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

8 departures available

August - October

Starting from

€1,300

€910

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

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

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

4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

€378

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!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

One departure available

August - September

€360

€324

Per person

cover image
avatar image

5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

6 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

cover image
avatar image

4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

cover image
avatar image

4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

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

18675 reviews

avatar image

Island of Elba and South Corsica fantastic week

08/22/2026

Myriam C.

-

IT

I would have liked to go a little sailing instead of always motoring! For the rest wonderful places, fun and nice people, captain a little too rigid with the crew!
avatar image

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/22/2026

Emanuele P.

-

IT

Beautiful experience, supercompetent skipper (Luca and Tommaso) who ensured most of the sailing even when many boats remained in port or roadstead. Program respected greatly. Beautiful crew and level kitchen and assistance. Absolutely to recommend

Flotilla Smeralda: La Maddalena Archipelago with Velasquez - MEN'S SEATS ONLY

08/22/2026

Luca A.

-

IT

Hello, Congratulations for the organization and management of the entire week. The destinations were very beautiful, the company on my boat Virgo and also on all the others that made up the flotilla was very pleasant. The management of the initial expense on the first day (for galley) needs to be deepened and reviewed. Anyway, congratulations. Greetings Luca .

Gargano National Park and Marine Protected Area of the Tremiti Islands

08/22/2026

Silvia D.

-

IT

A wonderful experience to experience the sea at 360 degrees. Crystal clear waters and amazing coastlines! The flagship: the skills and hospitality of the skipper! Although I didn't know anyone and was at my first experience on a sailing boat, after a few hours I felt like I was part of a family!

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