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.
497
experiences
497
experiences
5.0
Duration:
7 days - 6 nights
France:
French Riviera and Porquerolles
Give this experience a try!
Starting from
€711
€790
Per person
4.9
Super!
Duration:
7 days - 7 nights
Italy:
Pontine Islands
+71 travellers
have booked
Starting from
€621
€690
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Southern Sardinia
Give this experience a try!
€504
€560
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Aeolian Islands
+62 travellers
have booked
Starting from
€800
€890
Per person
4.9
Duration:
1 day - 0 nights
Italy:
Liguria
+55 travellers
have booked
Starting from
€126
€140
Per person
4.9
Duration:
3 days - 2 nights
Italy:
Liguria
+23 travellers
have booked
€324
€360
Per person
5.0
Duration:
2 days - 1 night
Italy:
Venice and the Gulf of Trieste
+8 travellers
have booked
Starting from
€171
€190
Per person
4.0
Duration:
6 days - 7 nights
Italy:
Aegadian islands
+15 travellers
have booked
Starting from
€630
€700
Per person
4.9
Super!
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
+29 travellers
have booked
Starting from
€990
€1,100
Per person
4.9
Super!
Duration:
7 days - 7 nights
Italy:
Aeolian Islands
+53 travellers
have booked
Starting from
€450
€500
Per person
4.8
Super!
Duration:
2 days - 2 nights
Italy:
Tuscany
+4 travellers
have booked
€189
€210
Per person
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
+10 travellers
have booked
Starting from
€1,440
€1,600
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
14736 reviews
Week between the Tuscan Islands and North Corsica
07/26/2024
Gianmarco N.
-
Italy
Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor
07/26/2024
Katia P.
-
Italy
4 days in the Pontine Islands (sailing school)
07/26/2024
valentina P.
-
Luxembourg
From Cinque Terre to Tigullio, discovering Ligurian pearls
07/26/2024
Chiara C.
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & SupportLet's talk Sailsquare!
Sailsquare
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964