header cover
sailsquare logo

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

4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

58 departures available

January - December

Starting from

€200

€180

Per person

cover image
avatar image

5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

November

€99

Per person

cover image
avatar image

4.9

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,400

Per person

cover image
avatar image

5.0

Sailing adventure in Guna Yala (San Blas Islands) - All inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

6 departures available

January - December

€860

Per person

cover image
avatar image

5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

Starting from

€3,000

€2,100

Per person

cover image
avatar image

4.4

From Sanremo sailing holiday to discover the Côte d'Azur

France: French Riviera and Porquerolles

4 days - 3 nights

One departure available

December

€380

€342

Per person

cover image
avatar image

4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

12 departures available

June - September

Starting from

€430

€409

Per person

cover image
avatar image

4.3

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

9 departures available

June - October

Starting from

€1,485

€1,337

Per person - min 2 pax

cover image
avatar image
Ocean Sailing Initiation in the Canary Islands: 7 days aboard a Pogo

Atlantic islands: Canary Islands

7 days - 7 nights

2 departures available

November - December

€1,200

Per person

cover image
avatar image

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

cover image
avatar image

4.5

Your holiday in the paradisiacal sea of Ibiza & Formentera

Spain: The Balearic Islands

6 days - 6 nights

14 departures available

June - September

Starting from

€790

Per person

cover image
avatar image

4.4

Easter sailing on the Côte d'Azur

France: French Riviera and Porquerolles

3 days - 3 nights

One departure available

April

€360

€324

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17615 reviews

avatar image

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

-

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
avatar placeholder

LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

-

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.
avatar placeholder

IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper and skipper and travel insurance

11/3/2025

Patrizia M.

-

Italy

*Return to the helm* A parenthesis of the long-awaited – and missed – summer holidays, in a late October... where everything was perfectly aligned: ☀️ sun, 💨 wind up to 30 knots, unfurled sails and breathtaking destinations, among the most varied shades of sunrises and sunsets. The skipper? What can I say... An excellence in terms of safety, handling and upwind and crosswind. Even at night: impeccable navigation, always under full sail! I left alone, with the courage and the awareness that it would be an experience to be savored to the fullest. To be discovered and then left a trace. And so it was! Mouth-watering lunches and dinners, a wonderful and intense boat holiday, lived following and supporting the wave motion. I was amazed at the sight of dolphins with Es Vedrà in the background... a boat all for me and for my unexpected furry friend, **Nao**, the skipper's affectionate dog: a sweet and ever-present companion, a real **unexpected pet therapy** that made every moment even more special. And then, **back at the helm**... feel the force of the wind in your hands, the thrill of the route, the freedom that only the sea can give! Thank you, Filippo, and thanks also to Nao — it's been a long time since I sailed with the genuine enthusiasm of feeling the wind flow between jib and mainsail...
avatar placeholder

End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

-

Italy

I come from the North Sea but I now live the Italian Alps and I’ve been really missing the ocean. So, after much thinking, I decided to treat myself to a little sailing holiday in October. [hidden] (the boat) is cozy yet has every comfort and the hosts really make you feel like you’re being treated to an Italian family gateway. Giacomo and Laura go above and beyond to fit everyone's need and requests. They exceeded my expectations! Great company, great food and insane landscapes! Nothing quite like sleeping under the stars, lulled by the gentle rocking of the boat. Thank you, I hope next time I can bring my family from Scotland!

Customer Support

nightLifeGeneralInfo

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!

search

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