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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

4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

October

€200

Per person

4.7

COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

Italy: Sicily

4 days - 3 nights

2 departures available

September

Starting from

€390

€351

Per person

4.9

Super!

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€440

Per person

4.8

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

4.7

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

September

€452

Per person

4.8

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

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€300

Per person

4.8

Cous cous Festival in San Vito lo Capo and the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

€570

Per person

5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

2 departures available

January - December

Starting from

€3,000

€2,550

Per person

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

€897

€807

Per person

5.0

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

Italy: Sicily

4 days - 3 nights

One departure available

September

€410

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

4.6

Barcolana - Mini-cruise to Trieste to see the regatta from the Sea

Italy: Venice and the Gulf of Trieste

2 days - 2 nights

One departure available

October

€371

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.

1315 reviews

Long weekend of whale watching with WWF guide on an 18-meter schooner

09/16/2025

Paolo S.

Italy

Wonderful experience

Trekking and sailing weekend on the island of Elba

09/16/2025

Fabio B.

Italy

Sailing holiday with yoga and SUP in the Saronic islands

09/15/2025

Nina S.

Finland

Awesome week at sea. Elias knows all the best places to go to. It was just amazing to have this possibility to enjoy yoga, sailing, swimming, Greek food & culture in a relaxing & safe way with good company. I would definetily like to do this soon again.

Sailing holiday with yoga and SUP in the Saronic islands

08/20/2025

madelaine w.

United Kingdom

What a fabulous trip! Everything I'd hoped for and more. A great mix of relaxation and adventure with fabulous company. It was great to learn a bit about sailing whilst exploring some beautiful islands.

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