alessandra were great people and made us feel at home!!! Thanks to Enrico we discovered amazing coves!! To be repeated absolutely absolute!! Thanks Enrico!!!!
Ornella V.

Ornella V.

review about Weekend on the island of Capraia June 2022

10 / 10
Wonderful holiday, Matteo a skipper of the highest level and excellent cook, involved us and made us participate throughout the weekend in the maneuvers during navigation and in the movements between one cove and another. Clean, comfortable and well maintained boat. In short, what about a SUPERVACANZA. An experience that will remain an unforgettable memory. Ready to organize another one immediately because for those who love the sea I think there is no better holiday. Thanks again for everything
Matteo G.

Matteo G.

review about Egadi sailing and snorkeling paradise! June 2022

8 / 10
Nice week in mixed group. Alessandro skipper experienced and patient made us sail and explore the Egadi in relaxation and with a smile!
Elena S.

Elena S.

review about Weekend among the pearls of the archipelago with hostess on board June 2022

10 / 10
Fantastic experience, what to say elba always beautiful but this time in particular, the skipper Edoardo and his partner Irene were very good I dare say of the travel companions albeit short. Edoardo very good and self-confident in steering the boat and Irene an excellent assistant but above all cook. Experience to be redone as soon as possible Everything above all expectations
Stefano S.

Stefano S.

review about Set off to discover the Ionian islands with the gastronomy of Davide, your skipper cook! June 2022

8 / 10
ON HOLIDAY WITH A SPECIAL PERSON My holiday with Davide was a nice holiday. The boat is wide and comfortable. The skipper a special person, sailor, chef, man of the world, a friend... The cruise was pleasant even if there was little wind in the area so mainly motorized. The places, especially PAXOS and ANTIPAXOS very nice. We traveled in a group of three boats for which the company was not lacking. Every day for lunch a Greek or Neapolitan dish cooked with skill. What can I say? I recommend it.
Ivano Antonio B.

Ivano Antonio B.

review about Long weekend of 2 June in Capraia and Corsica June 2022

8 / 10
Really fantastic boat and with an excellent livability, pity for the lack of the ladder, not a little thing .. and after what happened to our ominous reservation we can only be grateful to the organization for solving the problem So a big thank you to Sailsquare Good morning everyone
Alice Z.

Alice Z.

review about Bridge of 2 June - Sail with us 2 boats to discover Corsica and Capraia June 2022

10 / 10
Paolo is nice and caring, he is a great skipper and "roommate" for wonderful and carefree vacation days! I recommend it :)
Emanuele C.

Emanuele C.

review about Offshore navigation 370 nm. Sicily / Sardinia Nautical Education Vacation May 2022

10 / 10
Unique experience and amazing people! A trip full of emotions and that I will never forget, Marco and Valentina welcomed me on the boat, and immediately made me feel at home. During the three days of travel I had the pleasure of getting to know them better. Marco is a calm and kind person, a super competent and professional skipper. Always willing to teach his crew how to fix the course and sails, regardless of the level of experience. Master of sailing and unique life. Valentina, also very kind, is a bomb of energy and happiness, always ready to entertain and spoil the crew with aperitifs and delicious dishes. I will never forget the crossing of the Tyrrhenian Sea. Between naps tickled by the waves of the sea, aperitifs with traditional food and white wine, and shifts at the command during which to learn to manage the boat. And finally, three days of pure relaxation and fun in Sardinia immersed in unique coves with emerald water.
Alessandra N.

Alessandra N.

review about Wonderful weekend of 2 June in the Aeolian Islands June 2022

10 / 10
It was a magical holiday, out of time and out of the world!! I loved going full sails! Captain Maurizio was wonderful, he taught us so many things about sailing! Diomedes I already miss you!!
Luigi I.

Luigi I.

review about Weekend Lungo Ponte 2 June in Ponza and Palmarola on comfortable 4 cabins June 2022

10 / 10
We stayed at the Pontine Islands and it was a wonderful holiday. We did some sailing lessons, we fished and we saw some breathtaking coves. I was pleased to meet some nice people. The skipper gave us a lot of freedom of choice and we had a lot of fun. Experience to be redone
Carlo P.

