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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.

630

experiences

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5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

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+17 travellers

have booked

Starting from

€225

Per person

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4.9

A weekend in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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cosetta

has booked

€265

Per person

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4.9

Between Western Liguria and Côte d'Azur from Imperia - Stewardess on board

Duration:

2 days - 2 nights

Italy:

Liguria

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+2 travellers

have booked

€275

Per person

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4.2

Relaxing weekend between Portovenere and the 5 Terre

Duration:

2 days - 2 nights

Italy:

Liguria

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+5 travellers

have booked

Starting from

€250

Per person

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4.4

Weekend Riviera Ligure di Ponente and Côte d'Azur - skipper and hostess

Duration:

2 days - 1 night

Italy:

Liguria

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+6 travellers

have booked

€200

Per person

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4.5

A week with YOGA and SAILING lessons in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,350

Per person

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Sailing weekend in Camogli and Portofino from Genoa

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

€199

Per person

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5.0

The island of Ischia between sailing and trekking

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€200

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!

€250

Per person

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4.9

Sailing weekend in Istria

Duration:

2 days - 2 nights

Croatia:

Istrian peninsula

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Alberto B.

has booked

€249

Per person

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5.0

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

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+18 travellers

have booked

Starting from

€289

€340

Per person

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5.0

Weekend sailing course from Bandol

Duration:

2 days - 1 night

France:

French Riviera and Porquerolles

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+6 travellers

have booked

Starting from

€287

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

14273 reviews

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May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
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25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!
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LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

05/1/2024

Simone D.

-

Switzerland

Prima esperienza in barca a vela , Matteo oltre che essere una bellissima persona è veramente un capitano navigato che sa metterti subito a tuo agio ! Consigliato sia a giovani che famiglie ! Tutto veramente top
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Long weekend in Capraia and North Corsica

04/30/2024

Licio M.

-

Italy

Marco è uno skipper super professionale e accogliente.con l equipaggio. Barca pulita e in ordine. Grazie a Marco e a tutto l equipaggio, super simpatici

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