All Inclusive Sailing Holidays & skippered cruises

All Inclusive Sailing Holidays & skippered cruises

Experience an all-inclusive sailing holiday, pay the initial fee and forget about galley costs and skipper's services. Services offered by the skipper. The ideal way to be carefree once on board and keep your daily expenses under control.

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

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25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

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Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - All Inclusive Sailing Holidays & skippered cruises

363 reviews
20 / 10
Arturo M.

Arturo M.

review about Tartare, prawns and bubbles in Santa Margherita Ligure - all inclusive! March 2022

10 / 10
What can I say, beautiful We is beautiful company. Giorgio, in addition to being a very good skipper, is a fan of good food and bubbles. We drank and ate very well, really!! The boat is brand new and very comfortable. I recommend this experience to everyone!!
Barbara T.

Barbara T.

review about Unusual New Year between Elba and Corsica December 2021

10 / 10
I don't know if I won the tortellino in broth on December 31st, the grill in navigation or the homemade limoncello :') Fabrizio is of a goodness of soul and a rare cure. It was all a regenerating laugh! Beautiful. Very beautiful.
Delfine F.

Delfine F.

review about Red Sea: relax sailing and dolphins on SATAYAH reef - All Inclusive August 2021

10 / 10
A dream week in the Red Sea with Omar, a smiling young man, listening, who adapts to our requests. He is surrounded by a very efficient and welcoming crew. I highly recommend this trip. Thank you for a wonderful trip. One dream's week in the red sea with Omar, a smiling and attentive young man who adapts to our requests. He is surrounded by a very efficient crew. I highly recommend Omar and his trip. Thank you very much
Mary F.

Mary F.

review about Capri, Amalfi, Positano Tour 3 days - All inclusive July 2021

10 / 10
3 days on a sailing boat on the Amalfi Coast with skipper Alessandro, helpful, very discreet and excellent cook. Unforgettable sunrise at the Faraglioni of Capri and the night under the stars in the bay of Positano. Nice experience, thanks Ale!
Gianluca B.

Gianluca B.

review about IBIIZA - FORMENTERA - 6 nights in Half Board All Inclusive with skipper and hostess August 2021

10 / 10
Paradise on holiday! Recent and comfortable boat! We felt pampered both by the Skipper Santo (always ready to correct the route to the quieter coves to avoid rough seas and gatherings) and by the very kind and sunny companion Luisa (excellent cook and very active sailor). We would recommend anyone a holiday with them! We ourselves can't wait to be able to leave together to visit new islands!
Gino G.

Gino G.

review about Redentore 2019 Fireworks and seafood dinner. July 2021

10 / 10
Ernesto is a professional skipper, with great experience who has the ability to manage the boat safely and efficiently. We had a beautiful evening.
Silvia U.

Silvia U.

review about Weekend in Portofino and Santa Margherita July 2021

10 / 10
Paolo was very helpful and nice, the boat is clean and comfortable and made us spend a nice weekend. I recommend it and would do it again.
Josephine L.

Josephine L.

review about Gulf of Tigullio on a Sailboat - All inclusive! June 2021

10 / 10
It was a fantastic experience that I recommend everyone to do. Luca and his mother have transmitted to us in a few hours all their passion for the sea and sailing. They are very kind, helpful, prepared and attentive to detail. It was great to be part of this world for a day :)
Maria Grazia S.

Maria Grazia S.

review about Sailing with Siddhartha June 2021

10 / 10
Luigi and Federica were two fantastic skippers. They immediately made us feel comfortable and delighted us with interesting travel stories. The boat ride along the 5terre was not exactly as I would have imagined but this was dictated by factors not attributable to them. I highly recommend a travel experience with Luigi and Federica and hope to turn them back soon! Thank you!
ASTRID M.

ASTRID M.

review about Pelagie Islands of the high seas September 2020

10 / 10
Fantastic week! We sailed not only around Lampedusa, but also Linosa and Lampione. Snorkeling around this rocky islet perhaps one of the most beautiful of qs holiday. We stopped x baths and dives in coves with crystal clear and turquoise waters. I really liked the all inclusive formula, because the skippers in addition to being good cooks made us taste a lot of local specialties. In Linosa we had dinner with Cesare and Margaret who with the proceeds finance projects that they personally follow in Uganda. The skippers Emanuela and Lorenzo very good and always available. For those who like a sailing holiday, I can only recommend it.
Paolo B.

Paolo B.

review about Croatia - Gastro Route on a catamaran with hostess / Half-board included August 2020

10 / 10
Skipper attentive, professional, experienced, able to live the experience in the right way, good advice on what was better to visit. Very good and attentive also the hostess, nice, good cook who was able to share with us this beautiful experience. Bad assistance of Tajana, which contacted from the day before boarding, has never responded to our requests for information, neither via sailsquare, nor via whatsapp nor via phone. We were totally abandoned, looking for photos in hand for two hours inside the port of Trogir, asking right and missing if someone knew her, as we had not been given any info on what the charter company was, much less the name of the boat until someone managed to tell us something. The other guests were black for the fact that we did not arrive,they wanted to leave,but without us they could not. I was promised and assigned the stern cabin straight side and I had bow left side! Very bad experience.
Alexandra N.

Alexandra N.

review about 3 days – 2 nights lost in Paradise – ALL INCLUSIVE August 2020

10 / 10
The navigation through the Ionian Islands was incredible and exciting. It cannot be described in words. ?????????? We visit the most beautiful places of Lefkada, Meganisi Island, Kastos and beaches of the peninsula. Paradisiacal corners just for us. Mike is a crack and above all a great captain. You can tell that he is passionate about it, he taught us navigation concepts, such as hoisting sails according to the wind, how to sail the waves, how to drop anchor or anchor.???? Always attentive so that we did not lack anything, and with a smile always. Thanks Mike!!! Without a doubt, you are the best!!???? Thanks also to Viviana and Luca!!, without them it would not have been the same, we had a great time!!???????? A great experience that I would repeat one and a thousand times.????????
Cristiana S.

