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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

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Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

23 departures available

May - October

Starting from

€1,200

€1,080

Per person

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4.8

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

Italy: Northern Sardinia

6 days - 7 nights

17 departures available

June - October

Starting from

€660

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€460

Per person

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4.9

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Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

8 departures available

July - August

Starting from

€800

Per person

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4.9

Super!

Caribbean Escape – Sailing the Grenadines

Caribbean: Grenadines & Martinique

10 days - 10 nights

2 departures available

January - February

€2,100

Per person

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4.9

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SLOW SAIL - sailing from San Vincenzo to Capraia and Corsica

France: Corsica

7 days - 6 nights

4 departures available

August

Starting from

€750

Per person

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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

17 departures available

October - November

€150

Per person

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5.0

Super!

Dream Cruise Under Sail in the Society Islands 14 Days

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.9

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

9 departures available

July - September

Starting from

€1,550

€1,395

Per person

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4.9

Super!

Sailing adventure in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

7 days - 7 nights

7 departures available

January - November

Starting from

€1,200

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

15 departures available

June - September

Starting from

€754

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

2 departures available

October - November

€350

Per person

Why book a holiday with Sailsquare?

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

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

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

4598 reviews

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IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

10/17/2026

Elena V.

We really needed this holiday! Filippo is a wonderful host: attentive skipper (also ready to involve those who show interest in sailing), excellent cook, great entertainer and even singer. The weather was not the best, which changed the itinerary and it was a great shame, but it is the risk of every holiday, even more so in those by boat. The latter is equipped with interesting "pluses" (BBQ, fishing rods, SUP). It is comfortable, but it is "lived" practically all year round as it is basically Filippo's home and this means that it is not a 5-star hotel on the water where everything is impeccable. A thread of sporting spirit and sharing is needed, as clearly written in the announcement. Finally, I cannot fail to mention Nao, a wonderful sailing companion always ready to be cuddled and try to save you when you go down into the water. And if I loved it because I don't have any particular liking for dogs, you can trust it. Ps: you will go home with a couple of extra kilos on you, but it's worth it

Learn to sail in Liguria: First level sailing course

10/17/2026

Nicole C.

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IT

Unforgettable experience on the legendary [hidden]. Even before getting on board, Orazio, with great professionalism, deepened the previous experiences of his crew with whom he shared choices and organization. Once on board, we were greeted by wonderful people and we were amazed by the beauty of the boat, perfectly tidy, clean and welcoming. It is said that when you are at sea all your thoughts remain on land and so it was, between many laughs and exquisite company, we also learned new notions of sailing and life at sea in general. Super recommended experience. Nicole and Matteo from Aosta.
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/16/2026

Francesca D.

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CH

Aga and Jerry are excellent hosts and sailors. Aga goes above and beyond to make guests feel welcome, organising restaurant bookings, taxi boats, recommendations and gorgeous breakfasts. Jerry is an experienced sailor, always calm, with plenty of stories to share, and happy to offer hands-on sailing opportunities to those interested. The boat is comfortable, clean and well maintained. Unfortunately, I cannot give the highest rating due to the high overall cost, lack of transparency around the common fund and poor communication. Having experienced similar holidays, we found the price significantly higher than comparable offers. It was also the first time we encountered a flat per-person common fund with no breakdown of actual expenses. Given the additional €250 per person (including children), totalling €1,750, I would have appreciated a summary of costs, particularly as this covered bed linen, four nights in harbour, breakfasts and lunches, as well as a few restaurant dinners joined by Aga or Jerry. Finally, just days before departure, we were informed of an alleged bedbug outbreak in Athens, which we could not verify through any online sources. This meant sealing all our belongings before boarding, adding considerable packing time and taking up valuable luggage space. Had we been informed earlier, I might have chosen a different holiday.

Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/15/2026

Lara R.

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CH

We had a wonderful time and the crew took good care of everything we could have wished for. Thank you very much for the great experience!

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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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