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.

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

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.

A boat with a magnifier above it

Discover who’s already onboard

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

Two coins with a currency on top

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

433 reviews
20 / 10
Orsi P.

Orsi P.

review about Procida, Capri, Amalfi trekking, Positano, Sorrento - All inclusive August 2022

10 / 10
Alessandro is a highly qualified skipper with an excellent knowledge of the area. He organised a wonderful week-long trip , and prepared delicious meals for us day after day. Throughout the holiday he was very flexible, and adapted the programme to our needs.
Salvatore L.

Salvatore L.

review about Superb day on a boat between the Gulf of ALASSIO and the Gallinara island August 2022

10 / 10
Wonderful experience, Daniele and his family were very nice, I immediately felt part of them and pampered throughout the day, I even tried to the sails and drive the boat under Daniele's control. We stopped several times to take some great baths offshore. The final aperitif was excellent and plentiful, so much so as to skip dinner thanks to the delicacies prepared by his wife Carmen. I highly recommend it to everyone to have a great day on their wonderful boat which I will definitely return to.
Marianna C.

Marianna C.

review about Discovering the Riviera of Ulysses June 2022

10 / 10
Enrico and his wife are super pleasant people and always attentive to guests. For me it was the first outing on a sailboat and it couldn't be better. Highly recommend
Mauro D.

Mauro D.

review about A day of sailing in La Spezia - All inclusive June 2022

10 / 10
We had a great day thanks to Luigi and Federica. They managed to share with us their passion for sailing, always maintaining a great attention to passengers and details. We return home enriched with a beautiful experience. Thanks and congratulations !!!
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.
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

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!

Other travel ideas