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

4.5

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

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

€980

Per person

cover image
avatar image

4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

Per person

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

4 departures available

August

Starting from

€920

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

2 departures available

August - September

Starting from

€795

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

10 departures available

August - October

Starting from

€1,400

€1,120

Per person

cover image
avatar image

4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

August - October

Starting from

€590

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

3 departures available

August - September

Starting from

€600

€570

Per person

cover image
avatar image

4.8

Super!

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

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€900

Per person

cover image
avatar image

4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

cover image
avatar image

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

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

18163 reviews

The most spectacular islands of the Cyclades: from Athens to Milos

07/23/2026

Frank W.

-

DE

The cruise holiday in the Cyclades aboard the beautiful sailing yacht Anemeliá with skipper Alessio was spectacular! A perfect mix of pristine bays, crystal-clear blue waters, charming islands, and sailing whenever the wind allowed. The food on board was excellent, and the company of the other guests made the experience even more enjoyable. We had so much fun! Alessio is an experienced, professional, and friendly skipper who made us feel safe, relaxed, and welcome throughout the trip. Thanks to him, this holiday became a memory that will last a lifetime. We highly recommend this experience to anyone looking for an authentic sailing holiday in the Greek islands.

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

07/22/2026

chiara a.

-

IT

I had contacted the skipper beforehand to warn him that I did not eat fish and he had told me that there were no problems. It was not made WhatApp group before and no one was asked for preferences on breakfast, food, alcohol etc etc. We found ourselves with a galley made without sharing with a charge of 320 of wine, spirits well hidden in the shopping at the supermarket and about 500 euros of fish. I have never been offered any alternative but an egg omelette (with 50 euros spent on eggs) and twice a participant friend of the skipper made me a sauce with great controversy because the skipper imposed himself as a cook denying us to be able to cook. When I represented my need, I was literally pilloried and forced to eat salad that others ate as a side dish after succulent fish dishes. Now I'm wondering if I could get a refund??!! I had already used your platform and I had found it well, this is the reason why I used it again. I represent that we did not have the skipper indicated but there was a switch with his father Andrea who imposed the presence of his partner for two days (I do not know if he contributed to the galley). criticized me continuously because I did not eat fish and in general everyone for everything and in particular those who did not drink as much as he did. The whole group had difficulty communicating with the latter and in the last few days the situation has worsened. If you want further details write to me

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

Francesca C.

-

IT

It was an unforgettable experience, perfect from every point of view. The skipper is impeccable, an excellent cook and knows the sea and the Pontine islands perfectly. He is very nice and a person of heart. It is a trip that I recommend to anyone, even those who are at their first experience on a boat, like me. In addition, the places are magnificent and you will love them. Super recommended 😻

Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/22/2026

Giulio A.

-

GB

Dario made us live a unique experience and an unforgettable holiday. The Aeolian Islands are a wonderful place, but surely sailing with a person with so much experience made the holiday even more unforgettable. Dario is a very prepared captain, very professional but also welcoming and helpful. His boat is spotless and is maintained with a very high standard of cleanliness throughout the holiday. Dario was able to adapt the navigation and choices according to our needs and characteristics, and this was greatly appreciated. In addition, among Dario's many qualities I would certainly include his culinary skills: his prawns and pasta are difficult to forget! Dario's big heart can also be seen in the way he takes children to heart and gives them unforgettable experiences. We will never forget this holiday. Thank you again for everything you have allowed us to experience!

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