139

experiences

4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

September - October

Starting from

€230

Per person

4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

€790

Per person

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€300

Per person

5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

Per person

5.0

Super!

Weekend on Elba on a 16-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

September

€400

Per person

4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

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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