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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!

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€59

Per person

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4.8

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

17 departures available

April - July

Starting from

€210

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

One departure available

October

€1,325

Per person

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4.9

Super!

The most important squid festival in the world - Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€310

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

July - August

Starting from

€695

€626

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

One departure available

October

€265

€239

Per person

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5.0

Super!

A bordo con lo chef alle Egadi

Italy: Aegadian islands

7 days - 7 nights

9 departures available

June - September

Starting from

€800

€720

Per person

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5.0

Super!

Squid Festival in Capraia!

Italy: Tuscany

2 days - 2 nights

One departure available

October

€290

€270

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€460

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

12 departures available

June - September

Starting from

€450

€428

Per person

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5.0

Super!

South Sardinia

Italy: Southern Sardinia

6 days - 7 nights

16 departures available

June - September

Starting from

€790

€751

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

17592 reviews

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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/15/2025

Cinzia R.

-

Italy

Nice holiday, as described and above all the skipper Filippo is a marvel, he manages everything with the utmost naturalness, always in safety, and great surprise (sorry to spoil :D), he is a spectacular cook!! Its all-inclusive formula is really super, delicious dishes, without wasting anything! P.S. Nao is adorable :)
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Fantastic BARCOLANA: Racing in safety and joy!

10/15/2025

Giulia B.

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Italy

Beautiful experience with nice and heterogeneous crew! Paolo is a professional person who guided and taught us, transmitting his passion for sailing. Advised!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/15/2025

Elena L.

-

Germany

Everything was simply perfect! The crew was incredibly flexible and accommodated all of our individual requests. We felt comfortable, well looked after, and completely safe at all times. The food was excellent and always freshly prepared for us. An all-around wonderful experience that we would repeat anytime. Highly recommended!
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Barcolana weekend in Trieste and surroundings.

10/15/2025

Barbara M.

-

Italy

MARINO fantastic skipper, he pampered us ( swim in the blue included), he was very helpful for all our whims. The Barcolana is a grandiose spectacle, seen from the sea it excites a lot, if you like sailing you can not avoid being there at least once. The kitten on board, Lightning is a very sweet travel companion. After the restyling in the shipyard, the catamaran will also be up to the task.

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