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
56
experiences
Duration:
6 days - 7 nights
Greece:
Saronic Islands and Athens area
Starting from
€2,650
Per person
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
Saint Martin
Starting from
€2,490
Per person - min 2 pax
Duration:
6 days - 6 nights
Italy:
Southern Sardinia
Give this experience a try!
€1,290
Per person
4.3
Premium
Duration:
7 days - 7 nights
Croatia:
Split Archipelago
9 travellers
Starting from
€1,250
Per person
5.0
Super!
Duration:
1 day - 0 nights
Italy:
Tuscany
53 travellers
Starting from
€125
Per person
4.9
Duration:
2 days - 1 night
Italy:
Liguria
Give this experience a try!
Starting from
€200
Per person
5.0
Super!
Duration:
1 day - 0 nights
Italy:
Lake Garda
4 travellers
€69
Per person
4.3
Premium
Duration:
10 days - 10 nights
Pacific Ocean:
French Polynesia
2 travellers
Starting from
€3,205
Per person
5.0
Duration:
4 days - 4 nights
Africa:
Egypt & Red Sea
Give this experience a try!
€1,145
Per person
4.9
Duration:
2 days - 1 night
France:
French Riviera and Porquerolles
2 travellers
€260
Per person
5.0
Super!
Duration:
1 day - 0 nights
Italy:
Lake Garda
44 travellers
Starting from
€59
Per person
5.0
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
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
729 reviews
PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook
05/9/2025
Sara Angela R.
BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
04/12/2025
Carla P.
-
Italy
BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
03/18/2025
Patricia A. Mcmahon s.
BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
02/24/2025
Stefania T.
-
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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