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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

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

July

€410

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€780

€693

Per person

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5.0

Super!

"Born to Sail" - One Way from Tuscany to Sardinia

Italy: Northern Sardinia

6 days - 6 nights

One departure available

July - August

€900

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€750

€675

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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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€452

€429

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

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

One departure available

August

€900

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

Per person

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5.0

Super!

Weekend at 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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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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

18093 reviews

Four days wandering around the Ionian Islands

07/17/2026

Luca P.

-

IT

A short crossing and a few days of navigation between the Ionian islands. Dario is an extraordinary skipper, experienced and attentive to every need; but even before that, he is a person of excellent character. It was a great pleasure to meet you and I really hope that we will soon have new opportunities to sail together.

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

07/17/2026

Theo v.

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NL

nice skipper, nice destination, but this is not sailing but just sight seeing. Beautifull coast line, but sailing is something different.

Tuscany and Corsica: sailing sun adventure good food energy and well-being

07/17/2026

chiara s.

-

IT

First experience on a sailing boat, three unforgettable days: sea, sun, absolute relaxation. Daniele Skipper prepared and competent, Mariapia delighted us with her fresh and delicious cuisine. Both made us fully savor the essence of sailing! Experience to be repeated!!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

07/16/2026

Carlotta P.

-

IT

Wonderful experience! Joshua is an attentive, cautious, discreet and very kind skipper. We visited the north of Corsica and loved it. Joshua took us to different beaches and all really beautiful. Good winds!!

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