header cover

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.

615

experiences

cover image
avatar image

4.6

April 25 between the Tuscan islands and North Corsica.

Duration:

4 days - 4 nights

Italy:

Tuscany

avatar placeholder

Riccardo

has booked

€350

Per person

cover image
avatar image
Gulf of Poets, Portovenere, Palmaria and the island of Tino a Vela

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€120

Per person

cover image
avatar image

4.5

Sailing day Maddalena Archipelago

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€125

Per person

cover image
avatar image

4.9

Sailing & adventure among the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

avatar placeholder
avatar placeholder

+2 travellers

have booked

Starting from

€450

Per person

cover image
avatar image

4.6

Long weekend of April 25 Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€345

Per person

cover image
avatar image

4.8

Long weekend on board a brand new catamaran with hostess/chef in the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€590

Per person

cover image
avatar image

4.3

Wellness Cruise: Sailing and Yoga in Nature

Duration:

4 days - 5 nights

Italy:

Southern Sardinia

avatar placeholder
avatar placeholder
avatar placeholder

+3 travellers

have booked

€600

Per person

cover image
avatar image
Long weekend 25 April

Duration:

4 days - 4 nights

Italy:

Pontine Islands

avatar placeholder
avatar placeholder
avatar placeholder

+7 travellers

have booked

€550

Per person

cover image
avatar image

4.4

April 25 long weekend on the Western Ligurian Riviera and Côte d'Azur

Duration:

4 days - 4 nights

France:

French Riviera and Porquerolles

avatar placeholder
avatar placeholder
avatar placeholder

+4 travellers

have booked

€475

Per person

cover image
avatar image

5.0

April 25th long weekend between Elba and Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€450

Per person

cover image
avatar image

4.8

LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

avatar image
avatar placeholder
avatar placeholder

+4 travellers

have booked

€349

Per person

cover image
avatar image

4.2

Ponte del 25 Aprile in navigazione con rotta per la Capraia.

Duration:

4 days - 4 nights

Italy:

Tuscany

avatar image
avatar placeholder
avatar placeholder

+4 travellers

have booked

€435

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

132 reviews

avatar image

Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
avatar image

Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
avatar image

Sailing Cyclades

04/15/2024

yannis b.

-

France

Séjour incroyable avec Yann ! Très attentif, drôle et chill dans toutes les situations, dans un bateau très confortable !
avatar image

SEYCHELLES discovery experience - 7 nights on a Catamaran

04/14/2024

Giorgia C.

-

Italy

semplicemente fantastico. Francesco è uno skipper con tutte le qualità del mondo e anche di più, affidabile, capace di dare sicurezza, paziente e comprensivo, e anche molto compagnone, che in una vacanza del genere non guasta mai! è stata una settimana indimenticabile sia per i luoghi visitati che per la compagnia. Straconsigliato!!!

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964