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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

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

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!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - October

Starting from

€600

€540

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

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

6 departures available

July - September

Starting from

€690

€621

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!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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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!

Let's enjoy the wonders of the Tyrrhenian Sea - Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€801

€761

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

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

17923 reviews

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

06/30/2026

Simone L.

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IT

Let's talk about Antonio ... professional, helpful, nice and with many sea stories to tell. Not to mention how deliciously she cooks for her guests! And then he makes you discover all the caves of the islands by tender. You can't expect more. Book, leave and enjoy this experience 😊
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Weekend on a Sailing Boat in the Magical Gulf of Poets

06/30/2026

Margherita M.

-

IT

Nice weekend with pleasant crew and a prepared and nice skipper

Weekend of approach to sailing in the setting of the Gulf of Poets

06/30/2026

Lucia S.

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IT

Beautiful experience, everything according to expectations
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Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

06/30/2026

Iole D.

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BE

Magnificent experience, the Aeolian Islands are magical and exploring them on a sailboat was beautiful, between sunrises, sunsets and nights under the stars to leave you breathless. Not to mention Stromboli and its roars and trekking on the smoking crater of Vulcano. Antonio is an experienced skipper, attentive, kind and very nice (and then also a surfer 🤙🏼) and with the rest of the group we had a great time. You never got bored between swimming, diving, SUP and snorkeling in places with beautiful cobalt blue water and lots of laughter. Ah! And the dolphins! Everything really 🔝🐬🩵🌊⛵️

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