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.
BEST PRICE GUARANTEE
If you find the same experience for a lower price elsewhere, we’ll match the price.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
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.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
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!
I 2 giorni a bordo della barca di Andrea sono stati meravigliosi sia per me che per i miei 7 colleghi norvegesi. Grande conoscitore delle Eolie, aveva sempre pronte un paio di opzioni da proporci, a seconda delle condizioni meteo e dei nostri interessi. Non ci ha mai imposto niente, assecondando le nostre richieste, e dandoci comunque suggerimenti preziosi sui migliori ristoranti o su dove trovare la migliore granita dell'arcipelago. A bordo e' sempre stato gentile, disponibile, chiacchierone e pronto a dare spiegazioni se qualcosa non era chiaro. Ci ha preparato il caffe' a colazione e anche cucinato il pesce al bbq! In 2 parole, Andrea e' stato fondamentale x la felice riuscita del nostro weekend!
Gianni è stato il nostro quinto compagno di viaggio. Siamo stati fortunati con il tempo e abbiamo trascorso quattro splendide giornate: bagni in acque cristalline, aperitivi, giri in gommone e tante chiacchiere e risate. Una menzione particolare per la barca: spaziosa e unica nel suo genere. Ciao Gianni, fai il bravo e non ti perdere gli occhiali! :) A presto, Paola, Marco, Sara e il Fratellone.
Prima volta in barca a vela ed esperienza più che positiva. Stefano e Carolina super disponibili e attenti alle nostre esigenze. Abbiamo trascorso un week end a bordo, ma le dimensioni della barca consentono tranquillamente di passarvi più giorni. Promossi a pieni voti!
Abbiamo trascorso 6 gg su questa fantastica barca " ecologica" , in compagnia di Francesco e di suo figlio Alejandro, piacevoli compagni di viaggio.
Stare su questa barca è un viaggio nel viaggio, ti riporta alla consapevolezza del mondo in cui viviamo e come lo viviamo: consiglio a tutti di provare l' esperienza con mente e cuori aperti.
Buon viaggio!
The vacation was simply amazing! We had an amazing time with Ettore sailing around north Sardinia all the way to Corsica. My girlfriend and I decided to sail with Ettore around La Maddalena archipelago, and we slept over at different spots for 4 nights. Nothing compares to waking up in isolated crystal blue water all for yourself. Very well organized, and clean boat. Ettore has over 30 years of experience and he knows every single spot around (including some secluded beaches). Ettore is a very fun and easy going person who takes care of his guests very well.
La vacanza e stata bellissima. Ettore si e rivelato essere uno skipper di grande esperienza, una persona simpatica e divertente. Consigliatissimo!!
We had a fantastic time with Dominikus on his beautiful vessel! We were involved in the trip planning & Jessica lovely has taken care of us. As being a sailing enthusiast by myself Dominikus has given me many tipps how to handle a ship of this size & I learned a lot. All around we had a lot of fun, especially our daughter fell in love with ‚Adolf‘ the dog and played with him nonstop. From sailing fun, over to anchoring in beautiful bays, snorkeling, SUP paddling, cooking together and laughing...those were the perfect days...we had a wonderful time ! <3 We‘ll be back soon! Greetings & hugs of the LL family
Une semaine extraordinaire en voilier avec Christopher et Marie
Accueil sympa parcours extra baignade dans de superbes criques
Bonne musique le soir et repas délicieux
Que du bon temps
Adam et Allan pris leur premier cours de navigation avec le captain Christopher
N’hésitez pas à embarquer
Merci mille fois
Adam Allan Zena et Patrick
Week-end meraviglioso! Alessandro uno skipper gentile e attento. Accoglienza super! Anche il suo secondo davvero bravo. La barca accogliente, spaziosa e ben tenuta. Una breve vacanza piacevole e di volta in volta concordata. Consigliamo vivamente!!!
Gianpaolo è un ottimo skipper, navigare con lui dà sicurezza. Fa rispettare le regole , ma con gentilezza. Riesce a essere presente, ma mai invadente. È di compagnia, chiacchiera volentieri , e ci ha portato in posti molto belli. Bella e spaziosa la barca,
Insomma. Se cercate uno skipper in gamba , e una vacanza divertente e/o tranquilla , Gianpaolo fa al caso vostro.
Semaine inoubliable avec toute la famille sur le voilier de Charles très bien équipé, une vraie découverte pour nos enfants âgés de 14 à 23, le tout dans un cadre magnifique. Skipper très pro, avec beaucoup de sérénité et agréable à vivre, très expérimenté, toujours prêt à écouter nos souhaits et à nous dénicher de belles criques ! Chacun ayant le choix de participer ou non aux manoeuvres, voire même de prendre la barre, nous avons pu savourer des vacances très nature, chacun à son rythme, et gardons tous de très beaux moments en tête.
Che dire! Bellissima esperienza di vela alla scoperta del mare incontaminato dell'Isola di Capraia! Claudio e Nori sono persone che non si incontrano facilmente nella vita: solari, disponibili,ti mettono subito a tuo agio e ti fanno sentire dei veri "pirati"...alla conquista del mare! Week end perfetto ( Eolo poteva fare di più ma non ci lamentiamo)...siamo rimasti colpiti anche dalla bravura dello Chef Claudio, che ci ha coccolato con deliziose specialità! Tutto perfetto...peccato che il week end vola via! Grazie ...speriamo a presto! Buon Vento!
Giuseppe e Teresa sono stati molto simpatici e disponibili. Hanno organizzato la gita secondo le nostre richieste. La barca è comoda, pulita e tenuta molto bene. Da consigliare!
Siamo da poco ritornati da questo splendido viaggio e abbiamo ancora nel cuore e negli occhi i bellissimi luoghi che abbiamo visitato.
Un grazie enorme allo skipper Alessandro che ci ha condotti con maestria, simpatia e tanta pazienza nelle "perigliose" acque caraibiche, infestate da barracuda (purtroppo niente lampughe nè tonni). Se ci vorrai ancora a bordo con te, noi ci saremo!
Un grazie anche al co-skipper "zen", il pizzaiolo "in pectore", Carlo e alla sua compagna Mala che ci ha rallegrato con il suo stratripante buonumore e i suoi piatti luculliani.
Un grazie anche ai compagni di viaggio: Antonella, Carmen, Luisa, Renata, Danilo e Nerino, con cui abbiamo condiviso nel buonumore la vacanza.
Alla prossima. Valentina e Norberto
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!
