138

experiences

4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

September - October

Starting from

€585

€527

Per person

4.7

Feast of Santa Candida alle Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

4.6

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

4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€700

Per person

4.4

New Year's Eve in the Caribbean: Martinique and the Grenadines OneWay

Caribbean: Grenadines & Martinique

10 days - 11 nights

One departure available

December - January

€1,590

Per person

4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

Per person

5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

Per person

4.7

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

One departure available

September

€600

Per person

5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

3 departures available

September - October

€1,100

Per person

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Reviews - Sailboat holidays & skippered tours

19158 reviews

A week sailing in the most beautiful places in the world

09/18/2026

Davide G.

Fantastic experience! We got to discover incredible places traveling with the wind. Piero is a great skipper and a person of heart, he taught us the basics of sailing. We always felt safe even in strong winds. Giusy is a super cook and as a sailor she is no different. He spoiled us for a week! Comfortable, welcoming and organized boat in every detail. Super recommended experience for those who love the sea, nature and conviviality. Ps: LET PIERO WIN AT SCOPONE ahaha

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

09/17/2026

Cecilia A.

Beautiful, I absolutely recommend! Flavia and Gianni were top! Beautiful experience and we spotted Bottlenose Dolphins :)

Just relaxing while sailing on the Côte d'Azur

09/17/2026

Marco V.

Great experience

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/16/2026

Olivia C.

We had the best week with Capitano! He took us to the most beautiful places! The trip was a 10/10! No notes! You will not be disappointed if you book with him! Hope to sail with him again someday! :)

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