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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!

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

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

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5.0

Super!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€350

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

€470

Per person

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5.0

Super!

Maldive da sogno in barca a vela - Da Malé a Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

€2,385

Per person

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5.0

Super!

Seyschelles Islands... Welcome to paradise!

Indian Ocean: Seychelles

11 days - 11 nights

3 departures available

April - June

€2,400

€2,040

Per person

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5.0

Super!

Maldive da sogno in barca a vela - Da Kulhudhuffushi a Malé

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February - March

€2,650

€2,385

Per person

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5.0

Super!

Weekend Garda Lake 

Italy: Lake Garda

2 days - 2 nights

One departure available

May

€189

Per person

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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€69

Per person

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5.0

Super!

Sailing, early sun and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€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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4.9

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

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

17605 reviews

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Sailing in the Saronic Archipelago

10/26/2025

Lorenzo Z.

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Italy

I chose the boat trip precisely to live the experience of sailing. We always sailed by motor, except for a few hours, in the need to dry them after a heavy rain. this even when all the other boats were sailing
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North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

10/25/2025

Teresa B.

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Germany

We were very lucky to spend 7 days with Bledar on his sailboat around Sardinia and Corsica and it was unforgettable! Every day, Bledar surprised us with new, freshly prepared culinary highlights - fresh, creative and prepared with a lot of love. He took care of us touchingly, left nothing to be desired and led us to the most beautiful bays, islands and snorkeling spots. We got to know wonderful people and thanks to his warm nature, everything felt like a vacation with friends. This week was the perfect mix of relaxation, adventure and enjoyment. It was the best holiday we have ever had. Thank you, dear Bledar, for this magical time! ❤️⛵️ Tuttepossible!
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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/25/2025

Sara C.

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Italy

A week of relaxation, laughter, new friendships, baths, good food, karaoke, and slow life marked by the movements of the sea. Filippo is an expert, sunny captain, attentive to every need, super cook and master of the grill! His dog Nao is an adorable companion for travel and adventures in sup and cycling. The natural beauty of Ibiza and Formentera in October offers breathtaking views between rocky cliffs and blue sea, white sandy beaches and crystal clear water, perfect weather for exploring Formentera by bike and visiting its lighthouses overlooking the sea and well-kept villages. [hidden] comfortable, solid and spacious boat has given us beautiful sailing crossings.
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Barcolana weekend in Trieste and surroundings.

10/24/2025

Marilisa V.

-

Italy

Marino skipper of great experience and sympathy; Super event and experience just as much!

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