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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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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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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

May - October

Starting from

€800

€720

Per person

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5.0

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

Italy: Tuscany

3 days - 3 nights

2 departures available

July - September

Starting from

€350

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

One departure available

May

€350

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,134

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

€999

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June - July

Starting from

€440

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

11 departures available

May - October

Starting from

€500

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

8 departures available

June - October

€260

Per person

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5.0

Super!

Weekend of emotions in Ponza and Palmarola!

Italy: Pontine Islands

3 days - 2 nights

One departure available

June

€300

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

17678 reviews

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In the blue of Capri and the infinity of the Amalfi Coast

05/26/2026

Ludovica L.

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IT

Weekend on the coast on a sailing boat?! Totally worth it! Beautiful experience!
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Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

05/26/2026

Claudia M.

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IT

Beautiful weekend on Elba! The boat is spacious and very well maintained. Matteo's welcome was super! and the skipper Luca very nice, kind and helpful to explain how to collaborate in the various maneuvers on board. The company of the group was really pleasant! To be repeated soon

In the blue of Capri and the infinity of the Amalfi Coast

05/26/2026

Mariaelena P.

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IT

Wonderful experience, the first for me on a sailing boat. The boat is really very well kept, very clean, very pleasant crew, a nice group. Great credit must be given to the slipper, Gennaro, who was able to welcome and create an atmosphere of great collaboration and respect between everyone. Thank you Gennaro and the whole company.
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A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

05/26/2026

Michele P.

-

IT

Skipper available and attentive to the needs of each passenger, precise and organized, with valid experience of the sailing places. Large and well equipped boat. Recommended!

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