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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.

420

experiences

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4.9

Sailing in Las Palmas for the carnival

Duration:

3 days - 4 nights

Spain:

Galicia

Be the first one to book!

€150

Per person

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5.0

Sail with lunch on board

Duration:

1 day - 0 nights

Italy:

Lazio

Be the first one to book!

€89

Per person

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4.9

Weekend on Elba between Sailing and Trekking

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€280

Per person

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4.9

Trekking and sailing weekend on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+3 travellers

Have booked

Starting from

€228

€240

Per person

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Sailing day Genoa, Camogli and San Fruttuoso

Duration:

1 day - 0 nights

Italy:

Liguria

Be the first one to book!

Starting from

€110

Per person

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4.9

Weekend sailing from Imperia

Duration:

2 days - 1 night

Italy:

Liguria

Be the first one to book!

€190

Per person

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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+7 travellers

Have booked

Starting from

€190

Per person

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5.0

Sailing day in the Ligurian nature, boarding from Varazze

Duration:

1 day - 0 nights

Italy:

Liguria

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chiara c.

Has booked

€95

Per person

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5.0

Autour de Lanzarote, Isla de lobos and La Graciosa!

Duration:

6 days - 7 nights

Atlantic islands:

Canary Islands

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Fanny V.

Has booked

€725

Per person

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4.5

1 week professional catamaran training - Marina San Miguel - Tenerife

Duration:

7 days - 7 nights

Atlantic islands:

Canary Islands

Be the first one to book!

Starting from

€1,426

Per person

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5.0

Thailand and the Andaman Sea

Duration:

7 days - 7 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

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+2 travellers

Have booked

Starting from

€1,188

€1,250

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Be the first one to book!

Starting from

€500

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Private yacht vacations & whole boat skippered cruise

125 reviews

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Guadeloupe and its islands in ten days

02/10/2024

Caterina P.

-

Italy

At first, from my son Guglielmo , a special thanks to J.B. for his prompt interest and kind concern when we had problems to get in touch because of my smartphone (next time better an e sim). Than, even if i'm not exactly the best guest to have on bord, i received any kind of support to make me feel confortable and enjoy my stay.. You'll find someone who loves his job and who knows how to do it at best. Really good experience thanks also to Adriana, LuLu e Franco. See you soon!
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Guadeloupe and its islands in ten days

02/9/2024

Franck P.

-

France

J’ai passé un super séjour sur le Mango qui est un voilier de voyage hyper abouti. Des vrais sensations de Voile…..! Merci à Jean Baptiste pour son accueil authentique qui aime partager ces connaissances et qui m a fait les beaux sites traversés…. À très bientôt. Franck
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Guadeloupe and its islands in ten days

02/8/2024

Lucie C.

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France

Super accueil. Jean Baptiste est très agréable très professionnel et surtout très securisant en.mer. il connaît son bateau dans tous les détails. Très bon séjour avec une bonne ambiance. Jean Baptiste nous a fait decouvrir de très beaux endroits. . nous le recommandons vivement. Adriana Lucie et Franck
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Between aperitif sunsets and sailings on the island of Elba

09/19/2023

Lorenzo M.

-

Monaco

La nostra prima vacanza in barca a vela. La barca è perfetta, spaziosa e confortevole, con due bagni separati (skipper e ospiti). Luca il proprietario ha reso l'esperienza speciale, una persona eccezionale, cuoco straordinario e padrone di casa accogliente. Navigare tra Elba, Corsica e Capraia con lui è stato un autentico piacere. è stato come essere in barca con un amico di lunga data o uno zio. Nota per i futuri naviganti: è golossissimo (come noi) di gorgonzola! Esperienza super consigliata specialmente per chi è alla prima esperienza. Purtoppo non possiamo dire altrettanto di sailsquare, ad oggi non abbiamo ancora ricevuto documenti come ricevuta di pagamento o contratto di charter. Inoltre ad una richiesta di assistenza non siamo mai stati ricontattati.

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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!

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