
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.
501
experiences

4.6
Italy: Tuscany
7 days - 6 nights
2 departures available
July - August
Starting from
€800
€600
Per person

4.5
Italy: Aeolian Islands
7 days - 7 nights
12 departures available
August - November
Starting from
€540
€513
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
8 departures available
July - October
Starting from
€230
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
6 days - 6 nights
2 departures available
July - August
Starting from
€1,150
Per person

5.0
Super!
Greece: Sporades
7 days - 7 nights
One departure available
July - August
€890
€680
Per person

4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
6 departures available
July - October
Starting from
€420
€399
Per person

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
One departure available
September
€620
Per person

New
Italy: Pantelleria and Lampedusa
7 days - 7 nights
8 departures available
July - November
Starting from
€500
€425
Per person

5.0
New
Italy: Northern Sardinia
6 days - 6 nights
4 departures available
August - September
Starting from
€950
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
12 departures available
July - November
Starting from
€600
€540
Per person

5.0
Italy: Aeolian Islands
6 days - 7 nights
One departure available
August
€1,050
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
7 days - 7 nights
4 departures available
August
€990
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
17963 reviews
An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands
07/5/2026
Monica Sofia S.
-
IT
Four days in the Pontine Islands, just a stone's throw from Rome
07/5/2026
Cristina L.
-
IT
North Corsica & Tuscan Archipelago: we love to travel a lot
07/5/2026
Ilaria P.
-
IT
Capri Light Blue - Two boats in company!
07/5/2026
Roberta P.
-
IT
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