318

experiences

4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,180

€800

Per person

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€920

Per person

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

Per person

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

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

4.8

Super!

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

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

Per person

5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

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

18397 reviews

La Dolce Vita on a sailboat: discovering the Côte d'Azur

08/9/2026

Antonella B.

An experience that leaves a positive memory only for the excellent company and the beauty of the sea. The overall organization (rating: 2 stars) was unfortunately lacking: the itinerary was approximate, the ports were not booked and the management of on-board expenses (ports etc.) was not shared. Despite the favorable weather, we sailed for only a few hours. Skipper very attentive to safety, but rigid with limits of empathy with the group.

Sailing in Cilento

08/9/2026

Marina Serena T.

A sailing holiday is more than a moment of leisure .: it puts you (re)in contact with nature... it breaks the concrete walls that usually surround us and makes us feel part of the sun, the sea, the wind. Recommended for all those who want to remember what we are made of. Thank you Gabriele for giving us this opportunity and thank you to your travel companions for the serenity and harmony that characterized our days together

2 boats in Costa Smeralda and Bonifacio aboard a 16-meter traditional sailing yacht.

08/9/2026

Claudia D.

Super experience: relaxation, fun, safety, passion and so much to learn. Sailing with Vico is a guarantee! He has a very unique enthusiasm for sailing. He doesn't just set the course, but loves to share what he knows, explain the maneuvers and let those who want to get at the helm or the sheets try. Unforgettable days!

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/9/2026

Silvia S.

For the second year we chose the Pontine with the same boat. Lovely places!

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!