
Sailboat holidays & skippered tours
The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.
193
experiences

4.8
Super!
Italy: Tuscany
5 days - 4 nights
3 departures available
September
€490
€466
Per person

4.8
Super!
Italy: Tuscany
7 days - 7 nights
3 departures available
September - October
€650
Per person

4.9
Super!
North Sea: Norway
11 days - 11 nights
One departure available
December - January
€1,300
Per person
5.0
Super!
Greece: Cyclades
6 days - 6 nights
2 departures available
September
Starting from
€1,000
€750
Per person

4.9
Super!
North Sea: Norway
7 days - 7 nights
One departure available
October
€1,200
Per person

4.8
Super!
Italy: Southern Sardinia
5 days - 4 nights
One departure available
September
€1,200
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€940
Per person

5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€250
Per person

5.0
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€350
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
October
€453
€430
Per person

4.7
Spain: The Balearic Islands
6 days - 7 nights
2 departures available
September
€1,290
Per person

5.0
Italy: Pontine Islands
3 days - 2 nights
One departure available
September
€295
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 - Sailboat holidays & skippered tours
18971 reviews
A sailing holiday: discovering the Pontine Islands
08/31/2026
Matilde C.
-
IT
Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK
08/31/2026
Antonio C.
-
IT
Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica
08/31/2026
Giovanna B.
-
IT
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
08/31/2026
Luigi M.
-
IT
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