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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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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

Per person

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4.8

Super!

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - October

Starting from

€950

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

5 departures available

September - October

Starting from

€570

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

8 departures available

August - October

Starting from

€570

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

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5.0

Super!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

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

3956 reviews

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Egadi Islands, Zingaro Reserve and San Vito Lo Capo

08/15/2026

David V.

I lost David's place for the cruise. I needed rest. Actual sailing was restricted. When sailing, the boat often proceeded straight ahead without following the wind properly. I called my best friend who is a skipper several times with video calls and was speechless, telling me to leave the boat immediately. In the end, even my friends understood that we could not continue sailing after the boat stopped in the middle of the sea and Mario and Carmen were unable to manage the situation. Mario and Carmen struggle to coordinate with each other in maneuvers, also thanks to Mario's hearing problem, and give each other conflicting instructions. We suggested that they use walkie-talkies that they had purchased specially, but they never used them. The stick used to hook the buoys was lost at sea twice. Carmen was kind to me and tried to speak to me in French. However, Mario and Carmen quarreled with each other over the maneuvers and then the atmosphere was heavy. Mario snores very loudly during the night, significantly disturbing my rest for the duration of the cruise. For me this was a real problem as I needed to sleep and I spent sleepless nights. We found a total lack of flexibility: the one and only request for modification, minimal (stopping in the next bay), was met with disappointment (we were clearly told that they do not operate a "taxi"). On this occasion, we wanted to join friends who were with their catamaran near the beach and had a free buoy next to them. Mario and Carmen chose to moor on the buoy furthest from the beach despite the sea being calm. We were forced to swim about 300 meters without tender assistance, even on the way back late in the evening. Products have been added in particular for the hygiene/cleanliness of Carmen and Mario (about 35-40 €) and food (about 25-30 €) without submitting the list to us before sending. This is unacceptable to me. The worst, however, was the refusal to take us to Levanzo despite the optimal sea conditions, preventing us from visiting one of the three islands of the Egadi then that there are only 3 and we had 7 days of navigation. For me holiday ratées. Florence

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/15/2026

Francesca D.

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IT

It was a great experience and I was especially lucky with the group I shared the boat with. In a week, living in confined spaces, finding a close-knit group with whom to feel good is certainly an important aspect. The flotilla format is ideal for meeting many new people, many of them young, and always creates a very convivial and festive atmosphere. I also really appreciated the availability and attention of the skipper and co-skipper, always present and ready to meet the needs of the group.

Egadi Islands, Zingaro Reserve and San Vito Lo Capo

08/15/2026

Micaela V.

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CH

We are sorry to leave this comment, but we feel it is right to share our experience. On the site the profile is presented as "Carmen & Mario", with Carmen listed as 58 years old (but we believe she has more) and skipper. in reality the skipper is Mario who is 70 years old, overweight, motor and hearing problems. The boat is beautiful and Carmen and Mario can be very nice and friendly. Everything changes when they have to make maneuvers: insults between them and bad mood that involves the whole group. The slightest change of program creates tensions. Even before departure we had problems: we had a change in our flight with arrival at the port at 20h. This has already been a mini drama. We were written in harsh and unfriendly tones that they were making a "concession" to wait for us, despite the fact that we had booked the whole boat and the night was still scheduled in port. Both no longer have the energy and readiness necessary to manage weeks in a row with guests. We must point out a worrying lack of safety on board: on Monday the boat hit a rock without any hull check being carried out for two days and an engine failure at sea on Wednesday afternoon was handled disastrously, with Mario and Carmen refusing to contact the coast guard, who intervened anyway on our initiative (with Carmen verbally attacking us for doing so) The guard judged "crazy" the manoeuvre attempted by the skipper to pull the sailboat for many kilometres. we had to organize the end of the stay independently, with more than € 1500 at our expense as Mario and Carmen refused to take us to Levanzo once the boat was repaired stating that the weather conditions did not allow us to continue the tour then that the maritime guard had indicated that the conditions allowed navigation
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Aeolian Islands: between sea and authentic flavours

08/15/2026

Michela C.

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IT

Positive experience with a very comfortable boat having 1bathroom in each room and a spacious dinette, and equipped. Lq boat is clean and well maintained. . However, I would have preferred a greater use of the tender to get closer to the beaches instead of having to swim a lot all the time to get to rocks or the beach. I also find that in fact the issue of buoys to be paid / port etc is not very clear. I had read about this problem in advance.a and I can only confirm it. In addition, when we went down in the evening with the tender we were told that we could only be picked up until 23:30 which seems a bit early to me being summer and leaving the next day never before 10/10:30 in the morning, I don't say at 2 in the morning, but at least at midnight.

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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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