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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.

618

experiences

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4.7

Ibiza All Inclusive on an 18m ketch with skipper and skipper

Duration:

6 days - 7 nights

Spain:

The Balearic Islands

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35 travellers

Starting from

€960

€1,200

Per person

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5.0

Oslofjord - East Coast Norway - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

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5.0

Oslofjord - West Coast of Sweeden - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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51 travellers

€990

€1,190

Per person

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5.0

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

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5.0

Super!

Unspoilt Balearic Islands for max 4 guests: north Mallorca and south Menorca

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

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12 travellers

Starting from

€765

€900

Per person

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From Paros to Milos, the hidden gems of Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

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2 travellers

Starting from

€765

€900

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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28 travellers

Starting from

€667

€785

Per person

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5.0

Super!

To the Tremiti for the spring long weekends

Duration:

4 days - 3 nights

Italy:

Tremiti Islands

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4 travellers

€319

€375

Per person

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5.0

Sailing cruise on the French Riviera between the Lerins Islands

Duration:

6 days - 7 nights

France:

French Riviera and Porquerolles

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19 travellers

Starting from

€765

€900

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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6 travellers

Starting from

€170

€200

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

15798 reviews

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Relaxing weekend between Portovenere and the 5 Terre

04/11/2025

Fabio B.

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Italy

molto bello! Renato disponibile a condividere la sua esperienza
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Gone with the Wind: Corfu and the Ionian Islands

04/1/2025

jenna C.

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Canada

I was so excited to go sailing in Greece. This dream unfortunately took a quick turn into a nightmare. The captain didn’t take us to any of the sites listed on the itinerary. We stayed close to the original port the whole trip. We would ask him each day to go to one of the listed places and he would just ignore the suggestions. He would also blame it each day on the weather yet we had beautiful weather the whole trip, minus the first day. The boat itself was constantly breaking down. We had a broke toilet which was not a plus. But the worst part of the trip was when the captain used the outside shower in front of myself and a few of the other girls on the boat. He proceeded to take his swim shorts off deliberately flashing his private parts to us. All the lady’s became super uncomfortable on the boat afterwards. It was super inappropriate. Would highly recommended spending your money elsewhere. Was a horrific experience.
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Thailand and the Andaman Sea

03/29/2025

vincenzo P.

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Italy

Dal 2019 viaggio solo con Sailsquare e posso dire che mai ho fatto un esperienza cosi' intensa come questa fatta con il comandante Gianluca, conoscere la thailandia in tutte le sue piu' belle sfumature sia come spiaggie a pochi conosciute ed incantevoli come natura e colori sia come location serali e conviviali sempre ancorate alla cultura del posto e sempre con sorprese folkloristiche indimenticabili .Il comandante estrae dal cilindro una parte della thailandia che ad altri e' precluso ho sconosciuto ,in un escalation di bellezze che day by day lasciano senza fiato .Sempre lui riesce ad amalgamare i croceristi con sapienza , empatia e simpatia creando un ambiente idilliaco per armonia e divertimento giornaliero assicurato.Una esperienza da INCORNICIARE. grazie di e per tutto Comandante Gianluca
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

03/23/2025

Matt V.

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United States

Absolutely phenomenal sailing adventure with Alessandro and Andrea! From the moment we stepped aboard in Corfu with our three children (ages 7, 10 and 12), we knew we were in expert hands. They crafted the perfect itinerary, taking us to the stunning islands of Paxos and beyond, revealing the hidden gems of Greece. Our days were filled with unforgettable experiences: hiking to ancient temples, swimming and snorkeling in pristine bays, collecting sea shells, exploring historic castles, and wandering through charming seaside towns. The boat was incredibly comfortable, making our nights as enjoyable as our days. The meals onboard were all excellent as well and the accomodations were clean and cozy. Alessandro and Andrea's hospitality was truly exceptional. They are not only skilled sailors, but also passionate guides, sharing their love for Greece with us. They even played Uno with our kids every afternoon. Their knowledge and enthusiasm made this vacation one of the best we've ever had. Thank you, Alessandro and Andrea, for showing us the most beautiful side of Greece! You are simply the best! 5 stars without a doubt.

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