Carlo P.

review about Bridge of 2 June among the wonders of the Island of Elba June 2022

10 / 10
Giacomo is an experienced and prudent professional but also an excellent travel companion. With his boat, excellent and equipped, we sailed where possible and despite the variable weather we spent a perfect holiday.
Italia B.

Italia B.

review about Cruise to discover the Tuscan archipelago and northern Corsica May 2022

6 / 10
I state that I booked qst holiday seen the photo of "monia my boat" but I arrived there in the company of 3 men and I the only woman (skipper, owner and customer like me) average age 50 years I 35. I state that I have already been going on a sailboat for a while but I have never had to deal with a skipper so dictatorial and xnulla attentive to the needs of others (PAYING customers) but very experienced. In 5 days, I took 1 decent bath given the many hours of travel from place to place on average 6 hours a day. As soon as I arrived by boat, I was not given the opportunity to choose the cabin (skipper and owner took the best cabin with bathroom and shower much more capacious) usually the skipper sleeps on the outdoor sofas. The holiday is synonymous with relaxation (at night it was impossible to sleep given the infinity of noises made by the skipper who always came out of the boat checking I do not know what) Professionalism does so much as well as the experience but nowadays the ways are worth above all. --- SKIPPER ANSWER --- Good morning Bruna, I am really sorry that your experience was not optimal, thank you for bringing the problem to our attention, we will carefully examine your opinion to avoid future misunderstandings and to improve ourselves. Below my photo it is indicated that I am the organizer of the cruise, I manage the booking and the various requests of the customers, also always in the description it is highlighted that: "The skipper of this experience will be a professional and trusted skipper, who has been working with us for years: we will communicate more details before departure." No doubt it seems to me about the experience of our skipper. We are always available to clarify any doubt of the customer, before, during and after any booking. You were the first member of the crew, so it was difficult, if not impossible, to know what other members would come on board, men, women and of what age... I remember that the cruise is reserved for all those who like the sea and sailing, and in any case I have not received any request for information on the subject. A few days before the departure on whatsapp chat I put you in touch with the skipper (Stefano) and with the other members of the crew, to have the opportunity to exchange information but also and above all to have the opportunity to clarify any doubt. All the routes, places visited and landings were shared, first on the Sailsquare website and then with all the remaining guests who were very happy to have lived this experience, visiting the island of Elba, Corsica, Capraia and the coast of Tuscany. As mentioned above, I manage the booking, the booking is also part of the assignment of the cabins, we are always very careful when there are "single" travelers not to create situations of embarrassment by staying, always if possible, men with men and women with women, in this case being you in four (skipper included) I thought to do something welcome by entrusting you with the room with double bed for exclusive use and entrusting the cabin to you bow that has 2 beds singles to 2 men (thus avoiding making them sleep in a double bed).
Sabrina A.

Sabrina A.

review about Navigation to the Pontine Islands June 2022

10 / 10
Di Fabio I really appreciated the availability, kindness and flexibility in welcoming the requests of guests. Diego, our skipper, is a very experienced captain, as well as a patient and kind person, with a great spirit of initiative and ability to predict the needs of guests. Can't wait to get back on board!!
Giancarlo P.

Giancarlo P.

review about Traveling to the Gulf of Poets and the Cinque Terre June 2022

8 / 10
Vittorio was very hospitable, we had a very good time in his boat and he really treated us as guests, preparing delicious sauces and more. We highly recommend a boat experience with him, he will make you feel at home! Great Victor!!!
Andrea R.

Andrea R.

review about Bridge of 2 June to the Pontine Islands June 2022

10 / 10
Giovanni is a fantastic skipper, kind, professional, nice and discreet, attentive to detail. I had a great time.
Luigi M.

Luigi M.

review about Sailing in the Tuscan archipelago June 2022

10 / 10
The best skipper I've sailed with. Passionate about sailing and always ready to share and explain what happens on the boat and how to behave. Fun and nice but at the same time professional and balanced. A real sailor, with experiences of ocean crossing, really good and competent. I will be back on the boat with him for sure!
Corrado S.

