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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.

497

experiences

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Unspoilt Balearic Islands for up to 4 guests: North Mallorca and South Menorca

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

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+7 travellers

have booked

Starting from

€700

€1,400

Per person

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4.8

Super!

Wandering on a sailboat, sailing in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

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+40 travellers

have booked

Starting from

€450

€880

Per person

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4.5

Istria and Kornati Islands

Duration:

6 days - 7 nights

Croatia:

Istrian peninsula

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+7 travellers

have booked

€500

€850

Per person

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5.0

Super!

A dream adventure in the Tuscan Archipelago

Duration:

6 days - 6 nights

Italy:

Tuscany

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+30 travellers

have booked

Starting from

€390

€650

Per person

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4.6

Flottiglia Different: Party e nuovi amici alle isole Eolie

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+152 travellers

have booked

Starting from

€799

€1,175

Per person

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5.0

Ten days to the Egadi Islands (one-way from Marsala to Palermo)

Duration:

9 days - 10 nights

Italy:

Aegadian islands

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+10 travellers

have booked

€1,100

€1,500

Per person

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4.8

Discovering the Tuscan archipelago and Northern Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

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+3 travellers

have booked

€799

€1,099

Per person

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5.0

Gulf of Naples, Pontine, Amalfi Coast... Sailing in comfort!

Duration:

7 days - 7 nights

Italy:

Naples & Amalfi Coast

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+24 travellers

have booked

Starting from

€1,100

€1,490

Per person

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Chill & Adventure Sailing Greek Islands to Mykonos+DJ, sailing trainer

Duration:

8 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€593

€790

Per person

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5.0

FLEXIBLE DATES -  Blue Summer Week in Elba and Capraia

Duration:

6 days - 7 nights

Italy:

Tuscany

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+6 travellers

have booked

Starting from

€650

€830

Per person

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3.1

Greece Cruise in the Sporades - 2 Catamarans & 1 Sailboat

Duration:

10 days - 10 nights

Greece:

Sporades

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+15 travellers

have booked

Starting from

€1,312

€1,640

Per person

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4.9

Super!

Wine Experience with Sommelier on the Island of Elba

Duration:

4 days - 3 nights

Italy:

Tuscany

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+2 travellers

have booked

€479

€599

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

14736 reviews

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Week between the Tuscan Islands and North Corsica

07/26/2024

Gianmarco N.

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Italy

Meravigliosa vacanza con Franscesco, un vero lupo di mare ed un ottimo cuoco .Con lui ci siamo sentiti sicuri in mare, coccolati con gli ottimi pranzi che cucinava per noi. Simpaticcissimo sempre ma soprattutto quando strimpella la chitarra. Se volete vivere una vacanza spensierata in mare vi consiglio di farvi trasportare nel mare da lui e dalla sua confertevole barca a vela.
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Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor

07/26/2024

Katia P.

-

Italy

È stato il mio battesimo in barca, ne sono uscita assolutamente innamorata di questa esperienza…panorami fantastici, un grande senso di libertà, divertimento e attività a mare e a terra fantastiche… e poi che dire, il comandante è stato capace di far funzionare tutto alla meraviglia… oltre al fatto che sogno ancora la sua cucina…. Farei un’altro mese in barca solo per quello😅
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4 days in the Pontine Islands (sailing school) 

07/26/2024

valentina P.

-

Luxembourg

Grazie Dario e Grazie Seneghe che ci avete regalato giorni di pura meraviglia, relax, buonissima compagnia e scarsa voglia di tornare in porto! Dario e’ un professionista, uno skipper talentuoso e con una vera passione per il mare, centrato, che sa trasmettere competenza e tranquillita’, il tutto condito da senso dell’umorismo, pazienza, grande umanita’ e ottimi gusti musicali 😊. Isole pontine come sempre splendide e Dario ha fatto di tutto per farci vedere il piu’ possibile in questi 4 giorni. Noi siamo stati benissimo e consigliamo al 100% questo viaggio. A presto Seneghe e a presto Dario!
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From Cinque Terre to Tigullio, discovering Ligurian pearls

07/26/2024

Chiara C.

Giorgio è molto disponibile, una persona piacevole!

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