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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.

165

experiences

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4.8

Barefoot holiday: Weekend on Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+24 travellers

have booked

€240

€300

Per person

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4.6

ENDLESS SUMMER! Weekend in Flottiglia di Fine Estate a Ponza e Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+2 travellers

have booked

€299

€371

Per person

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4.3

7-day cruise on a 22 m maxi yacht with skipper from Pontine and Phlegraean

Duration:

7 days - 6 nights

Italy:

Pontine Islands

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+38 travellers

have booked

€927

€1,090

Per person

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4.9

Weekend tra Costiera Amalfitana e Isole Flegree

Duration:

3 days - 2 nights

Italy:

Naples & Amalfi Coast

Give this experience a try!

€340

€400

Per person

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5.0

The magic of the Egadi Islands on a Sailing Boat + couscous fest

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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+12 travellers

have booked

Starting from

€680

€800

Per person

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Live the sailboat experience

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€75

€85

Per person

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4.9

Super!

Sailing and Relaxation in the Gulf of Asinara

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+8 travellers

have booked

€810

€900

Per person

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5.0

New Year's Eve in Thailand

Duration:

9 days - 9 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

Give this experience a try!

€2,565

€2,850

Per person

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4.9

Sailing weekend in Ponza and Palmarola!

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+41 travellers

have booked

Starting from

€234

€260

Per person

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5.0

Summer in the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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+11 travellers

have booked

Starting from

€531

€590

Per person

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Experience among the Egadi Islands: a dream on a sailing boat

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€405

€450

Per person

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4.6

Two days at the Marine Protected Area of the Tremiti Islands

Duration:

2 days - 2 nights

Italy:

Tremiti Islands

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+16 travellers

have booked

€194

€216

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

15670 reviews

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

09/20/2024

Hollie D.

-

Australia

Alessandro made us feel seen and safe. He is quiet knowledgeable and did his best to try ensure we were all happy. Recommend
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/18/2024

elisa b.

-

Italy

Da quando ho assaporato per la prima volta la vacanza in barca a vela ho capito che non avrei più potuto farne a meno. Nello specifico questa vacanza é stata caratterizzata da un capitano davvero competente e disponibile (Andrea) nonché un equipaggio che tacitamente si é diviso le varie attività. É stato un peccato non poter vedere Capri ma il mere non lo consentiva. Le altre isole meravigliose! La barca pulita e spaziosa con una cucina super attrezzata dove la nostra deliziosa Carmen ha preparato tanti buoni manicaretti! Un’esperienza che consiglio a tutti almeno una volta nella vita!
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Amazing Pontine Islands in 4 days

09/18/2024

Niccolò T.

-

Italy

Tre giorni meravigliosi veleggiando tra le isole pontine. Silvio, skipper di esperienza, ha saputo guidarci sempre in sicurezza con la sua dolcezza e, soprattutto, col sorriso. Grande Silvio, spero di galleggiare nuovamente con te! La barca è un Beneteau 40.7 piedi ben armato con qualche chicca per i più tecnici: timone in carbonio (molto gradevole, specialmente con onda), sartie in tondino, scotta della randa "alla tedesca". Il comfort non è il massimo con un solo bagno, ma per pochi giorni può andare, soprattutto se c'è un buon equipaggio (personalmente mi sono trovato benissimo). Unico vero punto negativo è stato il frigo: emanava un odore difficile da gestire e descrivere. Consiglio una pulizia profonda prima delle prossime crociere.
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From Corfu sailing between turquoise sea and white beaches - hostess on board

09/17/2024

Florence D.

-

Spain

It was such a wonderful experience! We sailed to some beautiful spots, with crystal-clear water and some incredible shades of turquoise. This holiday is a great way to combine some relaxation: chilling on the deck, sunbathing, reading together with some water activities: SUP, swimming and snorkeling alongside some local culture and entertainment: visiting Corfu town and charming villages, shopping, having dinner in some local restaurants, exploring further by hiking/cycling/driving a scooter on land, Enrica and Omar are the best hosts and they form such a strong partnership. They made sure everything was perfect for all the guests. We all felt totally safe on board with Omar's experience and skills and Enrica cooked some tasty and healthy meals with an Italian touch. The boat was always kept perfectly clean and cosy. I will miss falling asleep to the gentle rocking motions of the sea ! Thanks for sharing your boat with us and for all your kindness!

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