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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!

  • 17 reviews
    confirmed

    Flotilla in the Aeolian Islands: Exciting sunsets and new friends - week 3

    from 20 August - 7 nights
    Aeolian Islands Italy
    9 people
    are onboard
    1.080€ Per person
  • 60 reviews
    confirmed

    La Maddalena archipelago: sailing between Budelli, Caprera and Lavezzi

    from 20 August - 7 nights
    Northern Sardinia Italy
    2 people
    are onboard
    764€ Per person
  • 2 reviews
    almost
    confirmed

    "Emotions on the Conero Riviera"

    from 20 August - One day
    Marche Italy
    Join in on this experience!
    98€ Per person
  • 26 reviews
    1 discounted
    spot

    LAST MINUTE: Aeolian Sailing Express by Sailboat

    from 20 August - 6 nights
    Aeolian Islands Italy
    7 people
    are onboard
    901 650€ Per person
  • 23 reviews
    confirmed

    Genoa -Sanremo - Antibes - Iles Lerin - St. Tropez - Cassis Calanques - Arcip. de Riou - Marseille

    from 20 August - 7 nights
    French Riviera and Porquerolles France
    2 people
    are onboard
    800€ Per person
  • confirmed

    Sailing between the Ionian islands Greece what a passion

    from 21 August - 6 nights
    Ionian Islands Greece
    4 people
    are onboard
    1.060€ Per person
  • 3 reviews
    confirmed

    Disconnect in South Brittany. Race-Cruise Sailing Course

    from 21 August - 5 nights
    Atlantic Coast France
    1 person
    is on board
    838€ Per person
  • confirmed

    Corsica cruise school - from Bastia to Calvi

    from 21 August - 7 nights
    Corsica France
    4 people
    are onboard
    689€ Per person
  • 2 reviews
    confirmed

    Week of relaxation, nature and navigation in the Aeolian Islands

    from 21 August - 7 nights
    Aeolian Islands Italy
    6 people
    are onboard
    954€ Per person
  • confirmed

    LAST MINUTE - Let's discover the Pontine Islands together !!!

    from 21 August - 7 nights
    Pontine Islands Italy
    6 people
    are onboard
    848€ Per person
  • 58 reviews

    Aeolian sailing on a spacious Comet 52 of 16 meters

    from 21 August - 7 nights
    Aeolian Islands Italy
    2 people
    are onboard
    1.200€ Per person
  • 6 reviews
    3 discounted
    spots

    Week of relaxation and nightlife in the Aeolian Islands

    from 21 August - 6 nights
    Aeolian Islands Italy
    3 people
    are onboard
    954 901€ 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 - Monohull yacht sailing holidays & skippered tours

12221 reviews
20 / 10
Vittoria F.

Vittoria F.

review about Between the Aeolian Islands and Capo Milazzo August 2022

10 / 10
Non potevamo trovare uno skipper migliore!!! Antonino ci ha fatto passare una settimana favolosa alle Eolie e oltre alla sua esperienza come skipper ci ha offerto anche la sua piacevolissima compagnia! Non vediamo l'ora di toranre!
Barbara B.

Barbara B.

review about Relax on a sailing boat in the Campania archipelago August 2022

10 / 10
Antonio an excellent skipper! With great skill he managed to handle all kinds of situations. Comfortable and well equipped boat. Absolutely recommended!
Barbara C.

Barbara C.

review about Relax and sail among the coves of southern Sardinia August 2022

10 / 10
10 laude...... to him and to all the crew. Relax fun and surf safely, you can not ask for more! "Pampered" is the best word to describe their attention to the crew...... free to relax when we wanted or to participate in the maneuvers when we felt like it ...... but most importantly, Paul is a man of the sea... you immediately perceive that he knows how to manage every situation, and he does it with serenity, without creating anxieties for the crew!! Congratulations to the team!!!
Giorgio N.

Giorgio N.

review about Let's live this fantastic experience together! August 2022

10 / 10
Fabio is a very experienced and friendly skipper who cares about the safety and well-being of his crew. He knows the Pontine Islands very well and has been a constant point of reference for all of us. Definitely recommend!
Mathilde M.

