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

9 departures available

July - September

Starting from

€700

Per person

cover image
avatar image

4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

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

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

July - 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

8 departures available

July - 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

11 departures available

July - October

Starting from

€1,200

€1,080

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

€1,260

€1,070

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

4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

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

4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

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

17921 reviews

Weekend of approach to sailing in the setting of the Gulf of Poets

06/30/2026

Lucia S.

-

IT

Beautiful experience, everything according to expectations
avatar image

Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

06/30/2026

Iole D.

-

BE

Magnificent experience, the Aeolian Islands are magical and exploring them on a sailboat was beautiful, between sunrises, sunsets and nights under the stars to leave you breathless. Not to mention Stromboli and its roars and trekking on the smoking crater of Vulcano. Antonio is an experienced skipper, attentive, kind and very nice (and then also a surfer 🤙🏼) and with the rest of the group we had a great time. You never got bored between swimming, diving, SUP and snorkeling in places with beautiful cobalt blue water and lots of laughter. Ah! And the dolphins! Everything really 🔝🐬🩵🌊⛵️

Cast off for a week at sea, a thousand ways to experience it!

06/30/2026

Marco B.

-

IT

I had been wanting a sailing holiday for a long time. The expectation was high and the experience proved to be up to the task. The highlight of the holiday in addition to the breathtaking places was certainly the skipper, unique in his kind, a peter pan with his head on his shoulders and a wealth of experience. The days passed pleasantly between laughter, dives, wind, sun and a sea of wonderful colors, perhaps too quickly. A special mention to the skipper's cuisine... To try, absolutely!!!!!! The boat carries its years well by connecting you with the sea, it makes this experience unique!
avatar image

Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

06/30/2026

Simona O.

-

IT

We couldn't ask for anything better! Beautiful holiday and exceptional skipper! Thank you Antonio!

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