header cover
logo

Log in

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.

cover image
avatar image

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€750

€675

Per person

cover image
avatar image

4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

cover image
avatar image

4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,180

€1,080

Per person

cover image
avatar image

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - October

Starting from

€590

Per person

cover image
avatar image

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

July - October

Starting from

€1,300

€1,170

Per person

cover image
avatar image

4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,134

Per person

cover image
avatar image

4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

€351

Per person

cover image
avatar image

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€795

Per person

cover image
avatar image

4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€620

€558

Per person

cover image
avatar image

4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

Per person

cover image
avatar image

4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

Per person

cover image
avatar image

4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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

17813 reviews

Midweek relaxing in the Pontine Islands

06/19/2026

roberta r.

-

IT

Beautiful ride. Mirko was great at 360 degrees, the best skipper I have ever had to deal with! Experienced, kind, nice and very proactive. He made us see very beautiful things and stop in beautiful bays. He is also a good cook. Bravo Mirko super skipper!
avatar image

Midweek in the Pontine Islands. Between Ponza, Palmarola and Zannone

06/19/2026

Silvia C.

-

IT

Really enjoyable experience. Marco and Giada accompanied us on a beautiful tour of the Pontine Islands making us discover beautiful bays also preparing excellent dishes. Marco is a very attentive and experienced skipper. Comfortable boat, a plus definitely the two sups at our disposal.

Long weekend of June 2 in the archipelago of La Maddalena and south of Corsica

06/19/2026

Marco R.

-

IT

It was a wonderful experience, from all points of view. The boat is kept in perfect condition and is very comfortable (availability of space, a bathroom for each cabin, for example). The care and attention of skipper Fabrizio in making guests feel at home are of a high level (towel and sheet kit, beautiful and quality, just to give an example). The destinations are beautiful, also thanks to the skipper's advice in finding the most beautiful, less crowded bays. An experience to be recommended and redone. Thank you Fabrizio.! Versione Italiana It was a truly wonderful experience in every respect. The boat, kept in perfect condition, is very comfortable (for example, thanks to the availability of space and a private bathroom for each cabin). The care and attention of the skipper, Fabrizio, in making guests feel at home are of a very high standard (just to give one example, the towel and linen kit provided is beautiful and of excellent quality). The destinations are stunning, also thanks to the skipper's advice in finding the most beautiful and less crowded bays. An experience highly recommended and definitely worth repeating. Thank you, Fabrizio!

Weekend of sea and colors between Ischia, Procida and Vivara

06/19/2026

FEDERICA L.

Really great sailing weekend! In addition to the beauty of the experience and the places visited, I had the opportunity to learn many things about the world of sailing. A special thanks to Emiliano, who with great competence and passion explained the operation of the boat, actively involving us and letting us try out different activities on board. It was a beautiful way to experience the sea not only as a passenger. Experience that I absolutely recommend to those who want to combine fun, adventure and learning!

Customer Support

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!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964