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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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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€1,150

€1,035

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

11 departures available

August - October

Starting from

€570

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

€999

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August - September

Starting from

€950

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

8 departures available

July - September

Starting from

€730

€657

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

14 departures available

July - November

Starting from

€700

€665

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

September

€280

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - October

Starting from

€700

Per person

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4.8

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€583

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

€585

Per person

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4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

August - September

Starting from

€400

€360

Per person

Why book a holiday with Sailsquare?

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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

3596 reviews

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

07/14/2026

Lidia Giulia D.

-

IT

An extremely prudent sailing experience, suitable for those seeking maximum tranquility. I state that I have several sailing holidays behind me, so I know the rhythms on board and the fundamental role of the skipper. Precisely for this reason, I would like to leave a balanced and objective review, which highlights both the positive sides and the aspects that have limited our experience. Starting from the positive notes, the boat itself is very comfortable and spacious, equipped with 4 cabins and 4 bathrooms, which guaranteed excellent livability on board even during an important crossing such as the one to reach Corsica. In addition, the skipper is an elderly and highly experienced person, who puts the safety of the crew and the boat first. He has always made himself available to accompany us ashore with the tender whenever we needed it, guaranteeing us comfortable and safe disembarkations. However, in other respects, the holiday was affected by a management that was perhaps too rigid. The aspects of navigation that most influenced the week were the management of the draft and the very conservative moorings. The boat has a large draft, which undoubtedly requires attention. However, the skipper's caution was in my opinion excessive. We stopped almost exclusively in roadsteads well known to him and very sheltered, often far from the most famous and evocative points, such as Isola Piana, which we were able to see only after much insistence. Coves with shallow waters and turquoise waters were systematically avoided, always keeping a safe distance well above what was necessary. In addition, there were few trips once at the destination. Although they covered an important route arriving in Corsica, once they arrived there, daily travel was reduced to a minimum. It became very difficult and rare to move to change bays or explore the surroundings once the anchor was dropped. During the journeys, navigation took place far offshore. Even during longer transfers, the skipper tended to always sail in very open seas, staying at a great distance from the mainland, which did not allow us to enjoy the coastal views. This also affected the logistics of the bathrooms and activities. Always mooring at a great distance from the shore, it was not possible to enjoy the sea swimming, and in SUP we struggled a lot to cover the distances starting directly from the boat. This has limited a bit the spontaneity and freedom typical of a holiday at sea. Finally, we did little sailing. Despite the days of good wind, navigation took place mainly by motor. In summary, it was a holiday with a very quiet pace and a strongly conservative approach. I think it is ideal for those who are at their first experience and are looking for very calm rhythms and maximum caution; those who already have experience and are looking for the spirit of sailing and active exploration of the coves may find this style a little too limiting.

Gulf of Poets

07/14/2026

Robin H.

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DE

We had an unforgettable sailing trip! It was an incredibly beautiful experience that we would do again at any time. Giovanni was incredibly warm, attentive and made sure we felt comfortable the whole time. Due to his open and friendly manner, we felt at home on the ship from the first moment. The atmosphere on board was relaxed, the landscape fantastic and the entire trip was simply perfectly organized. Thank you very much for this special experience – we can heartily recommend the sailing trip with Giovanni!
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2026

Stefano M.

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IT

Riccardo is a wonderful person, he fully infuses all his innate passion for the sea, nature and sailing. Excellent teacher, if interested he allows you to participate in the maneuvers of the boat explaining each step perfectly. Wonderful proposed itinerary, excellent cook who manages to satisfy all the dietary needs of his guests. Helpful and with excellent organizational skills.
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Catamaran between Costa Smeralda, Maddalena and Bonifacio!

07/14/2026

Simone T.

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IT

We had a fantastic week sailing through the Maddalena Archipelago. Alessandro is an excellent skipper who creates a relaxed and enjoyable atmosphere for everyone on board. Although we weren’t able to dock in Bonifacio as originally planned, and the catamaran could offer a few more features for its class, the overall experience was outstanding.

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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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