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!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€59

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

5 departures available

October

€1,325

Per person

cover image
avatar image

4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

October

€1,800

Per person

cover image
avatar image

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€69

Per person

cover image
avatar image

5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

3 departures available

October

€99

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

41 departures available

January - December

Starting from

€1,680

€1,512

Per person - min 2 pax

cover image
avatar image

4.3

Premium

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

Caribbean: Grenadines & Martinique

6 days - 7 nights

64 departures available

January - December

Starting from

€1,250

€1,125

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

62 departures available

January - December

Starting from

€1,760

€1,584

Per person

cover image
avatar image

4.7

IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

Spain: The Balearic Islands

6 days - 7 nights

One departure available

October

€690

Per person

cover image
avatar image

5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

2 departures available

October - November

€99

Per person

cover image
avatar image

5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

€3,000

€2,100

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

51 departures available

January - December

Starting from

€1,125

€1,013

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

788 reviews

avatar image

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

09/30/2025

MARIA GRAZIA P.

-

Italy

A wonderful sailing experience! 🚤⛵️ We spent Sunday in the company of nice people, with impeccable organization. Emanuele proved to be an exemplary professional: availability, kindness and attention to detail made us feel immediately at ease. Great food, stunning views and a relaxing atmosphere that made the experience truly unforgettable. Everything perfect: absolutely to try and recommend!
avatar placeholder

CORSICA SUD Dream - catamaran cruise with hostess FULL BOARD

09/28/2025

Michael L.

Please update your website to show the correct location of the new office. Very frustrating and stressful to find when it shows the old location. Mary (host) was exceptional and very hard working as was Fredric (Captain). The recently renovated boat (62ft Lagoon) was fantastic. Great routing with plenty of sailing and beautiful stops to swim. We will definitely use Dream Yacht again.
avatar image

Traveling and dreaming in the Gulf of Poets - All Inclusive

09/23/2025

Marta D.

-

Italy

The boat is comfortable (especially the bed!!) and in excellent condition The service is all inclusive, so on the one hand it is practical on the other hand it is not certain that you will find what you would like They were very kind to buy gluten-free pasta for me who is celiac A shame not to sleep in the roadstead and the sea points were not always wow, but it is a nice experience that I would repeat!
avatar placeholder

Traveling and dreaming in the Gulf of Poets - All Inclusive

09/23/2025

Luca P.

-

Italy

Fantastic weekend with Giorgio and Francesca who made us feel like special guests all the time

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