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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

One departure available

August

€390

Per person

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4.9

Sailing excursion to Capri / Positano

Italy: Naples & Amalfi Coast

1 day - 0 nights

7 departures available

August

€150

Per person

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New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

35 departures available

August - September

Starting from

€170

Per person

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New

Between the Ionian and the Adriatic where the seas meet

Italy: Puglia

1 day - 0 nights

14 departures available

August

€130

Per person

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New

Slow sailing in Portoferraio - daily trimaran trip

Italy: Tuscany

1 day - 0 nights

One departure available

August

€80

Per person

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Bachelorette Party

Italy: Liguria

1 day - 0 nights

7 departures available

September

Starting from

€145

€138

Per person

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New

Sailing in a trimaran to the rhythm of the wind

Italy: Tuscany

1 day - 0 nights

2 departures available

August

€100

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

One departure available

August

€149

Per person

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5.0

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

Italy: Lake Garda

1 day - 0 nights

15 departures available

August - October

Starting from

€59

Per person

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New

Gulf of Poets: Shared Sunset Tour by Catamaran

Italy: Liguria

1 day - 0 nights

36 departures available

August - September

Starting from

€140

Per person

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4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

2 departures available

August

€85

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

2 departures available

August

€150

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

646 reviews

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

08/10/2026

Paola P.

Excellent organization! Very nice skipper and prepared. Experience to be redone!!

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

08/10/2026

Christian B.

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IT

Great experience in the company of Daniele! We took a ride offshore with the sail which was a lot of fun. After this we made a stop at the gallinara with sup, lunch and relaxation on the boat and ended the day with a panoramic tour of the coast up to Capo Mele! Daniele is a very interesting person and the day flew by in his company! I absolutely recommend the tour!
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Sailing in Tigullio: Half-Day Experience from Rapallo

08/5/2026

Maurizio P.

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IT

Fantastic experience, very kind staff who made us feel at home. Highly recommend.

Sailing in Tigullio: Half-Day Experience from Rapallo

08/4/2026

LUCA ADRIANO B.

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IT

Well organized sailing excursion. We bathed, without haste, in two beautiful places.. Captain and crew treated us well with lots of focaccia and pizza for a snack!

Customer Support

customer support

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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