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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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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

July - September

Starting from

€370

€352

Per person

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5.0

Super!

Experience in the Egadi Islands: A Dream on a Sailing Boat

Italy: Aegadian islands

7 days - 7 nights

13 departures available

July - October

Starting from

€400

€360

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - November

Starting from

€650

€585

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€790

€751

Per person

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4.7

Dolphins & Whales cruise with WWF guide – Ligurian Sea

Italy: Liguria

5 days - 6 nights

4 departures available

July - September

Starting from

€830

€789

Per person

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4.8

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

7 departures available

August - October

€590

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

3 departures available

August - September

Starting from

€700

€665

Per person

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€640

Per person

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4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€550

€523

Per person

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4.8

Super!

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€910

€819

Per person - min 2 pax

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

2 departures available

July - August

Starting from

€395

€375

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

1957 reviews

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Dream sailing on a fully-equipped catamaran

07/9/2025

Alessandro B.

-

Italy

Per noi è stata la prima esperienza in barca e tutte le aspettative sono state soddisfatte! La parte più emozionante è stata aver potuto veleggiare insieme a [hidden]. L’ imbarcazione è in ottime condizioni e l'equipaggio che abbiamo incontrato è stato top. Sicuramente ripeteremo l’esperienza in futuro.
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Escape from the city for a weekend of sea and relaxation

07/9/2025

Monica v.

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Italy

Sono stata con i miei due figlii sulla barca di Carlo nel weekend tra il 4 e il 6 luglio. . La barca è splendida, praticamente nuova, con spazi ampi e confortevoli. Carlo è una persona squisita, socievole ma al tempo stesso discreta, attento alle esigenze degli ospiti. e felice di condividere le sue conoscenze con noi che eravamo alla prima esperienza.. Nonostante le condizioni meteo non fossero eccezionali abbiamo goduto appieno del mare e del vento, avvistato i delfini e dormito anche in rada una notte.. Nota positiva anche per il porto in cui è ormeggiata la barca , che offre servizi eccellenti
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Weekend only four guests - Elba Island

07/9/2025

Paola F.

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Italy

Bellissima esperienza! Pierpaolo skipper super disponibile sia nell’organizzazione sia nello strutturare le varie tappe per farci godere al meglio la barca a vela. Da rifare!
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Sailing weekend in the Pontine Islands

07/9/2025

Antonio F.

-

Italy

Abbiamo vissuto un'esperienza che porteremo nel cuore per molto tempo. Un weekend in barca a vela che è stato molto più di una semplice fuga dalla routine, è stato un tuffo in una dimensione fatta di silenzi, risate, salsedine e libertà. La barca era spaziosa, pulita, curata in ogni dettaglio e organizzata in modo impeccabile, si percepiva l’amore e la professionalità con cui viene gestita. Lo skipper? Straordinario. Presenza discreta ma sempre attenta, ci ha guidati con sicurezza e passione, rendendo ogni momento sereno e autentico. L’organizzazione è stata impeccabile dall’inizio alla fine, senza intoppi, con la sensazione costante di essere in ottime mani. Un’esperienza che consigliamo con il cuore.

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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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