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!

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

6 departures available

September - October

Starting from

€1,300

€1,040

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

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

cover image
avatar image

4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

cover image
avatar image

5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

cover image
avatar image

5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

Per person

cover image
avatar image

5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

€490

€441

Per person

cover image
avatar image

4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

3 departures available

September

Starting from

€441

€419

Per person

cover image
avatar image

4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

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

5 departures available

September - October

Starting from

€570

Per person

cover image
avatar image

4.8

Super!

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

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

18971 reviews

avatar image

A sailing holiday: discovering the Pontine Islands

08/31/2026

Matilde C.

-

IT

Fantastic experience! Fabio is a competent and attentive skipper, both to the weather conditions and to the needs of the group. He guided us between Palmarola, Ponza and Ventotene to discover beautiful bays and caves, also involving us in the maneuvers and handling of the boat and making us live the sailing experience to the fullest! The only flaw is the space: the boat is small and has only one bathroom, so in 6 plus the skipper it is a bit cramped.
avatar image

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

08/31/2026

Antonio C.

-

IT

To be clear: excellent experience, do it. Pros: - convenient departure, parking in Punta Ala, boarding and disembarking luggage directly in front of the boat; - A great skipper, nice, we sailed whenever we could, that is a lot of hours; - if you are sick of the sea, traveling by sail, only with the sound of the sea and the wind, is an experience; - the roadsteads visited are more than enchanting, so the dozens of baths taken are one better than the other; - the skipper guides the shopping and cooks VERY WELL. Fish couscous, hummus with octopus... So it optimized all the times and at the same time satisfied every palate. In addition, he went out of his way for every need. Cons: - serious voice: you sleep in extremely small spaces, several days it was hot and humid and the ventilation in the stern is entrusted to a small porthole. Fortunately, he has installed a fan in each room, but the noise is remarkable. In short, sleeping is a bit of a problem; - Not very relevant article: there is a lack of communication. Better to clarify, perhaps from Maps, which parking lot can be used. That on Mondays we need a car for shopping, what if we were all on the train? Extremely positive experience, I thank the skipper Riccardo. Don't deny it.
avatar image

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

08/31/2026

Giovanna B.

-

IT

Super positive sailing experience! Alberto took us to beautiful places... postcard sea and beaches.... exciting and numerous sails.... fairness and infinite availability in providing us with information and clarifications on the fabulous world of sailing !!! Top cleanliness .... !! Boat very well maintained !! The only flaw...... Time literally flew !!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

08/31/2026

Luigi M.

-

IT

Magnificent experience, perfect Joshua, beautiful places, wonderful travel companions... And I would definitely do it a thousand times over

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