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.
58
experiences
58
experiences
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
One departure available
July
€75
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
27 departures available
July - October
Starting from
€1,325
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
5 departures available
July - October
Starting from
€1,800
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
3 departures available
July - August
Starting from
€135
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
21 departures available
July - September
Starting from
€99
Per person
4.9
Italy: Liguria
1 day - 0 nights
2 departures available
August
€89
Per person
4.3
Premium
Indian Ocean: Seychelles
7 days - 7 nights
72 departures available
January - December
Starting from
€1,760
€1,584
Per person
4.3
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
53 departures available
January - December
Starting from
€1,680
€1,512
Per person - min 2 pax
4.9
Italy: Liguria
1 day - 0 nights
14 departures available
July - August
€150
Per person
4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
59 departures available
January - December
Starting from
€1,125
€1,013
Per person
4.3
Premium
Caribbean: BVI - British Virgin Islands
6 days - 7 nights
55 departures available
January - December
Starting from
€1,250
€1,125
Per person
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
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
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 more about the skipper and travellers who have already booked the holiday, to find out more about the
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
Weekend on a beautiful traditional schooner in the Tuscan archipelago
07/2/2025
Daniela C.
-
Italy
A day on a sailing boat to Gallinara Island or the Dianese Gulf
07/1/2025
Roberta M.
-
Italy
Sailing dreams in the Gulf of Poets and Cinque Terre
07/1/2025
Silvia S.
Sailing dreams in the Gulf of Poets and Cinque Terre
07/1/2025
Lorenzo M.
-
Italy
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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.
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.
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.
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.
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.
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.
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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