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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

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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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€719

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€900

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

4 departures available

August - 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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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€650

Per person

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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

One departure available

August - September

€660

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€583

€525

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€751

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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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

Starting from

€1,041

€989

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

2 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

2049 reviews

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Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Sabrina C.

-

Italy

First time on a sailboat, first time in Ponza, they were 4 days that I will remember and they will have a special place in my heart. Thanks to Leonardo and Elena for the perfect organization, and availability.. The navigation was perfect, despite the rough sea, I never had any doubts about the skipper's skills who showed confidence and experience. The destination and the surrounding areas that we visited with the tender are magnificent,.. I highly recommend this experience , the boat is very nice, clean and comfortable. We shared our holiday with unknown people but with the same desire to spend unforgettable days. Thank you all 🥰
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Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Laura D.

-

Italy

It was my first experience on a sailing boat, I was inspired to be able to travel by sea from cove to cove, but I was full of doubts, I was afraid of being sick. And instead I was practically always fine. I arrived at the port and the departure was unfortunately with very rough seas. Instead, I discovered that with the necessary precautions, i.e. the classic pill, I could feel good and enjoy the sea and navigation! We immediately sailed for five hours, the wind was blowing very strongly, the black waves pushed us and we arrived in Ponza at sunset fiery red. This was just the beginning, I then saw wonders, one after the other coves, rock cathedrals, natural arches, emerald green sea, I do not deny that I was unexpectedly moved by such a wonder .. I was lucky with the group that was bubbly and close-knit. I really appreciated Leonardo's ability to steer the boat with seriousness and palpable experience, he also took us with the tender everywhere, it was an exploration that I appreciated very much. During the day we also had fins, masks and sups available. Elena the wife was always present, very friendly and attentive with all of us. I also loved being able to cook for everyone, I wished I could have done so much more to be honest 😅 I was lucky to do my first sailing with them and I will certainly repeat a new experience shortly. Thanks for everything. 💙
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/18/2025

Nathalie B.

-

France

All the will Suddenly he leaves Faced with the obvious All this is immensity And work for 10 hours Always make choices of the heart Apologizing for a mistake This too is immensity All reality is immensity How the dream will then dissolve From tomorrow a new immensity will begin again From tomorrow From tomorrow From tomorrow •• Andrea Lazlo de Simone . Immensity And so, the mermaids disguised themselves as a birthday Elvis, the sea played at being the ocean and sailing did not challenge the fury of a capricious eole! New Odyssey, on a new parallel. For a parenthesis ... 'insolent'. And everything was ... immensity! Σας ευχαριστώ . Καλό ταξίδι …
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Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Jennifer D.

-

Italy

I put myself to the test because for me, it was my first experience on a sailing boat. Leonardo is a Captain who has been able, with his experience, to guide the whole group on this beautiful holiday, he has made us discover places of extraordinary beauty, willing to comply with our requests. Elena entertains the bench, helps her husband and takes care of all the guests. I feel lucky to have chosen this route and these people. The boat is beautiful, kept in impeccable condition, my cabin was delightful. On a boat there are many rules: you have to understand and respect them! This experience is for you if you're open, ready to share fun moments with a group of strangers. keyword: SHARING! A varied and bubbly group, I immediately empathized with most of them. I relaxed, tanned, explored with Sup, snorkeled etc. Beautiful location, the surreal sea! Things I didn't like: the sailor's 😅 shower and the rough sea, for the rest: I can't wait to do it again!!

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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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