
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.
560
experiences

4.8
Super!
Italy: Tuscany
5 days - 4 nights
3 departures available
July
€590
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: Tuscany
7 days - 7 nights
One departure available
August
€1,060
Per person

4.8
Italy: Naples & Amalfi Coast
3 days - 2 nights
2 departures available
September - October
€242
€218
Per person

5.0
New
Italy: Aegadian islands
7 days - 7 nights
6 departures available
June - September
Starting from
€650
€585
Per person

5.0
Super!
Italy: Southern Sardinia
4 days - 3 nights
2 departures available
July - September
€740
Per person

4.9
Super!
Italy: Liguria
2 days - 2 nights
2 departures available
July - September
€400
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
7 days - 7 nights
4 departures available
August
€990
Per person

4.8
Italy: Naples & Amalfi Coast
7 days - 7 nights
One departure available
August
€977
€879
Per person

4.8
Super!
Italy: Pontine Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€900
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
8 departures available
July - September
€1,600
Per person

5.0
Italy: Pontine Islands
7 days - 7 nights
2 departures available
August - September
€1,020
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
17837 reviews
Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola
06/22/2026
Angelica C.
-
IT
All-Inclusive Sailing: Capri, Positano, Amalfi
06/22/2026
Maria Grazia I.
-
IT
Weekend on the island of Elba: among dolphins, enchanting bays and relaxation
06/22/2026
Elisa M.
-
IT
Weekend between Ponza and Palmarola Comfortable - max 4 people
06/22/2026
MARIANO B.
-
IT
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