453

experiences

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

7 departures available

August - November

Starting from

€500

€348

Per person

5.0

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

€950

Per person

5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

5.0

Super!

Wandering between Tigullio and Cinque Terre

Italy: Liguria

7 days - 7 nights

One departure available

September

€700

Per person

4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

7 departures available

July - September

Starting from

€700

Per person

5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

Per person

4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

One departure available

July - August

€946

Per person

4.8

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

Per person

4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€850

Per person

5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

Why book a holiday with Sailsquare?

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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

18091 reviews

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

07/17/2026

chiara s.

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.

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!!

The North Dodecanese from Samos on a magnificent 15-meter boat

07/16/2026

Francesca T.

What a great experience! Fabio and Irene welcome you in their beautiful boat, making you feel immediately at ease. Expert guides of the Greek islands, take you to the most fascinating bays and places. Fabio, a captain with long experience, always makes you feel safe; Irene is an ideal travel companion. A holiday suitable for everyone, even those less used to sailing.

Magnificent weekend of approach to sailing on the island of Elba

07/16/2026

Alfredo M.

Nice experience, too bad the little wind for navigation but the important thing is to have been well in excellent company. Thank you Sandro for always indulging us and making us safe! Fair winds!

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