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

80 reviews
20 / 10
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. The Soledonna 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 most 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 Soledonna and 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.
Marco F.

Marco F.

review about Week end in the Gulf of Poets Portovenere and 5 lands May 2021

10 / 10
It couldn't have been better! A truly perfect weekend on board a wonderful boat. Alessandro and Paola are hospitable, nice, helpful and have been able to put us at ease right away. The experience at the helm was the eyelash on the cake. The boat is perfect, clean, livable, fun, fast and responsive. Despite being a cruise boat in all respects, the sail surface the jib carriage and other finesse make it extremely fun to steer, always with the tranquility of maximum safety on board. Five stars all deserved. I hope to get back on board soon!
Marco S.

Marco S.

review about Cruise or mini cruise in Northern Sardinia? You choose where to go and when to leave August 2020

10 / 10
Spectacular holiday! Antonio is a very good skipper both in navigation and in the rest of the moments on the boat, he cooked very well and we really enjoyed it. He knew how to take us to the most beautiful bays and we managed to go almost exclusively sailing, which was what we wanted. We slept in the harbor almost every night, as we wished, only one night in port, where we refueled with food. Special holiday, thank you very much!
Manuel G.

Manuel G.

review about Pontine Islands on a sailing boat - All Inclusive + chef on board August 2020

10 / 10
If you choose to take a holiday at the Pontine you must absolutely rely on Marco Umberto (also called Marco "baffetto" for the natives). Great connoisseur of the island for twenty years at least, lover of the sea, sailing and good food. Every day he delighted us with fish dishes (fresh from the day!) cooked properly. At the end of the holiday beyond the skipper (but never call him that) we found a friend! HIGHLY RECOMMENDED.
Eloise T.

Eloise T.

review about A week of pure relaxation, sea and strolls in the Tuscan Archipelago August 2020

10 / 10
Francesco is a very professional and prepared skipper attentive to his guests and with a particular dedication to the kitchen. We spent a beautiful week on the boat with our children and although it was our first experience we found ourselves very comfortable and thanks to the passion for sailing that Francesco has transmitted to us we are sure that there will be many other future experiences. Super recommended!
Margherita P.

Margherita P.

review about Sailing week with hostess on board. Flexible dates and itinerary. Relax, sea, adventure. August 2020

10 / 10
Vote 10: the best we could hope for! Great professionalism of Enrico and Daniela who are two great connoisseurs of the sea, you can immediately perceive it and you feel at ease from the beginning. Hospitality: friendly and pleasant make the holiday relaxing and at the same time fun. Kitchen: Daniela cooks very well always managing to meet everyone's needs. Itinerary: flexible here too depending on your needs. The most beautiful beaches and the blue sea are assured! We recommend 100%, even to those who, like us, are at the first experience on a sailing boat!
Federico S.

Federico S.

review about Sardinia South Coast August 2020

10 / 10
An exciting experience! We spent a wonderful week in southern Sardinia. The boat very clean and performing, Edoardo the skipper is a really pleasant person, a professional but at the same time affable and humble, he immediately put us at ease and really endorsed our every request during the cruise. We visited views and beaches difficult to reach from the ground, ate excellent typical dishes and made incredible baths. Definitely!
Andrea P.

Andrea P.

review about Sardinia among La Maddalena Islands & Corsica: sea, relax and adventure August 2020

10 / 10
Extraordinary experience with Francesco and Silvia. Very caring couple and attentive to details and to the realization of customer expectations. Francesco skipper expert, competent, fussy, methodical and deep connoisseur of the places and nuances of the most hidden corners. Experience to be repeated with a great crew very familiar and very intimate and special trip... highly recommend
Maria Elena P.

Maria Elena P.

review about Discovering the Gulf of Baratti July 2020

8 / 10
We traveled with Massimo and Joshua, two professional and helpful skippers. Beautiful experience. 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