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.

56

experiences

cover image
avatar image
Sail & Yoga Retreat: relaxing catamaran cruise with full board

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Starting from

€2,650

Per person

cover image
avatar image

4.4

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

Starting from

€2,490

Per person - min 2 pax

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!

€1,290

Per person

cover image
avatar image

4.3

Premium

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

Duration:

7 days - 7 nights

Croatia:

Split Archipelago

avatar image
avatar image
avatar image

9 travellers

Starting from

€1,250

Per person

cover image
avatar image

5.0

Super!

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

avatar image
avatar image
avatar image

53 travellers

Starting from

€125

Per person

cover image
avatar image

4.9

Traveling and dreaming in the Gulf of Poets - All Inclusive

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

Starting from

€200

Per person

cover image
avatar image

5.0

Super!

The awakening of the lake

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar placeholder
avatar placeholder
avatar placeholder

4 travellers

€69

Per person

cover image
avatar image

4.3

Premium

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

Duration:

10 days - 10 nights

Pacific Ocean:

French Polynesia

avatar placeholder
avatar placeholder

2 travellers

Starting from

€3,205

Per person

cover image
avatar image

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Duration:

4 days - 4 nights

Africa:

Egypt & Red Sea

Give this experience a try!

€1,145

Per person

cover image
avatar image

4.9

All-inclusive weekend in Porquerolles

Duration:

2 days - 1 night

France:

French Riviera and Porquerolles

avatar image
avatar placeholder

2 travellers

€260

Per person

cover image
avatar image

5.0

Super!

Sailing, early sun and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar image
avatar image

44 travellers

Starting from

€59

Per person

cover image
avatar image

5.0

San Blas Islands - All Inclusive

Duration:

7 days - 7 nights

Caribbean:

San Blas Islands - Panama

Give this experience a try!

€1,167

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

729 reviews

avatar placeholder

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

05/9/2025

Sara Angela R.

Ho partecipato a una crociera in catamarano con skipper e cuoco, ma purtroppo l’esperienza non è stata all’altezza delle aspettative. La destinazione e l’itinerario proposto sono davvero splendidi, così come la cucina a bordo, che è stata un punto di forza. Anche il modello dell’imbarcazione è di grande fascino, ma la barca non era in condizioni ottimali: l’aria condizionata funzionava a intermittenza, c’erano infiltrazioni d’acqua in cabina, e nel complesso non offriva il livello di comfort e lusso promesso. L’equipaggio, in particolare lo skipper, si è mostrato freddo e poco comunicativo, al punto che spiegare le tappe o semplicemente rivolgergli una domanda sembrava quasi un disturbo. Questo ha reso l’esperienza a bordo piuttosto piatta e poco coinvolgente. In sintesi, nonostante la bellezza dei luoghi visitati e la buona cucina, il servizio e le condizioni della barca non giustificano il prezzo pagato. Rapporto qualità/prezzo deludente.
avatar image

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

04/12/2025

Carla P.

-

Italy

ottimo skipper e ottimo servizio di bordo con eccellente cibo
avatar placeholder

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

03/18/2025

Patricia A. Mcmahon s.

Wonderful trip. I just wish we saw more of the islands we snorkel by.
avatar image

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

02/24/2025

Stefania T.

-

Italy

Altre esperienze con voi sono state effettuate con barche più nuove e confortevoli. Suggerisco di adeguare tutte le imbarcazioni così da giustificare il costo abbastanza elevato della crociera.

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

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964