
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.
201
experiences

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: Tuscany
4 days - 4 nights
2 departures available
September
€500
Per person

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

4.6
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€850
Per person

4.9
Greece: Cyclades
7 days - 7 nights
2 departures available
October
Starting from
€950
Per person

4.8
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

4.9
Italy: Aeolian Islands
3 days - 2 nights
7 departures available
September - October
€320
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
Starting from
€300
€270
Per person

5.0
Italy: Aegadian islands
7 days - 7 nights
One departure available
September
€620
Per person

4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€3,900
Per person

4.8
Italy: Aegadian islands
6 days - 7 nights
3 departures available
September - October
Starting from
€600
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
18934 reviews
Sailing among the Islands of Ulysses. Stewardess on board
08/30/2026
Giovanna Paola C.
-
IT
Southern Corsica & Maddalena - embarkation and disembarkation from Tuscany
08/30/2026
DEBORAH F.
-
IT
Sailing among the Islands of Ulysses. Stewardess on board
08/30/2026
Laura C.
-
IT
North Corsica & Tuscan Archipelago: we love to travel a lot
08/30/2026
Fiorella F.
-
IT
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