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.
31
experiences
31
experiences
5.0
Duration:
7 days - 7 nights
Africa:
Egypt & Red Sea
+3 travellers
Have booked
€784
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Lake Garda
+78 travellers
Have booked
€99
Per person
5.0
Duration:
5 days - 5 nights
Africa:
Egypt & Red Sea
Be the first one to book!
€784
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
Be the first one to book!
€90
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
+38 travellers
Have booked
Starting from
€85
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
+141 travellers
Have booked
€149
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
Be the first one to book!
€159
Per person
Why book a holiday with Sailsquare?
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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.
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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
624 reviews
Take part in the 55th Barcolana with everything included
10/11/2023
Peter C.
-
Italy
All inclusive weekend in the Gulf of Alassio
10/6/2023
John C.
-
Italy
Day Trip Sailing around the Golfo Di Paradiso towards Portofino ALL INCLUSIVE - FLEXIBLE DATES
10/5/2023
Pietro R.
-
Italy
LAST MINUTE! - Lampedusa and Linosa, Islands on the high seas - All Inclusive
10/2/2023
Angela Loredana D.
-
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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