Sailing day trips & getaways

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.

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Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Sailing day trips & getaways

372 reviews
20 / 10
Cristina O.

Cristina O.

review about Learn the art of sailing May 2022

10 / 10
Gianni is of few and punctual words when sailing but when the wind stops blowing, between a focaccia and a sparkling wine put on the table by Angela, he is of great company. And if he perceives interest and curiosity, he teaches you everything he can.
Romina V.

Romina V.

review about Relaxation and luxury sailing between Versilia and Liguria January 2022

10 / 10
Fabrizio is an excellent skipper with a great sailing experience and makes the crew feel in absolute safety. We spent a very pleasant day in wonderful company. The boat is brand new, comfortable and very performing! Five-star experience!!!
Fabrizio F.

Fabrizio F.

review about Sailing between nature and fun September 2021

10 / 10
Marco and Cristina were truly exceptional guests. They pampered us throughout the holiday time. Marco is a trained skipper who invites vacationers to try the boat, teaches and lets passengers experience the pleasures of sailing. The boat is very nice and impeccably maintained. Definitely will be back :)
Valeria A.

Valeria A.

review about "Emotions on the Conero Riviera" August 2021

10 / 10
With two friends we decided to take a ride on the Conero Riviera and we contacted Federico for more info. Federico was super helpful, very fast in the answers and getting organized with him was really easy. We had a beautiful boat ride, relaxing and we had lunch on the boat (all delicious!). Federico was not only an excellent skipper but also very kind and of excellent company. I highly recommend it, thanks Federico! Federico is knowledgeable, kind and super responsive. Planning this day out on the sea was a breeze, and my friends and I had a great time. Boat was perfect for our needs and lunch and drinks were great. Definitely recommended!
Gino G.

Gino G.

review about Redentore 2019 Fireworks and seafood dinner. July 2021

10 / 10
Ernesto is a professional skipper, with great experience who has the ability to manage the boat safely and efficiently. We had a beautiful evening.
Silvia A.

Silvia A.

review about On the dolphin route. June 2021

8 / 10
Despite the not exactly favorable weather, we had a nice day. Too bad we just didn't get to see the dolphins!
MARTINO B.

MARTINO B.

review about Sailing and aperitif at sunset in front of the suggestive Marina di Pisa August 2020

10 / 10
We gave this experience to our parents for their anniversary. They were thrilled!! The welcome, friendliness and friendliness have played a fundamental and complementary role to the already interesting sailing tour. I thank Romulus and Esther for everything!! Highly recommended!!!!!
Martina D.

Martina D.

review about - AN ALL INCLUSIVE DAY - In the Gulf of Poets August 2020

10 / 10
Wonderful day in the company of Alessandro and Giada! Relaxing to be lulled by the waves looking at the cliffs of Portovenere and Palmaria island and then devote yourself to diving and bathing! Testaroli with pesto cooked by Alessandro delicious, great company and atmosphere! Experience to be repeated!!
Paolo S.

Paolo S.

review about SAILING DAY August 2020

10 / 10
Perfect experience, according to the best expectations. Oscar was very good at nautical explanations and perfect reception. Not even the presence of little wind ruined the day.
Sara B.

Sara B.

review about Sailing day: La Maddalena archipelago August 2020

10 / 10
Wonderful day with Pietro and the other participants! Absolute relaxation, beautiful coves and although it was for everyone the first experience on a sailboat Pietro was very good! A very hospitable person, light and exquisite lunch cooked on site following everyone's needs. Highly recommended!!!
Lucio M.

Lucio M.

review about Living the sea August 2020

10 / 10
We had a lovely day, Emilio and his wife were really hospitable and helpful. It was like hanging out with friends. When possible we will repeat the experience
Cristina L.

Cristina L.

review about Gulf of Tigullio by Sailboat - Half Board July 2020

8 / 10
Very skilled skipper, expertly prepared. He put us at ease right away. Luca led us for a wonderful day in the Gulf of Tigullio. Magical places on a beautiful sunny day in good company. Thank you guys super mega experience recommended.
Luisa V.

Luisa V.

review about Day-Cruise Gulf of the Poets July 2020

10 / 10
Giacomo is very professional, polite and personable. He knows very well the Gulf of La Spezia in which he will take you with his boat kept very well!
Emanuela C.

Emanuela C.

review about Sailing and Wellness October 2019

10 / 10
In one word, a "fantastic" day that is all superlative!!! Umberto, the skipper, as well as being a very kind person and an excellent cicerone, is also an excellent cook. A tip ..... TRY WITHOUT HESITATION ps: a greeting to my travel companions :-)
Elia M.

Elia M.

review about PORTO VENERE AND 5 TERRE, BETWEEN WIND, HISTORY AND WINE ;) September 2019

10 / 10
You do not just go on a trip to the sea, but you live a continuous emotion made of history, stories and indescribable emotions. Davide and Damiano are patient and always available; they really know how to convey their passion for the sea. Experience certainly intense even if short, to be repeated for sure!
Elia B.

Elia B.

review about Between Portofino and Sestri Levante, Bay of Silence, Adventure, Relax, Spritz! Bavaria 50! August 2019

10 / 10
A fascinating experience undoubtedly, with Andrea and Nicole kind and always available. I recommend this excursion to everyone to those who, above all, want to disconnect from the routine to fully immerse themselves in the beauty of the sea and those fantastic places that can be admired along the sail!!! The boat is really great, clean and equipped with everything you may need. Mark: 10 laude!!! See you soon definitely!!!
Pascal V.

Pascal V.

review about Sailing around Ischia September 2019

10 / 10
Thank you Irene for this beautiful day. This gave us the idea to start with Sailsquare. Your boat is nickel clean and with you we are in total safety. Beats
ELENA B.

ELENA B.

review about Daily sailing between the most beautiful beaches of La Maddalena August 2019

10 / 10
Hello , nice experience , although we sailed little, there was no wind ????. Omar and Alessia were really nice, welcoming and available to various requests. The boat is large, clean and with all the comforts that a sailboat can afford, and maybe more. I recommend trying????
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8 reasons to choose a day trip on a sailing boat

  • To savour the magic of sailing for a day, and perhaps discover a new passion...
  • To explore secret destinations, islands, coves and dream beaches that can only be reached by sea.
  • The perfect solution for people who want a unique and authentic experience but have little time.
  • A unique opportunity to meet new people and share the experience with like-minded travellers.
  • Daily sailing trips throughout Italy and Europe, with a local skipper who will also be your guide during the day and will know how to lead you to the most beautiful corners of the destination.
  • Disconnect from everyday life on any day of the week to connect with nature and breathe in the peace and tranquillity of the sea.
  • Various possibilities for activities during the day, including: a short sailing course, an offshore swimming, a regatta, a boat party, a catamaran trip, specific sports and wellness activities such as yoga.....
  • For those with a limited budget and little time, you will find one-day boat experiences from €50.

Everything you need to know about organising a day sailing trip

When is the best time to charter a sailing boat for a day?

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.

How much does a boat trip cost?

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!

The best destinations for a sailing trip

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.

Sailing day trips

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!

Day trips: best destinations

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