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!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

cover image
avatar image

4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

cover image
avatar image

4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

cover image
avatar image

4.9

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

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

Starting from

€650

Per person

cover image
avatar image

5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

cover image
avatar image

4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

cover image
avatar image

5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€870

Per person

cover image
avatar image

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

Per person

cover image
avatar image

5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

cover image
avatar image

4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

3 departures available

August - September

Starting from

€312

Per person

cover image
avatar image

4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

5 departures available

August - September

€600

Per person

cover image
avatar image

5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

7 departures available

September - October

Starting from

€370

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

18617 reviews

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

08/18/2026

Eva R.

-

IT

A fantastic week on board "La [hidden]"! Super nice and close-knit group, great organization on board, delicious food and wonderful seats. Joshua was simply the perfect skipper: competent, super nice, super helpful and patient, always attentive to everyone's needs and great with the guys. He managed to involve us and make us learn a lot, from navigation to life underwater, always finding the ideal places to live every moment to the fullest. A holiday full of laughter, sea, discovery and unforgettable moments. Super recommended experience, to be done again absolutely!
avatar image

Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean

08/18/2026

federica s.

-

IT

Unfortunately, the skipper had severe back pain which, despite his commitment, affected the trip. I would have liked to visit more coves in the various islands, otherwise everything is ok.

North Corsica & Tuscan Archipelago: we love to travel a lot

08/18/2026

Eleonora M.

-

IT

Wonderful holiday. Marco is a skipper with a lot of experience, rely on him with your eyes closed.

Five days in Croatia with skipper, instructor and cook

08/18/2026

Alice P.

-

IT

It was a beautiful experience, far beyond expectations. Although I didn't know anyone in the group before the start, a great feeling and a relaxed and fun atmosphere were immediately created. Flavio was a super skipper: competent, attentive and always available, as well as cooking very well and not letting us miss anything throughout the holiday. I felt at ease from the first moment and I carry with me a wonderful memory of this experience. I would absolutely recommend it.

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