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

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

5 departures available

July - August

Starting from

€410

€369

Per person

cover image
avatar image

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

6 departures available

June - October

Starting from

€600

€540

Per person

cover image
avatar image

4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

3 departures available

July - August

Starting from

€800

Per person

cover image
avatar image

4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

Per person

cover image
avatar image

5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

cover image
avatar image

5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

4 departures available

June - September

€740

Per person

cover image
avatar image

4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

cover image
avatar image

5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

cover image
avatar image

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

Per person

cover image
avatar image

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

cover image
avatar image

4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

cover image
avatar image

4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

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

17779 reviews

avatar image

Midweek relaxing in the Pontine Islands

06/15/2026

Andrea G.

-

IT

Experience to frame! Mirko is a very prepared and helpful skipper, as well as a wonderful person and an excellent cook. The boat is large and equipped with every comfort and convenience. The scenery of the Pontine made everything superlative and unforgettable. SUPER RECOMMENDED!!
avatar image

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

06/15/2026

Kamil J.

-

GB

Our yacht trip with Alessandro was absolutely incredible. The weekly itinerary was perfectly planned, and every place we stayed was beautiful, with just the right amount of time spent at each destination. Carlo, our host, is the sweetest person on earth. He looked after us the entire time and made us feel truly welcome. The boat was very comfortable, and we never felt like there wasn’t enough space. Alessandro is extremely patient and such a genuinely nice person—it’s impossible not to like him. This has been one of the best experiences we’ve ever had, and we would highly recommend it to anyone considering this trip.

Midweek relaxing in the Pontine Islands

06/15/2026

Emanuele S.

-

IT

I would say everything perfect! Starting with the boat which is almost new, clean and efficient! Then special mention for the skipper Mirko who, in addition to being an excellent captain, is at the same time a cook, tour guide, entertainer, barman ... etc etc . super recommended holiday ! Fair winds to all !!

Dream weekend in the Pontine Islands

06/15/2026

Federico F.

-

IT

Beautiful experience! Breathtaking landscapes and crystal clear sea. Stefano, an expert commander, cheered us up during the day allowing us to sail and collaborate in maneuvers, and in the evening with guitar and songs in the moonlight; Francesca, the perfect hostess, pampered us by cooking delicacies and never letting us miss anything. When we spoke to her for the first time, she immediately made us feel welcomed, and so it was. The boat is comfortable and well maintained. In addition, the luck of having met sociable and expansive people on board made everything perfect. Highly recommended

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