
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.
149
experiences

5.0
Croatia: Split Archipelago
7 days - 7 nights
3 departures available
September - October
€1,100
Per person

4.7
Spain: The Balearic Islands
6 days - 7 nights
One departure available
October
€900
Per person

4.3
Malta: Malta
6 days - 6 nights
4 departures available
September - October
Starting from
€690
Per person

New
Italy: Tuscany
3 days - 2 nights
2 departures available
September - October
€275
Per person

5.0
Italy: Pontine Islands
3 days - 2 nights
One departure available
October
€295
Per person

4.5
Italy: Tuscany
2 days - 1 night
4 departures available
September - October
€220
Per person

New
Italy: Tuscany
4 days - 3 nights
One departure available
September
€424
Per person

4.0
Greece: Peloponnese
6 days - 6 nights
One departure available
September
€815
Per person

4.0
Atlantic islands: Canary Islands
6 days - 6 nights
One departure available
November
€660
Per person

5.0
Italy: Sicily
2 days - 1 night
5 departures available
September - October
Starting from
€215
€194
Per person

4.0
France: French Riviera and Porquerolles
6 days - 6 nights
One departure available
October
€550
Per person

5.0
Spain: The Balearic Islands
6 days - 6 nights
4 departures available
September - October
Starting from
€950
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
19150 reviews
Wellness, sun, sea and adventure: a weekend full of sailing!
09/15/2026
rosanna n.
-
IT
Sailing weekend in Istria
09/15/2026
Simona G.
-
IT
Week end in Costa Azzurra
09/15/2026
Massimiliano M.
-
CH
Week between the Tuscan Islands and Northern Corsica
09/15/2026
Silvia M.
-
IT
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