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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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4.4

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CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

26 departures available

May - October

Starting from

€1,320

€1,056

Per person - min 2 pax

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4.4

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DALMATIAN Paradise - Catamaran cruise with hostess FULL BOARD

Croatia: Split Archipelago

7 days - 7 nights

22 departures available

May - October

Starting from

€1,315

€1,184

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

2 departures available

October - November

€723

Per person

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4.4

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PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

39 departures available

January - December

Starting from

€1,390

Per person - min 2 pax

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4.4

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BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

74 departures available

January - December

Starting from

€1,535

Per person - min 2 pax

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4.4

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RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

26 departures available

January - December

Starting from

€2,330

Per person - min 2 pax

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5.0

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

8 departures available

October - December

Starting from

€1,925

€1,733

Per person

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4.4

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BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

46 departures available

January - December

Starting from

€1,415

€1,274

Per person - min 2 pax

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5.0

Grenadines Odyssey: Grenadines Islands Catamaran Cruise

Caribbean: Grenadines & Martinique

10 days - 11 nights

4 departures available

January - December

Starting from

€2,650

Per person - min 2 pax

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5.0

3 days sailing among the hidden gems of Palermo - All inclusive & flexible dates

Italy: Sicily

3 days - 2 nights

2 departures available

October

€315

Per person

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5.0

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

Italy: Lake Garda

1 day - 0 nights

2 departures available

October

€69

Per person

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4.4

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SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

23 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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

848 reviews

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IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

10/17/2026

Elena V.

We really needed this holiday! Filippo is a wonderful host: attentive skipper (also ready to involve those who show interest in sailing), excellent cook, great entertainer and even singer. The weather was not the best, which changed the itinerary and it was a great shame, but it is the risk of every holiday, even more so in those by boat. The latter is equipped with interesting "pluses" (BBQ, fishing rods, SUP). It is comfortable, but it is "lived" practically all year round as it is basically Filippo's home and this means that it is not a 5-star hotel on the water where everything is impeccable. A thread of sporting spirit and sharing is needed, as clearly written in the announcement. Finally, I cannot fail to mention Nao, a wonderful sailing companion always ready to be cuddled and try to save you when you go down into the water. And if I loved it because I don't have any particular liking for dogs, you can trust it. Ps: you will go home with a couple of extra kilos on you, but it's worth it
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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.

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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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