Mathilde M.

review about Aeolian Islands in the name of sailing, fishing and relaxation August 2022

10 / 10
Superb experience, the mini cruise was fabulous. Antonio always caring, flexibility +++ in the program. And I think one of the most beautiful sunsets of my life. I recommend +++ Thank you very much.
Francesca M.

Francesca M.

review about WEST SARDINIA in the name of total relaxation: sun, dives in crystal clear waters, nature and naturalness July 2022

10 / 10
If you are looking for a luxurious holiday served and revered it is not the holiday for you, but if you want to experience the sea in all its forms you will be on the right boat You will have the opportunity to always sleep in the harbor, see pristine places relax and go sailing. Vincenzo is an experienced skipper and if you know how to listen to him he can teach you many things. Despite having a pre-established itinerary Vincenzo is open to the possibility of changing the route, weather permitting, if you want to see other places. Thank you Vincenzo, it was a wonderful holiday !
Lavinia M.

Lavinia M.

review about Long weekend sailing to the fascinating Tremiti islands departing from Rodi Gargano August 2022

10 / 10
An exquisite person, kind-hearted, calm, humble, who transmits peace and manages to teach you so much .. There are few such people in the world, they are precious and remain in you forever...
Alessia C.

Alessia C.

review about July 15-21 Egadi islands week with skipper and mariania / hostess July 2022

10 / 10
Unique experience! Breathtaking scenery on board Rebelle, a brand new boat equipped with all comforts: from the coffee maker to the air conditioning for the hottest nights. The professionalism, competence, grace and hospitality of Clelia (the skipper) and Simona (as a sailor) made this experience unforgettable. Felt thanks to them, to my fellow adventurers and to the splendid Sicilian views :)
Paola S.

Paola S.

review about ISLAND OF ELBA: SAIL-SWING & DIVE - A week of sailing, swing dancing and diving July 2022

10 / 10
Beautiful holiday! Matteo is a very good skipper, safe and attentive. He perfectly understood the goal of our holiday. Always friendly and helpful! Sweet Silvia, the Hostess. He spoiled and pampered us! Priceless his presence to feel truly on vacation. ...... In short, everything is perfect. Too bad.... only..... that it did not last long!!!!!
Salvatore L.

Salvatore L.

review about Superb day on a boat between the Gulf of ALASSIO and the Gallinara island August 2022

10 / 10
Wonderful experience, Daniele and his family were very nice, I immediately felt part of them and pampered throughout the day, I even tried to the sails and drive the boat under Daniele's control. We stopped several times to take some great baths offshore. The final aperitif was excellent and plentiful, so much so as to skip dinner thanks to the delicacies prepared by his wife Carmen. I highly recommend it to everyone to have a great day on their wonderful boat which I will definitely return to.
Livia O.

Livia O.

review about To the Aeolian Islands on a 14 mt with Gabriella -skipper and mum- and Nicola -seaman and companion of adventures- July 2022

10 / 10
The memories from the week spent with Gabriella and Nicola on Eragon will stay with us forever! Gabriella is not only a skilful skipper but also a mum who knows how to engage and (when necessary) keep in check children if all ages. Nicola was a great companion for our 2 children, they had great fun together on the boat and on shore! The played board games, snorkelled, dived and fished together. It was beautiful to witness. The places Gabriella suggested for us to visit were spectacular and she always recommended things to do based on our interests and moods. The entire week was planned together with great flexibility on Gabriella's part. We wouldn't hesitate to recommend Gabrilella and Nicola if you are looking for a truly unique experience! Grazie Gabriella e Nicola!
Francesca W.

