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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.

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South Carribean - Dream cruise with skipper/cook

Caribbean: Trinidad and Tobago

14 days - 14 nights

One departure available

October

€2,300

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

6 departures available

August - October

Starting from

€1,260

Per person - min 2 pax

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5.0

Paradise on a sailing boat with All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

One departure available

July

€1,750

Per person

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4.3

Premium

New Year's Eve catamaran in the golden triangle of the Caribbean - Full board with hostess

Caribbean: Saint Martin

6 days - 7 nights

2 departures available

January

Starting from

€2,490

Per person - min 2 pax

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Full board South-East Sardinia Cruise with hostess

Italy: Southern Sardinia

6 days - 6 nights

One departure available

July

€1,290

Per person

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4.3

Premium

Dalmatian Dream - week on catamaran ALL INCLUSIVE with hostess/cook

Croatia: Split Archipelago

7 days - 7 nights

6 departures available

July - September

Starting from

€1,885

Per person

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4.3

Premium

ABACO Dream Premium - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

7 days - 7 nights

37 departures available

January - December

Starting from

€1,885

€1,697

Per person - min 2 pax

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4.3

Premium

PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

54 departures available

January - December

Starting from

€1,155

€1,040

Per person

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4.3

Premium

From RAIATEA to TAHITI Dream - by catamaran ALL INCLUSIVE with hostess/cook

Pacific Ocean: French Polynesia

10 days - 10 nights

30 departures available

January - December

Starting from

€2,295

Per person

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5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Africa: Egypt & Red Sea

4 days - 4 nights

One departure available

October

€1,145

Per person

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5.0

San Blas Islands - All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

3 departures available

July - August

€1,167

Per person

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5.0

San Blas Islands: Private Boat for 2 Persons - All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

12 departures available

January - December

Starting from

€1,625

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 - All Inclusive Sailing Holidays & skippered cruises

751 reviews

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Ibiza All Inclusive on an 18m ketch with skipper and skipper

07/8/2025

Donatella R.

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Italy

Five stars are not enough to honor the amazing holiday spent on [hidden]. Filippo, in addition to being an attentive sailor and an incredible cook, is a truly fantastic person, one of those who you hope life will bring you together. I literally fell in love with his assistant (and niece), Camilla: sunny, funny and beautiful. Last but not least... NAO, I knew it would brighten the week but I didn't imagine so much! Getting off the boat I thought: I'll get back on it
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Ibiza All Inclusive on an 18m ketch with skipper and skipper

07/7/2025

Margarita G.

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Germany

Very nice and very enriching experience: I recommend it! A boat with history and personality. Not the most modern, but robust, very well equipped, and taken care of with great care to keep it safe and as comfortable as possible, trying to avoid wasting energy or other resources. Skipper (Filippo, owner of the boat) very friendly, simple, flexible, calm, attentive and friendly. Instills confidence and security. It makes what needs to be made clear at the beginning, which avoids possible conflicts later. Diligent in resolving issues that may create problems. Obviously he enjoys cooking, and that he has a lot of talent for it. Many have said it before me, but it is worthy of all particular mention to highlight it. An attractive itinerary due to the beauty of the beaches, coves and islets that can be visited or seen from the sailboat. The different blues and greens of the sea water (and its transparency, especially on the beaches) are wonderful. A type of holiday for those who do not feel uncomfortable living closely with other people in a small space for a few days. Possibility of engaging in pleasant and fun conversations with others, and of carrying out activities (water, musical, playful) together or individually. Great opportunity to disconnect from the world, from the routine, and relax. Requirements: minimum physical condition and agility (some good balance, going up and down the ladder of the sailboat to the water or to the zodiac), swimming, tolerating the rocking of the boat with the waves... Good attitude and civic behavior (kindness, respect and consideration for the other. Good manners, come on) Ability to adapt and tolerance to unexpected changes (weather conditions, route, sailing mode, mood/mood in the group, schedule...) Destination and Season: in Ibiza and Formentera the week of 28.06-05.07.25 was quite hot and the sea water was warm. Quite a few boats and people were also beginning to arrive on the beaches. For those who prefer not to be so hot, the water is cool for swimming, or prefer more tranquility, they would enjoy more outside the high season, in May-early June or at the end of September.
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Ibiza All Inclusive on an 18m ketch with skipper and skipper

07/7/2025

Mercedes V.

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Spain

The missing star I remove because I don't have a good time on the boat and I got a little bored but otherwise the skipper a 10 and the destination too. And the boat with its unforgettable dog
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Traveling and dreaming in the Gulf of Poets - All Inclusive

07/7/2025

Michele T.

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Italy

Fantastic weekend, full of relaxation, sea, great company and fun. Francesca and Giorgio were welcoming, professional and pampered us by preparing us super delicacies and aperitifs. Definitely to be redone!!

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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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