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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.

632

experiences

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4.6

Ponza and its wonders

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€360

€400

Per person

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4.9

Long weekend sailing between Elba and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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+21 travellers

have booked

Starting from

€304

€320

Per person

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Get on board for an enchanting weekend in the Aeolian Islands!

Duration:

3 days - 2 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€290

Per person

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5.0

Gulf of Trieste and Istria

Duration:

4 days - 3 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€279

€310

Per person

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5.0

Weekend at the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€313

Per person

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4.6

Weekend a Capraia, trekking e natura

Duration:

2 days - 2 nights

Italy:

Tuscany

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+8 travellers

have booked

€200

Per person

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4.6

Moorings and manoeuvres course - Night Navigation and Signals - Anchorages

Duration:

2 days - 2 nights

Italy:

Liguria

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+10 travellers

have booked

€290

Per person

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5.0

From the first edges to offshore navigation from Ischia to Elba

Duration:

7 days - 8 nights

Italy:

Tuscany

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Philip J.

has booked

€500

Per person

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5.0

Weekend to discover the Pink Granite Coast

Duration:

2 days - 1 night

France:

Brittany and Normandy

Give this experience a try!

Starting from

€150

Per person

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5.0

Daily trip on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

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+7 travellers

have booked

€105

Per person

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5.0

Relaxing holiday on the Côte d'Azur

Duration:

7 days - 6 nights

France:

French Riviera and Porquerolles

Give this experience a try!

Starting from

€790

Per person

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Mini cruise Syracuse - Marzamemi

Duration:

3 days - 2 nights

Italy:

Sicily

Give this experience a try!

Starting from

€801

€890

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

14278 reviews

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1st May - Whale watching cruise with WWF researcher between Elba and Capraia

05/6/2024

Elettra B.

-

Italy

Esperienza ottima. Immersione totale nella vita da barca con una parte di spiegazioni sulla vita del mare e dei nostri stupendi mammiferi marini. Organizzato con cura, attenzione e andando incontro ai bisogni delle persone presente dove possibile. Barca stupenda, tenuta bene, cibo in abbondanza, persone speciali con cui condividere spazi e tempo. Silvia molto attenta, veloce e simpatica, con una conoscenza approfondita della vita marina e non solo che trasmette senza fatica. Giulia super preparata e ottima relatrice. Anche se il tempo ci è stato avverso è stata un'esperienza unica di cui sono molto soddisfatta. Consigliata. Il capitano della vela è stato il top. Elettra .
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1st May - Whale watching cruise with WWF researcher between Elba and Capraia

05/6/2024

Francesca S.

-

Italy

Il meteo i giorni precedenti alla partenza era sfavorevole con molta pioggia, vento e onde alte, inoltre ho scoperto sul posto che il porto di Viareggio ha anche la problematica della secca. Lo skipper avrebbe dovuto cancellare la partenza, credo sia stato scorretto far presentare tutti i partecipanti e poi stare consapevolmente dal mercoledì al sabato pomeriggio in porto ad aspettare ed uscire solo dal sabato pomeriggio alla domenica pomeriggio. È vero che il tempo non si comanda, ma il giorno prima ormai già si sapeva che non ci sarebbero state le condizioni. Questa situazione mi è dispiaciuta molto, così come agli altri miei compagni, perché è un'esperienza molto dispendiosa ed è stato davvero spiacevole. Per fortuna ho trovato un bel gruppo e una brava e simpatica guida.
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April 25th long weekend in Bastia

05/6/2024

Lisa V.

-

Italy

Bellissima esperienza. Lo Skipper Enrico oltre ad essere un ottimo uomo di mare ci ha deliziati di ottimi pranzetti e cene in barca.
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25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

-

Spain

Excellent sailing trip in a comfortable boat with a great captain!! Grazie per tutto Leo & Crew!!!

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