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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.

495

experiences

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4.6

Flottiglia Different: Party e nuovi amici alle isole Eolie

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+131 travellers

have booked

Starting from

€999

€1,175

Per person

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4.9

Super!

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+85 travellers

have booked

€998

€1,050

Per person

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4.7

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands

Duration:

7 days - 7 nights

Italy:

Naples & Amalfi Coast

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+44 travellers

have booked

Starting from

€1,253

Per person

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4.9

Super!

A week of sea, nature and fun in the Pontine Islands!

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+67 travellers

have booked

Starting from

€621

€690

Per person

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4.9

Super!

Adventure Flotilla in the Gulf of Athens and Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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+30 travellers

have booked

Starting from

€949

Per person

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4.8

Super!

Wandering on a sailboat, sailing in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

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+40 travellers

have booked

Starting from

€590

€850

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+52 travellers

have booked

Starting from

€799

€900

Per person

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4.7

The Wild Flotilla: dive into the wilderness of Tuscany

Duration:

7 days - 7 nights

Italy:

Tuscany

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+29 travellers

have booked

€990

€1,190

Per person

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4.7

Whale watching cruise with WWF in Liguria between Portofino and Cinque Terre

Duration:

6 days - 6 nights

Italy:

Liguria

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+49 travellers

have booked

Starting from

€749

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+53 travellers

have booked

Starting from

€450

€500

Per person

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4.9

Super!

Sailing & Adventure in the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+59 travellers

have booked

Starting from

€680

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+80 travellers

have booked

Starting from

€625

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

460 reviews

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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms plus crew

07/19/2024

Licia D.

-

United Kingdom

This was the first time sailing for me. Wasn’t sure what to expect at all. Booked the trip to see stunning Sardinia and Corsica from the sea as part of a birthday gift for my partner. We had noticed that hard cases weren’t recommended on board but we had no choice as on a three week Sardinia holiday. Luca (skipper) said it wasn’t an issue as we could unpack and then leave our cases in one of the other guests cars which was very kind. We arrived to meet a lovely group of people, mostly Italian, who made us feel very welcome. Unfortunately neither of us speak Italian which made it tricky knowing what was happening and when at times. The group did try to include us which was nice. We had a cabin towards the front of the boat which was small but perfectly formed. Sleeping area with en-suite bathroom. I did have great sleeps but my partner struggled a bit having big shoulders. It could get quite warm but we had rechargeable fans which made it nice and comfortable. The cabin was also equipped with modern usb points, perfect for keeping phones etc all charged up. We had 4g most of the time which was good. The kitchen area was a little bit crammed and with ten people on board could feel a bit chaotic at times. Luckily our group were great cooks and took the lead at meal times. We wish we could have made a meal for everybody however it just didn’t work out. Luca also cooked us a fantastic Carbonara when anchored at the stunning pink beach of Isola Budelli. A protected area. This was one of my favourite stops. Luca explained why the sand can look pink which was very interesting. A lovely story obviously close to his heart. When on the water with the sails up it was spectacular, feel very privileged to have experienced this. Luca and Calogero made us feel very safe and secure. The boat also had a paddle board available to use which was fab. We had our own snorkelling equipment. It was amazing to see these secluded islands. The clarity of the sea, unspoilt beauty and waking up each day to this was wonderful. Bonifacio is a beautiful town to see, it was great to have a night here too. The week overall was fantastic, great group of people to be around. I think if we’d been able to chat away in Italian it would have made it a bit easier but all in all very good. I would definitely recommend The Najaca for this type of trip and unforgettable memories.
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Midweek on Elba - from Monday to Thursday

07/19/2024

Celeste P.

È difficile trovare le parole adeguate per descrivere questa magnifica esperienza. Tre amici in cerca di relax, divertimento ed avventura hanno incontrato uno skipper preparato, di compagnia e coinvolgente. Paolo è una persona estremamente disponibile ed in grado di accogliere le richieste permettendo di vivere appieno lo spirito e la libertà che contraddistingue una vacanza in barca a vela. Sono stati giorni ricchi di racconti di vita, di grandi risate, di brindisi, di tentativi di pesca (mancati) e di SUP in un mare limpido e trasparente. Cenare in rada, al di sotto della fortezza illuminata, non ha prezzo. Rimarrà sicuramente nel cuore di ciascuno di noi. Grazie Paolo dal tuo equipaggio preferito!
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

07/19/2024

Elisabetta B.

-

Italy

Buongiorno, la vacanza è stata molto piacevole! Lo skipper Maurizio è stato paziente e competente, agevolando le nostre richieste. Un unico appunto diretto all'organizzazione: credo che la differenza delle cabine di prua e di poppa dovrebbe meritare anche una differenza di prezzo, gli ospiti pagano la stessa quota per una sistemazione alquanto diversa.
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Three days in Procida and Ischia: the pearls of the Gulf on a sailing boat

07/18/2024

gabriele b.

-

Italy

Esperienza molto positiva, sia perché la costa ischitana è unica, sia perchè siamo stati fortunati nel trovare Enzo, lo skipper, che è una persona esperta, sa guidarti e metterti a tuo agio (affidatevi ai suoi consigli).

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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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