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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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4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€420

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

5 departures available

July - August

Starting from

€410

€369

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

6 departures available

June - October

Starting from

€600

€540

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

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

4 departures available

June - September

€740

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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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

3 departures available

July - August

Starting from

€800

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

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

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

17772 reviews

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A sensory sailing journey between volcanoes and a marine paradise

06/14/2026

Diana B.

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IT

The experience spent on board was really positive. Mario was always very attentive and helpful. Every day spent on board was marked by big smiles, organization and relaxation. His boat is a SHOWSTOPPER, beautiful, comfortable and impeccably maintained. Special mention to the meals prepared on board that made the cruise look like an event organized by Slow food! Mario, with the precious help of Gaia, made a week of vacation special. Thank you
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North Sardinia and Corsica: blue seen from a sailboat

06/14/2026

Matteo B.

The most beautiful sailing holiday ever had! Absolutely recommended 🙌
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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/14/2026

Maddalena G.

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ES

We spent 6 days on a boat in the Aeolian Islands and it was a truly memorable experience. The itinerary allowed us to discover wonderful islands, spectacular bays and unforgettable sunsets. Life on board was pleasant and relaxing, and discovered fantastic places to take a dip. Bledar proved to be professional, helpful and attentive to safety, as well as knowing the area very well and being able to recommend the most beautiful places to visit. The boat was comfortable and well organized for a multi-day vacation. An experience that I recommend to those who want to experience the sea from a different perspective, and discover the Aeolian Islands in the most authentic way possible. Definitely a holiday that I will carry with me in my memories.

Egadi mon amour: seven days to fall in love, be amazed and relax.

06/14/2026

benedetta fosca a.

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IT

Beautiful experience! Giuseppe is a very prepared, attentive and helpful skipper! The boat is spacious and very well maintained The Egadi Islands are wonderful! Overall a super positive experience and one that I recommend!

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