Sailing day trips & getaways
The best way to break the routine and come back home refreshed is to experience a day's sailing. Give yourself 24 hours to discover the sea from a different perspective by choosing from hundreds of experiences offered by local skippers.
17
experiences
17
experiences
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
6 departures available
August - October
Starting from
€99
Per person
5.0
Super!
Italy: Tuscany
1 day - 0 nights
2 departures available
August
Starting from
€60
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
One departure available
October
€69
Per person
5.0
Super!
Italy: Aeolian Islands
3 days - 2 nights
2 departures available
August
€420
€378
Per person
5.0
Super!
Italy: Lake Garda
1 day - 0 nights
12 departures available
August - October
Starting from
€69
Per person
4.6
Spain: The Balearic Islands
1 day - 0 nights
11 departures available
August
Starting from
€100
Per person
4.9
France: French Riviera and Porquerolles
1 day - 0 nights
15 departures available
August
€88
Per person
Italy: Tremiti Islands
1 day - 0 nights
46 departures available
August - October
Starting from
€130
Per person
Italy: Liguria
1 day - 0 nights
4 departures available
August
Starting from
€290
Per person
Italy: Tuscany
1 day - 0 nights
49 departures available
August - November
Starting from
€115
Per person
5.0
Italy: Venice and the Gulf of Trieste
1 day - 0 nights
4 departures available
August - October
Starting from
€99
€94
Per person
Italy: Southern Sardinia
1 day - 0 nights
18 departures available
August - September
€160
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 - Sailing day trips & getaways
618 reviews
Sailing trip in the Côte Azure: aperitif and meal included
08/16/2025
Giovanni B.
-
Italy
A full day on a sailing boat in the Gulf of ALASSIO
08/14/2025
Lucia G.
-
Italy
A full day on a sailing boat in the Gulf of ALASSIO
08/13/2025
Diana B.
-
Italy
Aeolian Islands in the name of sailing, fishing and relaxation
08/13/2025
Simon H.
-
Australia
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Any time of year is a good time for a sailing trip. However, each season may be more or less suitable depending on the service required. A few examples:
if you want to learn to sail, we recommend that you board during the autumn or spring months and avoid the summer months, when prices are higher and there is more traffic at sea; if you want to take a trip, enjoy the view and take a swim, summer is perfect; if you are interested in trying out a regatta, the best time to participate is from April to November; if you are a fan of kitesurfing or windsurfing and would like to do it during your boat trip, the same time is ideal.
One-day boat trips are the most affordable of all the experiences available on sailsquare. For those who can't or don't want to take a skippered weekend or week-long sailing holiday, due to lack of time, money or simply because they're not sure they like it, the perfect alternative is to take one of our sailing trips. You'll find unique experiences from as little as €50 per day, and sometimes that's all it takes to have an unforgettable adventure!
Depending on your needs, each destination can offer you different things when discovered from a sailing boat. If you are in the maritime areas of the Bel Paese, you can take day sailing trips from the main coastal cities: a day sailing in the Gulf of Naples or Capri, Costiera Amalfitana; from Milan you can explore the Liguria in a day on a sailing boat, if you live in the north you can take a trip to the main lakes (Lake Garda, Lake Como, Lake Maggiore) or around Venice (Venetian Lagoon) etc etc. With a day on a boat in Tuscany you can discover the coast as well as the islands of Elba and Giglio. In Europe, wherever you are on holiday by land, you can also discover something from the sea: the Balearic Islands, the Croatia, any of the Greek islands or the Northern Sardinia.
The luxury of a day trip on a catamaran, a magical sunset, a dip in the turquoise waters of a paradise beach, a pleasant evening under the stars on the deck of the sailboat, a fun night dancing on the boat with new friends, the discovery of secret dream places accessible only by sea.....
No more excuses! Day trips by boat are really for everyone, even those who never have time but are looking for affordable experiences. Let yourself be enchanted by the magic of sailing!
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