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

5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

5 departures available

October - November

Starting from

€380

Per person

cover image
avatar image

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

cover image
avatar image

4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

Starting from

€325

€309

Per person

cover image
avatar image

4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

cover image
avatar image

New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

September - October

Starting from

€585

€527

Per person

cover image
avatar image

4.7

Feast of Santa Candida alle Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

cover image
avatar image

4.6

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

cover image
avatar image

4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€700

€630

Per person

cover image
avatar image

4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

cover image
avatar image

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

Per person

cover image
avatar image

5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

cover image
avatar image

4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

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

19141 reviews

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

09/14/2026

Dali G.

-

FR

Comfortable boat, serious skipper, lovely hostess, beautiful destination!
avatar image

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Evi (Paraskevi) P.

-

GR

[hidden] is a wonderful classy and spacious boat very well maintained so makes you feel safe and i couldn't get enough of the sunbathing on the lounge mattress on the bow of the boat. Captain Alessio is a down to earth,kind and calm person making this an Ideal combination for enjoying some relaxing holidays. Plus he has a lot's of knowledge around various subjects so it's really enjoyable talking to him. He made sure ,during our whole week in the Argosaronic gulf, to find for us the best anchorage with crystal clear waters. As i was the only person on board not speaking Italian captain Alessio and the rest of the crew never left me outside a conversation and always either translating or communicating in English.. Had a fantastic relaxing time, the chance to discover some sight seeing on the area make new friends and explore the local food culture. Thank You Captain.
avatar image

Long weekend on Elba: 4 days of sun and sailing

09/14/2026

Sara B.

Four wonderful days in which the wind and the sea were the splendid setting for a surprising human experience. Getting on board with strangers requires special chemistry. If this alchemy was created so naturally, the credit also goes to those who were able to guide not only his [hidden] through the waves, but also the human dynamics on board, far from being a simple "technician" of the sea. Don't be fooled by his being a bit "bear" initially, Paolo is an experience within the experience, an added value! More than a captain, he was the soul of our trip, adapting perfectly to the crew. He understood exactly what made us feel good and always looked for the best conditions to allow us to enjoy it to the fullest, transmitting a pure love for sailing even when the sea or the weather required us to adapt. He was a brilliant and reassuring guide when the group was looking for aggregation, capable of enriching the atmosphere with his unique personality and intuitions, but he also knew how to withdraw naturally when he perceived our need for tranquility and to live our spaces. Although it was his last weekend of sailing before a well-deserved break, he never spared his enthusiasm, working behind the scenes to ensure we had an impeccable experience from every point of view.

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

09/14/2026

Lucrezia F.

-

IT

I recommend this experience to everyone, we all had a very good time with Enrico who was a fantastic skipper! Super helpful and a great cook!

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