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.

cover image
avatar image

5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

July

€75

Per person

cover image
avatar image

4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

27 departures available

July - October

Starting from

€1,325

Per person

cover image
avatar image

4.8

Super!

Capri and Amalfi Coast by CATAMARAN BALI 4.3 ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

July - October

Starting from

€1,800

Per person

cover image
avatar image

5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

3 departures available

July - August

Starting from

€135

Per person

cover image
avatar image

5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

21 departures available

July - September

Starting from

€99

Per person

cover image
avatar image

4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

2 departures available

August

€89

Per person

cover image
avatar image

4.3

Premium

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

Indian Ocean: Seychelles

7 days - 7 nights

72 departures available

January - December

Starting from

€1,760

€1,584

Per person

cover image
avatar image

4.3

Premium

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

Caribbean: Grenadines & Martinique

9 days - 10 nights

53 departures available

January - December

Starting from

€1,680

€1,512

Per person - min 2 pax

cover image
avatar image

4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

14 departures available

July - August

€150

Per person

cover image
avatar image

4.3

Premium

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

Caribbean: Saint Martin

6 days - 7 nights

59 departures available

January - December

Starting from

€1,125

€1,013

Per person

cover image
avatar image

4.3

Premium

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

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

55 departures available

January - December

Starting from

€1,250

€1,125

Per person

cover image
avatar image
Discover the Egadi Islands on a sailboat with aperitif and hostess on board!

Italy: Aegadian islands

1 day - 0 nights

83 departures available

July - September

Starting from

€130

€117

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

742 reviews

avatar placeholder

Weekend on a beautiful traditional schooner in the Tuscan archipelago

07/2/2025

Daniela C.

-

Italy

Il capitano e l' equipaggio hanno reso questo weekend indimenticabile con la loro professionalità, gentilezza, allegria e umanità. Rimarrà un ricordo indelebile nella memoria mia e di mio figlio. È andata ogni oltre aspettativa. Il Capitano ha stabilito con noi un rapporto empatico e ci ha guidato in un' esperienza unica. L' equipaggio ci ha coccolati e coinvolti. Assolutamente consigliato.
avatar placeholder

A day on a sailing boat to Gallinara Island or the Dianese Gulf

07/1/2025

Roberta M.

-

Italy

Esperienza fantastica, io e i miei compagni di traversata siamo stati bene, Skipper Matteo preparato e davvero ospitale, ci ha dato nozioni sulla barca a vela e fatto un aperitivo top.
avatar placeholder

Sailing dreams in the Gulf of Poets and Cinque Terre

07/1/2025

Silvia S.

Abbiamo passato un weekend stupendo, Giorgio è un ottimo skipper e cuoco, e lui e sua moglie sono due persone meravigliose. Assolutamente consigliato!
avatar placeholder

Sailing dreams in the Gulf of Poets and Cinque Terre

07/1/2025

Lorenzo M.

-

Italy

Esperienza bellissima, la barca è molto bella e Giorgio e sua moglie sono delle persone fantastiche. Non vediamo l'ora di ripetere.

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

MastercardVisaGoogle PayApple Pay

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