Francesca W.

review about Ibiza and Formentera: mini cruise between relaxation, sea, comfort and nature - cook on board! July 2022

10 / 10
10 and praise for this wonderful holiday! We traveled on the beautiful elegant and comfortable sailboat. Olmo and Margherita are fantastic, impossible not to get along with them. Olmo has a great experience, knows how to advise with skill and has been able to accommodate our every request. It was great to modulate the holiday to our needs. Margherita delighted us with delicious dishes, satisfying our every taste and preference. We sailed almost exclusively on sailing and enjoyed a truly complete experience. Sailing is suggestive, romantic, in perfect harmony with nature and totally safe. In addition, to reach coves and beaches Olmo accompanied us with the tender, giving us unexpected views. I recommend this experience to all those who want to live a unique and unforgettable experience, in total relaxation, but also a little adventure, discovering wonderful places in companions of wonderful people.
Luca B.

Luca B.

review about Sporty and relaxing cruise between the Pontine islands July 2022

10 / 10
Nicola person very attentive to the needs of customers, kind and helpful, gave me the opportunity to make a holiday in perfect relaxation in maximum safety. Maximum seriousness
Nicola D.

Nicola D.

review about Living Ponza outside the weekend July 2022

10 / 10
A three-day holiday of perfect relaxation lulled by the sea among the beauties of the island of Ponza. Angelo is an experienced skipper and an excellent cook who makes you feel comfortable aboard a wide boat, well maintained and equipped with all the comforts. Too bad the days ended early and the lack of wind did not allow us to appreciate more the movements with the sails unfurled. Will be for next time!
Davide R.

Davide R.

review about Weekend to discover the Pontine Islands July 2022

10 / 10
The experience between a mix of relaxation and teaching on Matteo's sailboat was very relaxing and naturalistically perfect. Matteo is very competent and very experienced, he has been able to manage the guests on board very well, satisfying as much as possible the requests of all the participants!
Silvia C.

Silvia C.

review about Adventurous Pirates exploring the Cyclades Islands! July 2022

10 / 10
Tommaso and Laura are two very pleasant and welcoming people. and caring. They have a great passion for the sea. Skipper very attentive and prepared. Excellent their vegan cuisine, which they made us discover with simple but tasty and very varied recipes. On days of bad weather, when unfortunately we were forced to stand still in port, they organized tours by rental car. All great and highly recommended.
Massimiliano  P.

Massimiliano P.

review about Nordic Adventure - Stage 1: from Tromsø to Bodø (ALL INCLUSIVE) June 2022

10 / 10
Good morning, the premise of this holiday for me was to visit places unknown to me and pristine and I must say that I got the result. Nanni has proved to be a person with very high competence and great culture. Hearing him talk about his travels was fascinating. The only negative note I found in the boat, not for the seniority but for the hygienic conditions that left something to be desired, in addition to the persistent smell of diesel. However, I was overwhelmed by the experience I was preparing to have and the fact that I was the only passenger.
Giulia Z.

Giulia Z.

review about A weekend on Elba - Breakfast and lunch included! July 2022

10 / 10
We left with Antony and his sailboat for a weekend on the Island of Elba. Antony is a skipper of the real ones: he knows his boat and the wind, the sea is his home. He gave us confidence, tranquility and his passion for sailing. Witty, agile, excellent cook and with a heart of gold he made us spend beautiful days. We will carry with us forever this beautiful adventure where we learned a lot! The boat is beautiful and conveys just peace and quiet. Experience that we will definitely repeat, thank you very much Antony!! Until next time..
Alessandra R.

Alessandra R.

review about AROUND THE ISLAND OF ELBA practicing sailing July 2022

10 / 10
Very nice holiday and very pleasant company!
Giovanna C.

Giovanna C.

review about Paros-Small Cyclades-Amorgos June 2022

10 / 10
Giovanni and Stefania were amazing. Nice and super professional they made us safely discover the wonders of the Cyclades with a meltemi that did not give up on us for the whole week. Sailing, the real one!
Yasmina F.

Yasmina F.

review about Weekend of relaxation and swimming in clear waters June 2022

10 / 10
We were excellently welcomed by Paolo who is a pleasant, caring, patient and attentive man to his passengers. He is also a cautious skipper who does not make his teammates take unnecessary risks. The boat is top: super well maintained and very clean. Everything is planned so as not to lack anything. I highly recommend stays with Paolo!! We will probably leave with him!
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
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