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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.

588

experiences

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Mystic Shores: Exploring the Canaries

Duration:

7 days - 7 nights

Atlantic islands:

Canary Islands

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14 travellers

€833

€1,190

Per person

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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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32 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!

€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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10 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

Give this experience a try!

Starting from

€765

€900

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

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

Tour of Corsica

Duration:

14 days - 14 nights

France:

Corsica

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3 travellers

Starting from

€1,870

€2,200

Per person

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Paros-Naxos and Small Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€765

€900

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

15796 reviews

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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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Weekend of theoretical and practical course

03/11/2025

Domenico B.

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Italy

Corso efficace e a misura di studente: Giampaolo sa davvero tutto ed effettivamente se il vento fosse stato più intenso saremmo potuti uscire sapendo già come comandare una barca a vela. Fantastico!
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Thailand and the Andaman Sea

02/10/2025

Emanuele G.

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Italy

Se cercate una vacanza in barca a vela con un lupo di mare Gianluca è quello che fa per voi. La barca/la sua casa anche se ha qualche anno è sicura ed affidabile, Gianluca ha un'esperienza incredibile (si fra prima a fare la lista dei posti dove non ha navigato), l'ambiente tranquillo e rilassato e ottima cucina :) Vacanza super consigliata.
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Sailing adventure through the Caribbean: St Vincent & the Grenadines

02/8/2025

mara v.

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Italy

Avventura a bordo di un ketch meravigliosa, lo skipper Hernan una persona di assoluta professionalità ,competenza e dotato di grandissima esperienza nel mondo della navigazione ci ha portato alla scoperta di fantastici scorci di paradiso nei caraibi. E' stata una bella esperienza sotto ogni punto di vista. Prezzo molto competitivo del viaggio e barca dotata di tutto. Sicuramente mi affiderei nuovamente allo skipper Hernan per un'altra avventura a bordo di Palawan

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