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

4.6

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!

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!

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

8 departures available

August - October

Starting from

€590

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

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

cover image
avatar image

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

August - September

€1,041

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

18185 reviews

avatar image

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

07/26/2026

Marina S.

-

IT

Beautiful week, Favorable weather, fabulous travel companions, beautiful places and skipper Sandro kind, competent and always attentive. Thank you for this lovely holiday 👌👌👌
avatar image

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

07/26/2026

Paola M.

-

IT

Beautiful experience. The guide was very knowledgeable and created a great atmosphere on the boat. I have recommended this type of holiday to all friends. I will certainly repeat... Maybe to get to know other corners of the Mediterranean sea... Thank you

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

07/26/2026

Jerome B.

-

FR

A very nice week aboard [hidden]e with Fabio and Irène. an extraordinary discovery of the islands between Kos and Rhodes. If you are looking for a change of scenery with just beautiful places. Go ahead! Fabio is a good adviser and a good captain. note peculiar to the village NIkia on Nisyros. a postcard. And the island of Tylos. We will return to this boat for more adventures. Thank you Fabio and Irene!
avatar image

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

07/26/2026

Alessandro B.

-

IT

I had the pleasure of spending a week on a boat with a skipper who deeply loves the sea and sailing, and this passion can be felt in every moment of navigation. His experience, professionalism and competence convey safety, allowing you to experience the journey in total serenity. What I appreciated most was the constant attention to guests: always available, attentive to everyone's needs and able to create a pleasant atmosphere without ever neglecting safety. Every decision is taken seriously and responsibly, always putting the well-being of the crew first. If you are looking for an authentic experience, guided by a person who lives the sea with passion and who knows how to take care of his guests with great professionalism, I can only recommend it. It was a holiday that I will take with me and that I would do again without any doubt.

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