
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.
152
experiences

4.1
Italy: Aeolian Islands
6 days - 7 nights
One departure available
September - October
€680
Per person

4.8
Italy: Tuscany
3 days - 2 nights
3 departures available
September - October
Starting from
€325
€309
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€730
Per person

New
Italy: Northern Sardinia
7 days - 7 nights
4 departures available
September - October
Starting from
€585
€527
Per person

4.7
Italy: Pontine Islands
4 days - 3 nights
One departure available
September
€390
Per person

4.6
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - October
Starting from
€700
€630
Per person

4.7
Italy: Tuscany
2 days - 2 nights
One departure available
October
€180
Per person

4.0
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,290
Per person

5.0
Italy: Liguria
2 days - 1 night
One departure available
October
€350
Per person

4.4
Atlantic islands: Canary Islands
10 days - 10 nights
One departure available
November
€890
Per person

4.7
Spain: The Balearic Islands
6 days - 7 nights
One departure available
October
€900
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
19122 reviews
We have known the Aeolian Islands for 20 years, live them with us!
09/13/2026
MATTIA B.
-
IT
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
09/13/2026
Elisa V.
-
IT
Whale watching cruise with WWF guide between Northern Sardinia and South Corsica
09/13/2026
Matteo F.
-
IT
Sailing holiday in the archipelago of La Maddalena and Costa Smeralda
09/13/2026
Polyanne M.
-
ES
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