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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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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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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€750

€675

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

One departure available

September

€740

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!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

2 departures available

July

Starting from

€590

€531

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

8 departures available

July - September

€1,600

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

9 departures available

July - September

Starting from

€980

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

17963 reviews

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

07/5/2026

Monica Sofia S.

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IT

It was a beautiful week, Francesco is a very prepared skipper and transmits his passion for both the sea and cooking. In my opinion it should just be clearer with the rules on board.

Four days in the Pontine Islands, just a stone's throw from Rome

07/5/2026

Cristina L.

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IT

Beautiful 4-day holiday between Palmarola and Ponza The boat is large and with well-organized spaces and the skipper Antonio is a real sea dog: he has experience, passion and always has a story to tell us He made us discover the islands in a unique way, sailing between Palmarola and Ponza, sleeping in the roadstead, visiting various coves and even doing a few laps with the tender Impossible not to mention that he is also an excellent cook Highly recommended holiday Thank you Antonio and fair winds!
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North Corsica & Tuscan Archipelago: we love to travel a lot

07/5/2026

Ilaria P.

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IT

Exciting experience in total contact with nature. Marco, the skipper, is a very wise person and a great entertainer, he was able to manage every situation with great serenity. We visited magnificent places and we always slept under the stars.... Simply fantastic!
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Capri Light Blue - Two boats in company!

07/5/2026

Roberta P.

-

IT

Very nice destination, prepared skipper, homogeneous company all of the same age, very comfortable boat

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