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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€370

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

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 - Sailboat holidays & skippered tours

17989 reviews

Sailing weekend in Istria

07/7/2026

Silvia Z.

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IT

This was our first experience as sailing weekend and we enjoyed it a lot. Very relaxing. The boat was comfortable and well equipped. The skipper is great, very friendly, generous and we really enjoyed the company of Mirco.

Giglio or Elba the pearls of the Tuscan archipelago

07/7/2026

Benedetta S.

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IT

I gave the experience to my boyfriend, for us it was the very first time on a sailing boat and he exceeded all expectations! Simone and Milena made the experience incredible, making us feel immediately at ease. Simone is a great skipper and explained to us in detail how a sailboat works. This made the experience even more complete. We had the opportunity to see many beautiful coves and to enjoy good food in excellent company in an extremely serene environment. Really super recommended!!

A week sailing in the most beautiful places in the world

07/7/2026

Edoardo T.

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IT

A week that is simply unforgettable! The boat has its years, but this is what gives it a special charm. It is kept with great care and you can see the passion with which it is maintained. A special thanks to Piero and Giuseppina, as well as being very good they are two really nice people, able to create a familiar and relaxed atmosphere from the first day. Piero is an experienced skipper, always attentive and willing to share his passion for sailing. The choice to return to port one day due to the worsening weather turned out to be the right one, confirming all his experience. Giuseppina pampered us with abundant and delicious lunches and dinners. We sailed both north and south of Olbia, visiting wonderful places such as the Pink Beach, Cala Brandinchi and the Molara Pools, with the thrill of also spotting dolphins in the Golfo Aranci. The days were perfect: breakfast, a dip as soon as you woke up, sailing with some sailing lessons, lunch in spectacular bays in the shade of the bimini and lots of relaxation. In the evening aperitif, dinner, board games and lots of laughter with friends. An experience that I recommend to anyone who really wants to experience the sea and sailing. We will definitely be back... maybe for two weeks next time!

Sailing weekend in Alassio all-inclusive

07/7/2026

Massimiliano F.

-

IT

Daniele the skipper is a very funny person who knows how to put everyone at ease, a particularly happy note for the cleanliness of the boat and for the endless chats with him

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