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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.

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€719

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

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5.0

Super!

North and south Sardinia of Corsica sailing

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

July - August

Starting from

€900

€810

Per person

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4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

7 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Spain: The Balearic Islands

6 days - 6 nights

5 departures available

July - September

Starting from

€650

€585

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

September - November

Starting from

€530

€477

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

July - September

Starting from

€293

€264

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

July - August

Starting from

€780

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

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

1947 reviews

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Weekend on Elba Island

07/8/2025

Giovanna B.

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Italy

Weekend in barca a vela splendido! Tempo ottimo, vele spiegate e piacevoli compagnie . Anthony è skipper molto capace e sempre attivo oltre ad avere un sense of humour vincente!!! Ha cercato sempre di soddisfare ogni richiesta , ha dato indicazioni sui luoghi visti e sulla vita di barca, E' simpaticissimo e .... non ultimo.... un ottimo chef! Ha sempre cucinato piatti gustosi e vari, curandone anche la presentazione !!! E pensare che si i è trovato a bordo vegani , intolleranti al pesce e altro!
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Three-Day Sailing Tour to the Pontine Islands

07/8/2025

Serena R.

-

Italy

Mini vacanza bellissima! Antonio si è dimostrato un grande capitano e un grande uomo. Non solo ha una evidente competenza nautica ma ha anche grandi doti relazionali e ti fa sentire a proprio agio sulla sua confortevole barca. Si è dedicato a tutti noi con passione e gentilezza, portandoci con il suo gommone in tutte le calette e grotte possibili. Ci ha cucinato ottimi piatti e ci ha deliziato con tante storie che riguardavano le isole pontine. La sua barca è estremamente pulita e la cabina di prua una vera reggia! Inoltre la ciliegina sulla torta è il suo mitico tendalino, spazioso e in grado di offrire ampi spazi di ombra! Grazie Antonio, sceglieremmo sicuramente ancora te per una nuova avventura!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

-

Italy

-ho trascorso con Paolo e Bianca una vacanza stupenda . Loro sono gentilissimi simpaticissimi Bianca è una cuoca bravissima. Sono molto disponibili . La mia prima esperienza in barca a vela è stata piacevolissima. Ho visto posti stupendi, calette che altrimenti non avrei potuto vedere se non in barca . Consiglio vivamente una vacanza con Paolo e Bianca
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Ibiza All Inclusive on an 18m ketch with skipper and skipper

07/8/2025

Donatella R.

-

Italy

Cinque stelle non bastano per rendere onore alla strepitosa vacanza trascorsa su [hidden]. Filippo oltre ad essere un velista attento ed un cuoco incredibile è una persona davvero fantastica, di quelle che ti auguri che la vita ti faccia incontrare. Della sua assistente (e nipote), Camilla, mi sono letteralmente innamorata: solare, divertente e bellissima. Last but not least…NAO, sapevo avrebbe allietato la settimana ma non immaginavo così tanto! Scendendo dalla barca ho pensato: ci risalirò

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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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