header cover
sailsquare 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

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

August - September

Starting from

€1,041

€989

Per person

cover image
avatar image

5.0

Super!

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

Croatia: Split Archipelago

7 days - 7 nights

13 departures available

June - October

€1,250

Per person

cover image
avatar image

4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

10 departures available

May - September

Starting from

€550

€495

Per person

cover image
avatar image

4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

12 departures available

May - September

Starting from

€400

Per person

cover image
avatar image

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

7 departures available

June - August

Starting from

€680

Per person

cover image
avatar image

5.0

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

Greece: Ionian Islands

7 days - 7 nights

25 departures available

April - October

Starting from

€460

Per person

cover image
avatar image

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - August

Starting from

€480

€432

Per person

cover image
avatar image

5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

5 departures available

May - July

Starting from

€400

€360

Per person

cover image
avatar image

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

cover image
avatar image

4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

12 departures available

May - October

Starting from

€250

Per person

cover image
avatar image

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

June - October

Starting from

€700

Per person

cover image
avatar image

5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17620 reviews

avatar image

Sailing weekend to the Columbretes Islands

04/1/2026

Alicia W.

-

United States

Had such a fun time!!
avatar placeholder

Weekend a Capraia, trekking e natura

03/24/2026

Francesco V.

Francesco and Marco are two great professionals, but above all two great travel companions! Highly recommended experience
avatar placeholder

Weekend a Capraia, trekking e natura

03/23/2026

Niccolò S.

-

Italy

Francesco and Marco are two very prepared skippers and the perfect people with whom to embark on this type of adventure. Highly recommended.
avatar image

Four days in the paradise of the San Blas Islands - All inclusive

02/26/2026

Gianluca A.

-

United States

Luigina and Alessandro made us feel at home since the very first moment. They cooked incredible meals, were always attentive to our needs, and we truly enjoyed spending time with them. It was probably one of our best family sailing adventures. On top of that they made us discover the San Blas islands: crystal clear water, white sand beaches, snorkeling, paddle boarding and of course sailing between the islands. So much to do and a joy doing it with them especially thanks to their deep knowledge of the are. Definitely highly recommended!!

Customer Support

nightLifeGeneralInfo

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!

search

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