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.
50
experiences
50
experiences
4.6
Premium
Duration:
10 days - 10 nights
Thailand:
Phuket, Krabi and Phi Phi Islands
Starting from
€1,790
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Liguria
Claudia D.
has booked
Starting from
€224
€249
Per person
4.6
Premium
Duration:
7 days - 7 nights
Thailand:
Phuket, Krabi and Phi Phi Islands
+8 travellers
have booked
Starting from
€1,270
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
+2 travellers
have booked
Starting from
€1,150
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Bahamas
+16 travellers
have booked
Starting from
€1,430
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
BVI - British Virgin Islands
+4 travellers
have booked
Starting from
€1,420
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
+4 travellers
have booked
Starting from
€1,280
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
has booked
Starting from
€1,150
Per person
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
Give this experience a try!
€1,802
Per person
4.6
Premium
Duration:
10 days - 10 nights
Pacific Ocean:
French Polynesia
Starting from
€2,065
Per person
4.6
Premium
Duration:
10 days - 10 nights
Caribbean:
Grenadines & Martinique
+14 travellers
have booked
Starting from
€2,055
Per person
5.0
Duration:
1 day - 0 nights
Italy:
Liguria
Give this experience a try!
€180
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
616 reviews
PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
03/12/2024
Giancarlo A.