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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

5.0

Super!

Aeolian Islands - Volcanoes, Sail & Trekking - Mountain Guide on board

Italy: Aeolian Islands

5 days - 6 nights

One departure available

August

€1,430

€1,287

Per person

5.0

Super!

Sailing and yoga: discovering Elba and the north of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

July

€870

€820

Per person

5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

3 departures available

July - August

Starting from

€135

Per person

5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

13 departures available

July - October

Starting from

€990

Per person

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

Starting from

€997

€798

Per person

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Africa: Egypt & Red Sea

6 days - 6 nights

One departure available

August

€795

Per person

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

August - October

Starting from

€1,020

€816

Per person

Meditation and massage on a sailing boat in Corsica

France: Corsica

7 days - 7 nights

2 departures available

July - August

€1,100

Per person

5.0

Week in Corsica with wellness programme

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,559

Per person

4.5

Yoga and Sailing in Costa Smeralda

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

July - August

€1,250

Per person

Deep breathing: relaxation, reset and regeneration at the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

July - August

€700

€630

Per person

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Africa: Egypt & Red Sea

4 days - 4 nights

One departure available

October

€1,145

Per person

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 - Holidays and cruises on sailboats with organized activities.

1300 reviews

Weekend a Capraia, trekking e natura

06/22/2025

Leonardo D.

Italy

Consigliato!

Weekend a Capraia, trekking e natura

06/18/2025

Giovanni N.

Italy

Esperienza bellissima, Capraia Isola magari meno conosciuta di altre dell arcipelago della Toscana, ma affascinante, mare stupendo. Francesco persona competente , affidabile, disponibile, guida la ciurma con il giusto piglio del capitano perché a bordo tutto funzioni al meglio. Anche ottimo cuoco. Barca attrezzata di tutto,

Weekend a Capraia, trekking e natura

06/10/2025

Kristian G.

Italy

Esperienza positiva e skipper disponibile

Sailing WellEssere in Ionian Greece

09/14/2024

Barbara P.

Italy

Splendido viaggio nelle isole Ionie, veleggiando nel mare cristallino in tutto relax, tra bagni, snorkeling, il suo e visitando le isole più caratteristiche. Lo skipper Fabrizio, sua moglie Sari, col gatto Kekku, accoglienti e disponibili, amano profondamente queste isole e ci hanno portato nelle baie più belle, dove ci siamo svegliati nel silenzio; ci è capitato di essere accompagnati da una tartaruga o di provare un trattamento reiki con Fabrizio. La barca è curata in ogni dettaglio e molto confortevole. La cucina vegetariana di Sari è deliziosa. Molto consigliato!

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