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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.



Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

527 reviews

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Take part in the 55th Barcolana with everything included


Peter C.



Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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Sailing boat trip with aperitif on board!


Serena F.



Persona gradevolissima e skipper competente
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Day Trip Sailing around the Golfo Di Paradiso towards Portofino ALL INCLUSIVE - FLEXIBLE DATES


Pietro R.



Kit e sua moglie Alice sono stati degli ospiti eccezionali. Torneremo presto a trovarli.
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Free in the Wind!... perfumes and wonders in the upper Adriatic


Enzo B.



Ottimo skipper ma soprattutto bella persona; è stato un piacere passare una giornata in barca a vela con Paolo. Anche per le persone alle primissime armi è un tipo di esperienza super consigliata avendo la certezza che Paolo vi aiuterà a vivere al meglio questa diversa dimensione del mare. Buona navigazione a TUTTI

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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!

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