Homepage cover
logo

Log in

Whole boat with skipper yacht sailing holidays & tours in Split Archipelago

Discover more than 2 opportunities to get on board a Whole boat with skipper adventure in Split Archipelago . A unique experience with a local skipper, starting at €350 a week.

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 - Whole boat with skipper yacht sailing holidays & tours in Split Archipelago

34 reviews

Split archipelago, Hvar islands, Brac - with Hostess and full board

08/24/2026

Paola T.

-

IT

Beautiful experience: the attention, sympathy and friendliness of Cecilia combined with the skill (even as a chef!!) of the skipper Tommaso and a crystal clear sea and pristine bays made our first sailing holiday unforgettable.

Split Archipelago

08/17/2026

ENRICO MARIA B.

-

IT

It was our first family experience and we had a great time. Gianluca made us feel immediately at ease. We had a very good time with both the crew of our [hidden] and the rest of the flotilla. Excellent explanations on the use of sails and the overall management of the boat

Split archipelago, Hvar islands, Brac - with Hostess and full board

07/5/2026

Lise D.

-

US

Such a nice way to spend the extremely hot weather. Cute port towns are relaxing and the private nights in the bays are even better. Sadly we had to use the motor more than the sails. Cecilia, the host and owner, has a gift for making sure everyone has what they need. Italian wine was provided every day. 😊
avatar image

Split archipelago, Hvar islands, Brac - with Hostess and full board

07/5/2026

Massimo D.

-

IT

Beautiful week of relaxation. Tommaso and Cecilia, accompanied us to beautiful places, where mass tourism does not go and showed us beautiful bays. Sailing with Tommaso was pure tranquility, being assisted by Cecilia is like being in a 5-star hotel. For those who want to board a sailboat and never think about anything else, Cassiopeia is the perfect boat. Compatibly with the weather, Tommaso also made us sail, and it was pure magic, Thank you guys.

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