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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

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

Croatia: Split Archipelago

7 days - 7 nights

3 departures available

September - October

€1,100

Per person

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4.7

IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

One departure available

October

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

4 departures available

September - October

Starting from

€690

Per person

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New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€275

Per person

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5.0

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

October

€295

Per person

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4.5

Relaxing weekend and sailing school

Italy: Tuscany

2 days - 1 night

4 departures available

September - October

€220

Per person

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New

Four days of relaxation midweek on the island of Elba with hostess

Italy: Tuscany

4 days - 3 nights

One departure available

September

€424

Per person

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4.0

Outdoor and lifestyle exploration

Greece: Peloponnese

6 days - 6 nights

One departure available

September

€815

Per person

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4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

5 departures available

September - October

Starting from

€215

€194

Per person

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4.0

European Offshore Mile Builder - Leg 5: St Tropez to Malta

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€550

Per person

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5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

4 departures available

September - October

Starting from

€950

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

19150 reviews

Wellness, sun, sea and adventure: a weekend full of sailing!

09/15/2026

rosanna n.

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IT

We had a beautiful we on a sailing boat. Daniele and Maria Pia are wonderful in putting everyone at ease. Excellent company, the itinerary and the food prepared by Pia who is a wonderful cook, able to find any variation she is asked for. Daniele gladly lent himself to a change of cove for an unforgettable swim, due to the headwind compared to the established itinerary. Everything perfect.
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Sailing weekend in Istria

09/15/2026

Simona G.

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IT

Mirco top as captain 😊 you will only find out why by sailing with him 😝 boat in perfect conditions, cozy and equipped with all comforts. I will definitely be back at sea with Mirco. Thank you for everything !!

Week end in Costa Azzurra

09/15/2026

Massimiliano M.

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CH

Really beautiful experience! Alessandro was an extremely professional, competent and attentive commander, but above all kind and helpful. We were with three children under 4 years old, including a 10-month-old girl, and she was able to meet our needs with great patience and naturalness, making us experience and appreciate the boat (first time)! She took care of every organizational / logistical aspect to perfection, but her way of relating to the children was really an added value, fundamental to make the weekend serene and pleasant for everyone. An exquisite person and a captain of great professionalism. An experience that made us want to do it again soon! Thank you very much. Stefania + Massimiliano + Lori
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Week between the Tuscan Islands and Northern Corsica

09/15/2026

Silvia M.

-

IT

Beautiful experience, beautiful places, close-knit group and Francesco.. a real sea dog!

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