header cover
sailsquare logo

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.

48

experiences

cover image
avatar image

4.4

Premium

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

Duration:

10 days - 10 nights

Pacific Ocean:

French Polynesia

Starting from

€2,004

€2,505

Per person

cover image
avatar image

4.4

Premium

ANDAMAN Dream Premium - 11 days in ALL INCLUSIVE Catamaran with hostess/cook

Duration:

10 days - 10 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

avatar placeholder
avatar placeholder

2 travellers

Starting from

€2,394

€2,660

Per person - min 2 pax

cover image
avatar image

4.4

Premium

Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Grenadines & Martinique

avatar image
avatar image
avatar image

26 travellers

Starting from

€1,188

€1,320

Per person

cover image
avatar image

4.4

Premium

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

Duration:

6 days - 7 nights

Caribbean:

BVI - British Virgin Islands

avatar image
avatar image
avatar placeholder

20 travellers

Starting from

€1,188

€1,320

Per person

cover image
avatar image

4.4

Premium

PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Indian Ocean:

Seychelles

avatar image
avatar image
avatar placeholder

33 travellers

Starting from

€1,571

€1,745

Per person

cover image
avatar image

4.4

Premium

GRENADINES 11 days on a ALL INCLUSIVE catamaran with hostess/cook

Duration:

9 days - 10 nights

Caribbean:

Grenadines & Martinique

avatar image
avatar placeholder
avatar placeholder

20 travellers

Starting from

€1,629

€1,810

Per person - min 2 pax

cover image
avatar image

4.4

Premium

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

Duration:

7 days - 7 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

avatar image
avatar image
avatar image

42 travellers

Starting from

€1,040

€1,155

Per person

cover image
avatar image

4.4

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Guadeloupe

avatar image

Fabian M.

Starting from

€1,071

€1,190

Per person

cover image
avatar image

4.4

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

avatar image
avatar placeholder

2 travellers

Starting from

€1,071

€1,190

Per person

cover image
avatar image
Full board South-East Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,226

€1,290

Per person

cover image
avatar image

5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

avatar image
avatar image
avatar image

26 travellers

€94

€99

Per person

cover image
avatar image
Full board South Sardinia Cruise with hostess

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,226

€1,290

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

726 reviews

avatar placeholder

ANDAMAN Dream Premium - 11 days in ALL INCLUSIVE Catamaran with hostess/cook

02/20/2025

Delphine G.

-

France

Nous sommes très déçus (et en colère) de notre croisière. Le tarif n’est pas du tout en adéquation avec la qualité et le service proposé. 😡😡😡😡 Nous avons réservés une croisière de 11 jours en Thaïlande avec Sailsquare. Lors de notre réservation, j’avais lu plusieurs commentaires sur un problème de « toilettes ». J’ai donc demandé a Giulia, la représentante de Sailsquare, des précisions sur ce sujet. De là, elle m’a dit que tout était résolu. Mais je vous confirme que non. NOUS AVONS PASSÉ 11 JOURS AVEC DES TOILETTES REMPLIES D’EXCREMENTS A CÔTÉ DE NOTRE LIT. Impossible de dormir avec la porte fermée. Nous avons dû passer l’ensemble de notre séjours avec les fenêtres et les portes ouvertes pour atténuer un « peu » l’odeur. Inadmissible !!! A notre retour, j’ai souhaité joindre Sailsquare par le biais de Giulia, pour discuter de notre problème mais IMPOSSIBLE. Cela fait plus 10 jours que j’essaye de les joindre mais sans succès. Ils ne répondent plus. Le service après vente est donc tout simplement inexistant. A 6000€ les 11 jours, on ne s’attendaient pas à ça. 😡😡😡😡😡😡
avatar placeholder

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

02/18/2025

Simon E.

Brilliant cruise on the catamaran to Bond island and The Beach and favourite location being the small PAE island when the tide revealed the beach. Excellent overnight anchorages between the amazing sunsets and sunrises. Really well organised and great crew and food. Simon
avatar image

New Year's Eve 2024 on the Amalfi Coast - All inclusive

01/3/2025

Ilaria C.

-

Italy

Straordinario skipper , grande capacità di unire persone interessanti esperienza che intendo rifare proprio con questa barca questo skipper e la qualità delle sue scelte
avatar image

New Year's Eve 2024 on the Amalfi Coast - All inclusive

01/2/2025

Gabriella M.

-

Italy

È stata una piacevole vacanza in ottima compagnia. Lo skipper Fabrizio è una persona competente, simpatica e molto disponibile, oltre ad essere un ottimo cuoco

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964