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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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4.3

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

49 departures available

January - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

7 departures available

June - August

Starting from

€69

Per person

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5.0

Super!

From the sun to the moon - Afternoon All inclusive on Lake Garda

Italy: Lake Garda

1 day - 0 nights

5 departures available

June - August

Starting from

€135

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

52 departures available

April - August

Starting from

€59

Per person

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5.0

Super!

Spring on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€99

Per person

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5.0

Super!

A wonderful day.... sul Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

45 departures available

April - August

Starting from

€99

Per person

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4.3

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

32 departures available

February - December

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.3

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

39 departures available

January - December

Starting from

€1,125

€1,013

Per person - min 2 pax

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Caribbean: Guadeloupe

7 days - 7 nights

16 departures available

January - August

Starting from

€1,272

Per person - min 2 pax

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4.3

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

21 departures available

January - December

Starting from

€2,330

€2,097

Per person - min 2 pax

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4.8

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

16 departures available

May - September

€790

€711

Per person

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4.3

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CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

25 departures available

May - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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

798 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/19/2026

Elena B.

-

Italy

Amazing experience! Skipper (Medhi) and Cook (Kris) super capable smart and funny ♥️
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/17/2026

Paola C.

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Italy

Very nice experience overall the only thing for the destination maybe it is better to do more days as the last three days we did too much sailing in the afternoon, it would have been better to travel at night / early morning or possibly do more days in the Tobago cas area, Skipper very nice and quiet, the steward perhaps a little too young did not have a great desire to clean and lacked the eye of a person with more experience. Overall I would do it again
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Wellness Adventure Retreat

01/14/2026

Donna S.

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Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/11/2026

Elena Maria F.

-

Italy

The experience was wonderful. There were 2 inconveniences, the first was the wait in the port of departure of two guests who instead of arriving at 18.00 arrived at midnight and this led to a change of program on the first day, in fact we did not visit Bequia with Port Elizabeth at all. The second note is on the cook, who said she was at her first experience in that role and in the kitchen, in fact the management of the galley was bad. The dishes were too elaborate and used too many ingredients to the detriment of the quantities. After the middle of the week he realized that he could cook simpler and more abundant things. For the rest it was a wonderful experience.

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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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