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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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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September

€790

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€230

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

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

4 departures available

August - October

€650

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

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

2 departures available

September

€280

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€950

Per person

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4.3

La Dolce Vita on a sailboat: discovering the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 6 nights

One departure available

August

€649

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

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

18478 reviews

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A week sailing in the most beautiful places in the world

08/13/2026

Elena T.

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IT

Piero and Giusy are the best that a sailing experience can offer. Excellent sailors, they give the opportunity to try and apply themselves in maneuvers if you wish. Excellent guides and connoisseurs of the area, it is easy to get lost talking about anything with them. Finally, Giusy's ability in the kitchen and in the management of the kitchen / galley is something that borders on perfection. You can't ask for anything better. Priceless availability, patience and kindness!! ❤️❤️❤️
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Sailing cruise in the Greek islands - The Saronic Islands

08/13/2026

Bruno P.

Not even closer to the good experience we had last year.

Sailing paradise in Greece on a big 50 ft boat: the best local experience

08/13/2026

Florian H.

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DE

The Tour was great - we had a marvelous time with our family (including two 14-year-old boys) and the other guests. Skipper Tom and our host Aga are very kind and professional. We enjoyed the cuisine and the tour plan including a trip to Hydra. Tom was one of the best skippers I have been with, combining an eye for safety with calm and decisive seamanship. Aga made everything else possible be it recommending places and restaurants but also considering allergies and other specifics. The sea and the landscape are fantastic. Big thanks to the entire team!

Long weekend among the queens of the archipelago - Elba and Capraia

08/13/2026

Gabriele B.

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IT

Nice experience, Edoardo kind and helpful, to be done again.

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