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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.

631

experiences

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€650

Per person

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4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€490

Per person

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5.0

5-day sailing course: discovery and learning

Duration:

5 days - 4 nights

France:

French Riviera and Porquerolles

Give this experience a try!

Starting from

€630

Per person

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5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+25 travellers

have booked

€99

Per person

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5.0

Discover the beautiful scenery of the Pink Granite Coast

Duration:

4 days - 3 nights

France:

Brittany and Normandy

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Michel H.

has booked

€500

Per person

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4.5

Sailing on the Island of Elba

Duration:

3 days - 4 nights

Italy:

Tuscany

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+2 travellers

have booked

€350

Per person

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5.0

First dives in the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+11 travellers

have booked

Starting from

€400

Per person

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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

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+5 travellers

have booked

Starting from

€324

€360

Per person

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+42 travellers

have booked

Starting from

€99

Per person

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4.6

Meditation & Sailing

Duration:

5 days - 5 nights

Italy:

Tuscany

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+3 travellers

have booked

€480

Per person

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5.0

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€361

€380

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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