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
4.5
Premium
Duration:
7 days - 7 nights
Indian Ocean:
Seychelles
32 travellers
Starting from
€1,369
€1,825
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Bahamas
Starting from
€1,676
€2,095
Per person - min 2 pax
4.5
Premium
Duration:
10 days - 10 nights
Thailand:
Phuket, Krabi and Phi Phi Islands
Starting from
€2,144
€2,680
Per person - min 2 pax
4.5
Premium
Duration:
10 days - 10 nights
Pacific Ocean:
French Polynesia
Starting from
€1,736
€2,170
Per person
4.5
Premium
Duration:
7 days - 7 nights
Pacific Ocean:
French Polynesia
Starting from
€1,208
€1,510
Per person - min 2 pax
4.5
Premium
Duration:
7 days - 7 nights
Thailand:
Gulf of Thailand
Starting from
€1,692
€1,880
Per person - min 2 pax
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
BVI - British Virgin Islands
8 travellers
Starting from
€1,188
€1,320
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Saint Martin
2 travellers
Starting from
€1,071
€1,190
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Grenadines & Martinique
9 travellers
Starting from
€1,188
€1,320
Per person
4.5
Premium
Duration:
7 days - 7 nights
Thailand:
Phuket, Krabi and Phi Phi Islands
28 travellers
Starting from
€1,040
€1,155
Per person
4.5
Premium
Duration:
9 days - 10 nights
Caribbean:
Grenadines & Martinique
16 travellers
Starting from
€1,629
€1,810
Per person - min 2 pax
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
Starting from
€1,071
€1,190
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.
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
721 reviews
PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
12/7/2024
Jess L.
PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook
12/3/2024
Frauke K.
PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
12/1/2024
Edoardo F.
-
Italy
European Mile Builder Sao Jorge Leg 4 Gibraltar to Las Palmas
11/19/2024
Jan C.
-
Poland
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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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