Private yacht vacations & whole boat skippered cruise

Private yacht vacations & whole boat skippered cruise

Discover the magic of sailing holidays! Hire a whole boat: a new way of traveling with your loved one, friends or family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

FLEXIBLE CANCELLATION.

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

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

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

Two people with sailor hats

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.

A boat with a magnifier above it

Discover who’s already onboard

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

Two coins with a currency on top

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 - Private yacht vacations & whole boat skippered cruise

105 reviews
20 / 10
Ludovico S.

Ludovico S.

review about Between the Aeolian Islands and Capo Milazzo September 2022

10 / 10
I have taken many sailing holidays, and Antonino is one of the best and nicest skippers I have met. He puts passion, professionalism, has fun and entertains. It was a nice holiday, thank you Antonio from the whole group ????
Chiara M.

Chiara M.

review about Eolian Sailing- Max 4 guest for exclusivity and relax - Hostess on Board August 2022

10 / 10
Thanks to Mark and Adele we spent a wonderful family holiday: Mark, passionate and experienced skipper, made us relive the exciting experience of sailing, Adele always very careful not to miss anything and always ready to play cards with our children! They taught us and told us many things about life on the boat and the islands - we felt really welcomed and comfortable and we hope to repeat soon this experience that has no equal to fully experience the sea!
Roberto C.

Roberto C.

review about In the sea of Ulysses! Discovering the most beautiful islands August 2022

10 / 10
What can I say.... Beautiful holiday. Bays and marinas that Leo knows in a nutshell. He is an experienced sailor and has proven to be able to manage the boat safely even in adverse situations due to bad weather or the shortcomings of other nearby mooring boats. He is nice, sociable and eats well. Do not miss the marinated kid cooked on the grill on the berbecue of the boat. Thank you Leo.
Emiliano A.

Emiliano A.

review about Last minute Ponza and Palmarola on 52 feet August 2022

10 / 10
It was our first experience on a sailing boat, lived at 360 ° thanks to the skipper Emanuele, a professional and true sea wolf who was able to manage all situations making us always feel calm. A big fan of Taboo... but bad player :) SUPER RECOMMENDED!!!
Mascia V.

Mascia V.

review about Weekend on the island of Capraia July 2022

10 / 10
A good vote and above all a thank you! huge to Matteo by our whole group for helping us live an unforgettable holiday. I couldn't wish for a better birthday! Listing the qualities and skills would be too long... Matteo must be tried!!
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 their boat will stay with us forever! Gabriella is not only a skillful skipper but also a mum who knows how to engage and (when necessary) keep in check children of 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!
Francesco I.

Francesco I.

review about Blue Summer Week Flegree and Pontine July 2022

10 / 10
Skipper Mario has a great experience and has always made us feel in very good hands. At our request, he was very helpful in letting us participate in the maneuvers and conducting of the boat, allowing us to enjoy the beautiful sailing crossings, even arming the Gennaker when the wind and the route allowed it. He and his partner Antonella are of excellent company and, between dinners and evenings in the cockpit sipping a glass of wine, they have established a cheerful and convivial atmosphere, which has made the holiday truly unforgettable for all the crew :)
Roberto C.

Roberto C.

review about Elba island: beauty and relax July 2022

10 / 10
Fantastic experience thanks to Marcello and his boat. Very experienced and attentive to the needs of his guests, thanks to the valuable advice he made this holiday unforgettable. Highly recommended!
Fabrizio N.

Fabrizio N.

review about Sailboat cruise through the South Dalmatian islands July 2022

10 / 10
Armando immediately gave us a great impression, we felt like relying completely! Great food and excellent cook! The places he took us to were lovely! During the navigation we met a Sea turtle "caretta caretta" to whom we took many photos, in another route instead we were approached by a large group of dolphins and also to them we dedicated numerous photos! Experience definitely to be repeated
Antonio M.

Antonio M.

review about Egadi Islands: a dream between sea and land June 2022

10 / 10
My wife and I spent with Nicola a wonderful holiday to discover the Egadi Islands. It was our first sailing experience and, thanks to Nicola, it turned out fantastic. He will welcome you to his home with a smile, a lot of patience and (much appreciated) even some silence. Those who choose this type of trip do so to experience the sea, fully enjoy nature, relax, learn the basic principles of sailing and spend quality time. If you want to party 24 hours a day, it is not the right holiday for you! The boat is comfortable (x4 px), clean and equipped with every comfort but, not being a hotel, it will also be up to you to help make it so. Another super thanks to Nicola! We hope to be his guests again!
Nicla P.

Nicla P.

review about Sailing between the Costa Smeralda and the Maddalena Park May 2022

10 / 10
Stefano is a pleasant, discreet and balanced person. You have a great sense of security and run a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he proposes is a dream, every five minutes you find yourself saying "How beautiful!", A magical experience with a safe and very competent person both in practical management and on a relational level. Chapeau!
Elia B.

