
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.
108
experiences

4.1
Italy: Aeolian Islands
6 days - 7 nights
18 departures available
May - October
Starting from
€680
Per person

4.5
Spain: The Balearic Islands
6 days - 6 nights
14 departures available
June - September
Starting from
€790
Per person

4.9
Italy: Aeolian Islands
5 days - 4 nights
15 departures available
July - October
Starting from
€590
Per person

4.9
Italy: Tuscany
4 days - 3 nights
12 departures available
April - October
Starting from
€250
Per person

Atlantic islands: Canary Islands
7 days - 7 nights
9 departures available
January - December
€900
€630
Per person

Italy: Southern Sardinia
5 days - 4 nights
One departure available
May - June
€800
Per person

4.6
Italy: Aeolian Islands
7 days - 7 nights
8 departures available
July - August
Starting from
€910
€865
Per person - min 2 pax

North Sea: Norway
14 days - 14 nights
One departure available
December - January
€999
Per person

5.0
Caribbean: Guadeloupe
11 days - 11 nights
One departure available
January - February
Starting from
€1,795
Per person - min 2 pax

4.0
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€390
Per person

Italy: Naples & Amalfi Coast
1 day - 0 nights
6 departures available
October
€110
Per person

4.3
Premium
Greece: Ionian Islands
7 days - 7 nights
17 departures available
May - October
Starting from
€845
Per person - min 2 pax
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
17604 reviews
North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine
10/25/2025
Teresa B.
-
Germany
IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper
10/25/2025
Sara C.
-
Italy
Barcolana weekend in Trieste and surroundings.
10/24/2025
Marilisa V.
-
Italy
Weekend in Capraia, the island with timeless sunsets
10/22/2025
Don D.
-
Italy
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