Corrado S.

review about Sailboat cruise through the Kornati Islands Park May 2022

10 / 10
It is difficult to express in a few words such a complete emotional experience! ... Armando, in addition to being a good skipper, is an equally skilled cook, able to satisfy your tastes and your nautical and culinary preferences. Just let yourself go at the slow pace of the days and you will find yourself in a timeless and carefree world. Thanks Armando! Corrado
Sailor

Sailor

review about Week-end in the Gulf of Baratti May 2022

10 / 10
Great experience- Marcello was prudent and attentive regarding the management of the boat, very helpful for those who wanted to deepen the theory and practice of the sailboat. He had attention to our needs. Good conversationalist and organizer.
Robert M.

Robert M.

review about Weekend - Favignana, Levanzo May 2022

10 / 10
We had a nirvana sailing and spending time with Antonio and his Family . It's amazing experience that we highly recommend to you. You will cherish memories of it for a very, very long time. Thank you Antonio, and Pepe, and Aldo, and Katia, and Enza! We are so looking forward to hug you again!
Samantha B.

Samantha B.

review about May weekend on the island of Elba .... sailing, nature and characteristic villages May 2022

10 / 10
Magical experience Thank you then Skipper Marco who immediately put us at ease. A beautiful group for a truly dream weekend! Super recommended!
Spartaco M.

Spartaco M.

review about CrazySail Skipper Academy Lite: Punta Ala - April 30th April 2022

10 / 10
Great Inti! The most ''ganzo'' skipper (tuscan like me) I have met so far. Really engaging and dynamic person from a human point of view, but technical at the same time in pointing out some dangerous situations to the skipper or helmsman on duty, always with a smile or a joke that does not hurt. I hope to have the opportunity to sail with you again Good wind and see you soon
Giuseppe B.

Giuseppe B.

review about The Gargano and the Tremiti April 2022

10 / 10
Thank you guys for welcoming us in your boat with all its comforts and the precautions reserved for us you have made us this Easter special. Everything was perfect... The ability of andrea and his partner to sail even with sea always formed in maximum tranquility and carefree the enchanted places visited at the tremiti the walks in the villages evenings and dinners on the boat spent in joy with the fantastic companions ... leave an indelible memory and new true friendships Thank you for the wonderful holiday I highly recommend to try all these beautiful emotions
Sylvie G.

Sylvie G.

review about Easter in Morbihan April 2022

10 / 10
Easter in Morbihan with Benoit... nothing is wrong!! Great weekend in your company. You transported us to your world during these 4 days. Attentive, pedagogue and friendly, you managed to reconcile holidays and learning. You knew how to adapt to the lack of tone of the wind to make us discover a maximum of territory. Houat, Hoedic, Gulf of Morbihan, Belle Île, Groix were discussed. You had the patience to wait for us during our escapes on earth where you were kind enough to deposit us in annex. Your boat is a treat, it offers a real interior space. It's super comfortable... and we were able to discover on the return all its power with a tip at 14 knots. You have a very beautiful boat both sporty and very well designed for cruising ... enough to really enjoy yourself! Benoit... Thank you!!! We will come back to discover Les Glénans with you... and maybe cross dolphins... See you soon...
Norbert M.

Norbert M.

review about Are you a lover of nature and crystalline seas? This is the perfect relaxing holiday April 2022

10 / 10
Hello We had the pleasure of sailing with Alessandro. He is a very friendly boy who was very caring for us. Always wondering if everything was okay and if we needed anything. He knows the island of Corfu and its history very well. The meals prepared by himself, of local types were delicious. In addition we had the chance to be accompanied by his brother Andrea who usually pilots another boat and who is older and just as pleasant as his brother. We spent a very nice week in their company and are thinking of renewing the experience at a more summer time to enjoy swimming. I highly recommend this mini cruise especially with these two young people in love with nature, the sea and their job as sailors because we feel that it is really a passion for them.
Trustpilot

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