342

experiences

4.8

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

September

€333

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

8 departures available

August - October

Starting from

€230

Per person

4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€750

€675

Per person

4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

11 departures available

August - November

Starting from

€700

€665

Per person

4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

One departure available

August

€390

Per person

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€990

Per person

4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August - September

€1,600

Per person

4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

3 departures available

August - September

Starting from

€312

Per person

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€713

Per person

4.0

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

2 departures available

October - November

€500

€348

Per person

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

18363 reviews

The Island of Elba, to make you live a special experience!

08/5/2026

Gabriela A.

A sailing holiday is simply fantastic! Thanks to the skipper Livio is kind, professional and always available. He also delighted us with excellent meals cooked by him, really yummy!

Leave everything for the Island of Elba

08/5/2026

Sara U.

Overwhelming evaluation! We had a very good time with the Skipper, always very helpful and attentive to the needs of the participants. Authentic but comfortable boat! We spent only a short time (two full days and two nights), but we had a great time! For us it was the first time on a sailing boat. Highly recommended!

Face to face with the Archipelago(s)

08/5/2026

Francesca C.

Really great experience! Nice, engaging and very competent skipper. Spacious and nice fast boat, just the way I like it. Perfect day and impeccable organization. Absolutely recommended, I would do it again without a second thought!

Sailing cruise in the Greek islands - The Saronic Islands

08/5/2026

Donatella M.

The sea, the sun, the wind are nothing without a good captain and Periklis has proven to be one in all circumstances and above all human expectations.

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