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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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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

5 departures available

October

€150

Per person

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4.4

Premium

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

4 departures available

October - November

€723

Per person

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4.4

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

40 departures available

January - December

Starting from

€1,430

€1,144

Per person - min 2 pax

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4.4

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

76 departures available

January - December

Starting from

€1,535

€1,228

Per person - min 2 pax

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4.4

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

27 departures available

January - December

Starting from

€2,330

€1,864

Per person - min 2 pax

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4.4

Premium

BORA BORA PARADISE - Mini catamaran cruise with hostess and full board

Pacific Ocean: French Polynesia

4 days - 4 nights

One departure available

October

Starting from

€2,305

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

Premium

BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

47 departures available

January - December

Starting from

€1,565

€1,252

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

4 departures available

October

€315

Per person

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4.4

Premium

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

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4.4

Premium

ANDAMAN Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

10 days - 10 nights

17 departures available

January - December

Starting from

€2,700

€2,160

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

846 reviews

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.

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

09/10/2026

Alice M.

-

IT

Overall nice holiday but with some critical aspects. Initially the catamaran was not of the model confirmed for our trip, in fact our cabin had a shower without the glass cover so it flooded everything every day and there were no shutters for light on the windows. The sore point was the skipper, who did not meet the needs at all to make the group feel good. The first day before departure he told us the meal times (breakfast at 8 am, lunch at 1 pm and dinner at 7 pm), which immediately created general discontent. On vacation and especially with temperatures in August, thinking about respecting these holiday schedules becomes a nightmare. Although I pointed out, the answers on everything from the skipper were negative, so much so that I went so far as to shout in my husband's face for a trifle. Nothing was explained to us when we arrived on the islands and often to find a place in the ports we were forced to leave very early. Itinerary not with the sea that I would have expected. As for the hostess, on the other hand, she was very good and very attentive to our needs.

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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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