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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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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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4.4

Guadalupe to St. Martin via Antigua, Barbuda, St. Barth, and Anguilla

Caribbean: Saint Martin

14 days - 14 nights

One departure available

February

€1,490

€1,341

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

October - November

€723

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

October - November

€700

€665

Per person

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4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

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5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

3 departures available

October - November

Starting from

€220

€198

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€450

Per person

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4.7

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

Per person

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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

One departure available

April - May

€300

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

12 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

37 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

Why book a holiday with Sailsquare?

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

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

19244 reviews

Fast Sailing Experience between Authentic Islands and Good Food

10/1/2026

Alexandra C.

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CA

Great adventure, a mix of sailing, food and meeting new people! Usually, I get seasick but everything went well
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Cast off for a week at sea, a thousand ways to experience it!

09/30/2026

Lauren W.

-

AU

We had a wonderful time sailing with Alex on his boat Lady Sue. Alex is a very experienced Skipper and very attentive host who wanted to make sure we got the most from our trip. We were able to share stories and have a laugh with Alex. He is a fantastic cook if you are lucky enough for him to cook you a meal or two. On our first day, we had a coffee together and Alex made sure he understood what we wanted to experience so we could plan our week together. We then went food shopping together for the week and took off to our first spot to watch a beautiful sunset. We explored coves, visited islands, went paddle boarding, shared meals at little tavernas and connected with locals that our skipper knew. We had such beautiful days with perfect weather and some not so great weather days where we stayed docked at shore but we were able to adapt. Be flexible with expectations and keep ourselves entertained with exploring the port we were in, eating, resting and reading. We had some great sailing days with an opportunity to sail and skipper the boat and had other days where we just relaxed whilst Alex motored us to our next location. All up we had a great experience and would definitely do it again. It's a unique and special experience to be on a yacht travelling by water.

Sailing in the magical Sardinia of the South

09/30/2026

Moreno B.

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IT

The skippers Gianluca and Valeria are very prepared and professional, also good sailing instructors, nice and good cooks, a detail that should not be underestimated. A good friendship was immediately established. The itinerary to south-east Sardinia made us visit unforgettable bays and sea. I intend to have the same experience next year, perhaps on the west side.
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Sailing and Hiking in the Cyclades

09/30/2026

François-Gérald R.

-

FR

Fantastic waters for wind sailing, Island knowledge well shared. Some inshore activities may last longer.

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