Cristiana S.

review about Pontine islands on a sailing boat, all inclusive! July 2020

10 / 10
Just returned from this wonderful holiday. Everything was perfect, we relied on and trusted Umberto and his advice (never underestimate the experience and common sense of the "captain"). We were welcomed, pampered and delighted by the kitchen and the courtesy of the staff. The Pontine Islands are a magical place, an unexpected surprise, a place that at least once you have to visit. And I recommend doing it with Umberto!
Alessandro S.

Alessandro S.

review about Let's learn how to sail a boat August 2020

10 / 10
A fantastic day, Giorgio is an exceptional skipper always available for every need.
Lucio M.

Lucio M.

review about Living the sea August 2020

10 / 10
We had a lovely day, Emilio and his wife were really hospitable and helpful. It was like hanging out with friends. When possible we will repeat the experience
Matteo N.

Matteo N.

review about Sailing, relaxation and pampering between the Pontine islands All inclusive July 2020

10 / 10
I traveled with Stefano to the Pontine Islands on the first weekend of July. Stefano was really helpful and was able to put us at ease right away, he also allowed us to bring the boat when we wanted and to manage the itinerary to be able to reach friends in Ponza. The aperitifs and meals she prepared for us with Ornella (a friend of Francesca's who could not come) were always great and ready after every dip in the water. Traveling with Stefano was really nice and fun and, despite the weather did not always assist us, we managed to feel very good. An experience to be repeated also to get to know Francesca who, despite not being able to come, still followed us throughout the journey remotely, giving us advice and verifying that everything was fine.
Aleksandra Z.

Aleksandra Z.

review about ALL INCLUSIVE holiday at the Carribeans! (meals and beverage included & flexibles dates!)) February 2020

10 / 10
We had some amazing time with Giulia and Rodrigo in San Blas islands. They are most friendly and professional hosts that one can imagine. Giulias cooking is just great, while Rodrigo provides some fresh fish caught by himself. The boat was very comfortable and tidy. We can definitely recommend holidays with them!
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6 reasons for an all-inclusive sailing holiday:

  • If you're the kind of person who doesn't like organising trips, looking for restaurants and planning your next plans, this type of holiday is for you. Booking an all-inclusive sailing holiday will make you feel more relaxed and you won't have to worry about anything.
  • Whether family, with friends, couple or alone, you will find the skippered sailing holiday that best suits your tastes and needs.
  • You'll discover a multitude of secret corners that are difficult to reach by land, so you can explore incredible places without the presence of tourists.
  • You will have a unique experience on board a sailing boat or catamaran, discovering dream places from a different perspective
  • You will have no time for boredom, you can enjoy activities all day long, from excursions by sea and land, sailing courses to learn how to sail, leisure or sports activities such as surfing, diving, etc. and, of course, time to relax by sunbathing on the deck of your boat.
  • You'll be travelling in the company of a local skipper, who knows every corner of the region, to help you discover the secret gems of each place you visit - a sailing holiday that won't leave you indifferent!

The best destinations for sailing trips in the Mediterranean:

All-inclusive sailing holidays in the Balearic Islands

The leading sailing destination in Spain. On each of its islands you can breathe a different air, because they all have something different to offer. However, they are all beautiful islands with turquoise, almost paradise-like waters. Enjoy the Mediterranean landscape and its dream islands close to home.

All-inclusive trip to the Greek islands

Trace the history of this magnificent country on board a sailing boat or catamaran, discovering its past through its fascinating and almost endless islands, as there are some 3,054 islands of which only 80 are inhabited, so you won't be bored for a minute! Try their delicious traditional food: tzatziki, tarama, moussaka and their famous Gyros.

All-inclusive travel to Sardinia

Have you ever seen such crystal-clear waters as those of Sardinia? Its coasts have absolutely nothing to envy to those of the Caribbean. You will discover its most heavenly beaches so that you can take a swim and enjoy the sun at the same time. Don't forget to visit some beaches such as Playa Rosa, Playa del Cavaliere or the beaches of Cala Coticcio, famous for their enormous rocks of different shapes.

All-inclusive trip to the Maldives

One of the most desirable tropical countries in the world, located in the Indian Ocean. This idyllic destination will leave you speechless with its breathtaking wild landscapes and totally unspoilt turquoise waters. You won't want to wait a second to dive in. You can also enjoy extraordinary moments under the sea during a snorkelling or scuba diving session to explore the underwater flora and fauna.

Why go on an all-inclusive sailing holiday?

Goodbye worries

Accommodation, transport, skipper, hostess, meals... all this and more will be included in your trip, so you won't have to worry about a thing. You'll have a trip with all the comforts and your holiday skipper will organise everything exclusively for you, so you can relax and let go.

Ideal for families

Travelling with children can often be stressful when it comes to organising holidays because you have to plan activities, food etc. and look after the children at the same time. However, if you book an all-inclusive holiday, you can be sure that peace and quiet and relaxation are also included.

Price without surprises

We generally think that all-inclusive plans are expensive, but nothing could be further from the truth, we spend much more when we improvise and often have surprises when we check our bank account when we get home. On an all-inclusive holiday you'll have everything under control, you won't spend more than you set out to spend at the start of the experience.

All inclusive: best destinations

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