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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.

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

2 departures available

August

Starting from

€390

Per person

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New

Day trip to the island of Elba - Porto Azzurro

Italy: Tuscany

1 day - 0 nights

One departure available

August

€80

Per person

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New

Slow sailing in Portoferraio - daily trimaran trip

Italy: Tuscany

1 day - 0 nights

2 departures available

August

€80

Per person

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4.9

Sailing excursion to Capri / Positano

Italy: Naples & Amalfi Coast

1 day - 0 nights

13 departures available

August

€150

Per person

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5.0

From the sun to the moon - Afternoon All inclusive on Lake Garda

Italy: Lake Garda

1 day - 0 nights

3 departures available

July - August

€149

Per person

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4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

5 departures available

August

Starting from

€150

Per person

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4.5

New

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

Italy: Lake Maggiore

1 day - 0 nights

2 departures available

August

€100

Per person

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New

Between the Ionian and the Adriatic where the seas meet

Italy: Puglia

1 day - 0 nights

32 departures available

July - August

€130

Per person

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5.0

Sailing day in the beautiful Marine Protected Area of Capo Milazzo

Italy: Sicily

1 day - 0 nights

2 departures available

August

€118

Per person

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Bachelorette Party

Italy: Liguria

1 day - 0 nights

10 departures available

August - September

Starting from

€145

€138

Per person

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4.9

Sailing in Tigullio: Half-Day Experience from Rapallo

Italy: Liguria

1 day - 0 nights

3 departures available

August

€91

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

16 departures available

August - October

Starting from

€69

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

641 reviews

Aeolian Islands in the name of sailing, fishing and relaxation

07/25/2026

IRIS K.

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AT

Antonio was a very accommodating and competent captain. He fulfilled all requests and was able to give us a lot of information about the Isole Eolie. Thank you!
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Gulf of Alassio & Gallinara Island Full Day Experience

07/15/2026

Silvio R.

-

IT

Marco is a very skilled skipper, as well as being nice and easy-going! He was available to evaluate the route together based on sea and wind conditions and gave valuable advice to find the best places to anchor. In addition, in sailing he involved us in some maneuvers, under his careful supervision. On board nothing was missing for a lunch and various snacks. We sailed between Alassio and Gallinara, going around the island and it was very impressive. Marco has made inflatables available to let us relax even in the water. There were four friends of us all over the boat, and the space was suitable. It should be considered that being a boat also designed for regattas, some spaces are a bit small and many are a little closer, but it is part of the spirit of the sailboat. The boat is as pictured and as described! Thank you Marco!

A full day on a sailing boat in the Gulf of ALASSIO

07/5/2026

Raffaella F.

-

IT

Relaxing day!! Thank you Daniele and Edoardo

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/22/2026

daniela m.

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IT

I gave this experience to my husband who had dreamed of steering a sailboat for years and was satisfied! Stefano was super kind and helpful in advising me in the best possible way when and how to book and the experience itself was very nice

Customer Support

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Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

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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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