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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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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

€711

€790

Per person

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4.9

Super!

A week of sea, nature and fun in the Pontine Islands!

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+71 travellers

have booked

Starting from

€621

€690

Per person

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5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Duration:

3 days - 2 nights

Italy:

Southern Sardinia

Give this experience a try!

€504

€560

Per person

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4.8

Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+62 travellers

have booked

Starting from

€800

€890

Per person

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4.9

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

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+55 travellers

have booked

Starting from

€126

€140

Per person

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4.9

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

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+23 travellers

have booked

€324

€360

Per person

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5.0

Free in the Wind... scents and wonders in the upper Adriatic

Duration:

2 days - 1 night

Italy:

Venice and the Gulf of Trieste

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+8 travellers

have booked

Starting from

€171

€190

Per person

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4.0

Egadi Islands, Zingaro Nature Reserve, San Vito lo Capo

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+15 travellers

have booked

Starting from

€630

€700

Per person

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4.9

Super!

Flottiglia Smeralda: Arcipelago de La Maddalena con Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+29 travellers

have booked

Starting from

€990

€1,100

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+53 travellers

have booked

Starting from

€450

€500

Per person

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4.8

Super!

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

€189

€210

Per person

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North-east Sardinia and South Corsica on a beautiful 16m boat with HOSTESS

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+10 travellers

have booked

Starting from

€1,440

€1,600

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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