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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

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

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New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

July

€300

€270

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

July - August

Starting from

€950

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

One departure available

September

€740

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

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

17931 reviews

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

07/1/2026

Stefano A.

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IT

We had a great time, we were lucky enough to have good weather (a bit warm), a group to have fun with and a skipper who, in addition to being a nice storyteller, solves one of the main critical issues: he cooks! A great

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

07/1/2026

Rory D.

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IE

Francesco was incredibly nice, welcoming and good fun to be around. He was very accommodating, thoughtful and was always looking for a way to make our trip more enjoyable. He also sought to align the route with our preferences. The boat was very clean, well equipped and the beds were much larger than they appear in the photos! As a skipper, he was very organised and experienced. He was always tracking the weather and considered our safety a priority. On top of that, he knew the islands, bays, harbours and routes inside out!

Long live Elba and Capraia

07/1/2026

Marina M.

Beautiful experience. Filippo is a professional and experienced skipper. We sailed both under sail and by motor in complete safety, the skipper was available to explain the maneuvers, involving the crew members who wanted to do it in the management of the boat. Clean, comfortable, efficient, well-equipped boat. Very beautiful island of Capraia perfect for a three-day weekend.
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Four days in the Pontine Islands, just a stone's throw from Rome

07/1/2026

Gea O.

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IT

The experience with Antonio was beautiful. he took us to discover the Pontine Islands, between stories and making us explore the caves with the tenderino. In addition.... He is an excellent cook!! I hope to get back on his boat soon. Thank you Antonio!

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