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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!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

3 departures available

September - October

Starting from

€59

Per person

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5.0

Super!

Transfer to the Island of Elba

Italy: Tuscany

1 day - 0 nights

One departure available

September

€60

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

3 departures available

September - October

€279

Per person

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4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

10 departures available

September - October

Starting from

€1,325

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,400

Per person

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5.0

Super!

Island of Vulcano (Aeolian Islands) in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

2 days - 1 night

4 departures available

September - October

€265

€239

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

4 departures available

September - October

Starting from

€69

Per person

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4.9

Super!

Life-changing experiences: Four days in the Pontine Islands with photographer on board

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€420

€399

Per person

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5.0

5-day sailing course: discovery and learning

France: French Riviera and Porquerolles

5 days - 4 nights

5 departures available

September - October

€680

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

October

€220

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

7 departures available

October - December

€190

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17460 reviews

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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/16/2025

Renate D.

-

Italy

Stefano is a pleasant, discreet and balanced person. You have a great sense of security and manage a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he offers is dreamlike, every five minutes you find yourself saying "How beautiful!", A magical experience with a confident and very competent person both in practical management and on a relational level.
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/16/2025

Renate D.

-

Italy

Stefano is a pleasant, discreet and balanced person. You have a great sense of security and manage a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he offers is dreamlike, every five minutes you find yourself saying "How beautiful!", A magical experience with a confident and very competent person both in practical management and on a relational level.
avatar placeholder

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/16/2025

Renate D.

-

Italy

Stefano is a pleasant, discreet and balanced person. You have a great sense of security and manage a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he offers is dreamlike, every five minutes you find yourself saying "How beautiful!", A magical experience with a confident and very competent person both in practical management and on a relational level.
avatar placeholder

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/16/2025

Renate D.

-

Italy

Stefano is a pleasant, discreet and balanced person. You have a great sense of security and manage a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he offers is dreamlike, every five minutes you find yourself saying "How beautiful!", A magical experience with a confident and very competent person both in practical management and on a relational level.

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