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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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Arctic New Year: Sailing, Trekking, and Aurora adventures in Norway

North Sea: Norway

14 days - 14 nights

One departure available

December - January

€999

Per person

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5.0

12 days of sailing from Martinique to Guadeloupe

Caribbean: Guadeloupe

11 days - 11 nights

One departure available

January - February

Starting from

€1,795

Per person - min 2 pax

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Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

18 departures available

May - October

Starting from

€222

Per person

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5.0

We take a breath carried by the wind: we discover the sea in winter

Italy: Liguria

2 days - 1 night

12 departures available

January - March

€295

Per person

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4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€845

€761

Per person - min 2 pax

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4.4

Sailing holiday on the Côte d'Azur: discover the charms of the French Riviera

France: French Riviera and Porquerolles

7 days - 7 nights

10 departures available

June - September

Starting from

€700

€630

Per person

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Sails, Whales and ... Northern lights!

North Sea: Norway

7 days - 7 nights

One departure available

November

€980

Per person

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4.9

Sailing adventure in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

7 days - 7 nights

2 departures available

January - December

€1,200

Per person

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5.0

Weekend on Elba "Only for four" for maximum comfort

Italy: Tuscany

2 days - 2 nights

One departure available

November

€250

Per person

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4.4

New Year's Eve on the French Riviera between relaxation Provençal scents and sailing

France: French Riviera and Porquerolles

6 days - 5 nights

One departure available

December - January

€690

€621

Per person

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4.7

Amazing Pontine Islands in 4 days

Italy: Pontine Islands

4 days - 3 nights

5 departures available

June - August

Starting from

€450

Per person

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4.7

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

14 departures available

May - September

Starting from

€240

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

17615 reviews

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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

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Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
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LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

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Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.
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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper and skipper and travel insurance

11/3/2025

Patrizia M.

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Italy

*Return to the helm* A parenthesis of the long-awaited – and missed – summer holidays, in a late October... where everything was perfectly aligned: ☀️ sun, 💨 wind up to 30 knots, unfurled sails and breathtaking destinations, among the most varied shades of sunrises and sunsets. The skipper? What can I say... An excellence in terms of safety, handling and upwind and crosswind. Even at night: impeccable navigation, always under full sail! I left alone, with the courage and the awareness that it would be an experience to be savored to the fullest. To be discovered and then left a trace. And so it was! Mouth-watering lunches and dinners, a wonderful and intense boat holiday, lived following and supporting the wave motion. I was amazed at the sight of dolphins with Es Vedrà in the background... a boat all for me and for my unexpected furry friend, **Nao**, the skipper's affectionate dog: a sweet and ever-present companion, a real **unexpected pet therapy** that made every moment even more special. And then, **back at the helm**... feel the force of the wind in your hands, the thrill of the route, the freedom that only the sea can give! Thank you, Filippo, and thanks also to Nao — it's been a long time since I sailed with the genuine enthusiasm of feeling the wind flow between jib and mainsail...
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End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

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Italy

I come from the North Sea but I now live the Italian Alps and I’ve been really missing the ocean. So, after much thinking, I decided to treat myself to a little sailing holiday in October. [hidden] (the boat) is cozy yet has every comfort and the hosts really make you feel like you’re being treated to an Italian family gateway. Giacomo and Laura go above and beyond to fit everyone's need and requests. They exceeded my expectations! Great company, great food and insane landscapes! Nothing quite like sleeping under the stars, lulled by the gentle rocking of the boat. Thank you, I hope next time I can bring my family from Scotland!

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