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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

12 departures available

May - September

Starting from

€1,000

€890

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

€680

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - November

Starting from

€600

€540

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€550

€523

Per person

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4.7

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

Italy: Tuscany

6 days - 6 nights

4 departures available

August - September

Starting from

€1,041

€989

Per person

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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

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

6 departures available

July - August

Starting from

€1,094

€1,039

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August

Starting from

€1,100

€990

Per person

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4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

4 days - 4 nights

3 departures available

June

€400

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€1,041

€989

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

7 departures available

June - July

Starting from

€490

Per person

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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.

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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

403 reviews

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Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide

04/8/2026

Agnese F.

-

Italy

Unique experience, with excellent chances of whale sighting. In 3 days we made 3 close sightings of dolphins and bottlenose dolphins

Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide

04/7/2026

Sara B.

-

Italy

Competent and nice skipper. Biology as well. The experience was very nice and fun, even for my daughter despite being seasick at times. Nice collaboration with the other participants too
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IBIZA e FORMENTERA - ALL INCLUSIVE - su ketch 18m con 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.

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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