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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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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September

Starting from

€583

€525

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

€293

€264

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€550

Per person

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5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Spain: The Balearic Islands

6 days - 6 nights

5 departures available

July - September

Starting from

€650

€585

Per person

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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

3 departures available

July - September

Starting from

€680

€598

Per person

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4.9

Super!

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

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

9 departures available

August - October

Starting from

€850

€808

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

€989

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

July - October

Starting from

€530

€504

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

August - September

Starting from

€689

Per person

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4.8

Super!

ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

8 days - 7 nights

3 departures available

July - September

Starting from

€680

€544

Per person

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4.9

Super!

Tuscan Archipelago: An Oasis of Blue between Sea and Nature

Italy: Tuscany

6 days - 5 nights

6 departures available

July - August

Starting from

€650

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

16180 reviews

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Short sailing cruise in the Gulf of Naples

07/11/2025

Daniela D.

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Italy

My first experience on a sailing boat was an unforgettable experience, when the Universe puts the right people on your path at the right time. Every moment was intense, perfect and unforgettable, despite the rough sea, the change of tour due to the wind and the sea was all organized and managed calmly and with great professionalism and safety by Alessandro who was our skipper. Thank you for these three unforgettable days where we shared beautiful moments and the magic of being perfect strangers but immediately all old friends. A sensation never experienced. A gift like the breeze, the sun, the sea and the sense of touching freedom and embracing it totally.
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Life-changing experiences - Escape to the Pontine Islands

07/11/2025

Emanuela P.

First experience on a sailboat, fantastic!!!!!! perfect organization, our skipper Francesco attentive and professional,,made me feel safe at all times.,Thank you for everything
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Sailing weekend in the Pontine Islands

07/10/2025

Stefano M.

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Italy

Beautiful boat trip. I discovered two pearls: lucky those who can reach the Pontine islands habitually. Roberto is a unique skipper. Clearly an expert with many hours of navigation behind him: he knows how to command, manage the boat, put you at ease. Give great tips for living the best on the boat and on land. Excellent cook: he prepares delicious dishes and aperitifs, which make the trip more than pleasant. [hidden] is a super boat!!!! Excellent travel companions met. A real holiday. The head was freed to fully experience all the beauty that was around us. Thank you Roberto.
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Experience the sea at 360 degrees? embark with us in Kos

07/9/2025

Davide M.

-

Italy

Undecided about the choice of holiday to face, Gianfranco immediately put me at ease, so much so that it was difficult to get off his "[hidden]" on the last day. Crazy holiday with swimming in spectacular pristine coves not to mention the excellent restaurants he recommended. Gianfranco find me a location where you can dance Boogie boogie for June 2026 . Thanks again and we will see you again soon

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