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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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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

July - November

Starting from

€540

€513

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€750

€675

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

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5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

11 departures available

June - October

Starting from

€1,200

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

9 departures available

June - August

Starting from

€250

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

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5.0

Super!

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Italy: Liguria

2 days - 2 nights

One departure available

June

€289

€246

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

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!

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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5.0

Super!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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

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

17753 reviews

Weekend at the Pontine Islands

06/9/2026

Elisa P.

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IT

If you are looking for the perfect skipper for a sailing holiday, you have found it. Mirko is simply exceptional: an impeccable professional, incredibly capable and prepared, capable of transmitting absolute safety on board. But the real added value is his personality: he is funny, ironic and excellent company. In short, it has everything you need to turn a trip at sea into an unforgettable holiday. Highly recommended!

Weekend at the Pontine Islands

06/9/2026

MARCO P.

-

IT

A wonderful boat experience between Ponza and Palmarola. Comfortable boat, pleasant company and above all a skipper capable of making a real difference: safe in driving, available in explanations and always present without being intrusive. It made everything simple, natural and pleasant, even for those who perhaps face a boat holiday with some initial doubts. In the end, that's exactly what remains: not just a nice ride, but an experience lived well from start to finish. Absolutely recommended

Weekend on Elba, sea, colors and scents.

06/9/2026

Martina N.

-

IT

Ivo is a real sea dog, with his fantastic experience he welcomed my family on his boat and safely gave us a nice experience despite the possible unforeseen events. Thank you

Gulf of Poets and Cinque Terre

06/9/2026

Guido C.

-

IT

Wonderful holiday, magnificent skipper

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