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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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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

July - October

Starting from

€615

Per person

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4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

5 departures available

July - August

Starting from

€1,504

€1,128

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

July - November

Starting from

€650

€618

Per person

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4.5

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

July - September

Starting from

€1,040

€936

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

€950

Per person

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5.0

Super!

Kornati Islands: a week on a catamaran among the pearls of Croatia

Croatia: Kornati Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€1,400

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

€935

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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4.9

Super!

Tuscan Archipelago: An Oasis of Blue between Sea and Nature

Italy: Tuscany

6 days - 5 nights

7 departures available

July - August

Starting from

€650

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€420

€399

Per person

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4.8

Super!

Egadi Islands by catamaran Astrea 42 of 2020 - Stewardess/Cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

July

Starting from

€1,200

€1,080

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

1889 reviews

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4 weekdays in the Pontine Islands

07/3/2025

Danilo S.

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Italy

Vacanza indimenticabile! È stato tutto stupendo, praticamente perfetto! Lo skipper Stefano e il marinaio Adriano ci hanno fatto sentire a casa nostra dal primo all'ultimo istante. Ci siamo sentiti liberi, ma siamo stati guidati con grande sicurezza e conoscenza dei luoghi. Siamo stati molto fortunati anche con il gruppo. Posti stupendi, mare incredibile, barca molto bella e comoda. Per noi era la prima volta...sicuramente non l'ultima.
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Four days in the Pontine archipelago

07/2/2025

Eleonora F.

-

Italy

Abbiamo vissuto un'ottima esperienza! Abbiamo visto posti magnifici con buoni consigli di Antonio e abbiamo anche veleggiato!
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Enjoy: in the blue painted blue of the Aeolian Islands

07/2/2025

Loris C.

-

Italy

Giovanni è una persona che ha trovato nel mare la sua pace interiore ed è in grado una volta a bordo della sua barca di trasmetterti la sua passione e trasportarti attraverso la sua libertà e quiete in una navigazione confortevole tra le meraviglie della natura incontaminata . Grazie capitano.
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4 days relaxing in the Pontine Islands

07/2/2025

Simone S.

-

Italy

Tutto top tranne… ahimè… Sailsquare. Bruno è un ottimo skipper, ha grande esperienza e conosce bene le bellissime zone in cui naviga. La sua barca è bella, comoda e ben equipaggiata. Inoltre viverla massimo in 4 persone è un grande vantaggio… Maggiori spazi, maggiore comodità e maggiori comfort. Assolutamente una vacanza in barca TOP!!! Consigliata e da rifare assolutamente!!! Ahimè nella nostra vacanza abbiamo avuto un imprevisto non dipeso da nessuno. Cose che possono semplicemente accadere. Bruno l’ha gestito al meglio, ha cercato individuare la natura del problema, di riparare il danno, di trovare la soluzione migliore per l’equipaggio e per la sicurezza di tutti siamo rientrati con un giorno di anticipo rispetto al programma. Era assolutamente la cosa giusta da fare. Avendo prenotato tramite Sailsquare eravamo tutti convinti di poter contare su loro per compensare il giorno perso ma invece… nulla! Declino totale di ogni forma di assistenza e soluzione al problema. Abbiamo chiamato più volte e in modo educato e garbato ci hanno detto “vedetevela voi”. Grande grande grandissima delusione. Ho prenotato tramite Sailsquare, riconoscendo loro una commissione del 20%, convinto di poter contare sulla loro assistenza e supporto e invece, nel momento del bisogno a commissioni incassate, tanti saluti a voi. Bruno 5 stelle Barca 5 stelle Destinazione 5 stelle Sailsquare zero totale

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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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