581

experiences

4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

3 departures available

July - August

Starting from

€800

Per person

4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

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!

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

Italy: Southern Sardinia

4 days - 3 nights

4 departures available

June - September

€740

Per person

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

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

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - August

Starting from

€900

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

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

Per person

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

4.8

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

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

17794 reviews

Giglio or Elba the pearls of the Tuscan archipelago

06/16/2026

Moira C.

I spent 2 fantastic days, together with wonderful people, I couldn't ask for anything better. Cleanliness, kindness and safety assured! I have traveled a lot by sailboat and have always felt safe. I will definitely be back on the boat with Simone, an attentive, kind and polite skipper. Thank you!

Four days in Ponza and Palmarola

06/16/2026

laura B.

The days spent on the boat with skipper Fabio and all the other companions were a breath of serenity and lightness for me and my daughter. Exceptional skipper and unforgettable travel companions. Thank you for the wonderful experience.

Weekend in the Gulf of Alassio and Gallinara Island

06/16/2026

Anna Rosa C.

Alberto was a professional and helpful skipper. He met our every need. He organized a very nice ride. Experience to be repeated.

Three days of adventure in the Aeolian Islands

06/16/2026

Paolo B.

Just perfect!

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!