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.
25
experiences
25
experiences
4.9
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+67 travellers
have booked
€850
€1,308
Per person
4.8
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+3 travellers
have booked
€799
€999
Per person
4.8
Super!
Duration:
7 days - 7 nights
Greece:
Ionian Islands
+36 travellers
have booked
€1,000
€1,200
Per person
4.6
Duration:
7 days - 7 nights
Greece:
Peloponnese
+4 travellers
have booked
€675
€750
Per person
4.5
Duration:
7 days - 7 nights
Atlantic islands:
Canary Islands
Give this experience a try!
Starting from
€1,426
Per person
4.5
Duration:
8 days - 8 nights
Spain:
Andalusia
Give this experience a try!
€1,002
Per person
4.5
Duration:
7 days - 7 nights
Atlantic islands:
Canary Islands
Give this experience a try!
€949
Per person
4.5
Duration:
6 days - 6 nights
Spain:
The Balearic Islands
Give this experience a try!
€949
Per person
4.8
Duration:
6 days - 7 nights
Greece:
Ionian Islands
+19 travellers
have booked
€1,250
Per person
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+9 travellers
have booked
€1,600
Per person
4.8
Duration:
3 days - 2 nights
Italy:
Naples & Amalfi Coast
+2 travellers
have booked
€1,300
Per person
4.1
Duration:
7 days - 7 nights
Italy:
Aegadian islands
Give this experience a try!
€1,100
Per person
Why book a holiday with Sailsquare?
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
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
143 reviews
Egadi Islands - Sea, sun, relax on a brand new catamaran 2024
09/7/2024
Sergio andre r.
-
Italy
La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine
09/7/2024
roberto p.
-
Italy
Catamaran immersed in the nature of Sardinia in search of well-being, from Carloforte to Cagliari
09/6/2024
Barbara T.
-
Italy
Flottiglia Different: Party e nuovi amici alle isole Eolie
09/3/2024
vincenza c.
Customer Support
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!
Call us at
+44 2035144220Read our
Contact & SupportCan't find the perfect holiday for you?
Tell us what you are looking for and let our team find the right solution for you!
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.
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.
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.
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.
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.
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!
Sailsquare
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964