Holidays and cruises on sailboats with organized activities.
Do you love to relax but also need to stay active or pursue your greatest passions? On a sailboat, you can enjoy a week or weekend of sailing and sea, combining activities such as trekking, yoga, snorkeling, and even gastronomic tastings.
22
experiences
22
experiences
5.0
Duration:
2 days - 2 nights
Italy:
Gulf of Naples
Give this experience a try!
€200
Per person
4.3
Duration:
4 days - 5 nights
Italy:
Southern Sardinia
+3 travellers
have booked
€600
Per person
4.6
Duration:
4 days - 4 nights
Italy:
Tuscany
MARY
has booked
€510
Per person
4.8
Duration:
4 days - 4 nights
Italy:
Aegadian islands
+7 travellers
have booked
€490
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Tuscany
+2 travellers
have booked
€280
Per person
4.9
Duration:
5 days - 5 nights
Italy:
Tuscany
Give this experience a try!
€618
€650
Per person
5.0
Duration:
5 days - 5 nights
Africa:
Egypt & Red Sea
+6 travellers
have booked
Starting from
€795
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€1,350
Per person
5.0
Duration:
3 days - 3 nights
Italy:
Tuscany
Give this experience a try!
€361
€380
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Aeolian Islands
Give this experience a try!
€265
Per person
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
Starting from
€1,690
Per person
4.8
Duration:
6 days - 7 nights
Italy:
Southern Sardinia
Give this experience a try!
€711
€790
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 - Holidays and cruises on sailboats with organized activities.
1278 reviews
Wine Experience with Sommelier on the Island of Elba
10/4/2023
Davide Q.
-
Italy
All Inclusive Mallorca - Ibiza on large 18m Ketch with Insurance and Steward
10/1/2023
Stefano G.
-
Italy
Two boats together - Sailing on the island of Elba! Between the sea, courses and new friends... you forget everything! :-)
09/29/2023
Italy B.
-
Italy
Holistic Sail Aeolian in Catamaran - Sailing and Yoga for a Week of Relaxation and Energy
09/26/2023
Lorenza P.
-
Italy
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