512

experiences

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

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

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

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

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

4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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

4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

Per person

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

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

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?

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

17939 reviews

Weekend of emotions in Ponza and Palmarola!

07/3/2026

Francesco T.

The experience on board the [hidden] was truly splendid: well-kept boat, relaxed atmosphere and impeccable organization. Captain Valter proved to be professional, helpful and always attentive to make us experience the best of navigation in total safety. The coves of Ponza and Palmarola are wonderful, but what made everything even more special was the passion with which Valter accompanied us in this weekend of emotions. I recommend this experience to those looking for relaxation, beautiful sea and an authentic sail.

Sail in Menorca with a cook on board!

07/3/2026

Véronique S.

Everything was perfect! Very neat and very clean boat! Delicious Maussi's food and Alex the skipper very attentive and professional. You feel like part of a family. I recommend 100%.

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

07/3/2026

Simone G.

I spent fantastic days with Antonio: a true lover of the sea who knows what he is doing. Take it easy with him: he steers the boat safely and stress-free, always with a steady hand and a lot of experience. He knows perfectly the best places to anchor, the most hidden coves and the tricks of the weather, so every stop becomes a small treasure. Antonio is nice, helpful and knows how to put everyone at ease, even those who are at their first experience on a boat and, very importantly, he turned out to be an excellent cook!

From Mykonos to Milos

07/2/2026

Maximiliano S.

Great experience, we traveled 2 couples and we are very grateful for all the attention provided by Andrea, we sailed through all the cyclades and she made us enjoy and share great moments and know places. Unique and incredible and having fun with our travel companions Elena, Patrick and Toni, who were very funny. A sublime experience.

Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Call us at

+44 20 3514 4220

Read our

Contact & Support

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!