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Sailing and Catamaran Holidays for Families

Exploring the turquoise waters of the Mediterranean's most beautiful archipelagos by sailboat is a magical experience for the whole family. Each day becomes an unforgettable chapter of a sea adventure immersed in nature: children have fun exploring pristine bays, swimming with fish, learning to sail, while parents relax in complete serenity.

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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

10 departures available

July - October

Starting from

€1,100

€1,045

Per person

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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€625

Per person

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4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

5 days - 5 nights

4 departures available

June - September

€350

Per person

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5.0

Super!

A bordo con lo chef alle Egadi

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€800

€720

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

April - September

Starting from

€272

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

12 departures available

June - September

Starting from

€430

€409

Per person

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4.8

Set Sail with Family: 5 Days of Comfort & Adventure Around Elba Island

Italy: Tuscany

4 days - 4 nights

8 departures available

June - July

Starting from

€490

Per person

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4.5

SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

2 departures available

April - May

€990

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

Per person

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5.0

Family sailing Istria and Kvarner Bay

Croatia: Istrian peninsula

7 days - 7 nights

3 departures available

July - August

€900

Per person

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4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

€86

Per person

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4.6

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

11 departures available

June - September

Starting from

€750

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 - Sailing and Catamaran Holidays for Families

400 reviews

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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/25/2025

Sara C.

-

Italy

A week of relaxation, laughter, new friendships, baths, good food, karaoke, and slow life marked by the movements of the sea. Filippo is an expert, sunny captain, attentive to every need, super cook and master of the grill! His dog Nao is an adorable companion for travel and adventures in sup and cycling. The natural beauty of Ibiza and Formentera in October offers breathtaking views between rocky cliffs and blue sea, white sandy beaches and crystal clear water, perfect weather for exploring Formentera by bike and visiting its lighthouses overlooking the sea and well-kept villages. [hidden] comfortable, solid and spacious boat has given us beautiful sailing crossings.
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We have known the Aeolian Islands for 20 years. - Live them with us.

10/20/2025

Marco F.

-

Italy

Pasquale is a profound lover and connoisseur of the Aeolian Islands. Beyond the experience at sea, it also suggests excursions and places to visit on land
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IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper

10/15/2025

Cinzia R.

-

Italy

Nice holiday, as described and above all the skipper Filippo is a marvel, he manages everything with the utmost naturalness, always in safety, and great surprise (sorry to spoil :D), he is a spectacular cook!! Its all-inclusive formula is really super, delicious dishes, without wasting anything! P.S. Nao is adorable :)
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Poetic Gulf of Poets

10/9/2025

Massimo G.

-

Italy

Giovanni is a professional at his job,.. Expert, and collaborative with his customers... ADVICE....

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