Elia B.

review about We celebrate Easter on Elba April 2022

10 / 10
Thanks Claudio and Barbara!! Three magnificent days, fun and always sailing! Barbara and Claudio made an exceptional galley and a great menu for all three days.. The atmosphere on board is always pleasant with Barbara helping in the kitchen and Claudio making you try to steer! Very nice boat, always clean and well equipped! Until next time!
Caterina S.

Caterina S.

review about North Sardinia islands on a magnificent 15 meter boat September 2021

10 / 10
Fabio is a very pleasant person is a super experienced skipper who transmits tranquility and security on every occasion. I absolutely recommend an experience with his boat.
Margherita P.

Margherita P.

review about From the Zingaro reserve to the Egadi islands: sailing to discover north-western Sicily August 2021

10 / 10
Antonio and Bianca were extremely helpful and kind to us both in the pre-departure and during our first boat experience. We have been pampered and have always found a solution to satisfy our desires whether they were a destination to be reached or a culinary experience. They introduced us to the sea, the traditions of the sailor, taught us how a sailboat works. We had the opportunity to chat like among friends, giving us a fun, interesting and relaxing holiday. Being their home the boat was stocked with everything we needed, making us feel at home. We were really excited about the holiday not only for the lovely places we visited but for the company of two sea lovers like them.
MARIANGELA I.

MARIANGELA I.

review about Northern Sardinia and Southern Corsica on an exceptional 47-foot sailboat for 4 privileged people August 2021

10 / 10
Our holiday of almost 2 weeks between South Corsica and North-East of Sardinia was wonderful! Everything could not be better, enchanting places visited, protected bays, every day awakenings in enchanted places and sunsets over shimmering seas, despite it being August. Antoine's boat is really special with every possible sail imaginable, you will sail even with a thread of wind, a boat not for charter but for racing, with the added comforts to be able to make an extraordinarily comfortable holiday. The last but not the least Antoine and Fides special people, who made us feel at home from the first day, immediately tried to understand our needs and did everything to make us ferns! And they succeeded!! Leaving Antoine and Fides was hard, but we will meet again! I recommend everyone to travel with them, you really feel privileged! Good wind! Seas
Victoria M.

Victoria M.

review about South of Lefkas between pristine nature bays of Meganisi and myths of Ithaca July 2021

10 / 10
Our family of four (2 adults and two children aged 8 and 10) have just finished an amazing 14-day sailing trip with Francesco. We visited so many beautiful islands, coves and ports including Zakynthos, Kefalonia, Ithica, Lefkada, Kalamos, and Kastos. Francesco was a brilliant captain and we feel so grateful to have selected him. He was wonderful with our children, very relaxed whilst being extremely conscious of safety, and went out of his way to ensure that we had a well-balanced holiday that included sleeping in secluded bays, visiting charming fishing villages, eating in some wonderful tavernas and relaxing as a family. We would highly recommend Francesco for your Greek sailing adventure!
Giulia D.

Giulia D.

review about Full Charter - North Sardinia and Corsica July 2021

10 / 10
Wonderful experience of relaxation, fun but above all to discover the sea and life on a sailing boat. Massimo and Corinna made us live an unforgettable adventure! Our week aboard the beautiful and comfortable "you and me" has flown by! We think back with nostalgia to this wonderful holiday to discover the sea, the wind and good food! Thanks to their experience they took us to beautiful beaches and breathtaking coves where we could relax with a good book, walk on the islands, visit seaside towns and / or snorkel to discover the wonders of the Mediterranean, or again, have fun with windsurfing and SUP! In short, there is something for everyone! It was great to be able to participate in the maneuvers while sailing and we also had the privilege of seeing beautiful dolphins in their natural habitat! A big thank you it was great to live the sea with you! See you soon Giulia, Nathy, Mattia, Andrea and Giuliano
Isabelle S.

Isabelle S.

review about A dream for two ... Elba and its magic, bays and coves! July 2021

10 / 10
Everything was perfect Giacomo can make your dream comes true. He is very profesional and considérate with his customers. He cooks almost as a chief ???? The boat is not only very Nice but charming and each detail is made with Amore. I recommend Thais fabulosa Cruise +++++
Cristian C.

Cristian C.

review about The ideal holiday among the 7 pearls of the Tyrrhenian Sea in a true unspoiled paradise - Hostess on board July 2021

10 / 10
Our week in the Aeolian Islands with Luigi and Laura exceeded all expectations, we were immediately welcomed as friends and pampered and always listened to as special guests. Luigi has always been very careful to create an itinerary that was comfortable but that adapted to our desires and needs, while Laura always sweetened everything with lunches and snacks and delicious aperitifs and always attentive to our tastes. But obviously the real star is the sweet little dog Tancredi, a real dispenser of pampering and sweetness, the icing on the cake! The week has really flown by, we can say that we have met two special people who have always been attentive and present without ever being intrusive who have brought us with love and passion through some of the most beautiful landscapes in the world.
Luca C.

