604

experiences

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€750

€675

Per person

4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

11 departures available

June - October

Starting from

€1,200

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€650

Per person

4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

August

€510

€459

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!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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

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

17736 reviews

Midweek special between Capraia and Northern Corsica

06/7/2026

DANIELA C.

Thank you very much, Marco! You are an attentive, kind and always available skipper. From the first moment you manage to make everyone feel welcomed and at ease, sharing your beautiful boat with great generosity. Your experience and expertise convey safety and serenity, allowing everyone to fully enjoy every moment of navigation. The boat is perfect, spotless and equipped with every comfort. You know how to choose the best routes and spectacular destinations. Thanks also to my travel companions for the pleasant company.

Midweek special between Capraia and Northern Corsica

06/7/2026

Silvia G.

Thank you Marco, you were an excellent skipper, you told us so many interesting things, you led us safely to beautiful places.,Waking up in the morning and swimming in an emerald bay, all for us, is an unforgettable experience! Thanks also to all the travel companions who helped make this trip magical.....and thanks especially to [hidden]!

Midweek special between Capraia and Northern Corsica

06/7/2026

Samantha G.

Four unforgettable days between Capraia and North Corsica with fantastic travel companions! Marco is a perfect skipper: kind, professional, prudent, always available and caring with everyone! I hope to be able to travel with him again in the future

Midweek special between Capraia and Northern Corsica

06/7/2026

Maurizio Z.

Beautiful experience, the skipper Marco, prepared, helpful and caring. The boat is very beautiful and well cared for and above all very clean. The tour was very nice and Marco introduced us to places and legends of the Island of Capraia and Corsica. We felt pampered and above all safe throughout the trip. Definitely to be repeated in another itinerary!

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!