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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.

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

9 departures available

August - October

Starting from

€850

€808

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€550

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

July - September

Starting from

€689

Per person

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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

4 departures available

July - September

Starting from

€660

Per person

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4.9

Super!

Sailing dreams in the Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

August

€350

Per person

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4.9

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

4 departures available

July - September

Starting from

€1,041

€989

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

July - October

Starting from

€530

€504

Per person

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4.8

Super!

ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

8 days - 7 nights

3 departures available

July - September

Starting from

€680

€544

Per person

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4.9

Super!

Tuscan Archipelago: An Oasis of Blue between Sea and Nature

Italy: Tuscany

6 days - 5 nights

6 departures available

July - August

Starting from

€650

Per person

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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

July - September

Starting from

€370

€352

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

16167 reviews

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Weekend on Elba Island

07/8/2025

Giovanna B.

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Italy

Weekend in barca a vela splendido! Tempo ottimo, vele spiegate e piacevoli compagnie . Anthony è skipper molto capace e sempre attivo oltre ad avere un sense of humour vincente!!! Ha cercato sempre di soddisfare ogni richiesta , ha dato indicazioni sui luoghi visti e sulla vita di barca, E' simpaticissimo e .... non ultimo.... un ottimo chef! Ha sempre cucinato piatti gustosi e vari, curandone anche la presentazione !!! E pensare che si i è trovato a bordo vegani , intolleranti al pesce e altro!
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Three-Day Sailing Tour to the Pontine Islands

07/8/2025

Serena R.

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Italy

Mini vacanza bellissima! Antonio si è dimostrato un grande capitano e un grande uomo. Non solo ha una evidente competenza nautica ma ha anche grandi doti relazionali e ti fa sentire a proprio agio sulla sua confortevole barca. Si è dedicato a tutti noi con passione e gentilezza, portandoci con il suo gommone in tutte le calette e grotte possibili. Ci ha cucinato ottimi piatti e ci ha deliziato con tante storie che riguardavano le isole pontine. La sua barca è estremamente pulita e la cabina di prua una vera reggia! Inoltre la ciliegina sulla torta è il suo mitico tendalino, spazioso e in grado di offrire ampi spazi di ombra! Grazie Antonio, sceglieremmo sicuramente ancora te per una nuova avventura!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

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Italy

-ho trascorso con Paolo e Bianca una vacanza stupenda . Loro sono gentilissimi simpaticissimi Bianca è una cuoca bravissima. Sono molto disponibili . La mia prima esperienza in barca a vela è stata piacevolissima. Ho visto posti stupendi, calette che altrimenti non avrei potuto vedere se non in barca . Consiglio vivamente una vacanza con Paolo e Bianca
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Ibiza All Inclusive on an 18m ketch with skipper and skipper

07/8/2025

Donatella R.

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Italy

Cinque stelle non bastano per rendere onore alla strepitosa vacanza trascorsa su [hidden]. Filippo oltre ad essere un velista attento ed un cuoco incredibile è una persona davvero fantastica, di quelle che ti auguri che la vita ti faccia incontrare. Della sua assistente (e nipote), Camilla, mi sono letteralmente innamorata: solare, divertente e bellissima. Last but not least…NAO, sapevo avrebbe allietato la settimana ma non immaginavo così tanto! Scendendo dalla barca ho pensato: ci risalirò

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