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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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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

Starting from

€325

€309

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

September - October

Starting from

€585

€527

Per person

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4.7

Feast of Santa Candida alle Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€700

€630

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.9

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

€980

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

Per person

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4.7

IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

One departure available

October

€900

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

4448 reviews

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Luxury catamaran cruise in the Cyclades

09/13/2026

Gianluigi C.

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IT

Very disappointing experience and well below expectations. The skipper arrived more than two hours late, the boat was in very poor hygienic condition and unusable, without apologizing. We 10 guests had to clean it for about three hours. Despite the promise of reimbursement, we were only paid about 11 euros per person, just over 3 euros per hour. We also lost half a day in port due to technical problems and faced about 24 hours of inconvenience due to the malfunction of the generator, water system and toilet. When faced with problems, we were only told: "It's not my fault". As captain and manager of the boat, he should have handled the situation with greater professionalism. The itinerary was not respected for weather reasons, according to the skipper, although the forecast in the Saronic Islands was similar to that of the Cyclades. Positive aspects: the beauty of the boat and the possibility of using the equipment for diving and fishing, as well as the company that was created with the other guests during the week.

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

09/13/2026

Elisa V.

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IT

Super experience! Sleeping in the roadstead is exciting... swimming in the sea immediately after breakfast is priceless! Sunrise and sunset... too! Josuah was super, he shared with us all aspects of the boat and fishing, we shared pleasant and fun moments of adventure and relaxation. Thank you Josuah for this wonderful experience and congratulations on your [hidden]... a very cozy boat! We recommend it to everyone!

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

09/13/2026

Polyanne M.

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ES

A very disappointing experience and very different from what we expected from the contracted itinerary. We chose this one-week sailing trip precisely to get to know some of the most spectacular coves and landscapes of the La Maddalena archipelago and the south of Corsica. The itinerary included areas such as Caprera, Spargi, Budelli, Santa Maria, Lavezzi, Cavallo and Bonifacio, and our expectation was to sail, discover coves and enjoy those landscapes of turquoise blue water, light sand and large granite formations so characteristic of this area. However, by the end of the week we felt that we saw very little of all that this route had to offer. We passed through some places and were in Budelli, specifically in the Spiaggia del Cavaliere area, as well as other points and ports along the route, but many of the places that had made us choose this trip were left out. What disappointed us the most was that throughout the week we practically did not live the experience we imagined of anchoring the sailboat in front of a spectacular cove with turquoise blue waters. Nor did we get to enjoy those small coves surrounded by huge granite rocks that are one of the most representative images of the archipelago. We fully understand that on a boat trip wind, sea state and safety can force you to modify the itinerary, and we would never expect a skipper to sail when conditions were unsafe. But it is one thing to adapt a route for safety and another to end a week with the feeling of having spent too much time between ports and unspecial anchorages, leaving a huge part of the places that motivated our choice unknown. We had pending places such as Cala Corsara in Spargi, Cala Coticcio in Caprera, Lavezzi, Bonifacio and other coves along the route, in addition to a good part of that navigation between beaches and crystal clear waters that we expected to experience. After a week, our feeling was: we were in one of the most famous and beautiful archipelagos in the Mediterranean, but we could hardly get to know what makes it really special. And that, considering the price and the expectations created by the itinerary, was a huge disappointment. But the most difficult part of this experience was not only everything we missed. It was the constant feeling of helplessness for not being able to participate in decisions about our own journey. At no time did we feel that we could really choose, propose alternatives or give an opinion on how to make the most of the days. Every time we tried to ask about another cove, another anchorage or a different possibility, we had the feeling that any proposal ended up being redirected towards the option that the skipper Frederico considered most convenient. There came a time when we practically stopped asking and remained silent, because we felt that it didn't matter what we said. That dynamic generated a lot of anxiety and anguish during a vacation that we had hired precisely to enjoy, disconnect and experience something special with the family. We fully understand and respect that the final word on boating safety rests with the skipper. We do not question that. What we missed very much was communication, alternatives and the willingness to seek, within the possible conditions, options that also responded to what we wanted to know. Our perception for a good part of the trip was that the decisions ended up systematically favoring the easiest option for the skipper, instead of trying to build with us the best possible experience within the circumstances of each day. And that feeling ended up deeply affecting our experience. We were in an extraordinary place, had invested a lot of money and had a week to enjoy it, but we ended up feeling like voiceless passengers on our own journey.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/13/2026

Carolina V.

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US

We had the most incredible experience with Sailing with Andrea. He made us feel safe from day one while still keeping things fun and full of energy. You could tell right away how professional and experienced he is on the water. He took us to the most beautiful spots around Paxos, Anti Paxos, and Corfu, places we never would have found on our own. While other tours crowd into the same touristy spots, Andrea took us to the most secluded, hidden gems along the coast! Caroline, our hostess, was just as wonderful. She was warm, attentive to every detail, and her cooking was fantastic, every meal felt like a treat. Between the two of them, we felt like we were staying at a 1000-star hotel! We had a hilarious volleyball match in the shallow water, our boat against another, one of the most fun moments of the whole trip! If you're looking for a trip that combines beautiful places and genuinely lovely people taking care of you, this is it. We can't wait to sail with them 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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