
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.
122
experiences

Italy: Naples & Amalfi Coast
1 day - 0 nights
4 departures available
September
€180
Per person

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

5.0
New
France: French Riviera and Porquerolles
5 days - 4 nights
27 departures available
February - October
Starting from
€595
Per person

4.5
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€290
Per person

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

New
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
October
€600
Per person

4.5
Italy: Pontine Islands
3 days - 2 nights
One departure available
September
€380
€350
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
June
€625
Per person

5.0
New
Italy: Northern Sardinia
7 days - 7 nights
One departure available
September
€620
€590
Per person

Greece: Ionian Islands
7 days - 7 nights
2 departures available
October
€890
Per person

4.8
Italy: Lake Garda
1 day - 0 nights
8 departures available
September - October
€150
Per person

New
Premium
Greece: Ionian Islands
7 days - 7 nights
One departure available
September - October
Starting from
€1,645
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
19196 reviews
North Corsica & Tuscan Archipelago: we love to travel a lot
09/23/2026
Lodovica G.
-
IT
Wellness, sun, sea and adventure: a weekend full of sailing!
09/23/2026
Francesco G.
-
IT
Amazing Pontine Islands on a sailboat with private bathrooms
09/23/2026
Eleonora Santina Emma B.
-
IT
Sporades Experience: Freedom, Turquoise Sea and Greek Magic
09/23/2026
Miguel M.
-
ES
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