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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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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

€600

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

August - November

Starting from

€540

€513

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

8 departures available

July - October

Starting from

€230

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

July - August

Starting from

€1,150

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

6 departures available

July - October

Starting from

€420

€399

Per person

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5.0

Super!

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

8 departures available

July - November

Starting from

€500

€425

Per person

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5.0

New

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€950

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

July - November

Starting from

€600

€540

Per person

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5.0

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

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

17963 reviews

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

07/5/2026

Monica Sofia S.

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IT

It was a beautiful week, Francesco is a very prepared skipper and transmits his passion for both the sea and cooking. In my opinion it should just be clearer with the rules on board.

Four days in the Pontine Islands, just a stone's throw from Rome

07/5/2026

Cristina L.

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IT

Beautiful 4-day holiday between Palmarola and Ponza The boat is large and with well-organized spaces and the skipper Antonio is a real sea dog: he has experience, passion and always has a story to tell us He made us discover the islands in a unique way, sailing between Palmarola and Ponza, sleeping in the roadstead, visiting various coves and even doing a few laps with the tender Impossible not to mention that he is also an excellent cook Highly recommended holiday Thank you Antonio and fair winds!
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North Corsica & Tuscan Archipelago: we love to travel a lot

07/5/2026

Ilaria P.

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IT

Exciting experience in total contact with nature. Marco, the skipper, is a very wise person and a great entertainer, he was able to manage every situation with great serenity. We visited magnificent places and we always slept under the stars.... Simply fantastic!
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Capri Light Blue - Two boats in company!

07/5/2026

Roberta P.

-

IT

Very nice destination, prepared skipper, homogeneous company all of the same age, very comfortable boat

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