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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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4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

2 departures available

April - October

Starting from

€250

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

10 departures available

October - December

€1,400

Per person

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5.0

Sailing excursion from Naples to Procida or Sorrento

Italy: Naples & Amalfi Coast

1 day - 0 nights

32 departures available

October - December

€100

Per person

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4.4

The British Virgin Islands, an enchanted paradise

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

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4.1

Capraia & Corsica del Nord — 7 days of sailing in the blue

Italy: Tuscany

7 days - 6 nights

9 departures available

July - September

Starting from

€850

€723

Per person

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5.0

Raja Ampat: beyond the known routes

Indian Ocean: Indonesia

10 days - 10 nights

2 departures available

January - February

€1,570

Per person

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Sailing week of yesteryear in the clear waters of Sardinia

Italy: Southern Sardinia

6 days - 6 nights

One departure available

October

€750

Per person

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5.0

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

8 departures available

October - December

Starting from

€1,925

€1,733

Per person

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5.0

New

From the Côte d'Azur to Corsica: between wild coves and the open sea

France: Corsica

5 days - 4 nights

3 departures available

April - June

€795

Per person

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5.0

New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

2 departures available

October

Starting from

€1,200

€500

Per person

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4.6

School-holiday cruise from Marina di Pisa to Cagliari

Italy: Southern Sardinia

10 days - 10 nights

2 departures available

July

Starting from

€1,350

€1,282

Per person

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4.4

Caribbean by boat, the Grenadines and Tobago Cays

Caribbean: Grenadines & Martinique

7 days - 7 nights

3 departures available

January

€950

€855

Per person

Why book a holiday with Sailsquare?

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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

19269 reviews

Adventure weekend in the Egadi Islands

10/12/2026

Alessandro B.

-

IT

Route, stops and perfect overnight stays, skipper very helpful.
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Barcolana 58: a day at the most famous regatta in the world

10/12/2026

Sara B.

-

IT

5-star skipper: his experience and love for sailing can be seen in the naturalness with which he leads [hidden] and the serenity he transmits makes you want to continue sailing and never get off again! A 5-star destination: you have to experience the Barcolana to understand its extraordinariness... It is a regatta (where the competitive spirit comes out in a genuine way) and a party at the same time. 5-star boat: [hidden] performed very well... A true lady of the sea!

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

10/12/2026

Fiona B.

-

AU

Andrea was a fantastic skipper and Carol was a great hostess. The week was filled with beautiful beaches, delicious lunches and great conversations and was a perfect way to relax for a week. It was fun sailing along with the second yacht, and we had a great time playing volleyball together. The boat was comfortable and plenty of spots to relax above deck in the sunshine. I highly recommend this trip. Andrea and Alessandro are expert sailors who take the very best care of their customers and always put safety first - but maximize fun and stunning scenery throughout. The hosts on board (Carol and Carlo) were exceptional - making delicious and varied food each day. And little Mattias - the best boat poodle there ever was! What are you waiting for - book this adventure. Thank you Andrea, Carol and Marta for an unforgettable week.

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

10/12/2026

Lee T.

-

GB

Wow I had a fantastic week with Alessandro and Carlo, they both were so kind and caring and went out of their way to ensure we had a fantastic trip, even when the weather on the last 2 days meant we had to change the itinerary Ale found a way to ensure we didn’t miss out on visiting new places. Carlo was a fantastic host, his cooking was amazing and so much to eat every day as well as his friendly smile and always there to help. Alessandro, what a great guy, a great skipper, always ensuring we were happy and safe and would go out of his way to take us ashore and find the best restaurants. I have made a new friend for life and will be back next year 🤣 Thanks to you both for a memorable holiday

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