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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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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€716

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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5.0

Super!

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

6 departures available

September - October

Starting from

€950

€855

Per person

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

Per person

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€713

Per person

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4.7

Palma de Mallorca All Inclusive on 18m Ketch

Spain: The Balearic Islands

6 days - 7 nights

6 departures available

August - September

Starting from

€1,290

€1,117

Per person

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4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

3 departures available

August - October

Starting from

€860

€774

Per person

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5.0

Super!

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

11 departures available

August - November

Starting from

€1,099

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

Per person

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4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,080

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

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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

3770 reviews

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Whale watching cruise with WWF guide in the Corfu archipelago

08/2/2026

emanuela f.

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IT

This is my message already shared with the travel group and that I use here too. Thank you Sailsquer! Good morning everyone. This is a message that I feel I can make to close without hesitation or rancour a certainly unique experience. I am a kindergarten teacher where common rules, respect, kindness, knowing how to live civilly and sharing are mainly taught. I left with a load of enthusiasm due to the desire to travel (something I couldn't do for some time for family reasons) and a particularly hard year, so excuse me if I tried to live every single moment with an energy for you, probably, exaggerated. Working to make others feel good, like making a coffee, is an act of kindness that I gladly did but that, evidently, for those like Rocco who has been traveling for days and is perhaps tired of these dynamics, was not always welcoming😩 (dear Rocco, there were several things that upset you, perhaps with clearer indications given at the beginning of the trip you could have avoided several embarrassing situations). Having said that, and to return to the starting point. The review that is often done on the way back from a trip is done first here. Because we shared a journey that everyone chose for different reasons, of course, but all to be respected. I apologize therefore if I have been exaggerated for some, intrusive for others, too noisy at certain times or too silent at others. I just tried to live all the moments and take home as many memories as possible. Overall, for being a group trip with unknown people, it was definitely interesting. You can't please everyone or be friends with everyone but you can learn to recognize and accept diversity. The whale watching experience was the most unifying and exciting part. I thank, therefore, Don for being a prepared guide and extremely helpful and patient even with me and my difficulty in memorizing the names of the children. ceratacei😁 The most beautiful gift that nature has given us, not always forgiving, have certainly been the sightings. Wonderful experience to be surrounded by dozens of common dolphins in the beautiful mare nostrum 😉 Pure emotion!!!! Dear travelers, I appreciated the availability of some of you, the confidentiality of others and the patience of all. Yesterday Anna asked us if we would do this experience again, I immediately said no but, thinking about it, in another context that does not include long days of transfers, such as the Otranto channel, it is not to be excluded because you have less tight schedules it would also help those who have to face several weeks in a row like our skipper and our guide, in order to manage both the uncertainties of the weather and personal fatigue more serenely, to the benefit of a serene and relaxed climate on board. Praise to Rocco for his sailing skills and for sharing his Audace and his time that I know how difficult it can be for those who love boats and the sea. I greet and wish everyone fair winds, on the boat as in life Ad maiora Emanuela F. P.s. I still😉🌬⛵️🌊🐬 sway
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/2/2026

Antonella R.

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IT

Kindness:: there is no better word to describe this holiday week. We were literally inundated not only by the beauty of the places, but above all by the infinite care, attention and warmth that the crew reserved for us from the first to the last day. Alessandro the skipper: impeccable from every point of view, a person you can rely on with your eyes closed. He organized wonderful excursions every day, always leaving us maximum freedom of choice. Carlo, the steward: a true guardian angel! He pampered us with delicious dishes and more. Being a great swimmer, he accompanied us on beautiful swims in the most beautiful bays, enriching the trip with fascinating anecdotes about the various areas visited. Eros: the "little dog" of the crew, of infinite sweetness. Added value: sailing together with the boat of Andrea, Alessandro's brother, made the experience even more welcoming and familiar. A journey that leaves you with the memory of wonderful people and the value of small gestures. Super recommended holiday!!
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/2/2026

Tiziana L.

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IT

Every experience leaves its mark for better or for worse, it is always an absolutely subjective evaluation. I am an owner and I know how difficult it is to share your boat with others but from here to be jealous so much that it almost puts anxiety in your guests at every step is there. Sailing? A bit of just jib on the way back, sailing with the engine and with the pilot car for about 10/15 minutes on a boat that in any case to move would have had to open jib, staysail and mainsail and have at least 15/20 knots of real wind to move given its weight of 13 tons on 13 meters of boat, bowsprit included. The weather conditions, except during the first transfer to Ponza, have always been favorable for a very quiet sailing because 5 of us were experienced sailors, we would not even have caused damage. Disappointment for those who expected to sail. The boat is uncomfortable for eight people + skipper, there are a few ants everywhere, the kitchen set-up (non-tilting hob) and only one small refrigerator absolutely unsuitable for the number of people, the cabins and the small, unventilated berths are basically uncomfortable except perhaps one that I did not get to see that had already been assigned by the skipper to two friends even before we had all arrived (absolutely incorrect and out of the picture). regulation), Antonio decided everything, from the accommodation in the cabin, to the sleep/wake rhythms, to the daily menu in a nicely dictatorial manner. I am sure that he does his best in sympathy and hospitality but the level is a bit low, (my children, who do not know how to cook, cook better than Antonio). For the rest, the pontine are fantastic, the weather favorable and the travel companions almost all fabulous, We had so much fun and enjoyed the beauty that surrounded us, we were all in the same boat, so! You probably won't publish this review, I understand it and I don't care much but it's right that you know in the end in 6 out of 8 participants we said never again this man and this boat. In short: Beautiful holiday, the islands are a wonder and the company really fabulous, fortunately almost all seafarers! The weather was perfect and we were able to enjoy so much beauty, too bad we didn't sail because the boat itself, in addition to being small and uncomfortable for 8 + 1 adults, is absolutely not suitable for the times of a holiday and then, you know, skippers often reluctantly open the sails. I think Antonio gave the best of himself: he cooked, but he is not a chef, he put up with our presence by filming us nicely every 3/5 minutes for everything, and heroically with a knee out of order he took us around fantastic caves and coves.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/2/2026

Valentina B.

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IT

Alessandro is super nice and helpful. Plan the itinerary and organize the time and excursions by dinghy with great care to give the opportunity to explore the most beautiful places, all beautiful experiences. Carlo's care and cooking are pampering that you don't expect to find on a boat, a real gift! We cannot fail to mention Eros, a four-legged ☺️ skipper of infinite sweetness. Sailing in tandem with Andrea and his boat adds safety and liveliness to the cruise.

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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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