Holidays and cruises on sailboats with organized activities.

Do you love to relax but also need to stay active or pursue your greatest passions? On a sailboat, you can enjoy a week or weekend of sailing and sea, combining activities such as trekking, yoga, snorkeling, and even gastronomic tastings.

experiences

4.9

Super!

Ski & Sail at the end of the world!

North Sea: Norway

8 days - 7 nights

One departure available

April

€1,200

Per person

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

4.6

Yoga, Wind, Sailing and Freedom

Malta: Malta

5 days - 6 nights

One departure available

May - June

€990

€891

Per person

4.6

Cous Cous Fest: weekend of Sailing, Music and Cous Cous!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€350

€315

Per person

4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

June

€1,290

€1,161

Per person

4.7

Trekking & Sailing to discover Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

May

€299

€269

Per person

5.0

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

"Back to the Wild" Weekend Sail & Trek in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

May

€380

Per person

Being together - sailing passion

Croatia: Split Archipelago

7 days - 7 nights

One departure available

July - August

€1,100

€990

Per person

4.3

In the sea of Ulysses, all inclusive, yoga instructor on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€850

€765

Per person

4.6

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

9 departures available

April - October

Starting from

€200

Per person

5.0

For couples only: BenEssere in Greece!

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€2,000

Per person

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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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 - Holidays and cruises on sailboats with organized activities.

1323 reviews

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

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.

Wellness Adventure Retreat

01/14/2026

Donna S.

Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina

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