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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.

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 - All Inclusive Sailing Holidays & skippered cruises

847 reviews

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ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

10/11/2026

Lee P.

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GB

The Bali 52 was a fantastic boat, very comfortable clean and plenty of space, the itinerary was great and we visited beautiful places and it was a good mixture of staying in marinas and at bays so we could swim or explore the islands. But what made it really special was the crew, the captain Giannis and our hostess Eirini, they went above and beyond to make sure we all had a memorable and fabulous time

Sailing, swimming and aperitif at sunset ... What else?

10/3/2026

Victoire D.

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FR

Perfect afternoon with Emanuele! Wonderful host, generous food and drink and the boat is beautiful and welcoming Many thanks!!

All-Inclusive Sailing: Capri, Positano, Amalfi

09/28/2026

Nathalie P.

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FR

Very nice cruise with our skipper Alessandro who was very knowledgeable and very attentive. Highly recommend.

Palma de Mallorca All Inclusive on 18m Ketch

09/20/2026

Matteo E.

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IT

This was a really good sailing trip. It was well organized, relaxed, and enjoyable. A special mention goes to Filippo, our skipper. He is not only a highly capable and experienced sailor but also a genuinely kind and welcoming person. He was always happy to listen to everyone’s ideas, adapt the itinerary when possible, and make sure everyone felt comfortable and involved. One of the biggest surprises of the trip was his cooking! Every day he prepared delicious meals and snacks that went far beyond what we expected on a sailing holiday. He is truly an amazing chef, and every meal became another highlight of the experience. We visited beautiful coves and stunning spots around Mallorca, enjoyed great sailing conditions, and shared unforgettable moments together. The atmosphere on board was always friendly, relaxed, and fun. And of course, Noa was the real star of the trip! She won everyone’s heart, and we all had so much fun playing with her throughout the week.

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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.

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