Luca C.

review about Between Elba and Corsica-Boat 14 meters exclusively for 4 guests-Hostess on board. July 2021

10 / 10
Ganzissimi: Cinzia, Michel, the boat. Excellent holiday with exceptional skipper and hostess. Cinzia is very nice, always attentive and cooks divinely. Michael is a professional who knows the best places in the area, and is calm and always available. The boat is comfortable and impeccably clean. Return! Luca, Tracy, David, Maria Claudia
Sara Z.

Sara Z.

review about “Distinct & Distant” - 3 Cabins and 3 Bathrooms - Recent boat - Expert skipper June 2021

10 / 10
I would absolutely recommend this holiday even for those like us who were at the first experience of this kind. The Aeolian Islands undoubtedly deserve but doing them safely with an experienced skipper like Antonio certainly gives relaxation and peace. Antonio pleasant and nice person gave us some great advice on choosing places to see and restaurants to try. The boat is absolutely comfortable and well maintained, 3 dignified spacious rooms with attached bathroom, it is clean with the pots and pans necessary to prepare meals. I would say that everything went in the best way, an experience of 10 and praise, certainly to be redone.
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

6 reasons to choose a whole boat booking for your next sailing holiday

  • Benefit from a reduced price - when making a whole boat booking, the overall cost is generally substantially lower than when booking single berths or cabins.
  • Be totally free in the organisation and itinerary of your sailing holiday.
  • Fully embrace quality family or friend time and create unforgettable holiday memories.
  • Enjoy an original sailing holiday without worry or stress, with your skipper managing your day to day operations.
  • Holiday with confidence in your skipper’s local knowledge and sailing expertise.
  • Truly discover a region, travel from destination to destination at your own pace.

Discover the Caribbean or the Mediterranean in complete freedom

A sailing holiday offers an ideal setting to get together as a family and share special moments in serenity. Sleeping under the stars and a clear sky, taking the helm of the boat, sailing from island to island and waking up each morning in a new paradise are all wonderful components of sailing holidays that your family can share and create lasting memories.

Booking an entire sailboat with a skipper is a great option for groups of friends wishing for an original holiday. Diving, exploration, dinners, sunsets, parties under the stars - all of the ingredients for an exceptional adventure. Choose how involved you want to be in the sailing - whether you’d prefer to learn about sailing, or simply relax and enjoy the blissful atmosphere and scenery, embarking on a sailing trip with a skipper allows you ultimate holidaying freedom.

Some skippers offer experiences with other crew members - this might include a hostess or chef. Such listings are designed to offer holidaymakers another level of relaxation and comfort during their trip. If you are looking for an experience as worry free, with a little bit more luxury, consider a whole boat sailing holiday reservation with a crew.

All you need to know before renting a sailboat or catamaran with skipper

When is the best time to book an entire sailboat or catamaran?

There is no best specific period to rent an entire sailboat. Whenever you are looking for a sailing holiday, you can find whole boat booking options. The availability follows the seasonal peaks - for example, you can find a host of whole boat hire options through the European summer in the Mediterannean, and a host of options in the Caribbean and Indian Ocean during the European winter.

Renting a boat with a skipper: how much does it cost?

By booking the entire boat with a skipper, you can save up to 50% in comparison to the total sum of the individual spot price. The prices vary according to the period, the destination, and the type of boat. You can find periods of a week in the Mediterranean with skipper from €1,800.

What are the best destinations for a skippered boat rental?

Booking an entire sailboat is possible across the world. You can rent a catamaran with skipper in the Caribbean and discover the paradisiacal islands - or you can opt to rent a skippered sailboat in the Mediterranean where the coastlines offers countless beautiful destinations and itineraries.

Holiday concierge service

There is a sailing experience available for all. If you are in need of a little help to find the right holiday for you, you can use our holiday concierge service for free.

The best destinations for renting a sailboat or catamaran

You can find whole sailboats in all the seas of the world, at all different budgets and for all different tastes. Charter a whole boat with a skipper in the Mediterranean: discover the wonders of the sea, venture to the lesser known beaches and coves. The Mediterranean is shared by many countries, and has many stunning coastlines that make for some of the best destinations for sailing holidays in the world. Cities, towns, and villages home to a long history and rich culture, with picturesque natural wonders, with turquoise waters. The Côte d'Azur, Corsica, the Balearics, Greece, and Croatia - just to name a few!

Renting a skippered sailboat in the Caribbean: set sail aboard a catamaran in the Caribbean and discover the magical islands of Guadeloupe, Martinique, Grenadines, Cuba, San Blas, British Virgin Islands, and the Bahamas, where there are excellent sailing conditions, and in a unique atmosphere of relaxation and easygoing that is shared across the archipelago. This experience is topped off by the fresh, local cuisine of the area - that acts as an integral role of the experience. Whether you travel by catamaran or sailboat, your skipper will lead you to the special destinations of the region, making for a unique and unforgettable holidaying experience!

Whole boat with skipper: best destinations

Other travel ideas